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Showing NP-Card for 3-(3-Hydroxyphenyl)-2-propenoic acid, methyl (NP0045227)

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Record Information
Version2.0
Created at2022-03-10 19:01:37 UTC
Updated at2022-03-10 22:17:11 UTC
NP-MRD IDNP0045227
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-(3-Hydroxyphenyl)-2-propenoic acid, methyl
Description3-(3-Hydroxyphenyl)-2-propenoic acid, methyl, also known as methyl (E)-3-(3-hydroxyphenyl)prop-2-enoate, belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. 3-(3-Hydroxyphenyl)-2-propenoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045227 (3-(3-Hydroxyphenyl)-2-propenoic acid, methyl)


  Mrv1652303192001563D          

 13 13  0  0  0  0            999 V2000
    3.2845   -0.6901    1.9940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0661    0.9456   -1.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9031    0.4826   -1.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1406    1.1607    0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4053   -0.2685   -1.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5986   -0.6229   -1.4174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8745    0.4440    0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7519    0.2110   -0.9987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0568    0.9160    0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4991   -0.7654   -0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0827    1.1220    2.3057 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083   -1.1997   -0.5931 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2995   -0.5126    0.9672 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  2  3  0  0  0
  5  8  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
M  END
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3D MOL for NP0045227 (3-(3-Hydroxyphenyl)-2-propenoic acid, methyl)

     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
    4.6865    0.3341   -0.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2889    0.2319   -0.5461 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7045    0.3286    0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4163    0.5145    1.7246 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2646    0.2199    0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4951    0.0236   -0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9488   -0.1034   -0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6240   -0.3062   -1.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9931   -0.4344   -1.3712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6730   -0.3540   -0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423   -0.1543    1.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7277   -0.0719    2.2246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6661   -0.0285    1.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2235    0.7557    0.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0715   -0.6905   -0.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292    0.9362   -1.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092    0.2935    1.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9685   -0.0529   -1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632   -0.3690   -2.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4777   -0.5904   -2.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7554   -0.4517   -0.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7356   -0.1596    2.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1508    0.1288    1.9544 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7 13  2  0
 13 11  1  0
 11 12  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  6 18  1  0
 13 23  1  0
 12 22  1  0
 10 21  1  0
  9 20  1  0
  8 19  1  0
M  END
Download

3D SDF for NP0045227 (3-(3-Hydroxyphenyl)-2-propenoic acid, methyl)


  Mrv1652303192001563D          

 13 13  0  0  0  0            999 V2000
    3.2845   -0.6901    1.9940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0661    0.9456   -1.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9031    0.4826   -1.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1406    1.1607    0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4053   -0.2685   -1.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5986   -0.6229   -1.4174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8745    0.4440    0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7519    0.2110   -0.9987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0568    0.9160    0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4991   -0.7654   -0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0827    1.1220    2.3057 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083   -1.1997   -0.5931 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2995   -0.5126    0.9672 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  2  3  0  0  0
  5  8  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045227

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O3/c1-13-10(12)6-5-8-3-2-4-9(11)7-8/h2-7,11H,1H3

> <INCHI_KEY>
PKALKWFZXXGNJD-UHFFFAOYSA-N

> <FORMULA>
C10H10O3

> <MOLECULAR_WEIGHT>
178.187

> <EXACT_MASS>
178.062994182

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.025107750367802

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3-(3-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.2117483276666663

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.397337645167264

> <JCHEM_PKA_STRONGEST_BASIC>
-5.971943945247916

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
49.809900000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-(3-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0045227 (3-(3-Hydroxyphenyl)-2-propenoic acid, methyl)

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PDB for NP0045227 (3-(3-Hydroxyphenyl)-2-propenoic acid, methyl)
HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0       3.285  -0.690   1.994  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.066   0.946  -1.190  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.903   0.483  -1.750  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.141   1.161   0.142  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.405  -0.269  -1.687  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.599  -0.623  -1.417  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.875   0.444   0.348  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.752   0.211  -0.999  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.057   0.916   0.926  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.499  -0.765  -0.340  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.083   1.122   2.306  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.708  -1.200  -0.593  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.300  -0.513   0.967  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2    3    4                                                       
CONECT    3    2    8                                                       
CONECT    4    2    9                                                       
CONECT    5    6    8                                                       
CONECT    6    5   10                                                       
CONECT    7    8    9                                                       
CONECT    8    3    5    7                                                  
CONECT    9    4    7   11                                                  
CONECT   10    6   12   13                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
CONECT   13    1   10                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0045227 (3-(3-Hydroxyphenyl)-2-propenoic acid, methyl)
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SMILES for NP0045227 (3-(3-Hydroxyphenyl)-2-propenoic acid, methyl)
COC(=O)C=CC1=CC(O)=CC=C1
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INCHI for NP0045227 (3-(3-Hydroxyphenyl)-2-propenoic acid, methyl)
InChI=1S/C10H10O3/c1-13-10(12)6-5-8-3-2-4-9(11)7-8/h2-7,11H,1H3
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View in JSmol
Synonyms
ValueSource
Methyl 3-(3-hydroxyphenyl)-2-propenoic acidGenerator
Chemical FormulaC10H10O3
Average Mass178.1870 Da
Monoisotopic Mass178.06299 Da
IUPAC Namemethyl 3-(3-hydroxyphenyl)prop-2-enoate
Traditional Namemethyl 3-(3-hydroxyphenyl)prop-2-enoate
CAS Registry Number3943-95-1
SMILES
COC(=O)C=CC1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C10H10O3/c1-13-10(12)6-5-8-3-2-4-9(11)7-8/h2-7,11H,1H3
InChI KeyPKALKWFZXXGNJD-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
Cannabis sativaNULL
      Not Available
Typha angustifoliaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCinnamic acids and derivatives  
Sub ClassHydroxycinnamic acids and derivatives  
Direct ParentCoumaric acid esters  
Alternative Parents
Substituents
  • Coumaric acid ester
    • 

  • Coumaric acid or derivatives
    • 

  • Cinnamic acid ester
    • 

  • Styrene
    • 

  • Phenol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Fatty acid ester
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Fatty acyl
    • 

  • Benzenoid
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Methyl ester
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP2.41ALOGPS
logP2.21ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)9.4ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.81 m³·mol⁻¹ChemAxon
Polarizability18.03 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound94283  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available