版本
5.0
创建日期
2005-11-16 15:48:42 UTC
更新日期
2021-09-07 19:37:13 UTC
登录号
HMDB0000207
地位
quantified
二级访问
HMDB0002066

HMDB00207

HMDB02066

名称
Oleic acid
描述
Oleic acid (or 9Z)-Octadecenoic acid) is an unsaturated C-18 or an omega-9 fatty acid that is the most widely distributed and abundant fatty acid in nature. It occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. The name derives from the Latin word oleum, which means oil. Oleic acid is the most abundant fatty acid in human adipose tissue, and the second most abundant in human tissues overall, following palmitic acid. Oleic acid is a component of the normal human diet, being a part of animal fats and vegetable oils. Triglycerides of oleic acid represent the majority of olive oil (about 70%). Oleic acid triglycerides also make up 59–75% of pecan oil, 61% of canola oil, 36–67% of peanut oil, 60% of macadamia oil, 20–80% of sunflower oil, 15–20% of grape seed oil, sea buckthorn oil, 40% of sesame oil, and 14% of poppyseed oil. High oleic variants of plant sources such as sunflower (~80%) and canola oil (70%) also have been developed. consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly with increased high-density lipoprotein (HDL) cholesterol, however, the ability of oleic acid to raise HDL is still debated. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil that is considered a health benefit. Oleic acid is used in manufacturing of surfactants, soaps, plasticizers. It is also used as an emulsifying agent in foods and pharmaceuticals. Oleic acid is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent.
同义词
1:(9Z)-Octadecenoic acid

2:(Z)-Octadec-9-enoic acid

3:18:1 N-9

4:18:1DElta9cis

5:C18:1 N-9

6:cis-9-Octadecenoic acid

7:cis-Delta(9)-Octadecenoic acid

8:cis-Oleic acid

9:FA 18:1

10:Octadec-9-enoic acid

11:Oelsaeure

12:Oleate

13:(9Z)-Octadecenoate

14:(Z)-Octadec-9-enoate

15:cis-9-Octadecenoate

16:cis-delta(9)-Octadecenoate

17:cis-Δ(9)-octadecenoate

18:cis-Δ(9)-octadecenoic acid

19:cis-Oleate

20:Octadec-9-enoate

21:(9Z)-9-Octadecenoate

22:(9Z)-9-Octadecenoic acid

23:(Z)-9-Octadecanoate

24:(Z)-9-Octadecanoic acid

25:9,10-Octadecenoate

26:9,10-Octadecenoic acid

27:9-(Z)-Octadecenoate

28:9-(Z)-Octadecenoic acid

29:9-Octadecenoate

30:9-Octadecenoic acid

31:Century CD fatty acid

32:cis-Octadec-9-enoate

33:cis-Octadec-9-enoic acid

34:Distoline

35:Emersol 210

36:Emersol 211

37:Emersol 213

38:Emersol 220 white oleate

39:Emersol 220 white oleic acid

40:Emersol 221 low titer white oleate

41:Emersol 221 low titer white oleic acid

42:Emersol 233LL

43:Emersol 6321

44:Emersol 6333 NF

45:Emersol 7021

46:Glycon ro

47:Glycon wo

48:Groco 2

49:Groco 4

50:Groco 5l

51:Groco 6

52:Industrene 104

53:Industrene 105

54:Industrene 205

55:Industrene 206

56:L'acide oleique

57:Metaupon

58:Oelsauere

59:Oleic acid extra pure

60:Oleinate

61:Oleinic acid

62:Pamolyn

63:Pamolyn 100

64:Pamolyn 100 FG

65:Pamolyn 100 FGK

66:Pamolyn 125

67:Priolene 6900

68:Red oil

69:Tego-oleic 130

70:Vopcolene 27

71:Wecoline oo

72:Z-9-Octadecenoate

73:Z-9-Octadecenoic acid

74:Acid, 9-octadecenoic

75:Acid, oleic

76:9 Octadecenoic acid

77:Acid, cis-9-octadecenoic

78:cis 9 Octadecenoic acid

79:FA(18:1(9Z))

80:FA(18:1n9)

化学式
C18H34O2
平均分子量
282.4614
等位分子量
282.255880332
化学名称
(9Z)-octadec-9-enoic acid
传统名称
oleic acid
CAS 登记号
112-80-1
代谢物结构字符串
CCCCCCCC\C=C/CCCCCCCC(O)=O
inchi标识符
InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-
印记键
ZQPPMHVWECSIRJ-KTKRTIGZSA-N
分类学
description: belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

description:Long-chain fatty acids

kingdom:Organic compounds

super_class:Lipids and lipid-like molecules

class:Fatty Acyls

sub_class:Fatty acids and conjugates

molecular_framework:Aliphatic acyclic compounds

1:Carbonyl compounds

2:Carboxylic acids

3:Hydrocarbon derivatives

4:Monocarboxylic acids and derivatives

5:Organic oxides

6:Straight chain fatty acids

7:Unsaturated fatty acids

8:Aliphatic acyclic compound

9:Carbonyl group

10:Carboxylic acid

11:Carboxylic acid derivative

12:Hydrocarbon derivative

13:Long-chain fatty acid

14:Monocarboxylic acid or derivatives

15:Organic oxide

16:Organic oxygen compound

17:Organooxygen compound

18:Straight chain fatty acid

19:Unsaturated fatty acid

20:Monounsaturated fatty acids

21:Unsaturated fatty acids

22:Unsaturated fatty acids

23:octadec-9-enoic acid

本体论
term:Physiological effect

definition:The effect on an organism physiology, resulting from its exposure to a chemical.

parent_id:

level:1

type:parent

term:Health effect

definition:A health condition or observation associated with a stimuli or with a biological activity of a chemical.

parent_id:7693

*level:2

type:parent

term:Health condition

definition:A health effect that consists on short or long-term disease, condition, disorder, syndrome or constant abnormality.

parent_id:7694

**level:3

type:parent

term:Schizophrenia

definition:A psychotic disorder that is characterized by a disintegration of thought processes and of emotional responsiveness. (do).

parent_id:7695

***level:4

type:child

term:Gestational diabetes

definition:

parent_id:7695

***level:4

type:child

synonym:Gdm

synonym:Gestational diabetes mellitus

term:Disposition

definition:A concept that describes the origin of a chemical, its location within an organism, or its route of exposure.

parent_id:

level:1

type:parent

term:Route of exposure

definition:A mean by which a chemical agent comes in contact with an organism, either under intended or unintended circumstances.

parent_id:7724

*level:2

type:parent

term:Enteral

definition:Chemical exposure via the alimentary canal (mouth to anus).

parent_id:7743

**level:3

type:parent

term:Ingestion

definition:Chemical exposure facilitated by entry through the mouth.

parent_id:7744

***level:4

type:child

synonym:Digestion

term:Source

definition:Natural or synthetic origin of a chemical.

parent_id:7724

*level:2

type:parent

term:Endogenous

definition:

parent_id:7735

**level:3

type:child

term:Food

definition:

parent_id:7735

**level:3

type:child

term:Synthetic

definition:A man-made product or sample in which a chemical can be found.

parent_id:7735

**level:3

type:parent

term:Personal care product

definition:

parent_id:7742

***level:4

type:child

synonym:Pcp

synonym:Toiletries

synonym:Toiletry

synonym:Personal hygiene

synonym:Beautification product

term:Biological

definition:A living organism (species or a higher taxonomy rank), in which a chemical can be found.

parent_id:7735

**level:3

type:parent

term:Animal

definition:A living organism belonging to the kingdom animalia. it feeds on organic matter, typically having specialized sense organs and nervous system and able to respond rapidly to stimuli.

parent_id:7736

***level:4

type:child

synonym:Fauna

term:Plant

definition:A living organism belonging to the kingdom plantea. typically, it grows in a permanent site, absorbs water and inorganic substances through its roots, and synthesizes nutrients in its leaves by photosynthesis using the green pigment chlorophyll. examples incude trees, shrubs, herbs, grasses, ferns, and mosses.

parent_id:7736

***level:4

type:parent

synonym:Flora

term:Biological location

definition:The physiological origin within an organism, including anatomical compnents, biofluids and excreta.

parent_id:7724

*level:2

type:parent

term:Organ and components

definition:An anatomical organizational level including multiple tissues or substructures, which enables a common biological function.

parent_id:7725

**level:3

type:parent

term:Intestine

definition:The portion of the gastrointestinal tract that includes the small and large intestines.

parent_id:7727

***level:4

type:child

term:Liver

definition:An abdominal organ that has variable lobation which are composed mainly of hepatic lobules. (nci).

parent_id:7727

***level:4

type:child

term:Skin

definition:An organ that constitutes the external surface of the body. it consists of the epidermis, dermis, and skin appendages. (nci).

parent_id:7727

***level:4

type:child

term:Prostate

definition:The male reproductive accessory gland that produces prostatic fluid and is located adjacent to or around the urethra distal to the urinary bladder in mammals. (nci).

parent_id:7727

***level:4

type:child

synonym:Prostate gland

term:Pancreas

definition:A digestive organ in the abdomen that has both endocrine and exocrine functions. (nci).

parent_id:7727

***level:4

type:child

term:Tissue and substructures

definition:An anatomical organizational level including multiple cells yet not comprising a complete organ .

parent_id:7725

**level:3

type:parent

term:Placenta

definition:An organ present in some vertebrates during embryonic gestation that surrounds the fetus and provides it with nutrients and oxygen, facilitates gas and waste exchange between the fetus and mother, and provides parasitic cloaking from the mother's immune system by excretion of neurokinin b. (nci).

parent_id:7729

***level:4

type:child

term:Skeletal muscle

definition:Striated muscles that are under voluntary control of the organism. they are connected at either or both ends to a bone and are utilized for locomotion and other movements. (nci).

parent_id:7729

***level:4

type:child

synonym:Striated muscle

term:Adipose tissue

definition:A specialized form of connective tissue consisting primarily of adipocytes (fat cells), surrounded by a meshwork of collagen fibers. (NCI)

parent_id:7729

***level:4

type:child

synonym:Fat tissue

synonym:Body fat

synonym:Adipose

term:Muscle

definition:A fibrous soft tissue with the ability to contract to produce force and motion. (nci).

parent_id:7729

***level:4

type:child

term:Epidermis

definition:The epithelial portion of the skin (cutis). it consists of the following layers: stratum corneum (horny layer), stratum granulosum (granular layer), stratum spinosum (prickle cell layer), and stratum basale (basal cell layer). (nci).

parent_id:7729

***level:4

type:child

term:Biofluid and excreta

definition:A liquid, semi-solid or solid material originating in the body.

parent_id:7725

**level:3

type:parent

term:Saliva

definition:The watery fluid in the mouth made by the salivary glands. saliva moistens food to help digestion and it helps protect the mouth against infections. (nci).

parent_id:7731

***level:4

type:child

term:Feces

definition:The material discharged from the bowel during defecation. It consists of undigested food, intestinal mucus, epithelial cells, and bacteria.

parent_id:7731

***level:4

type:child

synonym:Fecal

synonym:Stool

synonym:Faecal

synonym:Faeces

term:Urine

definition:Excretion in liquid state processed by the kidney.

parent_id:7731

***level:4

type:child

term:Blood

definition:A liquid tissue with the primary function of transporting oxygen and carbon dioxide (nci). it supplies the tissues with nutrients, removes waste products, and contains various components of the immune system defending the body against infection.

parent_id:7731

***level:4

type:child

term:Cerebrospinal fluid

definition:The fluid that is contained within the brain ventricles, the subarachnoid space and the central canal of the spinal cord. (nci).

parent_id:7731

***level:4

type:child

synonym:Csf

term:Cell and elements

definition:An anatomical organizational level comprising of a single cell (or a fragment in some exceptions). a cell is defined by its type or function. it is the smallest unit of living structure capable of independent existence, composed of a membrane-enclosed mass of protoplasm and containing a nucleus or nucleoid.

parent_id:7725

**level:3

type:parent

term:Extracellular

definition:The space external to the outermost structure of a cell.

parent_id:7732

***level:4

type:child

synonym:Extracellular region

term:Subcellular

definition:An anatomical organizational level including a component within a biological cell .

parent_id:7725

**level:3

type:parent

term:Membrane

definition:

parent_id:7730

***level:4

type:child

term:Cell membrane

definition:A cellular compartment that separates a cellВ interiorВ from its exterior.

parent_id:7730

***level:4

type:child

synonym:Cellular membrane

term:Cytoplasm

definition:The portion of the cell contained within the plasma membrane but excluding the nucleus.

parent_id:7730

***level:4

type:child

synonym:Cytoplasma

term:Adiposome

definition:An intracellular non-membrane-bounded organelle comprising a matrix of coalesced lipids surrounded by a phospholipid monolayer. may include associated proteins.В source:В goc:tb,goc:mah.

parent_id:7730

***level:4

type:child

synonym:Lipid droplet

synonym:Lipid body

synonym:Lipid particle

term:Process

definition:Biological or chemical events, or a series thereof, leading to a known function or end-product.

parent_id:

level:1

type:parent

term:Naturally occurring process

definition:Naturally-occurring molecular events or a series thereof, leading to a known function or end-product.

parent_id:7659

*level:2

type:parent

term:Biological process

definition:Biological or chemical events or a series thereof, leading to a known function or end-product within an organism.

parent_id:7660

**level:3

type:parent

term:Biochemical process

definition:A biological process occurring at the subcellular level, involving biochemical reactions.

parent_id:7661

***level:4

type:parent

term:Chemical reaction

definition:A defined chemical event that occurs within or between organism cells.

parent_id:7661

***level:4

type:parent

term:Biochemical pathway

definition:A linked series of chemical reactions that occur in a defined order within or between organism cells, and lead to a known function or end product.

parent_id:7661

***level:4

type:parent

term:Cellular process

definition:A biological process occurring within a cell or its surroundings.

parent_id:7661

***level:4

type:parent

term:Role

definition:The purpose or function assumed by a chemical, either naturally or as intended by humans .

parent_id:

level:1

type:parent

term:Industrial application

definition:The assumed function of a chemical utilized by human.

parent_id:7671

*level:2

type:parent

term:Food and nutrition

definition:A chemical purpose related to manufacturing of food and nutrition products.

parent_id:7678

**level:3

type:child

term:Personal care products

definition:Cosmetics and personal hygene products in which a chemical was incorportaed during the manufacturing process.

parent_id:7678

**level:3

type:child

term:Surfactant

definition:A chemical substance that has the ability to lower the surface tension of water or to reduce the interfacial tension between two immiscible substances. in the cspa consumer product ingredients dictionary, surfactants are classified on the basis of their ionic characteristics, as amphoteric, anionic, cationic, or nonionic; and functions, which are subdivided into the following major groups: surfactant - cleaning agent, surfactant - conditioning agent, surfactant - emulsifying agent, surfactant - foam booster , surfactant hydrotrop , surfactant - solubility agent, surfactant - suspending agent.

parent_id:7678

**level:3

type:child

synonym:Surface-active agent

term:Emulsifier

definition:Substances that promote the formation and stability of a suspension of fine particles of a liquid in another liquid.

parent_id:7678

**level:3

type:child

term:Biological role

definition:The biological function of a chemical. the biological role answers the question how a chemical is involved in molecular processes in an organism. this can include biochemical effects of non-endogenous chemicals, which are also assigned an industrial application such as pharmaceuticals. the biological role is limited to cellular levls, and will not include role at system process level, such as a chemical which has a role in a disease.

parent_id:7671

*level:2

type:parent

term:Membrane stabilizer

definition:A chemical substance that supports the formation and maintenance of a structurally-sound and functioning cell or organelle membrane. Phospholipids form a bilayer and maintain the stability of the membrane structure together with proteins, and other lipids (i.e. cholesterol) which further strengthen it and decrease its permeability.

parent_id:7672

**level:3

type:child

synonym:Membrane stability agent

synonym:Membrane integrity agent

term:Energy source

definition:

parent_id:7672

**level:3

type:child

term:Energy storage

definition:A chemical substance which can be utilized for production of energy in the organism.

parent_id:7672

**level:3

type:child

term:Nutrient

definition:A chamical substance in food, further ingested and utilized by an organism for its well-being, growth and reproduction.

parent_id:7672

**level:3

type:child

状态
Liquid
实验性质
1:

kind:melting_point

value:13.4 °C

source:

预测性质
1:

kind:logp

value:7.68

source:ALOGPS

2:

kind:logs

value:-6.37

source:ALOGPS

3:

kind:solubility

value:1.210E-04 g/L

source:ALOGPS

4:

kind:logp

value:6.78

source:ChemAxon

5:

kind:pka_strongest_acidic

value:4.99

source:ChemAxon

6:

kind:iupac

value:(9Z)-octadec-9-enoic acid

source:ChemAxon

7:

kind:average_mass

value:282.4614

source:ChemAxon

8:

kind:mono_mass

value:282.255880332

source:ChemAxon

9:

kind:smiles

value:CCCCCCCC\C=C/CCCCCCCC(O)=O

source:ChemAxon

10:

kind:formula

value:C18H34O2

source:ChemAxon

11:

kind:inchi

value:InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-

source:ChemAxon

12:

kind:inchikey

value:ZQPPMHVWECSIRJ-KTKRTIGZSA-N

source:ChemAxon

13:

kind:polar_surface_area

value:37.3

source:ChemAxon

14:

kind:refractivity

value:87.4

source:ChemAxon

15:

kind:polarizability

value:37.09

source:ChemAxon

16:

kind:rotatable_bond_count

value:15

source:ChemAxon

17:

kind:acceptor_count

value:2

source:ChemAxon

18:

kind:donor_count

value:1

source:ChemAxon

19:

kind:physiological_charge

value:-1

source:ChemAxon

20:

kind:formal_charge

value:0

source:ChemAxon

21:

kind:number_of_rings

value:0

source:ChemAxon

22:

kind:bioavailability

value:No

source:ChemAxon

23:

kind:rule_of_five

value:No

source:ChemAxon

24:

kind:ghose_filter

value:No

source:ChemAxon

25:

kind:veber_rule

value:No

source:ChemAxon

26:

kind:mddr_like_rule

value:No

source:ChemAxon

1:

type:Specdb::EiMs

spectrum_id:1978

2:

type:Specdb::NmrOneD

spectrum_id:1190

3:

type:Specdb::CMs

spectrum_id:463

4:

type:Specdb::CMs

spectrum_id:1874

5:

type:Specdb::CMs

spectrum_id:2563

6:

type:Specdb::CMs

spectrum_id:27397

7:

type:Specdb::CMs

spectrum_id:30911

8:

type:Specdb::CMs

spectrum_id:31072

9:

type:Specdb::CMs

spectrum_id:37356

10:

type:Specdb::CMs

spectrum_id:153882

11:

type:Specdb::NmrTwoD

spectrum_id:1206

12:

type:Specdb::MsMs

spectrum_id:797

13:

type:Specdb::MsMs

spectrum_id:798

14:

type:Specdb::MsMs

spectrum_id:799

15:

type:Specdb::MsMs

spectrum_id:3612

16:

type:Specdb::MsMs

spectrum_id:285572

17:

type:Specdb::MsMs

spectrum_id:285573

18:

type:Specdb::MsMs

spectrum_id:285574

19:

type:Specdb::MsMs

spectrum_id:285575

20:

type:Specdb::MsMs

spectrum_id:373995

21:

type:Specdb::MsMs

spectrum_id:373996

22:

type:Specdb::MsMs

spectrum_id:373997

23:

type:Specdb::MsMs

spectrum_id:373998

24:

type:Specdb::MsMs

spectrum_id:373999

25:

type:Specdb::MsMs

spectrum_id:438646

26:

type:Specdb::MsMs

spectrum_id:440469

27:

type:Specdb::MsMs

spectrum_id:440470

28:

type:Specdb::MsMs

spectrum_id:440471

29:

type:Specdb::MsMs

spectrum_id:2229410

30:

type:Specdb::MsMs

spectrum_id:2230047

31:

type:Specdb::MsMs

spectrum_id:2234059

32:

type:Specdb::MsMs

spectrum_id:334

33:

type:Specdb::MsMs

spectrum_id:335

34:

type:Specdb::MsMs

spectrum_id:336

35:

type:Specdb::MsMs

spectrum_id:3613

36:

type:Specdb::MsMs

spectrum_id:2231721

光谱
生物学性质
1:

cellular:(1):Extracellular

cellular:(2):Membrane

2:

biospecimen:(1):Blood

biospecimen:(2):Cerebrospinal Fluid (CSF)

biospecimen:(3):Feces

biospecimen:(4):Saliva

biospecimen:(5):Urine

3:

tissue:(1):Adipose Tissue

tissue:(2):Epidermis

tissue:(3):Intestine

tissue:(4):Liver

tissue:(5):Pancreas

tissue:(6):Placenta

tissue:(7):Prostate

tissue:(8):Skeletal Muscle

4:

正常浓度
1:

biospecimen:Blood

concentration_value:11.42 +/- 1.67

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

2:

biospecimen:Blood

concentration_value:122 +/- 56

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

3:

biospecimen:Blood

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

4:

biospecimen:Blood

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

5:

biospecimen:Blood

concentration_value:346.950 +/- 38.943

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Male

subject_condition:Normal

6:

biospecimen:Blood

concentration_value:332.789 +/- 49.564

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Male

subject_condition:Normal

7:

biospecimen:Blood

concentration_value:339.869 +/- 42.484

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Male

subject_condition:Normal

8:

biospecimen:Blood

concentration_value:339.869 +/- 31.863

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Male

subject_condition:Normal

9:

biospecimen:Blood

concentration_value:130

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

10:

biospecimen:Blood

concentration_value:131

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

11:

biospecimen:Blood

concentration_value:158

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

12:

biospecimen:Blood

concentration_value:191

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

13:

biospecimen:Blood

concentration_value:202

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

14:

biospecimen:Blood

concentration_value:236

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

15:

biospecimen:Blood

concentration_value:240

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

16:

biospecimen:Blood

concentration_value:246

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

17:

biospecimen:Blood

concentration_value:248

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

18:

biospecimen:Blood

concentration_value:257

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

19:

biospecimen:Blood

concentration_value:267

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

20:

biospecimen:Blood

concentration_value:284

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

21:

biospecimen:Blood

concentration_value:476.384 +/- 146.817

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

22:

biospecimen:Blood

concentration_value:401.329 +/- 90.915

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Female

subject_condition:Normal

23:

biospecimen:Blood

concentration_value:49.243 +/- 19.314

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

24:

biospecimen:Blood

concentration_value:37.0 +/- 5.7

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

25:

biospecimen:Blood

concentration_value:32.5-41.3

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Female

subject_condition:Normal

26:

biospecimen:Blood

concentration_value:2135.4 +/- 665.5

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Not Specified

subject_condition:Normal

27:

biospecimen:Blood

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

28:

biospecimen:Blood

concentration_value:80.3 +/- 9.331

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

29:

biospecimen:Cerebrospinal Fluid (CSF)

concentration_value:36.0 +/- 36.0

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Not Specified

subject_condition:Normal

30:

biospecimen:Feces

concentration_value:

concentration_units:

subject_age:Not Specified

subject_sex:Not Specified

subject_condition:Normal

31:

biospecimen:Feces

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

32:

biospecimen:Feces

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

33:

biospecimen:Feces

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

34:

biospecimen:Feces

concentration_value:

concentration_units:

subject_age:Children (1-13 years old)

subject_sex:Both

subject_condition:Normal

35:

biospecimen:Feces

concentration_value:

concentration_units:

subject_age:Not Specified

subject_sex:Not Specified

subject_condition:Normal

36:

biospecimen:Feces

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

37:

biospecimen:Feces

concentration_value:

concentration_units:

subject_age:Infant (0-1 year old)

subject_sex:

subject_condition:Normal

38:

biospecimen:Feces

concentration_value:55.0518 +/- 80.0463

concentration_units:nmol/g wet feces

subject_age:Not Specified

subject_sex:Not Specified

subject_condition:Normal

39:

biospecimen:Feces

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

40:

biospecimen:Feces

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

41:

biospecimen:Feces

concentration_value:

concentration_units:

subject_age:Infant (0-1 year old)

subject_sex:Both

subject_condition:Normal

42:

biospecimen:Feces

concentration_value:

concentration_units:

subject_age:Infant (0-1 year old)

subject_sex:Not Specified

subject_condition:Normal

43:

biospecimen:Feces

concentration_value:

concentration_units:

subject_age:Infant (0-1 year old)

subject_sex:Not Specified

subject_condition:Normal

44:

biospecimen:Saliva

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Male

subject_condition:Normal

45:

biospecimen:Saliva

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Not Specified

subject_condition:Normal

46:

biospecimen:Saliva

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

47:

biospecimen:Urine

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

48:

biospecimen:Urine

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

49:

biospecimen:Urine

concentration_value:5.2 (0.3-13)

concentration_units:umol/mmol creatinine

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

50:

biospecimen:Urine

concentration_value:0.16 +/- 0.08

concentration_units:umol/mmol creatinine

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

异常浓度
1:

biospecimen:Blood

concentration_value:10.22 +/- 1.33

concentration_units:uM

patient_age:Adult (>18 years old)

patient_sex:Female

patient_information:Gestational diabetes mellitus (GDM)

2:

biospecimen:Blood

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Lung cancer

3:

biospecimen:Blood

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Colorectal cancer

4:

biospecimen:Blood

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Schizophrenia

5:

biospecimen:Blood

concentration_value:2365.1 +/- 844.5

concentration_units:uM

patient_age:Adult (>18 years old)

patient_sex:Not Specified

patient_information:Isovaleric acidemia

6:

biospecimen:Blood

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Schizophrenia

7:

biospecimen:Feces

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Colorectal cancer

8:

biospecimen:Feces

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Colorectal cancer

9:

biospecimen:Feces

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Colorectal Cancer

10:

biospecimen:Feces

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:CCD

11:

biospecimen:Feces

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Ileal Crohn's disease

12:

biospecimen:Feces

concentration_value:

concentration_units:

patient_age:Newborn (0-30 days old)

patient_sex:Not Specified

patient_information:Premature neonates

13:

biospecimen:Feces

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Colorectal cancer

14:

biospecimen:Feces

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Colorectal cancer

15:

biospecimen:Feces

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Colorectal cancer

16:

biospecimen:Feces

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Colorectal cancer

疾病参考
1:

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omim_id:

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2:

name:Lung Cancer

omim_id:211980

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4:

name:Isovaleric acidemia

omim_id:243500

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reference_text:Matern D, He M, Berry SA, Rinaldo P, Whitley CB, Madsen PP, van Calcar SC, Lussky RC, Andresen BS, Wolff JA, Vockley J: Prospective diagnosis of 2-methylbutyryl-CoA dehydrogenase deficiency in the Hmong population by newborn screening using tandem mass spectrometry. Pediatrics. 2003 Jul;112(1 Pt 1):74-8.

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reference_text:Korman SH, Andresen BS, Zeharia A, Gutman A, Boneh A, Pitt JJ: 2-ethylhydracrylic aciduria in short/branched-chain acyl-CoA dehydrogenase deficiency: application to diagnosis and implications for the R-pathway of isoleucine oxidation. Clin Chem. 2005 Mar;51(3):610-7. Epub 2004 Dec 22.

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5:

name:Colorectal cancer

omim_id:114500

[1]:

reference_text:Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8.

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reference_text:Monleon D, Morales JM, Barrasa A, Lopez JA, Vazquez C, Celda B: Metabolite profiling of fecal water extracts from human colorectal cancer. NMR Biomed. 2009 Apr;22(3):342-8. doi: 10.1002/nbm.1345.

pubmed_id:19006102

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reference_text:Weir TL, Manter DK, Sheflin AM, Barnett BA, Heuberger AL, Ryan EP: Stool microbiome and metabolome differences between colorectal cancer patients and healthy adults. PLoS One. 2013 Aug 6;8(8):e70803. doi: 10.1371/journal.pone.0070803. Print 2013.

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pubmed_id:24424155

[5]:

reference_text:Ritchie SA, Ahiahonu PW, Jayasinghe D, Heath D, Liu J, Lu Y, Jin W, Kavianpour A, Yamazaki Y, Khan AM, Hossain M, Su-Myat KK, Wood PL, Krenitsky K, Takemasa I, Miyake M, Sekimoto M, Monden M, Matsubara H, Nomura F, Goodenowe DB: Reduced levels of hydroxylated, polyunsaturated ultra long-chain fatty acids in the serum of colorectal cancer patients: implications for early screening and detection. BMC Med. 2010 Feb 15;8:13. doi: 10.1186/1741-7015-8-13.

pubmed_id:20156336

[6]:

reference_text:Qiu Y, Cai G, Su M, Chen T, Zheng X, Xu Y, Ni Y, Zhao A, Xu LX, Cai S, Jia W: Serum metabolite profiling of human colorectal cancer using GC-TOFMS and UPLC-QTOFMS. J Proteome Res. 2009 Oct;8(10):4844-50. doi: 10.1021/pr9004162.

pubmed_id:19678709

[7]:

reference_text:Cheng Y, Xie G, Chen T, Qiu Y, Zou X, Zheng M, Tan B, Feng B, Dong T, He P, Zhao L, Zhao A, Xu LX, Zhang Y, Jia W: Distinct urinary metabolic profile of human colorectal cancer. J Proteome Res. 2012 Feb 3;11(2):1354-63. doi: 10.1021/pr201001a. Epub 2011 Dec 28.

pubmed_id:22148915

[8]:

reference_text:Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14.

pubmed_id:25105552

[9]:

reference_text:Ikeda A, Nishiumi S, Shinohara M, Yoshie T, Hatano N, Okuno T, Bamba T, Fukusaki E, Takenawa T, Azuma T, Yoshida M: Serum metabolomics as a novel diagnostic approach for gastrointestinal cancer. Biomed Chromatogr. 2012 May;26(5):548-58. doi: 10.1002/bmc.1671. Epub 2011 Jul 20.

pubmed_id:21773981

[10]:

reference_text:Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18.

pubmed_id:25037050

[11]:

reference_text:Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016.

pubmed_id:27015276

[12]:

reference_text:Lin Y, Ma C, Liu C, Wang Z, Yang J, Liu X, Shen Z, Wu R: NMR-based fecal metabolomics fingerprinting as predictors of earlier diagnosis in patients with colorectal cancer. Oncotarget. 2016 May 17;7(20):29454-64. doi: 10.18632/oncotarget.8762.

pubmed_id:27107423

[13]:

reference_text:Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016.

pubmed_id:27275383

[14]:

reference_text:Wang X, Wang J, Rao B, Deng L: Gut flora profiling and fecal metabolite composition of colorectal cancer patients and healthy individuals. Exp Ther Med. 2017 Jun;13(6):2848-2854. doi: 10.3892/etm.2017.4367. Epub 2017 Apr 20.

pubmed_id:28587349

[15]:

reference_text:Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

KEGG数据库编号
C00712
DrugBank数据库编号
foodb数据库编号
FDB012858
ChemSpider数据库编号
393217
公共化学化合物编号
445639
PDB数据库编号
生物利益的化学实体数据库编号
16196
knapsack数据库编号
C00001232
维基百科编号
Oleic_acid
代谢途径的数据库编号
OLEATE-CPD
苯酚资源管理器化合物数据库编号
比格数据库编号
梅林编号
190
虚拟机身份证编号
OCDCEA
fbonto数据库编号
综合参考
Hu, Sheng; Yuan, Ji-rong; Zhu, Jin; Yin, Ying-sui. Preparation of high-purity oleic acid by selective reaction. Yingyong Huagong (2005), 34(12), 748-750, 753.
一般参考
1:

protein_accession:HMDBP00035

name:Fatty acid synthase

uniprot_id:P49327

gene_name:FASN

protein_type:Enzyme

2:

protein_accession:HMDBP00549

name:Bile acid-CoA:amino acid N-acyltransferase

uniprot_id:Q14032

gene_name:BAAT

protein_type:Enzyme

3:

protein_accession:HMDBP01046

name:Cytosolic acyl coenzyme A thioester hydrolase

uniprot_id:O00154

gene_name:ACOT7

protein_type:Enzyme

4:

protein_accession:HMDBP01047

name:Acyl-coenzyme A thioesterase 2, mitochondrial

uniprot_id:P49753

gene_name:ACOT2

protein_type:Enzyme

5:

protein_accession:HMDBP01048

name:Acyl-coenzyme A thioesterase 4

uniprot_id:Q8N9L9

gene_name:ACOT4

protein_type:Enzyme

6:

protein_accession:HMDBP01049

name:Acyl-coenzyme A thioesterase 8

uniprot_id:O14734

gene_name:ACOT8

protein_type:Enzyme

7:

protein_accession:HMDBP02888

name:Fatty-acid amide hydrolase 1

uniprot_id:O00519

gene_name:FAAH

protein_type:Enzyme

8:

protein_accession:HMDBP03089

name:2-acylglycerol O-acyltransferase 2

uniprot_id:Q3SYC2

gene_name:MOGAT2

protein_type:Enzyme

9:

protein_accession:HMDBP09234

name:Fatty-acid amide hydrolase 2

uniprot_id:Q6GMR7

gene_name:FAAH2

protein_type:Enzyme

10:

protein_accession:HMDBP11000

name:Acyl-coenzyme A thioesterase 1

uniprot_id:Q86TX2

gene_name:ACOT1

protein_type:Enzyme

11:

protein_accession:HMDBP11588

name:S-acyl fatty acid synthase thioesterase, medium chain

uniprot_id:Q9NV23

gene_name:OLAH

protein_type:Enzyme

蛋白质结合
1:

reference_text:Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.

pubmed_id:19212411

2:

reference_text:Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69.

pubmed_id:8412012

3:

reference_text:Takahashi K, Rytting JH: Novel approach to improve permeation of ondansetron across shed snake skin as a model membrane. J Pharm Pharmacol. 2001 Jun;53(6):789-94.

pubmed_id:11428654

4:

reference_text:Jensen MD: Gender differences in regional fatty acid metabolism before and after meal ingestion. J Clin Invest. 1995 Nov;96(5):2297-303.

pubmed_id:7593616

5:

reference_text:Russell AP, Somm E, Debigare R, Hartley O, Richard D, Gastaldi G, Melotti A, Michaud A, Giacobino JP, Muzzin P, LeBlanc P, Maltais F: COPD results in a reduction in UCP3 long mRNA and UCP3 protein content in types I and IIa skeletal muscle fibers. J Cardiopulm Rehabil. 2004 Sep-Oct;24(5):332-9.

pubmed_id:15602154

6:

reference_text:Crocker I, Lawson N, Daniels I, Baker P, Fletcher J: Significance of fatty acids in pregnancy-induced immunosuppression. Clin Diagn Lab Immunol. 1999 Jul;6(4):587-93.

pubmed_id:10391868

7:

reference_text:Colette C, Percheron C, Pares-Herbute N, Michel F, Pham TC, Brillant L, Descomps B, Monnier L: Exchanging carbohydrates for monounsaturated fats in energy-restricted diets: effects on metabolic profile and other cardiovascular risk factors. Int J Obes Relat Metab Disord. 2003 Jun;27(6):648-56.

pubmed_id:12833107

8:

reference_text:Christophe AB, De Greyt WF, Delanghe JR, Huyghebaert AD: Substituting enzymatically interesterified butter for native butter has no effect on lipemia or lipoproteinemia in Man. Ann Nutr Metab. 2000;44(2):61-7.

pubmed_id:10970994

9:

reference_text:de la Maza MP, Hirsch S, Nieto S, Petermann M, Bunout D: Fatty acid composition of liver total lipids in alcoholic patients with and without liver damage. Alcohol Clin Exp Res. 1996 Nov;20(8):1418-22.

pubmed_id:8947319

10:

reference_text:Droke EA, Briske-Anderson M, Lukaski HC: Fatty acids alter monolayer integrity, paracellular transport, and iron uptake and transport in Caco-2 cells. Biol Trace Elem Res. 2003 Dec;95(3):219-32.

pubmed_id:14665727

11:

reference_text:Valjakka-Koskela R, Hirvonen J, Monkkonen J, Kiesvaara J, Antila S, Lehtonen L, Urtti A: Transdermal delivery of levosimendan. Eur J Pharm Sci. 2000 Oct;11(4):343-50.

pubmed_id:11033078

12:

reference_text:Jones AE, Stolinski M, Smith RD, Murphy JL, Wootton SA: Effect of fatty acid chain length and saturation on the gastrointestinal handling and metabolic disposal of dietary fatty acids in women. Br J Nutr. 1999 Jan;81(1):37-43.

pubmed_id:10341674

13:

reference_text:Thielitz A, Helmdach M, Ropke EM, Gollnick H: Lipid analysis of follicular casts from cyanoacrylate strips as a new method for studying therapeutic effects of antiacne agents. Br J Dermatol. 2001 Jul;145(1):19-27.

pubmed_id:11453902

14:

reference_text:Richieri GV, Ogata RT, Kleinfeld AM: Equilibrium constants for the binding of fatty acids with fatty acid-binding proteins from adipocyte, intestine, heart, and liver measured with the fluorescent probe ADIFAB. J Biol Chem. 1994 Sep 30;269(39):23918-30.

pubmed_id:7929039

15:

reference_text:Lima WP, Carnevali LC Jr, Eder R, Costa Rosa LF, Bacchi EM, Seelaender MC: Lipid metabolism in trained rats: effect of guarana (Paullinia cupana Mart.) supplementation. Clin Nutr. 2005 Dec;24(6):1019-28. Epub 2005 Sep 22.

pubmed_id:16182414

16:

reference_text:Vinggaard AM, Provost JJ, Exton JH, Hansen HS: Arf and RhoA regulate both the cytosolic and the membrane-bound phospholipase D from human placenta. Cell Signal. 1997 Feb;9(2):189-96.

pubmed_id:9113419

17:

reference_text:Mittendorfer B, Liem O, Patterson BW, Miles JM, Klein S: What does the measurement of whole-body fatty acid rate of appearance in plasma by using a fatty acid tracer really mean? Diabetes. 2003 Jul;52(7):1641-8.

pubmed_id:12829627

18:

reference_text:Cater NB, Denke MA: Behenic acid is a cholesterol-raising saturated fatty acid in humans. Am J Clin Nutr. 2001 Jan;73(1):41-4.

pubmed_id:11124748

19:

reference_text:Bajaj M, Suraamornkul S, Romanelli A, Cline GW, Mandarino LJ, Shulman GI, DeFronzo RA: Effect of a sustained reduction in plasma free fatty acid concentration on intramuscular long-chain fatty Acyl-CoAs and insulin action in type 2 diabetic patients. Diabetes. 2005 Nov;54(11):3148-53.

pubmed_id:16249438

20:

reference_text:Andersen TC, Pedersen JF, Nordentoft T, Olsen O: Fat and mesenteric blood flow. Scand J Gastroenterol. 1999 Sep;34(9):894-7.

pubmed_id:10522608

21:

reference_text:Ayala-Bravo HA, Quintanar-Guerrero D, Naik A, Kalia YN, Cornejo-Bravo JM, Ganem-Quintanar A: Effects of sucrose oleate and sucrose laureate on in vivo human stratum corneum permeability. Pharm Res. 2003 Aug;20(8):1267-73.

pubmed_id:12948025

22:

reference_text:Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.

pubmed_id:32033212

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