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Showing metabocard for Isocrotonic acid (HMDB0034439)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:17:04 UTC
Update Date2023-02-21 17:24:14 UTC
HMDB IDHMDB0034439
Secondary Accession Numbers
  • HMDB34439
Metabolite 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. Based on a literature review a significant number of articles have been published on Isocrotonic acid.
Structure
Data?1677000254
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0034439 (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
Download

3D MOL for HMDB0034439 (Isocrotonic acid)

HMDB0034439
     RDKit          3D
Isocrotonic acid
 12 11  0  0  0  0  0  0  0  0999 V2000
   -1.2869   -0.6439    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8930    0.7617   -0.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539    1.1887   -0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4323    0.2289   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6107    0.6484   -0.1104 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2329   -1.1337    0.0719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9324   -1.3050   -0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3903   -0.7408    0.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9002   -1.0010    1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6687    1.5111   -0.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5807    2.2304   -0.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8610   -1.7448    0.5916 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  5  2  0
  4  6  1  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
Download

3D SDF for HMDB0034439 (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>
HMDB0034439

> <DATABASE_NAME>
hmdb

> <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

$$$$
Download

3D-SDF for HMDB0034439 (Isocrotonic acid)

HMDB0034439
     RDKit          3D
Isocrotonic acid
 12 11  0  0  0  0  0  0  0  0999 V2000
   -1.2869   -0.6439    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8930    0.7617   -0.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539    1.1887   -0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4323    0.2289   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6107    0.6484   -0.1104 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2329   -1.1337    0.0719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9324   -1.3050   -0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3903   -0.7408    0.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9002   -1.0010    1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6687    1.5111   -0.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5807    2.2304   -0.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8610   -1.7448    0.5916 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  5  2  0
  4  6  1  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
Download

PDB for HMDB0034439 (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 HMDB0034439 (Isocrotonic acid)

COMPND    HMDB0034439
HETATM    1  C1  UNL     1      -1.287  -0.644   0.018  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.893   0.762  -0.127  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.354   1.189  -0.170  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.432   0.229  -0.069  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.611   0.648  -0.110  1.00  0.00           O  
HETATM    6  O2  UNL     1       1.233  -1.134   0.072  1.00  0.00           O  
HETATM    7  H1  UNL     1      -0.932  -1.305  -0.791  1.00  0.00           H  
HETATM    8  H2  UNL     1      -2.390  -0.741   0.052  1.00  0.00           H  
HETATM    9  H3  UNL     1      -0.900  -1.001   1.017  1.00  0.00           H  
HETATM   10  H4  UNL     1      -1.669   1.511  -0.206  1.00  0.00           H  
HETATM   11  H5  UNL     1       0.581   2.230  -0.277  1.00  0.00           H  
HETATM   12  H6  UNL     1       1.861  -1.745   0.592  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3    3   10
CONECT    3    4   11
CONECT    4    5    5    6
CONECT    6   12
END
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SMILES for HMDB0034439 (Isocrotonic acid)

C\C=C/C(O)=O
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INCHI for HMDB0034439 (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 JSmolView Stereo Labels
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 Molecular Weight86.0892
Monoisotopic Molecular Weight86.036779436
IUPAC Name(2Z)-but-2-enoic acid
Traditional Nameisocrotonic acid
CAS Registry Number503-64-0
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
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
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point14.6 °CNot Available
Boiling Point169.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mL at 20 °CNot Available
LogP0.658 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility101 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+117.55231661259
DarkChem[M-H]-111.95631661259
DeepCCS[M+H]+127.23530932474
DeepCCS[M-H]-124.43730932474
DeepCCS[M-2H]-160.70530932474
DeepCCS[M+Na]+135.50730932474
AllCCS[M+H]+122.232859911
AllCCS[M+H-H2O]+117.732859911
AllCCS[M+NH4]+126.432859911
AllCCS[M+Na]+127.632859911
AllCCS[M-H]-125.032859911
AllCCS[M+Na-2H]-129.532859911
AllCCS[M+HCOO]-134.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isocrotonic acidC\C=C/C(O)=O1739.4Standard polar33892256
Isocrotonic acidC\C=C/C(O)=O960.7Standard non polar33892256
Isocrotonic acidC\C=C/C(O)=O839.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isocrotonic acid,1TMS,isomer #1C/C=C\C(=O)O[Si](C)(C)C934.7Semi standard non polar33892256
Isocrotonic acid,1TBDMS,isomer #1C/C=C\C(=O)O[Si](C)(C)C(C)(C)C1155.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isocrotonic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9000000000-824e2d62774bcbbebff02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocrotonic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0103-9100000000-bb87072a7225402c6d0e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocrotonic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocrotonic acid 10V, Positive-QTOFsplash10-00kr-9000000000-1dc3bc86132e739428612016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocrotonic acid 20V, Positive-QTOFsplash10-00ko-9000000000-d17c17c2c66a97ee9c272016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocrotonic acid 40V, Positive-QTOFsplash10-0006-9000000000-4cd5b916c7ee6039effc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocrotonic acid 10V, Negative-QTOFsplash10-000i-9000000000-dde621f263ff3ac728412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocrotonic acid 20V, Negative-QTOFsplash10-000l-9000000000-dce352f985fb5e1432632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocrotonic acid 40V, Negative-QTOFsplash10-00kf-9000000000-acd6176b8c6ebe2516352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocrotonic acid 10V, Negative-QTOFsplash10-000i-9000000000-ec20127c74818b1f634d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocrotonic acid 20V, Negative-QTOFsplash10-00kr-9000000000-acc7f4424bb0833d9f872021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocrotonic acid 40V, Negative-QTOFsplash10-014l-9000000000-f6cecaee0aa536b151602021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocrotonic acid 10V, Positive-QTOFsplash10-00kf-9000000000-1462d04bf056a8a82ccd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocrotonic acid 20V, Positive-QTOFsplash10-0006-9000000000-210cae383690d066d0e02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocrotonic acid 40V, Positive-QTOFsplash10-0006-9000000000-1aa1299c9e5efe8dc4212021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1099241
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.