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Showing NP-Card for pyroterebic acid (NP0296174)

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Record Information
Version2.0
Created at2022-09-10 05:36:30 UTC
Updated at2022-09-10 05:36:30 UTC
NP-MRD IDNP0296174
Secondary Accession NumbersNone
Natural Product Identification
Common Namepyroterebic acid
Description4-Methylpent-3-enoic acid, also known as pyroterebic acid or 4-methyl-3-pentenoate, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. pyroterebic acid is found in Calotropis procera. pyroterebic acid was first documented in 1965 (PMID: 4286899). 4-Methylpent-3-enoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0296174 (pyroterebic acid)


  Mrv1533004151514112D          

  8  7  0  0  0  0            999 V2000
    1.2375    0.7145    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    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  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  2  8  1  0  0  0  0
M  END
Download

3D MOL for NP0296174 (pyroterebic acid)

     RDKit          3D

 18 17  0  0  0  0  0  0  0  0999 V2000
   -2.0280    0.2961   -1.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150    0.0355   -0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2339    0.4595    1.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1037   -0.5784   -0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1397   -0.8510    0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3832   -0.1292   -0.0222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0328   -0.4498   -1.0502 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8289    0.9355    0.7531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0916    1.3798   -1.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7967   -0.2724   -2.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0398   -0.0504   -1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744    1.1304    1.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1841    1.0301    1.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2077   -0.4532    1.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2556   -0.8851   -1.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3763   -1.9356    0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8211   -0.5178    1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0298    0.8560    1.7443 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  1  0
  6  8  1  0
  6  7  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  8 18  1  0
M  END
Download

3D SDF for NP0296174 (pyroterebic acid)


  Mrv1533004151514112D          

  8  7  0  0  0  0            999 V2000
    1.2375    0.7145    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    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  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  2  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296174

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O2/c1-5(2)3-4-6(7)8/h3H,4H2,1-2H3,(H,7,8)

> <INCHI_KEY>
CQJHAULYLJXJNL-UHFFFAOYSA-N

> <FORMULA>
C6H10O2

> <MOLECULAR_WEIGHT>
114.144

> <EXACT_MASS>
114.068079562

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.461801292242473

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methylpent-3-enoic acid

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
1.247767077666667

> <ALOGPS_LOGS>
-0.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.9275155274721145

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
31.8712

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.87e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyroterebic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0296174 (pyroterebic acid)

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PDB for NP0296174 (pyroterebic acid)
HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.080  -2.667   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -3.080   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0296174 (pyroterebic acid)
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SMILES for NP0296174 (pyroterebic acid)
CC(C)=CCC(O)=O
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INCHI for NP0296174 (pyroterebic acid)
InChI=1S/C6H10O2/c1-5(2)3-4-6(7)8/h3H,4H2,1-2H3,(H,7,8)
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View in JSmol
Synonyms
ValueSource
4-Methyl-3-pentenoic acidChEBI
Pyroterebic acidChEBI
4-Methyl-3-pentenoateGenerator
PyroterebateGenerator
4-Methylpent-3-enoateGenerator
Chemical FormulaC6H10O2
Average Mass114.1440 Da
Monoisotopic Mass114.06808 Da
IUPAC Name4-methylpent-3-enoic acid
Traditional Namepyroterebic acid
CAS Registry NumberNot Available
SMILES
CC(C)=CCC(O)=O
InChI Identifier
InChI=1S/C6H10O2/c1-5(2)3-4-6(7)8/h3H,4H2,1-2H3,(H,7,8)
InChI KeyCQJHAULYLJXJNL-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
Calotropis proceraLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentMethyl-branched fatty acids  
Alternative Parents
Substituents
  • Methyl-branched fatty acid
    • 

  • Unsaturated 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
logP1.01ALOGPS
logP1.25ChemAxon
logS-0.6ALOGPS
pKa (Strongest Acidic)4.93ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity31.87 m³·mol⁻¹ChemAxon
Polarizability12.46 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
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 Compound68158  
PDB IDNot Available
ChEBI ID143856  
Good Scents IDNot Available
References
General References
  1. Shimizu K, Gut M: Formation of 4-methyl-3-pentenoic acid from cholesta-5, 24-dien-3-beta-ol by adrenal enzyme. Steroids. 1965 Sep;6(3):301-6. doi: 10.1016/0039-128x(65)90005-x. [PubMed:4286899  ] 
  2. LOTUS database [Link]