创建日期
2005-11-16 15:48:42 UTC
更新日期
2021-09-14 14:59:29 UTC
描述
Sphingosine, also known as (4E)-sphingenine or sphing-4-enine, belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Sphingosine is an 18-carbon amino alcohol with an unsaturated hydrocarbon chain, which forms a primary part of sphingolipids. Sphingolipids are a class of cell membrane lipids that include sphingomyelin. Thus, sphingosine is considered to be a sphingoid base lipid. Sphingosine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Sphingosine is found in all living organisms ranging from bacteria to plants to humans. Sphingosine is synthesized from palmitoyl CoA and serine in a condensation required to yield dehydrosphingosine. Dehydrosphingosine is then reduced by NADPH to dihydrosphingosine (sphinganine), and finally oxidized by FAD to sphingosine. Within humans and other mammals, sphingosine participates in a number of enzymatic reactions. In particular, sphingosine can be converted into sphingosine 1-phosphate through its interaction with the enzyme sphingosine kinase 2. sphingosine 1-phosphate is an important signaling molecule. In addition, sphingosine can be biosynthesized from sphingosine 1-phosphate; which is mediated by the enzyme sphingosine-1-phosphate phosphatase 2. Sphingosine and its derivative sphinganine are the major bases of the sphingolipids in mammals. In humans, sphingosine is involved in globoid cell leukodystrophy.
同义词
1:(2S,3R)-(e)-2-Amino-1,3-dihydroxy-4-octadecene
2:(2S,3R,4E)-2-Amino-3-hydroxyoctadec-4-ene-1-ol
3:(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol
4:(2S,3R,e)-2-Aminooctadec-4-ene-1,3-diol
5:(4E)-Sphing-4-enine
6:(4E)-Sphingenine
7:(e)-2-Amino-4-octadecan-1,3-diol
8:(e)-D-Erythro-4-octadecene-1,3-diol
9:2-Amino-4-octadecene-1,3-diol
10:C18 Sphingosine
11:D-(+)-Erythro-1,3-dihydroxy-2-amino-4-trans-octadecene
12:D-Erythro-sphingosine
13:Sph
14:Sphing-4-enine
15:Sphingenine
16:Sphingoid
17:Sphingosin
18:Sphingosine D18:1
19:trans-4-Sphingenine
20:trans-D-Erythro-2-amino-4-octadecene-1,3-diol
21:4-Sphingenine
22:4 Sphingenine
23:(-)-D-erythro-Sphingosine
24:(-)-Sphingosine
25:(2S,3R)-Sphingosine
26:4-trans-Sphingenine
27:C18-Sphingosine
28:D-(+)-erythro-4-trans-Sphingenine
29:D-Sphingosine
30:D-erythro-C18-Sphingosine
31:Erythrosphingosine
32:Sphingosine
33:erythro-4-Sphingenine
34:erythro-C18-Sphingosine
35:SP(d18:1)
化学名称
(2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol
代谢物结构字符串
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO
inchi标识符
InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1
印记键
WWUZIQQURGPMPG-KRWOKUGFSA-N
分类学
description: belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
description:1,2-aminoalcohols
kingdom:Organic compounds
super_class:Organic nitrogen compounds
class:Organonitrogen compounds
sub_class:Amines
molecular_framework:Aliphatic acyclic compounds
1:Hydrocarbon derivatives
2:Monoalkylamines
3:Organopnictogen compounds
4:Primary alcohols
5:Secondary alcohols
6:1,2-aminoalcohol
7:Alcohol
8:Aliphatic acyclic compound
9:Hydrocarbon derivative
10:Organic oxygen compound
11:Organooxygen compound
12:Organopnictogen compound
13:Primary alcohol
14:Primary aliphatic amine
15:Primary amine
16:Secondary alcohol
17:Sphing-4-enines (Sphingosines)
18:Sphing-4-enines (Sphingosines)
19:sphing-4-enine
本体论
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: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: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: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: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: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:Spleen
definition:An abdominal organ that is part of the hematopoietic and immune systems. it is composed of the white pulp and the red pulp and is surrounded by a capsule. (nci).
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:Kidney
definition:The organs of the urinary tract located in the retroperitoneal cavity adjacent to the spine and composed of the renal cortex and the renal medulla. (nci).
parent_id:7727
***level:4
type:child
synonym:Kidneys
term:Biofluid and excreta
definition:A liquid, semi-solid or solid material originating in the body.
parent_id:7725
**level:3
type:parent
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:Subcellular
definition:An anatomical organizational level including a component within a biological cell .
parent_id:7725
**level:3
type:parent
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:Membrane
definition:
parent_id:7730
***level:4
type:child
term:Lysosome
definition:В A sac-like compartment inside a cell that has enzymes that can break down cellular components that need to be destroyed. (NCI).
parent_id:7730
***level:4
type:child
term:Endoplasmic reticulum
definition:A network of tubular membranes within the cytoplasm of the cell, occurring either with a smooth surface (smooth endoplasmic reticulum) or studded with ribosomes (rough endoplasmic reticulum), involved in the transport of materials. (Infoplease Dictionary via NCI)
parent_id:7730
***level:4
type:child
synonym:Er
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:Mitochondria
definition:
parent_id:7730
***level:4
type:child
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:Element
definition:
parent_id:7732
***level:4
type:parent
term:Cell
definition:
parent_id:7732
***level:4
type:parent
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:Cellular process
definition:A biological process occurring within a cell or its surroundings.
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: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: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
实验性质
1:
kind:melting_point
value:81 °C
source:
预测性质
1:
kind:logp
value:5.15
source:ALOGPS
2:
kind:logs
value:-4.89
source:ALOGPS
3:
kind:solubility
value:0.0039 g/L
source:ALOGPS
4:
kind:logp
value:4.57
source:ChemAxon
5:
kind:pka_strongest_acidic
value:14.12
source:ChemAxon
6:
kind:pka_strongest_basic
value:9.23
source:ChemAxon
7:
kind:iupac
value:(2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol
source:ChemAxon
8:
kind:average_mass
value:299.4919
source:ChemAxon
9:
kind:mono_mass
value:299.282429433
source:ChemAxon
10:
kind:smiles
value:CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO
source:ChemAxon
11:
kind:formula
value:C18H37NO2
source:ChemAxon
12:
kind:inchi
value:InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1
source:ChemAxon
13:
kind:inchikey
value:WWUZIQQURGPMPG-KRWOKUGFSA-N
source:ChemAxon
14:
kind:polar_surface_area
value:66.48
source:ChemAxon
15:
kind:refractivity
value:91.89
source:ChemAxon
16:
kind:polarizability
value:39.37
source:ChemAxon
17:
kind:rotatable_bond_count
value:15
source:ChemAxon
18:
kind:acceptor_count
value:3
source:ChemAxon
19:
kind:donor_count
value:3
source:ChemAxon
20:
kind:physiological_charge
value:1
source:ChemAxon
21:
kind:formal_charge
value:0
source:ChemAxon
22:
kind:number_of_rings
value:0
source:ChemAxon
23:
kind:bioavailability
value:Yes
source:ChemAxon
24:
kind:rule_of_five
value:Yes
source:ChemAxon
25:
kind:ghose_filter
value:Yes
source:ChemAxon
26:
kind:veber_rule
value:No
source:ChemAxon
27:
kind:mddr_like_rule
value:No
source:ChemAxon
1:
type:Specdb::CMs
spectrum_id:1978
2:
type:Specdb::CMs
spectrum_id:32100
3:
type:Specdb::CMs
spectrum_id:32101
4:
type:Specdb::CMs
spectrum_id:160781
5:
type:Specdb::MsMs
spectrum_id:95370
6:
type:Specdb::MsMs
spectrum_id:95371
7:
type:Specdb::MsMs
spectrum_id:95372
8:
type:Specdb::MsMs
spectrum_id:159627
9:
type:Specdb::MsMs
spectrum_id:159628
10:
type:Specdb::MsMs
spectrum_id:159629
11:
type:Specdb::MsMs
spectrum_id:447488
12:
type:Specdb::MsMs
spectrum_id:451394
13:
type:Specdb::MsMs
spectrum_id:2236253
14:
type:Specdb::MsMs
spectrum_id:2248383
15:
type:Specdb::MsMs
spectrum_id:2250007
16:
type:Specdb::MsMs
spectrum_id:2250411
17:
type:Specdb::MsMs
spectrum_id:2251958
18:
type:Specdb::MsMs
spectrum_id:2385212
19:
type:Specdb::MsMs
spectrum_id:2385213
20:
type:Specdb::MsMs
spectrum_id:2385214
21:
type:Specdb::MsMs
spectrum_id:2577753
22:
type:Specdb::MsMs
spectrum_id:2577754
23:
type:Specdb::MsMs
spectrum_id:2577755
24:
type:Specdb::NmrTwoD
spectrum_id:2059
25:
type:Specdb::NmrOneD
spectrum_id:5241
生物学性质
1:
cellular:(1):Cytoplasm
cellular:(2):Endoplasmic reticulum
cellular:(3):Extracellular
cellular:(4):Lysosome
cellular:(5):Membrane
2:
biospecimen:(1):Blood
biospecimen:(2):Feces
biospecimen:(3):Urine
3:
tissue:(1):Epidermis
tissue:(2):Fibroblasts
tissue:(3):Intestine
tissue:(4):Kidney
tissue:(5):Leukocyte
tissue:(6):Liver
tissue:(7):Placenta
tissue:(8):Platelet
tissue:(9):Skeletal Muscle
tissue:(10):Spleen
4:
[1]:
name:Fabry disease
smpdb_id:SMP00525
kegg_map_id:
[2]:
name:Gaucher Disease
smpdb_id:SMP00349
kegg_map_id:
[3]:
name:Globoid Cell Leukodystrophy
smpdb_id:SMP00348
kegg_map_id:
[4]:
name:Krabbe disease
smpdb_id:SMP00526
kegg_map_id:
[5]:
name:Metachromatic Leukodystrophy (MLD)
smpdb_id:SMP00347
kegg_map_id:
[6]:
name:Starch and sucrose metabolism
smpdb_id:
kegg_map_id:map00500
正常浓度
1:
biospecimen:Blood
concentration_value:0.050 +/- 0.0013
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
2:
biospecimen:Feces
concentration_value:
concentration_units:
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
3:
biospecimen:Feces
concentration_value:
concentration_units:
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
4:
biospecimen:Feces
concentration_value:
concentration_units:
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
5:
biospecimen:Urine
concentration_value:0.000038485 (0.0000375-0.00003947)
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:
concentration_units:
patient_age:Adult (>18 years old)
patient_sex:Both
patient_information:Lung cancer
2:
biospecimen:Feces
concentration_value:
concentration_units:
patient_age:Adult (>18 years old)
patient_sex:Both
patient_information:Colorectal cancer
3:
biospecimen:Feces
concentration_value:
concentration_units:
patient_age:Adult (>18 years old)
patient_sex:Both
patient_information:Colorectal Cancer
4:
biospecimen:Feces
concentration_value:
concentration_units:
patient_age:Adult (>18 years old)
patient_sex:Both
patient_information:Colorectal cancer
疾病参考
1:
name:Lung Cancer
omim_id:211980
[1]:
reference_text:Stretch C, Eastman T, Mandal R, Eisner R, Wishart DS, Mourtzakis M, Prado CM, Damaraju S, Ball RO, Greiner R, Baracos VE: Prediction of skeletal muscle and fat mass in patients with advanced cancer using a metabolomic approach. J Nutr. 2012 Jan;142(1):14-21. doi: 10.3945/jn.111.147751. Epub 2011 Dec 7.
pubmed_id:22157537
[2]:
reference_text:Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25.
pubmed_id:18953024
[3]:
reference_text:Chen Y, Ma Z, Min L, Li H, Wang B, Zhong J, Dai L: Biomarker identification and pathway analysis by serum metabolomics of lung cancer. Biomed Res Int. 2015;2015:183624. doi: 10.1155/2015/183624. Epub 2015 Apr 16.
pubmed_id:25961003
2:
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.
pubmed_id:7482520
[2]:
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
[3]:
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.
pubmed_id:23940645
[4]:
reference_text:Phua LC, Chue XP, Koh PK, Cheah PY, Ho HK, Chan EC: Non-invasive fecal metabonomic detection of colorectal cancer. Cancer Biol Ther. 2014 Apr;15(4):389-97. doi: 10.4161/cbt.27625. Epub 2014 Jan 14.
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
综合参考
Obayashi, Michio; Schlosser, Manfred. An efficient synthesis of (2S,3R)- and (2S,3S)-sphingosine. Chemistry Letters (1985), (11), 1715-18.
一般参考
1:
protein_accession:HMDBP00231
name:Lipid phosphate phosphohydrolase 2
uniprot_id:O43688
gene_name:PPAP2C
protein_type:Unknown
2:
protein_accession:HMDBP00237
name:Lipid phosphate phosphohydrolase 1
uniprot_id:O14494
gene_name:PPAP2A
protein_type:Unknown
3:
protein_accession:HMDBP00242
name:Lipid phosphate phosphohydrolase 3
uniprot_id:O14495
gene_name:PPAP2B
protein_type:Unknown
4:
protein_accession:HMDBP00434
name:Globoside alpha-1,3-N-acetylgalactosaminyltransferase 1
uniprot_id:Q8N5D6
gene_name:GBGT1
protein_type:Unknown
5:
protein_accession:HMDBP00557
name:N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase
uniprot_id:Q9Y2B2
gene_name:PIGL
protein_type:Enzyme
6:
protein_accession:HMDBP00940
name:Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q
uniprot_id:Q9BRB3
gene_name:PIGQ
protein_type:Enzyme
7:
protein_accession:HMDBP00941
name:Phosphatidylinositol N-acetylglucosaminyltransferase subunit A
uniprot_id:P37287
gene_name:PIGA
protein_type:Enzyme
8:
protein_accession:HMDBP00942
name:Phosphatidylinositol N-acetylglucosaminyltransferase subunit H
uniprot_id:Q14442
gene_name:PIGH
protein_type:Enzyme
9:
protein_accession:HMDBP00943
name:Phosphatidylinositol N-acetylglucosaminyltransferase subunit P
uniprot_id:P57054
gene_name:PIGP
protein_type:Enzyme
10:
protein_accession:HMDBP00944
name:Phosphatidylinositol N-acetylglucosaminyltransferase subunit C
uniprot_id:Q92535
gene_name:PIGC
protein_type:Enzyme
11:
protein_accession:HMDBP01082
name:Sphingosine kinase 1
uniprot_id:Q9NYA1
gene_name:SPHK1
protein_type:Unknown
12:
protein_accession:HMDBP01083
name:Sphingosine kinase 2
uniprot_id:Q9NRA0
gene_name:SPHK2
protein_type:Unknown
13:
protein_accession:HMDBP01084
name:Acid ceramidase
uniprot_id:Q13510
gene_name:ASAH1
protein_type:Enzyme
14:
protein_accession:HMDBP01719
name:Ganglioside GM2 activator
uniprot_id:P17900
gene_name:GM2A
protein_type:Enzyme
15:
protein_accession:HMDBP02412
name:T-cell surface glycoprotein CD1e, membrane-associated
uniprot_id:P15812
gene_name:CD1E
protein_type:Enzyme
16:
protein_accession:HMDBP02561
name:Sphingosine 1-phosphate receptor 4
uniprot_id:O95977
gene_name:S1PR4
protein_type:Enzyme
17:
protein_accession:HMDBP02604
name:Sphingosine 1-phosphate receptor 2
uniprot_id:O95136
gene_name:S1PR2
protein_type:Enzyme
18:
protein_accession:HMDBP02675
name:Epididymal secretory protein E1
uniprot_id:P61916
gene_name:NPC2
protein_type:Enzyme
19:
protein_accession:HMDBP02679
name:Sphingosine 1-phosphate receptor 1
uniprot_id:P21453
gene_name:S1PR1
protein_type:Enzyme
20:
protein_accession:HMDBP02770
name:Sphingosine 1-phosphate receptor 5
uniprot_id:Q9H228
gene_name:S1PR5
protein_type:Enzyme
21:
protein_accession:HMDBP02779
name:Ceramide synthase 1
uniprot_id:P27544
gene_name:CERS1
protein_type:Enzyme
22:
protein_accession:HMDBP02783
name:Antigen-presenting glycoprotein CD1d
uniprot_id:P15813
gene_name:CD1D
protein_type:Enzyme
23:
protein_accession:HMDBP02955
name:GPI mannosyltransferase 1
uniprot_id:Q9H3S5
gene_name:PIGM
protein_type:Enzyme
24:
protein_accession:HMDBP02977
name:Phosphatidylinositol-glycan biosynthesis class W protein
uniprot_id:Q7Z7B1
gene_name:PIGW
protein_type:Enzyme
25:
protein_accession:HMDBP03084
name:Phosphatidylinositol-glycan biosynthesis class X protein
uniprot_id:Q8TBF5
gene_name:PIGX
protein_type:Enzyme
26:
protein_accession:HMDBP03088
name:GPI mannosyltransferase 4
uniprot_id:Q86VD9
gene_name:PIGZ
protein_type:Enzyme
27:
protein_accession:HMDBP06380
name:Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase
uniprot_id:Q9BYG0
gene_name:B3GNT5
protein_type:Enzyme
28:
protein_accession:HMDBP06939
name:Beta-1,3-galactosyltransferase 5
uniprot_id:Q9Y2C3
gene_name:B3GALT5
protein_type:Enzyme
29:
protein_accession:HMDBP07325
name:GPI mannosyltransferase 3
uniprot_id:Q92521
gene_name:PIGB
protein_type:Enzyme
30:
protein_accession:HMDBP07326
name:Phosphatidylinositol-glycan biosynthesis class F protein
uniprot_id:Q07326
gene_name:PIGF
protein_type:Enzyme
31:
protein_accession:HMDBP07327
name:GPI ethanolamine phosphate transferase 2
uniprot_id:Q5H8A4
gene_name:PIGG
protein_type:Enzyme
32:
protein_accession:HMDBP07328
name:GPI ethanolamine phosphate transferase 1
uniprot_id:O95427
gene_name:PIGN
protein_type:Enzyme
33:
protein_accession:HMDBP07329
name:GPI ethanolamine phosphate transferase 3
uniprot_id:Q8TEQ8
gene_name:PIGO
protein_type:Enzyme
34:
protein_accession:HMDBP07330
name:GPI transamidase component PIG-S
uniprot_id:Q96S52
gene_name:PIGS
protein_type:Enzyme
35:
protein_accession:HMDBP07331
name:GPI transamidase component PIG-T
uniprot_id:Q969N2
gene_name:PIGT
protein_type:Enzyme
36:
protein_accession:HMDBP07332
name:Phosphatidylinositol glycan anchor biosynthesis class U protein
uniprot_id:Q9H490
gene_name:PIGU
protein_type:Enzyme
37:
protein_accession:HMDBP07333
name:GPI mannosyltransferase 2
uniprot_id:Q9NUD9
gene_name:PIGV
protein_type:Enzyme
38:
protein_accession:HMDBP07334
name:Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y
uniprot_id:Q3MUY2
gene_name:PIGY
protein_type:Enzyme
39:
protein_accession:HMDBP07339
name:Pleckstrin homology domain-containing family A member 8
uniprot_id:Q96JA3
gene_name:PLEKHA8
protein_type:Unknown
40:
protein_accession:HMDBP07716
name:G-protein coupled receptor 6
uniprot_id:P46095
gene_name:GPR6
protein_type:Unknown
41:
protein_accession:HMDBP09162
name:Putative neutral ceramidase C
uniprot_id:P0C7U2
gene_name:ASAH2C
protein_type:Enzyme
42:
protein_accession:HMDBP09163
name:Alkaline ceramidase 2
uniprot_id:Q5QJU3
gene_name:ACER2
protein_type:Enzyme
43:
protein_accession:HMDBP09165
name:Neutral ceramidase
uniprot_id:Q9NR71
gene_name:ASAH2
protein_type:Enzyme
44:
protein_accession:HMDBP09169
name:Non-lysosomal glucosylceramidase
uniprot_id:Q9HCG7
gene_name:GBA2
protein_type:Enzyme
45:
protein_accession:HMDBP09386
name:Sphingosine kinase 1
uniprot_id:Q96GK1
gene_name:SPHK1
protein_type:Enzyme
46:
protein_accession:HMDBP10638
name:Alkaline ceramidase 1
uniprot_id:Q8TDN7
gene_name:ACER1
protein_type:Enzyme
47:
protein_accession:HMDBP10797
name:Sphingosine 1-phosphate receptor 3
uniprot_id:Q99500
gene_name:S1PR3
protein_type:Unknown
48:
protein_accession:HMDBP10978
name:Ceramide synthase 5
uniprot_id:Q8N5B7
gene_name:CERS5
protein_type:Unknown
49:
protein_accession:HMDBP11012
name:GPI-anchor transamidase
uniprot_id:Q92643
gene_name:PIGK
protein_type:Enzyme
50:
protein_accession:HMDBP11439
name:Glycosylphosphatidylinositol anchor attachment 1 protein
uniprot_id:O43292
gene_name:GPAA1
protein_type:Unknown
51:
protein_accession:HMDBP11440
name:Protein PLEKHA9
uniprot_id:O95397
gene_name:PLEKHA9
protein_type:Unknown
52:
protein_accession:HMDBP11441
name:Glycolipid transfer protein domain-containing protein 2
uniprot_id:A6NH11
gene_name:GLTPD2
protein_type:Unknown
53:
protein_accession:HMDBP11442
name:Putative uncharacterized protein PLEKHA8
uniprot_id:B5MDU3
gene_name:PLEKHA8
protein_type:Unknown
54:
protein_accession:HMDBP11443
name:T-cell surface glycoprotein CD1a
uniprot_id:P06126
gene_name:CD1A
protein_type:Unknown
55:
protein_accession:HMDBP11444
name:Glycolipid transfer protein domain-containing protein 1
uniprot_id:Q5TA50
gene_name:GLTPD1
protein_type:Unknown
56:
protein_accession:HMDBP11445
name:T-cell surface glycoprotein CD1c
uniprot_id:P29017
gene_name:CD1C
protein_type:Unknown
57:
protein_accession:HMDBP11446
name:Lipopolysaccharide-binding protein
uniprot_id:P18428
gene_name:LBP
protein_type:Unknown
58:
protein_accession:HMDBP11447
name:Putative uncharacterized protein DKFZp434L0435
uniprot_id:Q9UFH6
gene_name:DKFZp434L0435
protein_type:Unknown
59:
protein_accession:HMDBP11448
name:T-cell surface glycoprotein CD1b
uniprot_id:P29016
gene_name:CD1B
protein_type:Unknown
60:
protein_accession:HMDBP11449
name:Glycolipid transfer protein
uniprot_id:Q9NZD2
gene_name:GLTP
protein_type:Unknown
61:
protein_accession:HMDBP11558
name:Sphingosine-1-phosphate phosphatase 2
uniprot_id:Q8IWX5
gene_name:SGPP2
protein_type:Enzyme
62:
protein_accession:HMDBP11630
name:Ceramide synthase 2
uniprot_id:Q96G23
gene_name:CERS2
protein_type:Unknown
63:
protein_accession:HMDBP11631
name:Ceramide synthase 3
uniprot_id:Q8IU89
gene_name:CERS3
protein_type:Unknown
64:
protein_accession:HMDBP11632
name:Ceramide synthase 4
uniprot_id:Q9HA82
gene_name:CERS4
protein_type:Unknown
65:
protein_accession:HMDBP11633
name:Ceramide synthase 6
uniprot_id:Q6ZMG9
gene_name:CERS6
protein_type:Unknown
蛋白质结合
1:
reference_text:Qiu M, Liu X: Determination of sphinganine, sphingosine and Sa/So ratio in urine of humans exposed to dietary fumonisin B1. Food Addit Contam. 2001 Mar;18(3):263-9.
pubmed_id:11304035
2:
reference_text:Ribar S, Mesaric M, Bauman M: High-performance liquid chromatographic determination of sphinganine and sphingosine in serum and urine of subjects from an endemic nephropathy area in Croatia. J Chromatogr B Biomed Sci Appl. 2001 Apr 25;754(2):511-9.
pubmed_id:11339295
3:
reference_text:Wong K, Kwan-Yeung L: Sphingosine mobilizes intracellular calcium in human neutrophils. Cell Calcium. 1993 Jun;14(6):493-505.
pubmed_id:8358772
4:
reference_text:Wertz PW, Downing DT: Free sphingosine in human epidermis. J Invest Dermatol. 1990 Feb;94(2):159-61.
pubmed_id:2299191
5:
reference_text:Rusakov SA, Filippova GN, Pushkareva MIu, Korobko VG, Alesenko AV: [The effect of tumor necrosis factor on the free sphingosine level and sphingomyelinase in murine liver cells and nuclei]. Biokhimiia. 1993 May;58(5):724-32.
pubmed_id:8338884
6:
reference_text:Hisano N, Yatomi Y, Fujino MA, Igarashi Y, Kume S, Ozaki Y: Quantification of sphingosine derivatives in human platelets: inducible formation of free sphingosine. J Biochem. 1998 Feb;123(2):263-8.
pubmed_id:9538201
7:
reference_text:Arikawa J, Ishibashi M, Kawashima M, Takagi Y, Ichikawa Y, Imokawa G: Decreased levels of sphingosine, a natural antimicrobial agent, may be associated with vulnerability of the stratum corneum from patients with atopic dermatitis to colonization by Staphylococcus aureus. J Invest Dermatol. 2002 Aug;119(2):433-9.
pubmed_id:12190867
8:
reference_text:Gorska M, Dobrzyn A, Baranowski M: Concentrations of sphingosine and sphinganine in plasma of patients with type 2 diabetes. Med Sci Monit. 2005 Jan;11(1):CR35-8.
pubmed_id:15614193
9:
reference_text:Authors unspecified: Toxicology and carcinogenesis studies of fumonisin B1 (cas no. 116355-83-0) in F344/N rats and B6C3F1 mice (feed studies). Natl Toxicol Program Tech Rep Ser. 2001 Dec;(496):1-352.
pubmed_id:11852482
10:
reference_text:Alessenko AV, Korobko VG, Khrenov AV, Rozhnova UA, Soloviev AS, Shingarova LN: Relation of biological activity of mutant forms of recombinant human tumor necrosis factor alpha and accumulation of sphingosine in murine liver. Biochem Mol Biol Int. 1997 Jun;42(1):143-54.
pubmed_id:9192094
11:
reference_text:Sweeney EA, Sakakura C, Shirahama T, Masamune A, Ohta H, Hakomori S, Igarashi Y: Sphingosine and its methylated derivative N,N-dimethylsphingosine (DMS) induce apoptosis in a variety of human cancer cell lines. Int J Cancer. 1996 May 3;66(3):358-66.
pubmed_id:8621258
12:
reference_text:Shin Y, Daly JW, Choi OH: Diverse effects of sphingosine on calcium mobilization and influx in differentiated HL-60 cells. Cell Calcium. 2000 May;27(5):269-80.
pubmed_id:10859593
13:
reference_text:van der Westhuizen L, Shephard GS, van Schalkwyk DJ: The effect of repeated gavage doses of fumonisin B1 on the sphinganine and sphingosine levels in vervet monkeys. Toxicon. 2001 Jul;39(7):969-72.
pubmed_id:11223085
14:
reference_text:van der Westhuizen L, Brown NL, Marasas WF, Swanevelder S, Shephard GS: Sphinganine/sphingosine ratio in plasma and urine as a possible biomarker for fumonisin exposure in humans in rural areas of Africa. Food Chem Toxicol. 1999 Dec;37(12):1153-8.
pubmed_id:10654591
15:
reference_text:Khan WA, Mascarella SW, Lewin AH, Wyrick CD, Carroll FI, Hannun YA: Use of D-erythro-sphingosine as a pharmacological inhibitor of protein kinase C in human platelets. Biochem J. 1991 Sep 1;278 ( Pt 2):387-92.
pubmed_id:1898331
16:
reference_text:Cuvillier O, Pirianov G, Kleuser B, Vanek PG, Coso OA, Gutkind S, Spiegel S: Suppression of ceramide-mediated programmed cell death by sphingosine-1-phosphate. Nature. 1996 Jun 27;381(6585):800-3.
pubmed_id:8657285
17:
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