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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-02-23 13:32:29 UTC

Update Date

2023-02-21 17:17:33 UTC

HMDB ID

HMDB0011714

Secondary Accession Numbers

HMDB11714

Metabolite Identification

Common Name

Vanilpyruvic acid

Description

Vanilpyruvic acid, also known as vanilpyruvate or HMPPA, belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. Vanilpyruvic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make vanilpyruvic acid a potential biomarker for the consumption of these foods. Vanilpyruvic acid, with regard to humans, has been linked to the inborn metabolic disorder aromatic l-amino acid decarboxylase deficiency. Based on a literature review very few articles have been published on Vanilpyruvic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241201522D          

 15 15  0  0  0  0            999 V2000
   13.2291   -9.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4043   -9.9324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9918   -9.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4043   -8.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9918   -7.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1669   -7.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7544   -8.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1669   -9.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9296   -8.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5171   -9.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6921   -9.2179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9296   -9.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5171  -10.6463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7544   -9.9324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2291   -8.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4 15  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011714

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(CC(=O)C(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O5/c1-15-9-5-6(2-3-7(9)11)4-8(12)10(13)14/h2-3,5,11H,4H2,1H3,(H,13,14)

> <INCHI_KEY>
YGQHQTMRZPHIBB-UHFFFAOYSA-N

> <FORMULA>
C10H10O5

> <MOLECULAR_WEIGHT>
210.1834

> <EXACT_MASS>
210.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
19.527225955044084

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-hydroxy-3-methoxyphenyl)-2-oxopropanoic acid

> <ALOGPS_LOGP>
1.36

> <JCHEM_LOGP>
1.4389771856666662

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.938980989596994

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7287034069368934

> <JCHEM_PKA_STRONGEST_BASIC>
-4.892288896643812

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
51.15570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(4-hydroxy-3-methoxyphenyl)-2-oxopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      24.694 -18.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      23.155 -18.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      22.385 -17.207   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.155 -15.873   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.385 -14.539   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.845 -14.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.075 -15.873   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.845 -17.207   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.535 -15.873   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.765 -17.207   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      16.225 -17.207   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      18.535 -18.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      17.765 -19.873   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      20.075 -18.540   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      24.694 -15.873   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    3    7                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    4                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Vanilpyruvate	Generator
3-Methoxy-4-hydroxyphenylpyruvic acid	MeSH
4-Hydroxy-3-methoxyphenylpyruvic acid	MeSH
HMPPA	MeSH
Vanilpyruvic acid, (14)C-labeled	MeSH
3-(4-Hydroxy-3-methoxyphenyl)-2-oxopropanoate	Generator, HMDB
Vanilpyruvic acid	MeSH

Chemical Formula

C₁₀H₁₀O₅

Average Molecular Weight

210.1834

Monoisotopic Molecular Weight

210.05282343

IUPAC Name

3-(4-hydroxy-3-methoxyphenyl)-2-oxopropanoic acid

Traditional Name

3-(4-hydroxy-3-methoxyphenyl)-2-oxopropanoic acid

CAS Registry Number

1081-71-6

SMILES

COC1=C(O)C=CC(CC(=O)C(O)=O)=C1

InChI Identifier

InChI=1S/C10H10O5/c1-15-9-5-6(2-3-7(9)11)4-8(12)10(13)14/h2-3,5,11H,4H2,1H3,(H,13,14)

InChI Key

YGQHQTMRZPHIBB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpyruvic acid derivatives

Direct Parent

Phenylpyruvic acid derivatives

Alternative Parents

Substituents

Phenylpyruvate
3-phenylpropanoic-acid
Methoxyphenol
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Alpha-keto acid
Keto acid
Alpha-hydroxy ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

a small molecule (CPD-11830 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.3 g/L	ALOGPS
logP	1.36	ALOGPS
logP	1.44	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	2.73	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	51.16 m³·mol⁻¹	ChemAxon
Polarizability	19.53 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	149.959	31661259
DarkChem	[M-H]-	148.721	31661259
DeepCCS	[M+H]+	148.896	30932474
DeepCCS	[M-H]-	146.538	30932474
DeepCCS	[M-2H]-	179.664	30932474
DeepCCS	[M+Na]+	154.989	30932474
AllCCS	[M+H]+	145.5	32859911
AllCCS	[M+H-H2O]+	141.4	32859911
AllCCS	[M+NH4]+	149.2	32859911
AllCCS	[M+Na]+	150.3	32859911
AllCCS	[M-H]-	143.7	32859911
AllCCS	[M+Na-2H]-	144.2	32859911
AllCCS	[M+HCOO]-	144.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.67 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9871 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.83 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1368.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	290.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	108.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	68.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	378.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	337.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	121.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	796.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	314.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	996.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	237.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	307.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	455.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	270.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	143.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vanilpyruvic acid	COC1=C(O)C=CC(CC(=O)C(O)=O)=C1	3232.7	Standard polar	33892256
Vanilpyruvic acid	COC1=C(O)C=CC(CC(=O)C(O)=O)=C1	1727.1	Standard non polar	33892256
Vanilpyruvic acid	COC1=C(O)C=CC(CC(=O)C(O)=O)=C1	1830.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vanilpyruvic acid,1TMS,isomer #1	COC1=CC(CC(=O)C(=O)O)=CC=C1O[Si](C)(C)C	2024.9	Semi standard non polar	33892256
Vanilpyruvic acid,1TMS,isomer #2	COC1=CC(CC(=O)C(=O)O[Si](C)(C)C)=CC=C1O	1962.3	Semi standard non polar	33892256
Vanilpyruvic acid,1TMS,isomer #3	COC1=CC(C=C(O[Si](C)(C)C)C(=O)O)=CC=C1O	2156.3	Semi standard non polar	33892256
Vanilpyruvic acid,2TMS,isomer #1	COC1=CC(CC(=O)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2040.0	Semi standard non polar	33892256
Vanilpyruvic acid,2TMS,isomer #2	COC1=CC(C=C(O[Si](C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C	2199.6	Semi standard non polar	33892256
Vanilpyruvic acid,2TMS,isomer #3	COC1=CC(C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O	2112.0	Semi standard non polar	33892256
Vanilpyruvic acid,3TMS,isomer #1	COC1=CC(C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2150.5	Semi standard non polar	33892256
Vanilpyruvic acid,3TMS,isomer #1	COC1=CC(C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2146.6	Standard non polar	33892256
Vanilpyruvic acid,3TMS,isomer #1	COC1=CC(C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2232.6	Standard polar	33892256
Vanilpyruvic acid,1TBDMS,isomer #1	COC1=CC(CC(=O)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	2303.4	Semi standard non polar	33892256
Vanilpyruvic acid,1TBDMS,isomer #2	COC1=CC(CC(=O)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	2223.8	Semi standard non polar	33892256
Vanilpyruvic acid,1TBDMS,isomer #3	COC1=CC(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O	2409.5	Semi standard non polar	33892256
Vanilpyruvic acid,2TBDMS,isomer #1	COC1=CC(CC(=O)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2515.3	Semi standard non polar	33892256
Vanilpyruvic acid,2TBDMS,isomer #2	COC1=CC(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	2701.8	Semi standard non polar	33892256
Vanilpyruvic acid,2TBDMS,isomer #3	COC1=CC(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	2598.1	Semi standard non polar	33892256
Vanilpyruvic acid,3TBDMS,isomer #1	COC1=CC(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2854.1	Semi standard non polar	33892256
Vanilpyruvic acid,3TBDMS,isomer #1	COC1=CC(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2792.1	Standard non polar	33892256
Vanilpyruvic acid,3TBDMS,isomer #1	COC1=CC(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2596.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Vanilpyruvic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-3900000000-dafbcec2d38954fef85e	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanilpyruvic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00ri-9432000000-3d55712bbfe9bdc7e323	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanilpyruvic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilpyruvic acid 10V, Positive-QTOF	splash10-029f-0930000000-0b172389e3c947156f73	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilpyruvic acid 20V, Positive-QTOF	splash10-029l-0900000000-ad02a787e85a9f49fb5e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilpyruvic acid 40V, Positive-QTOF	splash10-052r-2900000000-940a4f4bf06342206ef6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilpyruvic acid 10V, Negative-QTOF	splash10-0a4i-1590000000-e50dd99429a7ccc4dc9c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilpyruvic acid 20V, Negative-QTOF	splash10-07bf-1910000000-34be49b6f1e377c3b80a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilpyruvic acid 40V, Negative-QTOF	splash10-01ot-2900000000-38792c690b55d020d815	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilpyruvic acid 10V, Negative-QTOF	splash10-0ab9-5490000000-87ff334d9c765af556b7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilpyruvic acid 20V, Negative-QTOF	splash10-00di-1900000000-9a789246b1b70fb792b7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilpyruvic acid 40V, Negative-QTOF	splash10-006y-5900000000-41ded4bdb04a6a46395b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilpyruvic acid 10V, Positive-QTOF	splash10-01p9-0940000000-063224a36815c236d0d3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilpyruvic acid 20V, Positive-QTOF	splash10-052r-0900000000-b1b3201ed43aec49a25a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilpyruvic acid 40V, Positive-QTOF	splash10-0a4r-4900000000-98f11828d3fafa8b3c11	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	10 +/- 2 umol/mmol creatinine	Infant (0-1 year old)	Male	Aromatic L-amino acid decarboxylase deficiency	16288991	details

Associated Disorders and Diseases

Disease References

Aromatic L-amino acid decarboxylase deficiency
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:16288991 ]

Associated OMIM IDs

608643 (Aromatic L-amino acid decarboxylase deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028400

KNApSAcK ID

Not Available

Chemspider ID

13501

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14124

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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:16288991 ]
Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Vanilpyruvic acid → 6-[4-(2-carboxy-2-oxoethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Vanilpyruvic acid → 3,4,5-trihydroxy-6-{[3-(4-hydroxy-3-methoxyphenyl)-2-oxopropanoyl]oxy}oxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

Vanilpyruvic acid → 3-[3-methoxy-4-(sulfooxy)phenyl]-2-oxopropanoic acid	details

Showing metabocard for Vanilpyruvic acid (HMDB0011714)

MOL for HMDB0011714 (Vanilpyruvic acid)

3D MOL for HMDB0011714 (Vanilpyruvic acid)

3D SDF for HMDB0011714 (Vanilpyruvic acid)

3D-SDF for HMDB0011714 (Vanilpyruvic acid)

PDB for HMDB0011714 (Vanilpyruvic acid)

3D PDB for HMDB0011714 (Vanilpyruvic acid)

SMILES for HMDB0011714 (Vanilpyruvic acid)

INCHI for HMDB0011714 (Vanilpyruvic acid)

Structure for HMDB0011714 (Vanilpyruvic acid)

3D Structure for HMDB0011714 (Vanilpyruvic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

Reactions

Reactions