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Showing NP-Card for Vanilloylglycine (NP0339469)

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Record Information
Version2.0
Created at2024-09-11 22:00:15 UTC
Updated at2024-09-11 22:00:16 UTC
NP-MRD IDNP0339469
Secondary Accession NumbersNone
Natural Product Identification
Common NameVanilloylglycine
DescriptionVanilloylglycine belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine. Vanilloylglycine is a moderately basic compound (based on its pKa). 3-Methoxy-4-hydroxyhippuric acid is one of the main catechins metabolites found in humans after consumption of green tea infusions.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339469 (Vanilloylglycine)


  Mrv0541 02271201352D          

 16 16  0  0  0  0            999 V2000
   -0.7145    2.0625    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
    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
   -0.7145   -2.8875    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   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
  3  2  2  0  0  0  0
  6  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  4  0  0  0
 11 10  2  0  0  0  0
 12  7  1  0  0  0  0
 13  9  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16  1  1  0  0  0  0
 16  8  1  0  0  0  0
M  END
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3D MOL for NP0339469 (Vanilloylglycine)

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3D SDF for NP0339469 (Vanilloylglycine)

  Mrv0541 02271201352D          

 16 16  0  0  0  0            999 V2000
   -0.7145    2.0625    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
    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
   -0.7145   -2.8875    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   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
  3  2  2  0  0  0  0
  6  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  4  0  0  0
 11 10  2  0  0  0  0
 12  7  1  0  0  0  0
 13  9  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16  1  1  0  0  0  0
 16  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339469

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO5/c1-16-8-4-6(2-3-7(8)12)10(15)11-5-9(13)14/h2-4,12H,5H2,1H3,(H,11,15)(H,13,14)

> <INCHI_KEY>
LOODYTDRRBLQNH-UHFFFAOYSA-N

> <FORMULA>
C10H11NO5

> <MOLECULAR_WEIGHT>
225.198

> <EXACT_MASS>
225.063722467

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
21.528841470573557

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{[hydroxy(4-hydroxy-3-methoxyphenyl)methylidene]amino}acetic acid

> <ALOGPS_LOGP>
0.74

> <JCHEM_LOGP>
0.7508571253923307

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.856394458088623

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2185434702614533

> <JCHEM_PKA_STRONGEST_BASIC>
1.3711306928118185

> <JCHEM_POLAR_SURFACE_AREA>
99.35000000000001

> <JCHEM_REFRACTIVITY>
55.08350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[hydroxy(4-hydroxy-3-methoxyphenyl)methylidene]amino}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0339469 (Vanilloylglycine)
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PDB for NP0339469 (Vanilloylglycine)
HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   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  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2    3    6                                                       
CONECT    3    2    7                                                       
CONECT    4    6    8                                                       
CONECT    5    9   11                                                       
CONECT    6    2    4   10                                                  
CONECT    7    3    8   12                                                  
CONECT    8    4    7   16                                                  
CONECT    9    5   13   14                                                  
CONECT   10    6   11   15                                                  
CONECT   11    5   10                                                       
CONECT   12    7                                                            
CONECT   13    9                                                            
CONECT   14    9                                                            
CONECT   15   10                                                            
CONECT   16    1    8                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

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3D PDB for NP0339469 (Vanilloylglycine)
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SMILES for NP0339469 (Vanilloylglycine)
COC1=C(O)C=CC(=C1)C(O)=NCC(O)=O
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INCHI for NP0339469 (Vanilloylglycine)
InChI=1S/C10H11NO5/c1-16-8-4-6(2-3-7(8)12)10(15)11-5-9(13)14/h2-4,12H,5H2,1H3,(H,11,15)(H,13,14)
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Synonyms
ValueSource
2-[(4-Hydroxy-3-methoxybenzoyl)amino]acetic acidHMDB
3-Methoxy-4-hydroxyhippuric acidHMDB
2-{[hydroxy(4-hydroxy-3-methoxyphenyl)methylidene]amino}acetateGenerator
Chemical FormulaC10H11NO5
Average Mass225.1980 Da
Monoisotopic Mass225.06372 Da
IUPAC Name2-{[hydroxy(4-hydroxy-3-methoxyphenyl)methylidene]amino}acetic acid
Traditional Name{[hydroxy(4-hydroxy-3-methoxyphenyl)methylidene]amino}acetic acid
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC(=C1)C(O)=NCC(O)=O
InChI Identifier
InChI=1S/C10H11NO5/c1-16-8-4-6(2-3-7(8)12)10(15)11-5-9(13)14/h2-4,12H,5H2,1H3,(H,11,15)(H,13,14)
InChI KeyLOODYTDRRBLQNH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentHippuric acids  
Alternative Parents
Substituents
  • Hippuric acid
    • 

  • N-acyl-alpha amino acid or derivatives
    • 

  • N-acyl-alpha-amino acid
    • 

  • Alpha-amino acid or derivatives
    • 

  • Methoxyphenol
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Benzoyl
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Carboxamide group
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Ether
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.74ALOGPS
logP0.75ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.22ChemAxon
pKa (Strongest Basic)1.37ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area99.35 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.08 m³·mol⁻¹ChemAxon
Polarizability21.53 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0060026  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030006  
KNApSAcK IDNot Available
Chemspider ID2340857  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Methoxy-4-hydroxyhippuric acid  
METLIN IDNot Available
PubChem Compound3083688  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available