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Showing NP-Card for Methyl 4-hydroxycinnamate (NP0137516)

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Record Information
Version2.0
Created at2022-05-30 16:54:47 UTC
Updated at2022-05-30 16:54:47 UTC
NP-MRD IDNP0137516
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethyl 4-hydroxycinnamate
Description Methyl 4-hydroxycinnamate is found in Allium cepa, Alpinia roxburghii, Anisomeles indica, Annona cherimola, Aralia bipinnata, Aristolochia kaempferi, Aristolochia zollingeriana, Artemisia capillaris, Artemisia fragrans, Balanophora japonica, Boenninghausenia albiflora, Boschniakia rossica, Calocedrus formosana, Cinnamomum reticulatum, Clausena excavata, Comptonia peregrina, Cucumis sativus, Diphasiastrum alpinum, Echinacea purpurea, Tetradium glabrifolium, Fagraea gracilipes, Gmelina asiatica, Goniothalamus laoticus, Grevillea robusta, Haplopteris anguste-elongata, Harpullia pendula, Hibiscus taiwanensis, Hydrangea chinensis, Idesia polycarpa, Marshallia obovata, Melicope semecarpifolia, Microtropis fokienensis, Muntingia calabura, Oxalis pes-caprae, Parastrephia lepidophylla, Persicaria lapathifolia, Phyllostachys edulis, Plumeria obtusa, Pueraria montana, Richterago polymorpha, Rohdea chinensis, Stereospermum acuminatissimum, Viburnum dilatatum, Wikstroemia canescens, Zanthoxylum ailanthoides and Zanthoxylum schinifolium.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0137516 (Methyl 4-hydroxycinnamate)


  Mrv0541 02241221472D          

 13 13  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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
    1.4289    0.0000    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   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  2  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
M  END
Download

3D MOL for NP0137516 (Methyl 4-hydroxycinnamate)

     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
    4.8486   -0.2454    0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4349   -0.1704    0.2525 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6015   -1.2550    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1642   -2.3724    0.6335 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1493   -1.1595    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5612   -0.0007    0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8750    0.2169    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4057    1.4659   -0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7666    1.7038   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6448    0.6544    0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0384    0.8520   -0.0208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1295   -0.6019    0.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7568   -0.8213    0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2570   -0.8220   -0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1856   -0.6516    1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2067    0.8138    0.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -2.0294    0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1912    0.8983    0.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7098    2.2962   -0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1305    2.7072   -0.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3997    1.7805   -0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8374   -1.4154    0.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461   -1.8440    0.4897 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  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13  7  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  6 18  1  0
  8 19  1  0
  9 20  1  0
 11 21  1  0
 12 22  1  0
 13 23  1  0
M  END
Download

3D SDF for NP0137516 (Methyl 4-hydroxycinnamate)


  Mrv0541 02241221472D          

 13 13  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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
    1.4289    0.0000    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   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  2  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137516

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
NITWSHWHQAQBAW-UHFFFAOYSA-N

> <FORMULA>
C10H10O3

> <MOLECULAR_WEIGHT>
178.1846

> <EXACT_MASS>
178.062994186

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
18.41550371623222

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
2.2117483276666663

> <ALOGPS_LOGS>
-2.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.398704446238039

> <JCHEM_PKA_STRONGEST_BASIC>
-5.954730133757686

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
49.80990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0137516 (Methyl 4-hydroxycinnamate)

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PDB for NP0137516 (Methyl 4-hydroxycinnamate)
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  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   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  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0137516 (Methyl 4-hydroxycinnamate)
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SMILES for NP0137516 (Methyl 4-hydroxycinnamate)
COC(=O)C=CC1=CC=C(O)C=C1
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INCHI for NP0137516 (Methyl 4-hydroxycinnamate)
InChI=1S/C10H10O3/c1-13-10(12)7-4-8-2-5-9(11)6-3-8/h2-7,11H,1H3
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View in JSmol
Synonyms
ValueSource
Methyl p-coumaric acidGenerator
4-Coumaric acid methyl ester, (e)-isomerMeSH
4-Coumaric acid methyl esterMeSH
Para-coumaric acid methyl esterMeSH
Chemical FormulaC10H10O3
Average Mass178.1846 Da
Monoisotopic Mass178.06299 Da
IUPAC Namemethyl 3-(4-hydroxyphenyl)prop-2-enoate
Traditional Namemethyl 3-(4-hydroxyphenyl)prop-2-enoate
CAS Registry NumberNot Available
SMILES
COC(=O)C=CC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C10H10O3/c1-13-10(12)7-4-8-2-5-9(11)6-3-8/h2-7,11H,1H3
InChI KeyNITWSHWHQAQBAW-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
Allium cepaLOTUS Database
Alpinia roxburghiiLOTUS Database
Anisomeles Anisomeles indicaLOTUS Database
Annona cherimolaLOTUS Database
Aralia bipinnataLOTUS Database
Aristolochia kaempferiLOTUS Database
Aristolochia zollingerianaLOTUS Database
Artemisia capillarisLOTUS Database
Artemisia fragransLOTUS Database
Balanophora japonicaLOTUS Database
Boenninghausenia albifloraLOTUS Database
Boschniakia rossicaLOTUS Database
Calocedrus formosanaLOTUS Database
Cinnamomum reticulatumLOTUS Database
Clausena excavataLOTUS Database
Comptonia peregrinaLOTUS Database
Cucumis sativusLOTUS Database
Diphasiastrum alpinumLOTUS Database
Echinacea purpureaLOTUS Database
Euodia fargesiiLOTUS Database
Fagraea gracilipesLOTUS Database
Gmelina asiaticaLOTUS Database
Goniothalamus laoticusLOTUS Database
Grevillea robustaLOTUS Database
Haplopteris anguste-elongataLOTUS Database
Harpullia pendulaLOTUS Database
Hibiscus taiwanensisLOTUS Database
Hydrangea chinensisLOTUS Database
Idesia polycarpaLOTUS Database
Marshallia obovataLOTUS Database
Melicope semecarpifoliaLOTUS Database
Microtropis fokienensisLOTUS Database
Muntingia calaburaLOTUS Database
Oxalis pes-capraeLOTUS Database
Parastrephia lepidophyllaLOTUS Database
Persicaria lapathifoliaLOTUS Database
Phyllostachys edulisLOTUS Database
Plumeria obtusaLOTUS Database
Pueraria montanaLOTUS Database
Richterago polymorphaLOTUS Database
Rohdea chinensisLOTUS Database
Stereospermum acuminatissimumLOTUS Database
Viburnum dilatatumLOTUS Database
Wikstroemia canescensLOTUS Database
Zanthoxylum ailanthoidesLOTUS Database
Zanthoxylum schinifoliumLOTUS 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
    • 

  • Fatty acid ester
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Fatty acyl
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Methyl ester
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • 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
logP2.42ALOGPS
logP2.21ChemAxon
logS-2.3ALOGPS
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
Polarizability18.42 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 IDFDB001825  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92203  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available