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Showing NP-Card for p-Hydroxymandelic acid (NP0086655)

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Record Information
Version1.0
Created at2022-05-11 16:27:16 UTC
Updated at2024-04-19 10:04:03 UTC
NP-MRD IDNP0086655
Secondary Accession NumbersNone
Natural Product Identification
Common Namep-Hydroxymandelic acid
DescriptionP-Hydroxymandelic acid, also known as 4-hydroxymandelate or 4-hydroxyphenylglycolate, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. It was first documented in 1979 (PMID: 487594). P-Hydroxymandelic acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 8087979) (PMID: 3706738) (PMID: 22770225) (PMID: 3091293).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086655 (p-Hydroxymandelic acid)


  Mrv1652305231920442D          

 12 12  0  0  1  0            999 V2000
    0.7145   -0.4125    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    0.4125    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    0.4125    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
    2.1433   -0.4125    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
    2.1433    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  2  1  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  4  1  0  0  0  0
  5 12  1  0  0  0  0
  2  6  1  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
M  END
Download

3D MOL for NP0086655 (p-Hydroxymandelic acid)

     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.2959    0.0312   -1.8315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4345    0.4100   -0.6429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2353    1.4990   -0.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7121   -0.3557    0.4203 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0317    0.2627    1.6295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2542   -0.3486    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4313   -1.4653   -0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856   -1.4462   -0.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4846   -0.2787   -0.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8542   -0.2317   -0.5396 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8090    0.8356    0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421    0.8142    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    2.3982   -0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0826   -1.3939    0.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9063   -0.1035    1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1048   -2.3948   -0.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3455   -2.3081   -0.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4070    0.6018   -0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740    1.7380    0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0180    1.7359    0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12  6  1  0
  5 15  1  0
  4 14  1  1
  3 13  1  0
  7 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

3D SDF for NP0086655 (p-Hydroxymandelic acid)


  Mrv1652305231920442D          

 12 12  0  0  1  0            999 V2000
    0.7145   -0.4125    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    0.4125    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    0.4125    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
    2.1433   -0.4125    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
    2.1433    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  2  1  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  4  1  0  0  0  0
  5 12  1  0  0  0  0
  2  6  1  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086655

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(C(O)=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O4/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)

> <INCHI_KEY>
YHXHKYRQLYQUIH-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.1467

> <EXACT_MASS>
168.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.644347996836352

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-2-(4-hydroxyphenyl)acetic acid

> <ALOGPS_LOGP>
0.86

> <JCHEM_LOGP>
0.5922703229999999

> <ALOGPS_LOGS>
-1.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.475213707677849

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3028147671822787

> <JCHEM_PKA_STRONGEST_BASIC>
-4.105652938089659

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
40.6847

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.69e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxymandelic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0086655 (p-Hydroxymandelic acid)

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PDB for NP0086655 (p-Hydroxymandelic acid)
HEADER    PROTEIN                                 23-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAY-19         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   0.770   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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    8    2    3                                                  
CONECT    2    1    6                                                       
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4   12    6                                                  
CONECT    6    2    5                                                       
CONECT    7    8    9   10                                                  
CONECT    8    1    7   11                                                  
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    5                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0086655 (p-Hydroxymandelic acid)
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SMILES for NP0086655 (p-Hydroxymandelic acid)
OC(C(O)=O)C1=CC=C(O)C=C1
Download
INCHI for NP0086655 (p-Hydroxymandelic acid)
InChI=1S/C8H8O4/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)
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View in JSmol
Synonyms
ValueSource
4-Hydroxyphenylglycolic acidChEBI
4-Hydroxymandelic acidKegg
4-HydroxyphenylglycolateGenerator
4-HydroxymandelateGenerator
p-HydroxymandelateGenerator
(+/-)-alpha,4-dihydroxy-benzeneacetateHMDB
(+/-)-alpha,4-dihydroxy-benzeneacetic acidHMDB
(R)-4-HydroxymandelateHMDB
(RS)-p-HydroxymandelateHMDB
(RS)-p-Hydroxymandelic acidHMDB
(S)-4-HydroxymandelateHMDB
2-(4-Hydroxyphenyl)-2-hydroxyacetateHMDB
2-(4-Hydroxyphenyl)-2-hydroxyacetic acidHMDB
3-Dimethylallyl-4-hydroxymandelateHMDB
3-Dimethylallyl-4-hydroxymandelic acidHMDB
4-Hydroxy-DL-mandelateHMDB
4-Hydroxy-DL-mandelic acidHMDB
alpha,4-Dihydroxy-benzeneacetateHMDB
alpha,4-Dihydroxy-benzeneacetic acidHMDB
alpha,4-DihydroxybenzeneacetateHMDB
alpha,4-Dihydroxybenzeneacetic acidHMDB
D-4-HydroxymandelateHMDB
D-p-HydroxymandelateHMDB
delta-4-HydroxymandelateHMDB
delta-p-HydroxymandelateHMDB
DL-4-HydroxymandelateHMDB
DL-4-Hydroxymandelic acidHMDB
DL-p-HydroxymandelateHMDB
DL-p-Hydroxymandelic acidHMDB
DL-p-HydroxyphenylglycolateHMDB
DL-p-Hydroxyphenylglycolic acidHMDB
Hydroxy(4-hydroxyphenyl)acetateHMDB
Hydroxy(4-hydroxyphenyl)acetic acidHMDB
L-4-HydroxymandelateHMDB
L-p-HydroxymandelateHMDB
p-Hydroxy-mandelateHMDB
p-Hydroxy-mandelic acidHMDB
p-HydroxyphenylglycolateHMDB
p-Hydroxyphenylglycolic acidHMDB
Para-hydroxymandelic acidHMDB
4-Hydroxymandelic acid, (D)-isomerHMDB
Pisolithin bHMDB
2-Hydroxy-2-(4'-hydroxyphenyl)acetic acid
(4-Hydroxyphenyl)-2-hydroxyacetic acid
(4-Hydroxyphenyl)-2-hydroxyethanoic acid
2-Hydroxy-2-(4'-hydroxyphenyl)ethanoic acid
4-Hydroxy-D-mandelic acid
4-Hydroxy-L-mandelic acid
4'-Hydroxymandelic acid
Chemical FormulaC8H8O4
Average Mass168.1467 Da
Monoisotopic Mass168.04226 Da
IUPAC Name2-hydroxy-2-(4-hydroxyphenyl)acetic acid
Traditional Name4-hydroxymandelic acid
CAS Registry NumberNot Available
SMILES
OC(C(O)=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O4/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)
InChI KeyYHXHKYRQLYQUIH-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableSumner lab, University of MissouriZach Tretter2024-01-10View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableSumner lab, University of MissouriZach Tretter2024-01-10View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableSumner lab, University of MissouriZach Tretter2024-01-10View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableSumner lab, University of MissouriZach Tretter2024-01-10View Spectrum
1D NMR[13C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)Not AvailableSumner lab, University of MissouriZach Tretter2024-01-10View Spectrum
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 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenols  
Sub Class1-hydroxy-2-unsubstituted benzenoids  
Direct Parent1-hydroxy-2-unsubstituted benzenoids  
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alpha-hydroxy acid
    • 

  • Monocyclic benzene moiety
    • 

  • Hydroxy acid
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Aromatic alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • 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
logP0.86ALOGPS
logP0.59ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.68 m³·mol⁻¹ChemAxon
Polarizability15.64 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000822  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022267  
KNApSAcK IDNot Available
Chemspider ID321  
KEGG Compound IDC11527  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Hydroxymandelic acid  
METLIN ID5785  
PubChem Compound328  
PDB IDNot Available
ChEBI ID16388  
Good Scents IDNot Available
References
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979  ] 
  2. Higa S, Kishimoto S: Isolation of 2-hydroxycarboxylic acids with a boronate affinity gel. Anal Biochem. 1986 Apr;154(1):71-4. [PubMed:3706738  ] 
  3. 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  ] 
  4. Couch MW, Greer DM, Williams CM: Excretion of octopamine metabolites in neuroblastoma. Clin Chim Acta. 1986 Jul 15;158(1):109-14. doi: 10.1016/0009-8981(86)90121-x. [PubMed:3091293  ] 
  5. Niwa T, Ohki T, Maeda K, Saito A, Ohta K, Kobayashi K: A gas chromatographic-mass spectrometric assay for nine hydroxyphenolic acids in uremic serum. Clin Chim Acta. 1979 Sep 3;96(3):247-54. doi: 10.1016/0009-8981(79)90435-2. [PubMed:487594  ]