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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:47:11 UTC

HMDB ID

HMDB0000913

Secondary Accession Numbers

HMDB00913

Metabolite Identification

Common Name

Vanillactic acid

Description

Vanillactic acid, also known as vanillactate or VLA, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Vanillactic acid is a potentially toxic compound. Vanillactic acid has been linked to the inborn metabolic disorders including aromatic l-amino acid decarboxylase deficiency. Vanillactic acid is an acidic catecholamine metabolite present in normal human urine (PMID 7524950 ), in normal human CSF (PMID 7914240 ), and increased in the CSF of newborns with neonatal epileptic encephalopathy mimicking aromatic L-amino acid decarboxylase deficiency (PMID 12200739 ).

Structure

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

Vanillactic acid.mol
  Mrv1652305271900322D          

 15 15  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    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
  2  4  1  0  0  0  0
  1  5  2  0  0  0  0
  1  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  7 12  2  0  0  0  0
 13 14  1  0  0  0  0
  9 13  1  0  0  0  0
 10 15  1  0  0  0  0
  4  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000913

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(CC(O)C(O)=O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O5/c1-15-9-5-6(2-3-7(9)11)4-8(12)10(13)14/h2-3,5,8,11-12H,4H2,1H3,(H,13,14)

> <INCHI_KEY>
SVYIZYRTOYHQRE-UHFFFAOYSA-N

> <FORMULA>
C10H12O5

> <MOLECULAR_WEIGHT>
212.1993

> <EXACT_MASS>
212.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.57879576486937

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.08

> <JCHEM_LOGP>
0.7232602623333333

> <ALOGPS_LOGS>
-1.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.944267618539813

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3720183154089307

> <JCHEM_PKA_STRONGEST_BASIC>
-3.835551710250905

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
51.90290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vanillactic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Vanillactic acid.mol                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    7                                                       
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    8   12    4                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   14    9                                                       
CONECT   14   13                                                            
CONECT   15   10                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0000913
HETATM    1  C1  UNL     1      -3.229  -1.980  -0.415  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.296  -0.578  -0.285  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.154   0.206  -0.263  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.885  -0.369  -0.368  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.246   0.419  -0.344  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.619  -0.159  -0.454  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.170  -0.494   0.934  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.196   0.706   1.639  1.00  0.00           O  
HETATM    9  C7  UNL     1       3.530  -1.009   0.773  1.00  0.00           C  
HETATM   10  O3  UNL     1       4.503  -0.370   1.248  1.00  0.00           O  
HETATM   11  O4  UNL     1       3.831  -2.192   0.111  1.00  0.00           O  
HETATM   12  C8  UNL     1       0.069   1.781  -0.214  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.156   2.388  -0.108  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.272   1.577  -0.134  1.00  0.00           C  
HETATM   15  O5  UNL     1      -3.529   2.149  -0.029  1.00  0.00           O  
HETATM   16  H1  UNL     1      -2.940  -2.467   0.538  1.00  0.00           H  
HETATM   17  H2  UNL     1      -4.190  -2.400  -0.809  1.00  0.00           H  
HETATM   18  H3  UNL     1      -2.471  -2.245  -1.206  1.00  0.00           H  
HETATM   19  H4  UNL     1      -0.753  -1.430  -0.469  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.641  -1.085  -1.036  1.00  0.00           H  
HETATM   21  H6  UNL     1       2.278   0.628  -0.871  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.487  -1.215   1.449  1.00  0.00           H  
HETATM   23  H8  UNL     1       2.863   1.300   1.188  1.00  0.00           H  
HETATM   24  H9  UNL     1       4.406  -2.214  -0.743  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.942   2.431  -0.192  1.00  0.00           H  
HETATM   26  H11 UNL     1      -1.262   3.479  -0.005  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.642   3.145   0.065  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3
CONECT    3    4    4   14
CONECT    4    5   19
CONECT    5    6   12   12
CONECT    6    7   20   21
CONECT    7    8    9   22
CONECT    8   23
CONECT    9   10   10   11
CONECT   11   24
CONECT   12   13   25
CONECT   13   14   14   26
CONECT   14   15
CONECT   15   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Vanillactate	Generator
3-(3-Methoxy-4-hydroxyphenyl)lactate	HMDB
3-(3-Methoxy-4-hydroxyphenyl)lactic acid	HMDB
3-(4-Hydroxy-3-methoxyphenyl)-lactate	HMDB
3-(4-Hydroxy-3-methoxyphenyl)-lactic acid	HMDB
3-(4-Hydroxy-3-methoxyphenyl)lactate	HMDB
3-(4-Hydroxy-3-methoxyphenyl)lactic acid	HMDB
3-Methoxy-4-hydroxyphenyllactate	HMDB
3-Methoxy-4-hydroxyphenyllactic acid	HMDB
4-Hydroxy-3-methoxyphenyllactic acid	HMDB
b-(4-Hydroxy-3-methoxyphenyl)lactate	HMDB
b-(4-Hydroxy-3-methoxyphenyl)lactic acid	HMDB
beta-(4-Hydroxy-3-methoxyphenyl)lactate	HMDB
beta-(4-Hydroxy-3-methoxyphenyl)lactic acid	HMDB
Vanillyllactate	HMDB
Vanillyllactic acid	HMDB
VLA	HMDB
Vanillylactic acid	HMDB
2-Hydroxy-3-(4-hydroxy-3-methoxyphenyl)propanoate	HMDB
Vanillactic acid	MeSH

Chemical Formula

C₁₀H₁₂O₅

Average Molecular Weight

212.1993

Monoisotopic Molecular Weight

212.068473494

IUPAC Name

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

Traditional Name

vanillactic acid

CAS Registry Number

2475-56-1

SMILES

COC1=CC(CC(O)C(O)=O)=CC=C1O

InChI Identifier

InChI=1S/C10H12O5/c1-15-9-5-6(2-3-7(9)11)4-8(12)10(13)14/h2-3,5,8,11-12H,4H2,1H3,(H,13,14)

InChI Key

SVYIZYRTOYHQRE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Alpha-hydroxy acid
Benzenoid
Monocyclic benzene moiety
Hydroxy acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Organooxygen compound
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

a small molecule (CPD-11831 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000913)

Excreta

Biofluid or Excreta

Urine (PMID: 7524950)

Cellular substructure

Cytoplasm (HMDB: HMDB0000913)
Extracellular (HMDB: HMDB0000913)

Source

Endogenous

Endogenous (HMDB: HMDB0000913)

Plant

Plant (HMDB: HMDB0000913)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Hawkinsinuria (HMDB: HMDB0000913)

Role

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	4.3 g/L	ALOGPS
logP	1.08	ALOGPS
logP	0.72	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	51.9 m³·mol⁻¹	ChemAxon
Polarizability	20.58 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]+	150.756	31661259
DarkChem	[M-H]-	149.15	31661259
AllCCS	[M+H]+	147.585	32859911
AllCCS	[M-H]-	145.242	32859911
DeepCCS	[M+H]+	145.455	30932474
DeepCCS	[M-H]-	143.097	30932474
DeepCCS	[M-2H]-	177.656	30932474
DeepCCS	[M+Na]+	152.859	30932474
AllCCS	[M+H]+	147.6	32859911
AllCCS	[M+H-H2O]+	143.6	32859911
AllCCS	[M+NH4]+	151.3	32859911
AllCCS	[M+Na]+	152.4	32859911
AllCCS	[M-H]-	145.2	32859911
AllCCS	[M+Na-2H]-	145.8	32859911
AllCCS	[M+HCOO]-	146.5	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.	2.92 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9615 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.27 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	103.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1171.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	265.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	91.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	315.3 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	287.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	255.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	684.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	294.7 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	907.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	202.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	258.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	469.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	311.4 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	200.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vanillactic acid	COC1=CC(CC(O)C(O)=O)=CC=C1O	3545.4	Standard polar	33892256
Vanillactic acid	COC1=CC(CC(O)C(O)=O)=CC=C1O	1921.9	Standard non polar	33892256
Vanillactic acid	COC1=CC(CC(O)C(O)=O)=CC=C1O	1889.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vanillactic acid,1TMS,isomer #1	COC1=CC(CC(O[Si](C)(C)C)C(=O)O)=CC=C1O	1969.9	Semi standard non polar	33892256
Vanillactic acid,1TMS,isomer #2	COC1=CC(CC(O)C(=O)O[Si](C)(C)C)=CC=C1O	1904.4	Semi standard non polar	33892256
Vanillactic acid,1TMS,isomer #3	COC1=CC(CC(O)C(=O)O)=CC=C1O[Si](C)(C)C	1958.9	Semi standard non polar	33892256
Vanillactic acid,2TMS,isomer #1	COC1=CC(CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O	1947.8	Semi standard non polar	33892256
Vanillactic acid,2TMS,isomer #2	COC1=CC(CC(O[Si](C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C	1999.1	Semi standard non polar	33892256
Vanillactic acid,2TMS,isomer #3	COC1=CC(CC(O)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1988.3	Semi standard non polar	33892256
Vanillactic acid,3TMS,isomer #1	COC1=CC(CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2006.6	Semi standard non polar	33892256
Vanillactic acid,1TBDMS,isomer #1	COC1=CC(CC(O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O	2240.4	Semi standard non polar	33892256
Vanillactic acid,1TBDMS,isomer #2	COC1=CC(CC(O)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	2169.6	Semi standard non polar	33892256
Vanillactic acid,1TBDMS,isomer #3	COC1=CC(CC(O)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	2233.3	Semi standard non polar	33892256
Vanillactic acid,2TBDMS,isomer #1	COC1=CC(CC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	2449.8	Semi standard non polar	33892256
Vanillactic acid,2TBDMS,isomer #2	COC1=CC(CC(O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	2500.0	Semi standard non polar	33892256
Vanillactic acid,2TBDMS,isomer #3	COC1=CC(CC(O)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2479.5	Semi standard non polar	33892256
Vanillactic acid,3TBDMS,isomer #1	COC1=CC(CC(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	2690.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillactic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ku-2900000000-69c1daf79bf136cbeda8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillactic acid GC-MS (3 TMS) - 70eV, Positive	splash10-03ki-9135400000-66bd27980748dec48932	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillactic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillactic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillactic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillactic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillactic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillactic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillactic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillactic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillactic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillactic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillactic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillactic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillactic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillactic acid GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vanillactic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-014j-0900000000-286fd6a398d981fb304b	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vanillactic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-004l-9500000000-e5d908b43c53fa144f04	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vanillactic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-00or-9000000000-9c1d1b75d20954fa5e7f	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillactic acid 10V, Positive-QTOF	splash10-029b-0930000000-358780a634f9b76c8ffd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillactic acid 20V, Positive-QTOF	splash10-00ks-0900000000-a0c9e1c6055d07eff5fb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillactic acid 40V, Positive-QTOF	splash10-0abi-4900000000-98f74ecb570f22a3ab2e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillactic acid 10V, Negative-QTOF	splash10-03di-2590000000-950900f4d05879b38813	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillactic acid 20V, Negative-QTOF	splash10-01bl-2910000000-04db11413f60bdfdb560	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillactic acid 40V, Negative-QTOF	splash10-00dr-5900000000-470f97906aa1018f9b73	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillactic acid 10V, Negative-QTOF	splash10-03fr-9480000000-528dd14b88a108965ec9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillactic acid 20V, Negative-QTOF	splash10-05g0-5900000000-4c7476268c7a3c11a131	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillactic acid 40V, Negative-QTOF	splash10-0ab9-3930000000-2725f9ff3e03c2076f86	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillactic acid 10V, Positive-QTOF	splash10-03ds-0950000000-178e1e266b1f63c6ec8e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillactic acid 20V, Positive-QTOF	splash10-000i-0900000000-95be65594bf90008ecaa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillactic acid 40V, Positive-QTOF	splash10-00kr-9800000000-46f5d9fc7bb2d38b6766	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected and Quantified	0.0933 (0.00-0.187) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	7524950	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.83-1.2 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	0.75-0.93 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	11.3 umol/mmol creatinine	Infant (0-1 year old)	Female	Aromatic L-amino acid decarboxylase deficiency	9686366	details
Urine	Detected and Quantified	12.7 umol/mmol creatinine	Children (1-13 years old)	Female	Aromatic L-amino acid decarboxylase deficiency	9686366	details

Associated Disorders and Diseases

Disease References

Aromatic L-amino acid decarboxylase deficiency
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:9686366 ]

Associated OMIM IDs

608643 (Aromatic L-amino acid decarboxylase deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022315

KNApSAcK ID

Not Available

Chemspider ID

141152

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5868

PubChem Compound

160637

PDB ID

Not Available

ChEBI ID

1240674

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Wong, Henry N. C.; Xu, Zun Le; Chang, Hson Mou; Lee, Chi Ming. Compounds from Danshen. 6. A modified synthesis of (±)-b-aryllactic acids. Synthesis (1992), (8), 793-7.

Material Safety Data Sheet (MSDS)

Not Available

General References

Javors MA, Bowden CL, Maas JW: 3-methoxy-4-hydroxyphenylglycol, 5-hydroxyindoleacetic acid, and homovanillic acid in human cerebrospinal fluid. Storage and measurement by reversed-phase high-performance liquid chromatography and coulometric detection using 3-methoxy-4-hydroxyphenyllactic acid as an internal standard. J Chromatogr. 1984 Dec 12;336(2):259-69. [PubMed:6085084 ]
Mashige F, Ohkubo A, Matsushima Y, Takano M, Tsuchiya E, Kanazawa H, Nagata Y, Takai N, Shinozuka N, Sakuma I: High-performance liquid chromatographic determination of catecholamine metabolites and 5-hydroxyindoleacetic acid in human urine using a mixed-mode column and an eight-channel electrode electrochemical detector. J Chromatogr B Biomed Appl. 1994 Aug 5;658(1):63-8. [PubMed:7524950 ]
Hyland K, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10. [PubMed:1281049 ]
Muskiet FA, Fremouw-Ottevangers DC, van der Meulen J, Wolthers BG, de Vries JA: Determination of some L-3,4-dihydroxyphenylalanine and dopamine metabolites in urine by means of mass fragmentography. Clin Chem. 1978 Jan;24(1):122-7. [PubMed:73430 ]
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 ]
Ikeda H, Matsuyama S, Suzuki N, Takahashi A, Kuroiwa M: 3,4-dihydroxyphenylalanine (DOPA) decarboxylase deficiency and resultant high levels of plasma DOPA and dopamine in unfavorable neuroblastoma. Hypertens Res. 1995 Jun;18 Suppl 1:S209-10. [PubMed:8529065 ]
Kinoshita Y, Yamada S, Haraguchi K, Takayanagi T, Mori Y, Takahashi T, Haruki E: Determination of vanillylmandelic acid, vanillactic acid, and homovanillic acid in dried urine on filter-paper discs by high-performance liquid chromatography with coulometric electrochemical detection for neuroblastoma screening. Clin Chem. 1988 Nov;34(11):2228-30. [PubMed:3180413 ]
Jouve J, Bakri D, Herault J, Muh JP: Determination of urinary vanillactic acid and plasma dihydroxyphenylalanine as markers of non-secreting neuroblastoma by high-performance liquid chromatography with electrochemical detection. J Chromatogr. 1991 Jul 5;567(2):331-41. [PubMed:1939466 ]
Tuchman M, Stoeckeler JS: Conjugated versus "free" acidic metabolites of catecholamines in random urine samples: significance for the diagnosis of neuroblastoma. Pediatr Res. 1988 Jun;23(6):576-9. [PubMed:3393388 ]
Mashige F, Takai N, Matsushima Y, Ito A, Takano M, Tsuchiya E, Kanazawa H, Nagata Y, Shinozuka N, Wada H, et al.: [Simultaneous determination of catecholamines, serotonin, and their precursors and metabolites in body fluid by an HPLC system with multi-electrode electrochemical detector]. Rinsho Byori. 1994 Jun;42(6):591-9. [PubMed:7914240 ]
Brautigam C, Hyland K, Wevers R, Sharma R, Wagner L, Stock GJ, Heitmann F, Hoffmann GF: Clinical and laboratory findings in twins with neonatal epileptic encephalopathy mimicking aromatic L-amino acid decarboxylase deficiency. Neuropediatrics. 2002 Jun;33(3):113-7. [PubMed:12200739 ]

Enzymes

Enzyme Details

1. Sulfotransferase family cytosolic 2B member 1

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:: SULT2B1
Uniprot ID:: O00204
Molecular weight:: 39598.595

Reactions

Vanillactic acid → 3-(4-hydroxy-3-methoxyphenyl)-2-(sulfooxy)propanoic acid	details

Enzyme Details

2. 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

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

Enzyme Details

3. 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

Vanillactic acid → 2-hydroxy-3-[3-methoxy-4-(sulfooxy)phenyl]propanoic acid	details

Showing metabocard for Vanillactic acid (HMDB0000913)

MOL for HMDB0000913 (Vanillactic acid)

3D MOL for HMDB0000913 (Vanillactic acid)

3D SDF for HMDB0000913 (Vanillactic acid)

3D-SDF for HMDB0000913 (Vanillactic acid)

PDB for HMDB0000913 (Vanillactic acid)

3D PDB for HMDB0000913 (Vanillactic acid)

SMILES for HMDB0000913 (Vanillactic acid)

INCHI for HMDB0000913 (Vanillactic acid)

Structure for HMDB0000913 (Vanillactic acid)

3D Structure for HMDB0000913 (Vanillactic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions