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Showing NP-Card for 4-hydroxycinnamoylmethane (NP0295165)

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Record Information
Version2.0
Created at2022-09-10 04:01:28 UTC
Updated at2022-09-10 04:01:28 UTC
NP-MRD IDNP0295165
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-hydroxycinnamoylmethane
Description(3E)-4-(4-hydroxyphenyl)but-3-en-2-one, also known as p-hydroxybenzalacetone or methyl p-hydroxycinnamyl ketone, belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated (3E)-4-(4-hydroxyphenyl)but-3-en-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-hydroxycinnamoylmethane is found in Alpinia roxburghii, Phlomis bovei, Scopalina ruetzleri and Scutellaria barbata. It is generated by cyp2b6, cyp2e1, and cyp3a4 enzymes via a p-hydroxylation-of-monosubstituted-benzene reaction.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0295165 (4-hydroxycinnamoylmethane)


  Mrv1652304272019262D          

 12 12  0  0  0  0            999 V2000
    2.8875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4290    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    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    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    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2  3  2  0  0  0  0
  2  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4  6  2  0  0  0  0
  4  9  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  2  0  0  0  0
  6 10  1  0  0  0  0
  7 10  2  0  0  0  0
  8 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0295165 (4-hydroxycinnamoylmethane)

     RDKit          3D

 22 22  0  0  0  0  0  0  0  0999 V2000
    4.1810   -0.9104    0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1136    0.1091    0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4795    1.2646    0.6883 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6982   -0.2112    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8166    0.7439    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5973    0.4819    0.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4764    1.5435    0.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8146    1.3554    0.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2983    0.1080   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6552   -0.0587   -0.1854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4312   -0.9402   -0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0491   -0.7678   -0.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3063   -1.4720    1.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1403   -0.4336   -0.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8212   -1.5812   -0.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4587   -1.2173   -0.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1492    1.7674    0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011    2.5303    0.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4938    2.2069    0.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0282   -0.9611   -0.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8038   -1.9375   -0.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4154   -1.6200   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  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
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  0
  7 18  1  0
  8 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

3D SDF for NP0295165 (4-hydroxycinnamoylmethane)


  Mrv1652304272019262D          

 12 12  0  0  0  0            999 V2000
    2.8875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4290    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    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    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    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2  3  2  0  0  0  0
  2  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4  6  2  0  0  0  0
  4  9  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  2  0  0  0  0
  6 10  1  0  0  0  0
  7 10  2  0  0  0  0
  8 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0295165

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h2-7,12H,1H3/b3-2+

> <INCHI_KEY>
OCNIKEFATSKIBE-NSCUHMNNSA-N

> <FORMULA>
C10H10O2

> <MOLECULAR_WEIGHT>
162.188

> <EXACT_MASS>
162.068079562

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.58601503992003

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-4-(4-hydroxyphenyl)but-3-en-2-one

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
2.162146461

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.685179967376577

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.043404918738084

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6920094632367215

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
48.59190000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxycinnamoylmethane

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0295165 (4-hydroxycinnamoylmethane)

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PDB for NP0295165 (4-hydroxycinnamoylmethane)
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       5.390   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.080   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   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      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.850   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.080   5.335   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.540  -2.667   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    3    8                                                       
CONECT    3    2    9                                                       
CONECT    4    6    9                                                       
CONECT    5    7    9                                                       
CONECT    6    4   10                                                       
CONECT    7    5   10                                                       
CONECT    8    1    2   11                                                  
CONECT    9    3    4    5                                                  
CONECT   10    6    7   12                                                  
CONECT   11    8                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0295165 (4-hydroxycinnamoylmethane)
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SMILES for NP0295165 (4-hydroxycinnamoylmethane)
CC(=O)\C=C\C1=CC=C(O)C=C1
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INCHI for NP0295165 (4-hydroxycinnamoylmethane)
InChI=1S/C10H10O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h2-7,12H,1H3/b3-2+
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View in JSmol
Synonyms
ValueSource
p-HydroxybenzalacetoneKegg
4-(p-Hydroxyphenyl)-3-buten-2-oneKegg
Methyl p-hydroxycinnamyl ketoneHMDB
4-Hydroxycinnamoylmethane, (e)-isomerHMDB
4-Hydroxycinnamoyl methaneHMDB
4-Hydroxycinnamoylmethane, (Z)-isomerHMDB
Chemical FormulaC10H10O2
Average Mass162.1880 Da
Monoisotopic Mass162.06808 Da
IUPAC Name(3E)-4-(4-hydroxyphenyl)but-3-en-2-one
Traditional Name4-hydroxycinnamoylmethane
CAS Registry NumberNot Available
SMILES
CC(=O)\C=C\C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C10H10O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h2-7,12H,1H3/b3-2+
InChI KeyOCNIKEFATSKIBE-NSCUHMNNSA-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
Alpinia roxburghiiLOTUS Database
Phlomis boveiLOTUS Database
Scopalina ruetzleriLOTUS Database
Scutellaria barbataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCinnamic acids and derivatives  
Sub ClassHydroxycinnamic acids and derivatives  
Direct ParentHydroxycinnamic acids and derivatives  
Alternative Parents
Substituents
  • Hydroxycinnamic acid or derivatives
    • 

  • Styrene
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Acryloyl-group
    • 

  • Enone
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Ketone
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP2.21ALOGPS
logP2.16ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)9.04ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.59 m³·mol⁻¹ChemAxon
Polarizability17.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0133749  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID696947  
KEGG Compound IDC12088  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound796857  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]