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Showing NP-Card for Isohomovanillic acid (NP0086555)

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Record Information
Version1.0
Created at2022-05-11 16:24:17 UTC
Updated at2022-05-11 16:24:17 UTC
NP-MRD IDNP0086555
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsohomovanillic acid
DescriptionIsohomovanillic acid, also known as homoisovanillate, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. It was first documented in 1978 (PMID: 621233). Isohomovanillic acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 22770225) (PMID: 476919).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086555 (Isohomovanillic acid)

3-Hydroxy-4-methoxyphenylacetic acid.mol
  Mrv0541 02231218272D          

 13 13  0  0  0  0            999 V2000
    0.7145   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
  5 10  2  0  0  0  0
  2  5  1  0  0  0  0
 11 12  1  0  0  0  0
  8 11  1  0  0  0  0
  7 13  1  0  0  0  0
M  END
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3D MOL for NP0086555 (Isohomovanillic acid)

     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
    3.7271    1.0070    0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0319   -0.2140   -0.0977 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6572   -0.2447    0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763    0.9067    0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3831    0.9495    0.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0911   -0.2286    0.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5492   -0.2100    0.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2876    0.0622   -0.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6299    0.2343   -1.5239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6594    0.1288   -0.5099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4283   -1.4059    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9329   -1.4130   -0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5734   -2.6130   -0.3423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7676    1.3626    1.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2594    1.8294   -0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7501    0.8652   -0.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5333    1.8353    0.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8893    1.8910    0.9377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8009    0.5382    1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8333   -1.2197    1.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2151    0.9532   -0.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9894   -2.3306    0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475   -2.6841   -0.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  6 11  1  0
 11 12  2  0
 12 13  1  0
 12  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
  7 20  1  0
 10 21  1  0
 11 22  1  0
 13 23  1  0
M  END
Download

3D SDF for NP0086555 (Isohomovanillic acid)

3-Hydroxy-4-methoxyphenylacetic acid.mol
  Mrv0541 02231218272D          

 13 13  0  0  0  0            999 V2000
    0.7145   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
  5 10  2  0  0  0  0
  2  5  1  0  0  0  0
 11 12  1  0  0  0  0
  8 11  1  0  0  0  0
  7 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086555

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c1-13-8-3-2-6(4-7(8)10)5-9(11)12/h2-4,10H,5H2,1H3,(H,11,12)

> <INCHI_KEY>
BWXLCOBSWMQCGP-UHFFFAOYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.1733

> <EXACT_MASS>
182.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
17.719256927378964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.88

> <JCHEM_LOGP>
1.1497575179999997

> <ALOGPS_LOGS>
-1.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.910032800229548

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.744853115039856

> <JCHEM_PKA_STRONGEST_BASIC>
-4.890936914925856

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
45.8097

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isohomovanillic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0086555 (Isohomovanillic acid)

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PDB for NP0086555 (Isohomovanillic acid)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3-Hydroxy-4-methoxyphenylacetic acid.mol          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       1.334  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -4.620   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.667  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334   4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    6   10    2                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11   12    8                                                       
CONECT   12   11                                                            
CONECT   13    7                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0086555 (Isohomovanillic acid)
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SMILES for NP0086555 (Isohomovanillic acid)
COC1=CC=C(CC(O)=O)C=C1O
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INCHI for NP0086555 (Isohomovanillic acid)
InChI=1S/C9H10O4/c1-13-8-3-2-6(4-7(8)10)5-9(11)12/h2-4,10H,5H2,1H3,(H,11,12)
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View in JSmol
Synonyms
ValueSource
Homoisovanillic acidChEBI
HomoisovanillateGenerator
IsohomovanillateGenerator
3-Hydroxy-4-methoxyphenylacetateHMDB
3-Hydroxy-4-methoxyphenylacetic acidHMDB
4-Methoxy-3-hydroxyphenylacetateHMDB
4-Methoxy-3-hydroxyphenylacetic acidHMDB
Homo-iso-vanillic acidHMDB
Chemical FormulaC9H10O4
Average Mass182.1733 Da
Monoisotopic Mass182.05791 Da
IUPAC Name2-(3-hydroxy-4-methoxyphenyl)acetic acid
Traditional Nameisohomovanillic acid
CAS Registry NumberNot Available
SMILES
COC1=CC=C(CC(O)=O)C=C1O
InChI Identifier
InChI=1S/C9H10O4/c1-13-8-3-2-6(4-7(8)10)5-9(11)12/h2-4,10H,5H2,1H3,(H,11,12)
InChI KeyBWXLCOBSWMQCGP-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenols  
Sub ClassMethoxyphenols  
Direct ParentMethoxyphenols  
Alternative Parents
Substituents
  • Methoxyphenol
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Monocyclic benzene moiety
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Carboxylic acid
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
logP0.88ALOGPS
logP1.15ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.74ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.81 m³·mol⁻¹ChemAxon
Polarizability17.72 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000333  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021958  
KNApSAcK IDNot Available
Chemspider ID141092  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5322  
PubChem Compound160562  
PDB IDNot Available
ChEBI ID70818  
Good Scents IDNot Available
References
General References
  1. Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225  ] 
  2. Takahashi S, Yoshioka M, Yoshiue S, Tamura Z: Mass fragmentographic determination of vanilmandelic acid, homovanillic acid and isohomovanillic acid in human body fluids. J Chromatogr. 1978 Jan 1;145(1):1-9. doi: 10.1016/s0378-4347(00)81663-1. [PubMed:621233  ] 
  3. Muskiet FA, Fremouw-Ottevangers DC, Nagel GT, Wolthers BG: Determination of 4-O-methylated catecholamine metabolites in urine by mass fragmentography. Clin Chem. 1979 Oct;25(10):1708-13. [PubMed:476919  ]