NP-MRD: Showing NP-Card for Vanilpyruvic acid (NP0091570)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-11 18:41:35 UTC

Updated at

2022-05-11 18:41:35 UTC

NP-MRD ID

NP0091570

Secondary Accession Numbers

None

Natural Product 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). Vanilpyruvic acid was first documented in 2006 (PMID: 16288991). Vanilpyruvic acid, with regard to humans, has been linked to the inborn metabolic disorder aromatic l-amino acid decarboxylase deficiency.

Structure

MOL 3D MOL SDF 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>
NP0091570

> <DATABASE_NAME>
NP-MRD

> <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

Synonyms

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

Chemical Formula

C₁₀H₁₀O₅

Average Mass

210.1834 Da

Monoisotopic Mass

210.05282 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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

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 )

Physical Properties

State

Not Available

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
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

External Links

HMDB ID

HMDB0011714

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028400

KNApSAcK ID

Not Available

Chemspider ID

Not Available

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

Good Scents ID

Not Available

References

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 ]

Showing NP-Card for Vanilpyruvic acid (NP0091570)

MOL for NP0091570 (Vanilpyruvic acid)

3D MOL for NP0091570 (Vanilpyruvic acid)

3D SDF for NP0091570 (Vanilpyruvic acid)

3D-SDF for NP0091570 (Vanilpyruvic acid)

PDB for NP0091570 (Vanilpyruvic acid)

3D PDB for NP0091570 (Vanilpyruvic acid)

SMILES for NP0091570 (Vanilpyruvic acid)

INCHI for NP0091570 (Vanilpyruvic acid)

Structure for NP0091570 (Vanilpyruvic acid)

3D Structure for NP0091570 (Vanilpyruvic acid)