NP-MRD: Showing NP-Card for Vanillactic acid (NP0000280)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-06-29 00:46:42 UTC

NP-MRD ID

NP0000280

Secondary Accession Numbers

None

Natural Product 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>
NP0000280

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

212.1993 Da

Monoisotopic Mass

212.06847 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Homo sapiens (Urine)	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0000913

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022315

KNApSAcK ID

C00052426

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

Good Scents ID

Not Available

References

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 ]
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 ]

Showing NP-Card for Vanillactic acid (NP0000280)

MOL for NP0000280 (Vanillactic acid)

3D MOL for NP0000280 (Vanillactic acid)

3D SDF for NP0000280 (Vanillactic acid)

3D-SDF for NP0000280 (Vanillactic acid)

PDB for NP0000280 (Vanillactic acid)

3D PDB for NP0000280 (Vanillactic acid)

SMILES for NP0000280 (Vanillactic acid)

INCHI for NP0000280 (Vanillactic acid)

Structure for NP0000280 (Vanillactic acid)

3D Structure for NP0000280 (Vanillactic acid)