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Showing NP-Card for isocrotonic acid (NP0152424)

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Record Information
Version2.0
Created at2022-09-02 08:53:48 UTC
Updated at2022-09-02 08:53:48 UTC
NP-MRD IDNP0152424
Secondary Accession NumbersNone
Natural Product Identification
Common Nameisocrotonic acid
DescriptionIsocrotonic acid, also known as perisocrotonate or (Z)-2-butenoic acid, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. isocrotonic acid is found in Coffea arabica. Isocrotonic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0152424 (isocrotonic acid)


  Mrv0541 02241215182D          

  6  5  0  0  0  0            999 V2000
   -0.8987    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5302    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2447    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8987    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5302    0.0000    0.0000 O   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
  1  5  1  0  0  0  0
  3  6  2  0  0  0  0
M  END
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3D MOL for NP0152424 (isocrotonic acid)

     RDKit          3D

 12 11  0  0  0  0  0  0  0  0999 V2000
   -1.6173    0.3944   -0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6444   -0.5494   -0.6731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6327   -0.5630   -0.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1828    0.3944    0.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4359    1.2476    1.0617 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524    0.3372    0.7968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6430    0.2034   -0.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4114    1.4584   -0.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778    0.2827    0.9886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0130   -1.3042   -1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2590   -1.3140   -0.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440   -0.5876    0.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  6  1  0
  4  5  2  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  3 11  1  0
  6 12  1  0
M  END
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3D SDF for NP0152424 (isocrotonic acid)


  Mrv0541 02241215182D          

  6  5  0  0  0  0            999 V2000
   -0.8987    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5302    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2447    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8987    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5302    0.0000    0.0000 O   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
  1  5  1  0  0  0  0
  3  6  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0152424

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C/C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2-

> <INCHI_KEY>
LDHQCZJRKDOVOX-IHWYPQMZSA-N

> <FORMULA>
C4H6O2

> <MOLECULAR_WEIGHT>
86.0892

> <EXACT_MASS>
86.036779436

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
8.384724269366616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-but-2-enoic acid

> <ALOGPS_LOGP>
0.94

> <JCHEM_LOGP>
0.9195822873333331

> <ALOGPS_LOGS>
0.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.900895626912272

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
22.9649

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isocrotonic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0152424 (isocrotonic acid)

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PDB for NP0152424 (isocrotonic acid)
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  C   UNK     0      -1.678   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.344   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.990   1.540   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.323   2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.678   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.990   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3                                                            
CONECT    5    1                                                            
CONECT    6    3                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

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3D PDB for NP0152424 (isocrotonic acid)
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SMILES for NP0152424 (isocrotonic acid)
C\C=C/C(O)=O
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INCHI for NP0152424 (isocrotonic acid)
InChI=1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2-
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View in JSmol
Synonyms
ValueSource
(Z)-2-Butenoic acidChEBI
(Z)-But-2-enoic acidChEBI
(Z)-Crotonic acidChEBI
cis-2-Butenoic acidChEBI
cis-Crotonic acidChEBI
Perisocrotonic acidChEBI
(Z)-2-ButenoateGenerator
(Z)-But-2-enoateGenerator
(Z)-CrotonateGenerator
cis-2-ButenoateGenerator
cis-CrotonateGenerator
PerisocrotonateGenerator
IsocrotonateGenerator
(2Z)-2-Butenoic acidHMDB
(2Z)-But-2-enoic acidHMDB
b-Crotonic acidHMDB
Chemical FormulaC4H6O2
Average Mass86.0892 Da
Monoisotopic Mass86.03678 Da
IUPAC Name(2Z)-but-2-enoic acid
Traditional Nameisocrotonic acid
CAS Registry NumberNot Available
SMILES
C\C=C/C(O)=O
InChI Identifier
InChI=1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2-
InChI KeyLDHQCZJRKDOVOX-IHWYPQMZSA-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
Coffea arabicaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentStraight chain fatty acids  
Alternative Parents
Substituents
  • Unsaturated fatty acid
    • 

  • Straight chain fatty acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
logP0.94ALOGPS
logP0.92ChemAxon
logS0.07ALOGPS
pKa (Strongest Acidic)4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.96 m³·mol⁻¹ChemAxon
Polarizability8.38 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034439  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012845  
KNApSAcK IDNot Available
Chemspider ID558890  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsocrotonic acid  
METLIN IDNot Available
PubChem Compound643792  
PDB IDNot Available
ChEBI ID36253  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]