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Showing metabocard for But-2-enoic acid (HMDB0010720)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-10-15 12:12:16 UTC
Update Date2021-09-07 17:05:27 UTC
HMDB IDHMDB0010720
Secondary Accession Numbers
  • HMDB10720
Metabolite Identification
Common NameBut-2-enoic acid
DescriptionBut-2-enoic acid, also known as (2E)-2-butenoate or alpha-crotonic acid, belongs to the class of organic compounds known as straight chain organic acids. These are organic acids with a straight aliphatic chain. But-2-enoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Data?1582752865
MOLSDF3D-SDFPDBSMILESInChI

MOL for HMDB0010720 (But-2-enoic acid)


  Mrv1652305271900042D          

  6  5  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
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   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
  4  6  2  0  0  0  0
M  END
Download

SDF for HMDB0010720 (But-2-enoic acid)


  Mrv1652305271900042D          

  6  5  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
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   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
  4  6  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0010720

> <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-NSCUHMNNSA-N

> <FORMULA>
C4H6O2

> <MOLECULAR_WEIGHT>
86.0892

> <EXACT_MASS>
86.036779436

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
8.443178849897404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-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>
butenoic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0010720 (But-2-enoic acid)

637090
  -OEChem-10221920493D

 12 11  0     0  0  0  0  0  0999 V2000
    2.0046    0.9556   -0.0002 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3674   -1.2284   -0.0001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3803   -0.3347   -0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7807    0.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3006    0.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0896   -0.0380    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2643   -1.4150   -0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8180    1.2805    0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3113   -0.1726   -0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3113   -0.1729    0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4222    1.5387    0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9229    0.6105   -0.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 12  1  0  0  0  0
  2  6  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  5 11  1  0  0  0  0
M  END
> <PUBCHEM_COMPOUND_CID>
637090

> <PUBCHEM_CONFORMER_RMSD>
0.4

> <PUBCHEM_CONFORMER_DIVERSEORDER>
1

> <PUBCHEM_MMFF94_PARTIAL_CHARGES>
9
1 -0.65
11 0.15
12 0.5
2 -0.57
3 -0.29
4 0.14
5 -0.14
6 0.71
7 0.15

> <PUBCHEM_EFFECTIVE_ROTOR_COUNT>
1

> <PUBCHEM_PHARMACOPHORE_FEATURES>
4
1 1 acceptor
1 2 acceptor
1 4 hydrophobe
3 1 2 6 anion

> <PUBCHEM_HEAVY_ATOM_COUNT>
6

> <PUBCHEM_ATOM_DEF_STEREO_COUNT>
0

> <PUBCHEM_ATOM_UDEF_STEREO_COUNT>
0

> <PUBCHEM_BOND_DEF_STEREO_COUNT>
1

> <PUBCHEM_BOND_UDEF_STEREO_COUNT>
0

> <PUBCHEM_ISOTOPIC_ATOM_COUNT>
0

> <PUBCHEM_COMPONENT_COUNT>
1

> <PUBCHEM_CACTVS_TAUTO_COUNT>
1

> <PUBCHEM_CONFORMER_ID>
0009B8A200000001

> <PUBCHEM_MMFF94_ENERGY>
6.3892

> <PUBCHEM_FEATURE_SELFOVERLAP>
20.354

> <PUBCHEM_SHAPE_FINGERPRINT>
139733 1 9222934981040815587
14390081 3 18273212040686103465
20096714 4 18342176721262595816
21040471 1 18338516464244102726
23552449 11 18188196603198550010
24536 1 18337659845922890497
29004967 10 18187089463793141745
5460574 1 9295293841602344769

> <PUBCHEM_SHAPE_MULTIPOLES>
111.74
3.34
0.97
0.58
1.53
0.11
0
-0.3
0
-0.47
0
0.06
0
0

> <PUBCHEM_SHAPE_SELFOVERLAP>
203.591

> <PUBCHEM_SHAPE_VOLUME>
71.4

> <PUBCHEM_COORDINATE_TYPE>
2
5
10

$$$$
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PDB for HMDB0010720 (But-2-enoic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         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  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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SMILES for HMDB0010720 (But-2-enoic acid)

C\C=C\C(O)=O
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INCHI for HMDB0010720 (But-2-enoic 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
(2E)-2-Butenoic acidChEBI
(e)-2-Butenoic acidChEBI
(e)-But-2-enoic acidChEBI
(e)-Crotonic acidChEBI
2-Butenoic acidChEBI
3-Methylacrylic acidChEBI
alpha-Butenoic acidChEBI
alpha-Crotonic acidChEBI
BEOChEBI
beta-Methacrylic acidChEBI
beta-Methylacrylic acidChEBI
trans-2-Butenoic acidChEBI
trans-Crotonic acidChEBI
Crotonic acidKegg
(2E)-2-ButenoateGenerator
(e)-2-ButenoateGenerator
(e)-But-2-enoateGenerator
(e)-CrotonateGenerator
2-ButenoateGenerator
3-MethylacrylateGenerator
a-ButenoateGenerator
a-Butenoic acidGenerator
alpha-ButenoateGenerator
Α-butenoateGenerator
Α-butenoic acidGenerator
a-CrotonateGenerator
a-Crotonic acidGenerator
alpha-CrotonateGenerator
Α-crotonateGenerator
Α-crotonic acidGenerator
b-MethacrylateGenerator
b-Methacrylic acidGenerator
beta-MethacrylateGenerator
Β-methacrylateGenerator
Β-methacrylic acidGenerator
b-MethylacrylateGenerator
b-Methylacrylic acidGenerator
beta-MethylacrylateGenerator
Β-methylacrylateGenerator
Β-methylacrylic acidGenerator
trans-2-ButenoateGenerator
trans-CrotonateGenerator
CrotonateGenerator
But-2-enoateGenerator
(2E)-But-2-enoateHMDB
(2E)-But-2-enoic acidHMDB
3-Methyl-acrylic acidHMDB
ButenoateHMDB
Butenoic acidHMDB
Kyselina krotonovaHMDB
Solid crotonic acidHMDB
Chemical FormulaC4H6O2
Average Molecular Weight86.0892
Monoisotopic Molecular Weight86.036779436
IUPAC Name(2E)-but-2-enoic acid
Traditional Namebutenoic acid
CAS Registry Number3724-65-0
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-NSCUHMNNSA-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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point72 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.72HANSCH,C ET AL. (1995)
Predicted 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
Polarizability8.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000l-9000000000-c066ee0b8aa28cc564f52017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000l-9000000000-c066ee0b8aa28cc564f52018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9000000000-dcef1149fbd6447033ad2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0103-9100000000-bb87072a7225402c6d0e2017-10-06View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-139e86f163451c657b842017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-b1e1c9a0bcfd328b1cd92017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-e0d8bcef7823a57ace6b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-f496e2b96544aa9df21d2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-9000000000-1dc3bc86132e739428612016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ko-9000000000-d17c17c2c66a97ee9c272016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4cd5b916c7ee6039effc2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-dde621f263ff3ac728412016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-9000000000-dce352f985fb5e1432632016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-acd6176b8c6ebe2516352016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-ec20127c74818b1f634d2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-9000000000-acc7f4424bb0833d9f872021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9000000000-f6cecaee0aa536b151602021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kf-9000000000-1462d04bf056a8a82ccd2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-210cae383690d066d0e02021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-1aa1299c9e5efe8dc4212021-09-07View Spectrum
MSMass Spectrum (Electron Ionization)splash10-000f-9000000000-824e2d62774bcbbebff02021-09-05View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2016-09-19View Spectrum
Biological Properties
Cellular Locations
  • 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 IDDB02074
Phenol Explorer Compound IDNot Available
FooDB IDFDB003283
KNApSAcK IDNot Available
Chemspider ID552744
KEGG Compound IDC01771
BioCyc IDCROTONATE
BiGG IDNot Available
Wikipedia LinkCrotonic_acid
METLIN IDNot Available
PubChem Compound637090
PDB IDBEO
ChEBI ID41131
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.