版本
5.0
创建日期
2005-11-16 15:48:42 UTC
更新日期
2021-09-14 14:57:28 UTC
登录号
HMDB0000291
地位
quantified
二级访问
HMDB00291

HMDB0133489

名称
Vanillylmandelic acid
描述
Vanillylmandelic acid, also known as vanillylmandelate or VMA, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Vanillylmandelic acid is a sweet and vanilla tasting compound. Vanillylmandelic acid (VMA) is a chemical intermediate in the synthesis of artificial vanilla flavorings and is an end-stage metabolite of the catecholamines (dopamine, epinephrine, and norepinephrine). Vanillylmandelic acid exists in all living organisms, ranging from bacteria to plants to humans. Within humans, vanillylmandelic acid participates in a number of enzymatic reactions. In particular, vanillylmandelic acid can be biosynthesized from 3-methoxy-4-hydroxyphenylglycolaldehyde through its interaction with the enzyme aldehyde dehydrogenase. In addition, vanillylmandelic acid and pyrocatechol can be biosynthesized from 3,4-dihydroxymandelic acid and guaiacol through the action of the enzyme catechol O-methyltransferase. Urinary VMA is elevated in patients with tumors that secrete catecholamines. Urinary VMA tests may also be used to diagnose neuroblastomas, and to monitor treatment of these conditions. VMA urinalysis tests can be used to diagnose an adrenal gland tumor called pheochromocytoma, a tumor of catecholamine-secreting chromaffin cells. Vanillylmandelic acid (VMA) is produced in the liver and is a major product of norepinephrine and epinephrine metabolism excreted in the urine.
同义词
1:Vanillylmandelate

2:(4-Hydroxy-3-methoxyphenyl)glycolate

3:(4-Hydroxy-3-methoxyphenyl)glycolic acid

4:3-Methoxy-4-hydroxy-mandelic acid

5:3-Methoxy-4-hydroxymandelate

6:3-Methoxy-4-hydroxymandelic acid

7:3-Methoxy-4-hydroxyphenylhydroxyacetate

8:3-Methoxy-4-hydroxyphenylhydroxyacetic acid

9:4'-Hydroxy-3'-methoxymandelate

10:4'-Hydroxy-3'-methoxymandelic acid

11:4-Hydroxy 3-methoxymandelic acid

12:4-Hydroxy-3-methoxy-DL-mandelate

13:4-Hydroxy-3-methoxy-DL-mandelic acid

14:4-Hydroxy-3-methoxy-mandelate

15:4-Hydroxy-3-methoxy-mandelic acid

16:4-Hydroxy-3-methoxymandelate

17:4-Hydroxy-3-methoxymandelic acid

18:DL-3-Methoxy-4-hydroxymandelate

19:DL-3-Methoxy-4-hydroxymandelic acid

20:DL-4-Hydroxy-3-methoxymandelate

21:DL-4-Hydroxy-3-methoxymandelic acid

22:DL-Vanillomandelate

23:DL-Vanillomandelic acid

24:DL-Vanillylmandelate

25:DL-Vanillylmandelic acid

26:HMMA

27:Hydroxymethoxymandelic acid

28:Lopac-H-0131

29:Vainillylmandelic acid

30:Vanillinmandelate

31:Vanillinmandelic acid

32:Vanillomandelate

33:Vanillomandelic acid

34:Vanillyl-mandelic acid

35:Vanillylmandellic acid

36:Vanillymandelic acid

37:Vanilmandelate

38:Vanilmandelic acid

39:Vanilylmandelic acid

40:Vanyl-mandelic acid

41:Vanylmandelic acid

42:VMA

43:2-Phenyllactic acid

44:VMA CPD

45:Atrolactic acid

46:Atrolactic acid monosodium salt, (S)-isomer

47:Atrolactic acid, (+-)-isomer

48:Hydroxymethylmandelic acid

49:(+)-4-Hydroxy-3-methoxymandelic acid

50:(+)-Vanilmandelic acid

51:(2S)-2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid

52:(S)-4-Hydroxy-3-methoxymandelic acid

53:(alphaS)-alpha,4-Dihydroxy-3-methoxybenzeneacetic acid

54:(αS)-α,4-Dihydroxy-3-methoxybenzeneacetic acid

55:2-(4'-Hydroxy-3'-methoxyphenyl)-2-hydroxyethanoic acid

56:2-(4’-Hydroxy-3’-methoxyphenyl)-2-hydroxyethanoic acid

57:2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid

58:4’-Hydroxy-3’-methoxymandelic acid

59:L-(+)-3-Methoxy-4-hydroxymandelic acid

60:Vanillylmandelic acid

61:alpha,4-Dihydroxy-3-methoxybenzeneacetic acid

62:α,4-Dihydroxy-3-methoxybenzeneacetic acid

化学式
C9H10O5
平均分子量
198.1727
等位分子量
198.05282343
化学名称
(2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
传统名称
(S)-hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid
CAS 登记号
13244-77-4
代谢物结构字符串
COC1=C(O)C=CC(=C1)[C@H](O)C(O)=O
inchi标识符
InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)/t8-/m0/s1
印记键
CGQCWMIAEPEHNQ-QMMMGPOBSA-N
分类学
description: belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

description:Methoxyphenols

kingdom:Organic compounds

super_class:Benzenoids

class:Phenols

sub_class:Methoxyphenols

molecular_framework:Aromatic homomonocyclic compounds

1:1-hydroxy-2-unsubstituted benzenoids

2:Alkyl aryl ethers

3:Alpha hydroxy acids and derivatives

4:Anisoles

5:Aromatic alcohols

6:Carbonyl compounds

7:Carboxylic acids

8:Hydrocarbon derivatives

9:Methoxybenzenes

10:Monocarboxylic acids and derivatives

11:Organic oxides

12:Phenoxy compounds

13:Secondary alcohols

14:1-hydroxy-2-unsubstituted benzenoid

15:Alcohol

16:Alkyl aryl ether

17:Alpha-hydroxy acid

18:Anisole

19:Aromatic alcohol

20:Aromatic homomonocyclic compound

21:Carbonyl group

22:Carboxylic acid

23:Carboxylic acid derivative

24:Ether

25:Hydrocarbon derivative

26:Hydroxy acid

27:Methoxybenzene

28:Methoxyphenol

29:Monocarboxylic acid or derivatives

30:Monocyclic benzene moiety

31:Organic oxide

32:Organic oxygen compound

33:Organooxygen compound

34:Phenol ether

35:Phenoxy compound

36:Secondary alcohol

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:Aromatic l-amino acid decarboxylase deficiency

definition:An inherited metabolic disorder characterized by reduced production of serotonin and dopamine resulting in hypotonia, hypokinesia, ptosis oculogyric crises, and signs of autonomic dysfunction with onset in infancy or childhood that has material basis in homozygous or compound heterozygous mutation in the ddc gene on chromosome 7p12. (do).

parent_id:7695

***level:4

type:child

synonym:Aadc deficiency

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: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: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: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: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:Endocrine gland

definition:

parent_id:7727

***level:4

type:parent

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: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: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 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

状态
Solid
实验性质
1:

kind:melting_point

value:132 - 134 °C

source:

预测性质
1:

kind:logp

value:0.94

source:ALOGPS

2:

kind:logs

value:-1.58

source:ALOGPS

3:

kind:solubility

value:5.16 g/L

source:ALOGPS

4:

kind:logp

value:0.43

source:ChemAxon

5:

kind:pka_strongest_acidic

value:3.11

source:ChemAxon

6:

kind:pka_strongest_basic

value:-4.1

source:ChemAxon

7:

kind:iupac

value:(2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid

source:ChemAxon

8:

kind:average_mass

value:198.1727

source:ChemAxon

9:

kind:mono_mass

value:198.05282343

source:ChemAxon

10:

kind:smiles

value:COC1=C(O)C=CC(=C1)[C@H](O)C(O)=O

source:ChemAxon

11:

kind:formula

value:C9H10O5

source:ChemAxon

12:

kind:inchi

value:InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)/t8-/m0/s1

source:ChemAxon

13:

kind:inchikey

value:CGQCWMIAEPEHNQ-QMMMGPOBSA-N

source:ChemAxon

14:

kind:polar_surface_area

value:86.99

source:ChemAxon

15:

kind:refractivity

value:47.15

source:ChemAxon

16:

kind:polarizability

value:18.45

source:ChemAxon

17:

kind:rotatable_bond_count

value:3

source:ChemAxon

18:

kind:acceptor_count

value:5

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:1

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::NmrTwoD

spectrum_id:1258

2:

type:Specdb::CMs

spectrum_id:18510

3:

type:Specdb::CMs

spectrum_id:37406

4:

type:Specdb::CMs

spectrum_id:137982

5:

type:Specdb::CMs

spectrum_id:145716

6:

type:Specdb::MsMs

spectrum_id:492

7:

type:Specdb::MsMs

spectrum_id:493

8:

type:Specdb::MsMs

spectrum_id:494

9:

type:Specdb::MsMs

spectrum_id:307027

10:

type:Specdb::MsMs

spectrum_id:307028

11:

type:Specdb::MsMs

spectrum_id:307029

12:

type:Specdb::MsMs

spectrum_id:350860

13:

type:Specdb::MsMs

spectrum_id:350861

14:

type:Specdb::MsMs

spectrum_id:350862

15:

type:Specdb::MsMs

spectrum_id:2257896

16:

type:Specdb::MsMs

spectrum_id:2258707

17:

type:Specdb::MsMs

spectrum_id:2259884

18:

type:Specdb::MsMs

spectrum_id:2706638

19:

type:Specdb::MsMs

spectrum_id:2706639

20:

type:Specdb::MsMs

spectrum_id:2706640

21:

type:Specdb::MsMs

spectrum_id:2999575

22:

type:Specdb::MsMs

spectrum_id:2999576

23:

type:Specdb::MsMs

spectrum_id:2999577

24:

type:Specdb::NmrOneD

spectrum_id:1315

25:

type:Specdb::NmrOneD

spectrum_id:6462

26:

type:Specdb::NmrOneD

spectrum_id:6463

27:

type:Specdb::NmrOneD

spectrum_id:6464

28:

type:Specdb::NmrOneD

spectrum_id:6465

29:

type:Specdb::NmrOneD

spectrum_id:6466

30:

type:Specdb::NmrOneD

spectrum_id:6467

31:

type:Specdb::NmrOneD

spectrum_id:6468

32:

type:Specdb::NmrOneD

spectrum_id:6469

33:

type:Specdb::NmrOneD

spectrum_id:6470

34:

type:Specdb::NmrOneD

spectrum_id:6471

35:

type:Specdb::NmrOneD

spectrum_id:6472

36:

type:Specdb::NmrOneD

spectrum_id:6473

37:

type:Specdb::NmrOneD

spectrum_id:6474

38:

type:Specdb::NmrOneD

spectrum_id:6475

39:

type:Specdb::NmrOneD

spectrum_id:6476

40:

type:Specdb::NmrOneD

spectrum_id:6477

41:

type:Specdb::NmrOneD

spectrum_id:6478

42:

type:Specdb::NmrOneD

spectrum_id:6479

43:

type:Specdb::NmrOneD

spectrum_id:6480

44:

type:Specdb::NmrOneD

spectrum_id:6481

光谱
生物学性质
1:

cellular:(1):Cytoplasm

2:

biospecimen:(1):Blood

biospecimen:(2):Feces

biospecimen:(3):Saliva

biospecimen:(4):Urine

3:

tissue:(1):Adrenal Gland

tissue:(2):Epidermis

tissue:(3):Thyroid Gland

4:

[1]:

name:Alkaptonuria

smpdb_id:SMP00169

kegg_map_id:

[2]:

name:Disulfiram Action Pathway

smpdb_id:SMP00429

kegg_map_id:

[3]:

name:Dopamine beta-hydroxylase deficiency

smpdb_id:SMP00498

kegg_map_id:

[4]:

name:Hawkinsinuria

smpdb_id:SMP00190

kegg_map_id:

[5]:

name:Monoamine oxidase-a deficiency (MAO-A)

smpdb_id:SMP00533

kegg_map_id:

[6]:

name:Tyrosine metabolism

smpdb_id:

kegg_map_id:map00350

[7]:

name:Tyrosinemia Type I

smpdb_id:SMP00218

kegg_map_id:

[8]:

name:Tyrosinemia, transient, of the newborn

smpdb_id:SMP00494

kegg_map_id:

正常浓度
1:

biospecimen:Blood

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

2:

biospecimen:Blood

concentration_value:0.035 +/- 0.008

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Male

subject_condition:Normal

3:

biospecimen:Feces

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

4:

biospecimen:Saliva

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Not Specified

subject_condition:Normal

5:

biospecimen:Urine

concentration_value:4.906 +/- 1.769

concentration_units:umol/mmol creatinine

subject_age:Infant (0-1 year old)

subject_sex:Both

subject_condition:Normal

6:

biospecimen:Urine

concentration_value:5.0776 +/- 1.712

concentration_units:umol/mmol creatinine

subject_age:Infant (0-1 year old)

subject_sex:Both

subject_condition:Normal

7:

biospecimen:Urine

concentration_value:5.135 +/- 1.826

concentration_units:umol/mmol creatinine

subject_age:Infant (0-1 year old)

subject_sex:Both

subject_condition:Normal

8:

biospecimen:Urine

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

9:

biospecimen:Urine

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

10:

biospecimen:Urine

concentration_value:6.2

concentration_units:umol/mmol creatinine

subject_age:Infant (0-1 year old)

subject_sex:Both

subject_condition:Normal

11:

biospecimen:Urine

concentration_value:1.585 +/- 1.095

concentration_units:umol/mmol creatinine

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:

12:

biospecimen:Urine

concentration_value:3.67 +/- 2.12

concentration_units:umol/mmol creatinine

subject_age:Infant (0-1 year old)

subject_sex:Both

subject_condition:Normal

13:

biospecimen:Urine

concentration_value:7.758 +/- 2.944

concentration_units:umol/mmol creatinine

subject_age:Children (1 - 13 years old)

subject_sex:Not Specified

subject_condition:Normal

14:

biospecimen:Urine

concentration_value:13.24 +/- 5.3

concentration_units:umol/mmol creatinine

subject_age:Infant (6 months - <1 year old)

subject_sex:Both

subject_condition:Normal

15:

biospecimen:Urine

concentration_value:5.38 +/- 1.83

concentration_units:umol/mmol creatinine

subject_age:Infant (6 months - <1 year old)

subject_sex:Both

subject_condition:Normal

16:

biospecimen:Urine

concentration_value:4.18 +/- 1.55

concentration_units:umol/mmol creatinine

subject_age:Newborn (0-30 days old)

subject_sex:Both

subject_condition:Normal

17:

biospecimen:Urine

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

18:

biospecimen:Urine

concentration_value:6.19 +/- 2.014

concentration_units:umol/mmol creatinine

subject_age:Infant (1 - 6 months old)

subject_sex:Both

subject_condition:Normal

19:

biospecimen:Urine

concentration_value:6.22 +/- 2.32

concentration_units:umol/mmol creatinine

subject_age:Infant (0-1 year old)

subject_sex:Both

subject_condition:Normal

20:

biospecimen:Urine

concentration_value:10.0 (0.3-20.0)

concentration_units:umol/mmol creatinine

subject_age:Infant (0-1 year old)

subject_sex:Not Specified

subject_condition:Normal

21:

biospecimen:Urine

concentration_value:3.22-9.08

concentration_units:umol/mmol creatinine

subject_age:Infant (0-1 year old)

subject_sex:Both

subject_condition:Normal

22:

biospecimen:Urine

concentration_value:5.68 +/- 2.19

concentration_units:umol/mmol creatinine

subject_age:Infant (6 months - <1 year old)

subject_sex:Both

subject_condition:Normal

23:

biospecimen:Urine

concentration_value:5.93 +/- 3.016

concentration_units:umol/mmol creatinine

subject_age:Children (1 - 13 years old)

subject_sex:Not Specified

subject_condition:Normal

24:

biospecimen:Urine

concentration_value:1.6-2.2

concentration_units:umol/mmol creatinine

subject_age:Adult (>18 years old)

subject_sex:Female

subject_condition:Normal

25:

biospecimen:Urine

concentration_value:2.3 (1.0-3.4)

concentration_units:umol/mmol creatinine

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

26:

biospecimen:Urine

concentration_value:1.2 +/- 0.5

concentration_units:umol/mmol creatinine

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

27:

biospecimen:Urine

concentration_value:0.300-19.700

concentration_units:umol/mmol creatinine

subject_age:Children (1-13 years old)

subject_sex:Female

subject_condition:Normal

28:

biospecimen:Urine

concentration_value:1.1-1.7

concentration_units:umol/mmol creatinine

subject_age:Adult (>18 years old)

subject_sex:Male

subject_condition:Normal

29:

biospecimen:Urine

concentration_value:0.5-7.6

concentration_units:umol/mmol creatinine

subject_age:Adult (>18 years old)

subject_sex:Male

subject_condition:Normal

30:

biospecimen:Urine

concentration_value:12.5 (3.7-21.8)

concentration_units:umol/mmol creatinine

subject_age:Newborn (0-30 days old)

subject_sex:Both

subject_condition:Normal

31:

biospecimen:Urine

concentration_value:12.4 (11.6-25.9)

concentration_units:umol/mmol creatinine

subject_age:Infant (0-1 year old)

subject_sex:Both

subject_condition:Normal

32:

biospecimen:Urine

concentration_value:6.5 (1.3-11.5)

concentration_units:umol/mmol creatinine

subject_age:Children (1-13 years old)

subject_sex:Both

subject_condition:Normal

33:

biospecimen:Urine

concentration_value:6.5 (2.9-13.0)

concentration_units:umol/mmol creatinine

subject_age:Children (1-13 years old)

subject_sex:Both

subject_condition:Normal

34:

biospecimen:Urine

concentration_value:5.2 (2.5-16.1)

concentration_units:umol/mmol creatinine

subject_age:Children (1-13 years old)

subject_sex:Both

subject_condition:Normal

35:

biospecimen:Urine

concentration_value:<=3.289

concentration_units:umol/mmol creatinine

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

36:

biospecimen:Urine

concentration_value:1.6 (0.6-2.8)

concentration_units:umol/mmol creatinine

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

异常浓度
1:

biospecimen:Feces

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Colorectal cancer

2:

biospecimen:Urine

concentration_value:9.128 +/- 4.450

concentration_units:umol/mmol creatinine

patient_age:Children (1-13 years old)

patient_sex:Both

patient_information:Phenylketonuria

3:

biospecimen:Urine

concentration_value:7.586 +/- 3.852

concentration_units:umol/mmol creatinine

patient_age:Children (1 - 13 years old)

patient_sex:Not Specified

patient_information:Eosinophilic esophagitis

4:

biospecimen:Urine

concentration_value:7.332 +/- 3.711

concentration_units:umol/mmol creatinine

patient_age:Children (1 - 13 years old)

patient_sex:Not Specified

patient_information:Gastroesophageal reflux disease

5:

biospecimen:Urine

concentration_value:0.15 (0.00-0.30)

concentration_units:umol/mmol creatinine

patient_age:Infant (0-1 year old)

patient_sex:Male

patient_information:Aromatic L-amino acid decarboxylase deficiency

6:

biospecimen:Urine

concentration_value:6.869 +/- 2.756

concentration_units:umol/mmol creatinine

patient_age:Children (1 - 13 years old)

patient_sex:Not Specified

patient_information:Eosinophilic esophagitis

7:

biospecimen:Urine

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Hypertension (mild)

8:

biospecimen:Urine

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Hypertension (mild)

9:

biospecimen:Urine

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Bladder cancer

10:

biospecimen:Urine

concentration_value:0.2-0.4

concentration_units:umol/mmol creatinine

patient_age:Adult (>18 years old)

patient_sex:Male

patient_information:Brunner Syndrome

11:

biospecimen:Urine

concentration_value:0.5

concentration_units:umol/mmol creatinine

patient_age:Children (1-13 years old)

patient_sex:Female

patient_information:Aromatic L-amino acid decarboxylase deficiency

12:

biospecimen:Urine

concentration_value:0.9

concentration_units:umol/mmol creatinine

patient_age:Infant (0-1 year old)

patient_sex:Female

patient_information:Aromatic L-amino acid decarboxylase deficiency

13:

biospecimen:Urine

concentration_value:15.404 +/- 14.833

concentration_units:umol/mmol creatinine

patient_age:Children (1-13 years old)

patient_sex:Both

patient_information:Phenylketonuria

14:

biospecimen:Urine

concentration_value:4.564 +/- 1.369

concentration_units:umol/mmol creatinine

patient_age:Children (1-13 years old)

patient_sex:Both

patient_information:Phenylketonuria

疾病参考
1:

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

2:

name:Aromatic L-amino acid decarboxylase deficiency

omim_id:608643

[1]:

reference_text:Abdenur JE, Abeling N, Specola N, Jorge L, Schenone AB, van Cruchten AC, Chamoles NA: Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis. Mol Genet Metab. 2006 Jan;87(1):48-53. Epub 2005 Nov 9.

pubmed_id:16288991

[2]:

reference_text:Hyland K, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10.

pubmed_id:1281049

[3]:

reference_text:Abeling NG, van Gennip AH, Barth PG, van Cruchten A, Westra M, Wijburg FA: Aromatic L-amino acid decarboxylase deficiency: a new case with a mild clinical presentation and unexpected laboratory findings. J Inherit Metab Dis. 1998 Jun;21(3):240-2.

pubmed_id:9686366

3:

name:Eosinophilic esophagitis

omim_id:610247

[1]:

reference_text:Mordechai, Hien, and David S. Wishart

pubmed_id:

4:

name:Phenylketonuria

omim_id:261600

[1]:

reference_text:Perry TL, Hansen S: Cystinylglycine in plasma: diagnostic relevance for pyroglutamic acidemia, homocystinuria, and phenylketonuria. Clin Chim Acta. 1981 Nov 25;117(1):7-12.

pubmed_id:7333014

[2]:

reference_text:Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24.

pubmed_id:2091926

[3]:

reference_text:Deng C, Shang C, Hu Y, Zhang X: Rapid diagnosis of phenylketonuria and other aminoacidemias by quantitative analysis of amino acids in neonatal blood spots by gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Jul 25;775(1):115-20.

pubmed_id:12101068

[4]:

reference_text:Elvers LH, Loeber JG, Dhondt JL, Fukushi M, Hannon WH, Torresani T, Webster D: First ISNS Reference Preparation for Neonatal Screening for thyrotropin, phenylalanine and 17alpha-hydroxyprogesterone in blood spots. J Inherit Metab Dis. 2007 Aug;30(4):609. Epub 2007 Jun 14.

pubmed_id:17574536

[5]:

reference_text:Langenbeck U, Behbehani A, Luthe H: Renal transport of aromatic acids in patients with phenylketonuria. J Inherit Metab Dis. 1981;4(2):69-70.

pubmed_id:6790852

[6]:

reference_text:Peck H, Pollitt RJ: The occurrence of gamma-glutamylphenylalanine in the urine of newborn phenylketonurics. Clin Chim Acta. 1979 Jun 15;94(3):237-40.

pubmed_id:466810

[7]:

reference_text:Clemens PC, Schunemann MH, Hoffmann GF, Kohlschutter A: Plasma concentrations of phenyllactic acid in phenylketonuria. J Inherit Metab Dis. 1990;13(2):227-8.

pubmed_id:2116554

[8]:

reference_text:Gronwald W, Klein MS, Kaspar H, Fagerer SR, Nurnberger N, Dettmer K, Bertsch T, Oefner PJ: Urinary metabolite quantification employing 2D NMR spectroscopy. Anal Chem. 2008 Dec 1;80(23):9288-97. doi: 10.1021/ac801627c.

pubmed_id:19551947

[9]:

reference_text:Jansen RS, Addie R, Merkx R, Fish A, Mahakena S, Bleijerveld OB, Altelaar M, IJlst L, Wanders RJ, Borst P, van de Wetering K: N-lactoyl-amino acids are ubiquitous metabolites that originate from CNDP2-mediated reverse proteolysis of lactate and amino acids. Proc Natl Acad Sci U S A. 2015 May 26;112(21):6601-6. doi: 10.1073/pnas.1424638112. Epub 2015 May 11.

pubmed_id:25964343

[10]:

reference_text:Swarna M, Jyothy A, Usha Rani P, Reddy PP: Amino acid disorders in mental retardation: a two-decade study from Andhra Pradesh. Biochem Genet. 2004 Apr;42(3-4):85-98.

pubmed_id:15168722

[11]:

reference_text:Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9.

pubmed_id:4837567

[12]:

reference_text:MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

pubmed_id:

5:

name:Brunner Syndrome

omim_id:300615

[1]:

reference_text:Brunner HG, Nelen MR, van Zandvoort P, Abeling NG, van Gennip AH, Wolters EC, Kuiper MA, Ropers HH, van Oost BA: X-linked borderline mental retardation with prominent behavioral disturbance: phenotype, genetic localization, and evidence for disturbed monoamine metabolism. Am J Hum Genet. 1993 Jun;52(6):1032-9.

pubmed_id:8503438

KEGG数据库编号
C05584
DrugBank数据库编号
foodb数据库编号
FDB021931
ChemSpider数据库编号
643307
公共化学化合物编号
736172
PDB数据库编号
生物利益的化学实体数据库编号
1127735
knapsack数据库编号
维基百科编号
Vanillylmandelic acid
代谢途径的数据库编号
苯酚资源管理器化合物数据库编号
比格数据库编号
46071
梅林编号
697
虚拟机身份证编号
3MOX4HOXM
fbonto数据库编号
综合参考
Recondo, E. F.; Rinderknecht, H. Preparation of epinephrine and norepinephrine metabolites, 3-methoxy-4-hydroxymandelic acid and 3,4-dihydroxymandelic acid. Journal of Organic Chemistry (1960), 25 2248-50.
一般参考
1:

protein_accession:HMDBP00272

name:Catechol O-methyltransferase

uniprot_id:P21964

gene_name:COMT

protein_type:Unknown

2:

protein_accession:HMDBP00292

name:Aldehyde dehydrogenase, dimeric NADP-preferring

uniprot_id:P30838

gene_name:ALDH3A1

protein_type:Unknown

3:

protein_accession:HMDBP00294

name:Aldehyde dehydrogenase family 1 member A3

uniprot_id:P47895

gene_name:ALDH1A3

protein_type:Unknown

4:

protein_accession:HMDBP00541

name:Aldehyde dehydrogenase family 3 member B2

uniprot_id:P48448

gene_name:ALDH3B2

protein_type:Unknown

5:

protein_accession:HMDBP00542

name:Aldehyde dehydrogenase family 3 member B1

uniprot_id:P43353

gene_name:ALDH3B1

protein_type:Unknown

蛋白质结合
1:

reference_text:Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6.

pubmed_id:8087979

2:

reference_text:Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9.

pubmed_id:6085021

3:

reference_text:Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20.

pubmed_id:12649306

4:

reference_text:Silbergeld EK, Chisolm JJ Jr: Lead poisoning: altered urinary catecholamine metabolites as indicators of intoxication in mice and children. Science. 1976 Apr 9;192(4235):153-5.

pubmed_id:1257763

5:

reference_text:Frank K, Raue F, Gottswinter J, Heinrich U, Meybier H, Ziegler R: Importance of early diagnosis and follow-up in multiple endocrine neoplasia (MEN II B). Eur J Pediatr. 1984 Dec;143(2):112-6.

pubmed_id:6394335

6:

reference_text:Takahashi S, Godse DD, Warsh JJ, Stancer HC: A gas chromatographic-mass spectrometric (GC-MS) assay for 3-methoxy-4-hydroxyphenethyleneglycol and vanilmandelic acid in human serum. Clin Chim Acta. 1977 Dec 1;81(2):182-92.

pubmed_id:589798

7:

reference_text:Suga K, Shimizu K, Nishigauchi K, Kume N, Kawamura T, Matsunaga N: [A case of bilateral adrenal neuroblastomas detected by bone scintigraphy]. Kaku Igaku. 1996 Dec;33(12):1337-42.

pubmed_id:9023440

8:

reference_text:Hartleb J, Eue S, Kemper A: Simultaneous analysis of homovanillic acid, 5-hydroxyindoleacetic acid, 3-methoxy-4-hydroxyphenylethylene glycol and vanilmandelic acid in plasma from alcoholics by high-performance liquid chromatography with electrochemical detection. Critical comparison of solid-phase and liquid-liquid extraction methods. J Chromatogr. 1993 Dec 22;622(2):161-71.

pubmed_id:7512090

9:

reference_text:Dias PL, Amarasiri AA: 4-hydroxy-3-methoxymandelic acid (HMMA) excretion in retinoblastoma. Br J Ophthalmol. 1978 Aug;62(8):525-7.

pubmed_id:687548

10:

reference_text:Saran RK, Sahuja RC, Gupta NN, Hasan M, Bhargava KP, Shanker K, Kishor K: 3-Methoxy-4-hydroxyphenylglycol in cerebrospinal fluid and vanillylmandelic acid in urine of humans with hypertension. Science. 1978 Apr 21;200(4339):317-8.

pubmed_id:635588

11:

reference_text:Strittmatter M, Grauer M, Isenberg E, Hamann G, Fischer C, Hoffmann KH, Blaes F, Schimrigk K: Cerebrospinal fluid neuropeptides and monoaminergic transmitters in patients with trigeminal neuralgia. Headache. 1997 Apr;37(4):211-6.

pubmed_id:9150615

12:

reference_text:Zambotti F, Blau K, King GS, Campbell S, Sandler M: Monoamine metabolites and related compounds in human amniotic fluid: assay by gas chromatography and gas chromatography-mass spectrometry. Clin Chim Acta. 1975 Jun 20;61(3):247-56.

pubmed_id:1149252

13:

reference_text:Drebing CJ, Freedman R, Waldo M, Gerhardt GA: Unconjugated methoxylated catecholamine metabolites in human saliva. Quantitation methodology and comparison with plasma levels. Biomed Chromatogr. 1989 Sep;3(5):217-20.

pubmed_id:2804429

14:

reference_text:Bostrom B, Mirkin BL: Elevation of cerebrospinal fluid catecholamine metabolites in patients with intracranial tumors of neuroectodermal origin. J Clin Oncol. 1987 Jul;5(7):1090-7.

pubmed_id:3598613

15:

reference_text:Afonso D, Castellanos MA, Rodriguez M: Determination of monoamines and indoles in amniotic fluid by high-performance liquid chromatography-electrochemical detection. J Chromatogr. 1990 Jun 8;528(1):101-9.

pubmed_id:1696583

16:

reference_text:Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5.

pubmed_id:30612223

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