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Showing NP-Card for 2-Phenylpropionate (NP0091581)

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Record Information
Version2.0
Created at2022-05-11 18:41:51 UTC
Updated at2022-05-11 18:41:51 UTC
NP-MRD IDNP0091581
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Phenylpropionate
Description2-Phenylpropionate, also known as (+-)-hydratropasaeure or (+-)-hydratropic 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-Phenylpropionate is found in Aloe africana, Alpinia officinarum, Glycyrrhiza glabra, Hoya latifolia and Populus alba. 2-Phenylpropionate was first documented in 1976 (PMID: 939327). 2-Phenylpropionate is a weakly acidic compound (based on its pKa) (PMID: 11159807) (PMID: 2865113) (PMID: 412331).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0091581 (2-Phenylpropionate)


  Mrv1652304272019252D          

 11 11  0  0  0  0            999 V2000
   -2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8876   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5  8  2  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for NP0091581 (2-Phenylpropionate)

     RDKit          3D

 21 21  0  0  0  0  0  0  0  0999 V2000
   -1.6305   -1.3273   -0.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2149    0.0988   -0.3538 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0533    0.5008    0.7738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5374    0.8424    1.8560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4237    0.5036    0.6440 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2379    0.1516   -0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1044    0.8648   -0.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4678    0.9261   -0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9644    0.2573    0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279   -0.4634    1.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7671   -0.5071    1.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7221   -1.7703   -1.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8582   -1.8396    0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4785   -1.2722   -1.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4015    0.7035   -1.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9432    1.2271    0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7697    1.4108   -1.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1540    1.4912   -1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0154    0.2666    0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5276   -0.9868    2.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271   -1.0780    1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  6
  5 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
M  END
Download

3D SDF for NP0091581 (2-Phenylpropionate)


  Mrv1652304272019252D          

 11 11  0  0  0  0            999 V2000
   -2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8876   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5  8  2  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0091581

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O2/c1-7(9(10)11)8-5-3-2-4-6-8/h2-7H,1H3,(H,10,11)

> <INCHI_KEY>
YPGCWEMNNLXISK-UHFFFAOYSA-N

> <FORMULA>
C9H10O2

> <MOLECULAR_WEIGHT>
150.1745

> <EXACT_MASS>
150.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.774604993351875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-phenylpropanoic acid

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.1539803836666667

> <ALOGPS_LOGS>
-1.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.587870280133123

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
41.9401

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.85e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-phenylpropionic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0091581 (2-Phenylpropionate)

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PDB for NP0091581 (2-Phenylpropionate)
HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0      -3.850   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.850  -1.334   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.390  -1.334   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -3.080  -2.667   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    8                                                       
CONECT    6    4    8                                                       
CONECT    7    1    8    9                                                  
CONECT    8    5    6    7                                                  
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

Download
3D PDB for NP0091581 (2-Phenylpropionate)
Download
SMILES for NP0091581 (2-Phenylpropionate)
CC(C(O)=O)C1=CC=CC=C1
Download
INCHI for NP0091581 (2-Phenylpropionate)
InChI=1S/C9H10O2/c1-7(9(10)11)8-5-3-2-4-6-8/h2-7H,1H3,(H,10,11)
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View in JSmol
Synonyms
ValueSource
(+-)-HydratropasaeureChEBI
(+-)-Hydratropic acidChEBI
2-Phenylpropionic acidChEBI
alpha-Methylbenzeneacetic acidChEBI
alpha-Methylphenylacetic acidChEBI
alpha-Phenylpropionic acidChEBI
HydratropasaeureChEBI
(+-)-HydratropateGenerator
a-MethylbenzeneacetateGenerator
a-Methylbenzeneacetic acidGenerator
alpha-MethylbenzeneacetateGenerator
Α-methylbenzeneacetateGenerator
Α-methylbenzeneacetic acidGenerator
a-MethylphenylacetateGenerator
a-Methylphenylacetic acidGenerator
alpha-MethylphenylacetateGenerator
Α-methylphenylacetateGenerator
Α-methylphenylacetic acidGenerator
a-PhenylpropionateGenerator
a-Phenylpropionic acidGenerator
alpha-PhenylpropionateGenerator
Α-phenylpropionateGenerator
Α-phenylpropionic acidGenerator
2-PhenylpropanoateHMDB
2-Phenylpropanoic acidHMDB
alpha-PhenylpropioateHMDB
alpha-Phenylpropioic acidHMDB
Hydratropic acidHMDB
PhenylpropionateHMDB
Hydratropic acid, (R)-isomerHMDB
Hydratropic acid, (+-)-isomerHMDB
Hydratropic acid, (S)-isomerHMDB
HydratropateHMDB
2-PhenylpropionateGenerator
Chemical FormulaC9H10O2
Average Mass150.1745 Da
Monoisotopic Mass150.06808 Da
IUPAC Name2-phenylpropanoic acid
Traditional Name2-phenylpropionic acid
CAS Registry NumberNot Available
SMILES
CC(C(O)=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H10O2/c1-7(9(10)11)8-5-3-2-4-6-8/h2-7H,1H3,(H,10,11)
InChI KeyYPGCWEMNNLXISK-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
Aloe africanaLOTUS Database
Alpinia officinarumLOTUS Database
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
Glycyrrhiza glabraLOTUS Database
Hoya latifoliaLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Populus albaLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
  • 2-phenylpropanoic-acid
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP2.17ALOGPS
logP2.15ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)4.59ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.94 m³·mol⁻¹ChemAxon
Polarizability15.77 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0011743  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028418  
KNApSAcK IDNot Available
Chemspider ID9874  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenylpropanoic acid  
METLIN IDNot Available
PubChem Compound10296  
PDB IDNot Available
ChEBI ID48526  
Good Scents IDNot Available
References
General References
  1. De Costa KS, Black SR, Thomas BF, Burgess JP, Mathews JM: Metabolism and disposition of alpha-methylstyrene in rats. Drug Metab Dispos. 2001 Feb;29(2):166-71. [PubMed:11159807  ] 
  2. Yamaguchi T, Nakamura Y: Stereoselective disposition of hydratropic acid in rat. Drug Metab Dispos. 1985 Sep-Oct;13(5):614-9. [PubMed:2865113  ] 
  3. Dixon PA, Caldwell J, Smith RL: Metabolism of arylacetic acids. 2. The fate of [14C]hydratropic acid and its variation with species. Xenobiotica. 1977 Nov;7(11):707-15. doi: 10.3109/00498257709038700. [PubMed:412331  ] 
  4. Borgna P, Vicarini L, Gandini C: [Preparation and study of phytotoxic activity of anilides of the (+/-) hydratropic acid]. Farmaco Sci. 1976 Apr;31(4):284-90. [PubMed:939327  ]