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Showing NP-Card for 4-hydroxy-3-(3-methylbut-2-enoyl)benzoic acid (NP0160089)

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Record Information
Version2.0
Created at2022-09-02 17:58:14 UTC
Updated at2022-09-02 17:58:14 UTC
NP-MRD IDNP0160089
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-hydroxy-3-(3-methylbut-2-enoyl)benzoic acid
Description4-Hydroxy-3-(3-methylbut-2-enoyl)benzoic acid belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 4-hydroxy-3-(3-methylbut-2-enoyl)benzoic acid is found in Piper dilatatum. 4-Hydroxy-3-(3-methylbut-2-enoyl)benzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0160089 (4-hydroxy-3-(3-methylbut-2-enoyl)benzoic acid)


  Mrv1533004241510142D          

 16 16  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 C   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
    0.0000    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
    1.4289    2.4750    0.0000 O   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
    0.0000    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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  2 16  1  0  0  0  0
M  END
Download

3D MOL for NP0160089 (4-hydroxy-3-(3-methylbut-2-enoyl)benzoic acid)

     RDKit          3D

 28 28  0  0  0  0  0  0  0  0999 V2000
    3.1441   -0.0744    0.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7568    0.0945   -0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9847    0.3202   -1.6633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6050    0.0865   -1.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2240   -0.0490   -1.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4018    0.2655   -2.3172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7658   -0.3977   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0682    0.1896   -0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0112    0.1700    0.6150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3438    0.7820    0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2295    0.7808    1.2708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6570    1.3818   -0.8229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7976   -0.3987    1.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5788   -0.9735    2.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6204   -0.9543    1.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5799   -1.6054    1.3532 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4530   -1.0988    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4043    0.3382    1.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0728    0.5433    0.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7487   -0.4010   -1.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6245    0.0861   -2.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2748    1.3707   -1.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8512    0.2749   -2.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3115    0.6560   -1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2295    2.2207   -0.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5899   -0.3709    2.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3565   -1.4375    3.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376   -1.7995    0.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
  9 10  1  0
 10 12  1  0
 10 11  2  0
 15  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  8 24  1  0
 13 26  1  0
 14 27  1  0
 16 28  1  0
 12 25  1  0
M  END
Download

3D SDF for NP0160089 (4-hydroxy-3-(3-methylbut-2-enoyl)benzoic acid)


  Mrv1533004241510142D          

 16 16  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 C   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
    0.0000    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
    1.4289    2.4750    0.0000 O   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
    0.0000    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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  2 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0160089

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC(=O)C1=CC(=CC=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H12O4/c1-7(2)5-11(14)9-6-8(12(15)16)3-4-10(9)13/h3-6,13H,1-2H3,(H,15,16)

> <INCHI_KEY>
KKTUVLDFZYQTIU-UHFFFAOYSA-N

> <FORMULA>
C12H12O4

> <MOLECULAR_WEIGHT>
220.224

> <EXACT_MASS>
220.073558866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.012105351578583

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3-(3-methylbut-2-enoyl)benzoic acid

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
2.921200194333333

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.354199275684644

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.219340207274117

> <JCHEM_PKA_STRONGEST_BASIC>
-7.312231225138484

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
60.30110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3-(3-methylbut-2-enoyl)benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0160089 (4-hydroxy-3-(3-methylbut-2-enoyl)benzoic acid)

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PDB for NP0160089 (4-hydroxy-3-(3-methylbut-2-enoyl)benzoic acid)
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11                                                            
CONECT   13    8   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    2                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

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3D PDB for NP0160089 (4-hydroxy-3-(3-methylbut-2-enoyl)benzoic acid)
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SMILES for NP0160089 (4-hydroxy-3-(3-methylbut-2-enoyl)benzoic acid)
CC(C)=CC(=O)C1=CC(=CC=C1O)C(O)=O
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INCHI for NP0160089 (4-hydroxy-3-(3-methylbut-2-enoyl)benzoic acid)
InChI=1S/C12H12O4/c1-7(2)5-11(14)9-6-8(12(15)16)3-4-10(9)13/h3-6,13H,1-2H3,(H,15,16)
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View in JSmol
Synonyms
ValueSource
4-Hydroxy-3-(3-methylbut-2-enoyl)benzoateGenerator
TaboganateGenerator
Chemical FormulaC12H12O4
Average Mass220.2240 Da
Monoisotopic Mass220.07356 Da
IUPAC Name4-hydroxy-3-(3-methylbut-2-enoyl)benzoic acid
Traditional Name4-hydroxy-3-(3-methylbut-2-enoyl)benzoic acid
CAS Registry NumberNot Available
SMILES
CC(C)=CC(=O)C1=CC(=CC=C1O)C(O)=O
InChI Identifier
InChI=1S/C12H12O4/c1-7(2)5-11(14)9-6-8(12(15)16)3-4-10(9)13/h3-6,13H,1-2H3,(H,15,16)
InChI KeyKKTUVLDFZYQTIU-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
Piper dilatatumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentHydroxybenzoic acid derivatives  
Alternative Parents
Substituents
  • Hydroxybenzoic acid
    • 

  • Benzoic acid
    • 

  • Benzoyl
    • 

  • Aryl ketone
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Acryloyl-group
    • 

  • Vinylogous acid
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Enone
    • 

  • Ketone
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • 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
logP2.14ALOGPS
logP2.92ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.3 m³·mol⁻¹ChemAxon
Polarizability22.01 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 Compound15840545  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]