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Showing NP-Card for dl-o-hydroxyphenyllactic acid (NP0265431)

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Record Information
Version2.0
Created at2022-09-08 09:24:28 UTC
Updated at2022-09-08 09:24:28 UTC
NP-MRD IDNP0265431
Secondary Accession NumbersNone
Natural Product Identification
Common Namedl-o-hydroxyphenyllactic acid
Description(±)-2-Hydroxy-3-(2-hydroxyphenyl)propanoic acid 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 (±)-2-Hydroxy-3-(2-hydroxyphenyl)propanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (±)-2-Hydroxy-3-(2-hydroxyphenyl)propanoic acid has been detected, but not quantified in, fruits. dl-o-hydroxyphenyllactic acid is found in Prunus cerasus. This could make (±)-2-hydroxy-3-(2-hydroxyphenyl)propanoic acid a potential biomarker for the consumption of these foods.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0265431 (dl-o-hydroxyphenyllactic acid)


  Mrv0541 02241208422D          

 13 13  0  0  0  0            999 V2000
   -0.7135    0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147    0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432   -0.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291    1.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147   -0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7135   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  2  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
Download

3D MOL for NP0265431 (dl-o-hydroxyphenyllactic acid)

     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
   -3.5302    0.0169   -0.8303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2984    0.2935   -0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5009    0.5502   -1.6223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8910    0.2987    0.8484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9703   -0.2256    1.6409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6903   -0.5800    1.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5033   -0.1292    0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6907    1.1803   -0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8440    1.5468   -0.8042 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8105    0.5875   -1.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6107   -0.7133   -0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4800   -1.0969    0.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3830   -2.4095    0.4447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6307    0.2632   -2.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6930    1.2893    1.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1699    0.4105    2.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9275   -1.6199    0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5572   -0.8029    2.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0608    1.9374    0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9115    2.5663   -1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6871    0.8882   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3834   -1.4540   -0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6162   -2.7977    0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  6  1  0
  6  7  1  0
  7 12  2  0
 12 13  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  8  7  1  0
  5 16  1  0
  4 15  1  1
  6 17  1  0
  6 18  1  0
 13 23  1  0
 11 22  1  0
 10 21  1  0
  9 20  1  0
  8 19  1  0
  3 14  1  0
M  END
Download

3D SDF for NP0265431 (dl-o-hydroxyphenyllactic acid)


  Mrv0541 02241208422D          

 13 13  0  0  0  0            999 V2000
   -0.7135    0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147    0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432   -0.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291    1.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147   -0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7135   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  2  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0265431

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(CC1=C(O)C=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c10-7-4-2-1-3-6(7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)

> <INCHI_KEY>
HXQBZGMVGIDZAJ-UHFFFAOYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.1733

> <EXACT_MASS>
182.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
17.4828050508278

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-3-(2-hydroxyphenyl)propanoic acid

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
0.8809315280000001

> <ALOGPS_LOGS>
-1.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.349579848121353

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.586307951631448

> <JCHEM_PKA_STRONGEST_BASIC>
-3.857633495474226

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
45.4397

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.83e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-3-(2-hydroxyphenyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0265431 (dl-o-hydroxyphenyllactic acid)

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PDB for NP0265431 (dl-o-hydroxyphenyllactic acid)
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      -1.332   0.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.001   0.769   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.668   0.769   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001  -0.001   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.668   2.310   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.334  -1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667   0.769   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   0.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.332  -1.540   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    8   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3                                                            
CONECT    8    1    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    1   11                                                       
CONECT   13    8                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0265431 (dl-o-hydroxyphenyllactic acid)
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SMILES for NP0265431 (dl-o-hydroxyphenyllactic acid)
OC(CC1=C(O)C=CC=C1)C(O)=O
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INCHI for NP0265431 (dl-o-hydroxyphenyllactic acid)
InChI=1S/C9H10O4/c10-7-4-2-1-3-6(7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)
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View in JSmol
Synonyms
ValueSource
(±)-2-hydroxy-3-(2-hydroxyphenyl)propanoateGenerator
2-Hydroxy-3-(2-hydroxyphenyl)propanoateGenerator
Chemical FormulaC9H10O4
Average Mass182.1733 Da
Monoisotopic Mass182.05791 Da
IUPAC Name2-hydroxy-3-(2-hydroxyphenyl)propanoic acid
Traditional Name2-hydroxy-3-(2-hydroxyphenyl)propanoic acid
CAS Registry NumberNot Available
SMILES
OC(CC1=C(O)C=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C9H10O4/c10-7-4-2-1-3-6(7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)
InChI KeyHXQBZGMVGIDZAJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Prunus cerasusLOTUS Database
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.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassPhenylpropanoic acids  
Sub ClassNot Available
Direct ParentPhenylpropanoic acids  
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Alpha-hydroxy acid
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Hydroxy acid
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organic oxygen 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
logP0.9ALOGPS
logP0.88ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.59ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.44 m³·mol⁻¹ChemAxon
Polarizability17.48 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033624  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011712  
KNApSAcK IDNot Available
Chemspider ID2341107  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3083977  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]