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Showing NP-Card for umbellic acid (NP0276519)

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Record Information
Version2.0
Created at2022-09-09 00:42:01 UTC
Updated at2022-09-09 00:42:01 UTC
NP-MRD IDNP0276519
Secondary Accession NumbersNone
Natural Product Identification
Common Nameumbellic acid
Description3-(2,4-Dihydroxyphenyl)prop-2-enoic acid belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. umbellic acid is found in Chamaecyparis formosensis and Dipteryx odorata. 3-(2,4-Dihydroxyphenyl)prop-2-enoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0276519 (umbellic acid)


  Mrv1652308221904192D          

 13 13  0  0  0  0            999 V2000
    1.4289    0.0000    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
    0.0000   -1.6500    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
    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 C   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   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
  8  6  2  0  0  0  0
  4  9  1  4  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
M  END
Download

3D MOL for NP0276519 (umbellic acid)

     RDKit          3D

 21 21  0  0  0  0  0  0  0  0999 V2000
    2.4612   -0.8972   -1.5765 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9635   -0.0030   -0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3796    0.1864   -1.0301 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2846    0.8325    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0769    1.0056    0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1746    0.4440    0.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0506    0.1667    1.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2309   -0.4909    0.9721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6034   -0.9054   -0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7928   -1.5721   -0.4907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7676   -0.6413   -1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5467    0.0391   -1.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2445    0.2963   -2.2810 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7688    1.1113   -1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0649    1.5261    0.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9804    1.8140    1.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7489    0.4947    2.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9125   -0.7140    1.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4089   -1.7717    0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0097   -0.9431   -2.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0220    0.0220   -3.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6 12  2  0
 12 13  1  0
 12 11  1  0
 11  9  2  0
  9 10  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
 13 21  1  0
 11 20  1  0
 10 19  1  0
  8 18  1  0
  7 17  1  0
M  END
Download

3D SDF for NP0276519 (umbellic acid)


  Mrv1652308221904192D          

 13 13  0  0  0  0            999 V2000
    1.4289    0.0000    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
    0.0000   -1.6500    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
    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 C   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   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
  8  6  2  0  0  0  0
  4  9  1  4  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0276519

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O4/c10-7-3-1-6(8(11)5-7)2-4-9(12)13/h1-5,10-11H,(H,12,13)

> <INCHI_KEY>
HGEFWFBFQKWVMY-UHFFFAOYSA-N

> <FORMULA>
C9H8O4

> <MOLECULAR_WEIGHT>
180.159

> <EXACT_MASS>
180.042258738

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
17.281626603565154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,4-dihydroxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
1.5289556166666665

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.164488176663289

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.842622541397255

> <JCHEM_PKA_STRONGEST_BASIC>
-5.649442592457466

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
47.0217

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2,4-dihydroxyphenyl)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0276519 (umbellic acid)

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PDB for NP0276519 (umbellic acid)
HEADER    PROTEIN                                 22-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-AUG-19         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    9                                                       
CONECT    5    7    8                                                       
CONECT    6    1    2    8                                                  
CONECT    7    3    5   10                                                  
CONECT    8    5    6   11                                                  
CONECT    9    4   12   13                                                  
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0276519 (umbellic acid)
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SMILES for NP0276519 (umbellic acid)
OC(=O)C=CC1=C(O)C=C(O)C=C1
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INCHI for NP0276519 (umbellic acid)
InChI=1S/C9H8O4/c10-7-3-1-6(8(11)5-7)2-4-9(12)13/h1-5,10-11H,(H,12,13)
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View in JSmol
Synonyms
ValueSource
3-(2,4-Dihydroxyphenyl)prop-2-enoateGenerator
Chemical FormulaC9H8O4
Average Mass180.1590 Da
Monoisotopic Mass180.04226 Da
IUPAC Name3-(2,4-dihydroxyphenyl)prop-2-enoic acid
Traditional Name3-(2,4-dihydroxyphenyl)prop-2-enoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C=CC1=C(O)C=C(O)C=C1
InChI Identifier
InChI=1S/C9H8O4/c10-7-3-1-6(8(11)5-7)2-4-9(12)13/h1-5,10-11H,(H,12,13)
InChI KeyHGEFWFBFQKWVMY-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
Chamaecyparis formosensisLOTUS Database
Dipteryx odorataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCinnamic acids and derivatives  
Sub ClassHydroxycinnamic acids and derivatives  
Direct ParentHydroxycinnamic acids  
Alternative Parents
Substituents
  • Cinnamic acid
    • 

  • Hydroxycinnamic acid
    • 

  • Styrene
    • 

  • Resorcinol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organooxygen 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
logP1.49ALOGPS
logP1.53ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.84ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m³·mol⁻¹ChemAxon
Polarizability17.28 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0132508  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB089684  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3359493  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]