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Showing metabocard for cis-Acetylacrylate (HMDB0060461)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:22:25 UTC
Update Date2023-02-21 17:30:01 UTC
HMDB IDHMDB0060461
Secondary Accession Numbers
  • HMDB60461
Metabolite Identification
Common Namecis-Acetylacrylate
Descriptioncis-Acetylacrylate belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. cis-Acetylacrylate is an extremely weak basic (essentially neutral) compound (based on its pKa). cis-Acetylacrylate exists in all living organisms, ranging from bacteria to humans. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
Structure
Data?1677000601
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0060461 (cis-Acetylacrylate)

  Mrv0541 08131209282D          

 10  9  0  0  0  0            999 V2000
    2.0625   -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
    1.2375   -0.7145    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
    0.8250   -1.4289    0.0000 O   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
    1.2375    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
M  END
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3D MOL for HMDB0060461 (cis-Acetylacrylate)

HMDB0060461
     RDKit          3D
cis-Acetylacrylate
 14 13  0  0  0  0  0  0  0  0999 V2000
   -2.3623   -0.1222   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8390   -0.2545   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4523   -1.4107   -0.3546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0624    0.9227    0.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2431    0.9484    0.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1373   -0.1401   -0.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3919    0.1034    0.0678 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8080   -1.4401   -0.2883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7882   -0.9813    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7229   -0.1129   -1.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362    0.8071    0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5848    1.8982    0.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7440    1.9290    0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1240   -2.1470    0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  5 13  1  0
  8 14  1  0
M  END
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3D SDF for HMDB0060461 (cis-Acetylacrylate)

  Mrv0541 08131209282D          

 10  9  0  0  0  0            999 V2000
    2.0625   -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
    1.2375   -0.7145    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
    0.8250   -1.4289    0.0000 O   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
    1.2375    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060461

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(=C(/[H])C(O)=O)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H6O3/c1-4(6)2-3-5(7)8/h2-3H,1H3,(H,7,8)/b3-2-

> <INCHI_KEY>
XGTKSWVCNVUVHG-IHWYPQMZSA-N

> <FORMULA>
C5H6O3

> <MOLECULAR_WEIGHT>
114.0993

> <EXACT_MASS>
114.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
10.497647390902229

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-4-oxopent-2-enoic acid

> <ALOGPS_LOGP>
0.31

> <JCHEM_LOGP>
0.2887111913333334

> <ALOGPS_LOGS>
-0.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.870271336347308

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.226656271176779

> <JCHEM_PKA_STRONGEST_BASIC>
-6.922879032454119

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
28.1581

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.85e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cis-acetylacrylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0060461 (cis-Acetylacrylate)

HMDB0060461
     RDKit          3D
cis-Acetylacrylate
 14 13  0  0  0  0  0  0  0  0999 V2000
   -2.3623   -0.1222   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8390   -0.2545   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4523   -1.4107   -0.3546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0624    0.9227    0.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2431    0.9484    0.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1373   -0.1401   -0.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3919    0.1034    0.0678 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8080   -1.4401   -0.2883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7882   -0.9813    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7229   -0.1129   -1.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362    0.8071    0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5848    1.8982    0.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7440    1.9290    0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1240   -2.1470    0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  5 13  1  0
  8 14  1  0
M  END
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PDB for HMDB0060461 (cis-Acetylacrylate)

HEADER    PROTEIN                                 13-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    9  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   10  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2    3    4    9                                                  
CONECT    3    2    5   10                                                  
CONECT    4    1    2    6                                                  
CONECT    5    3    7    8                                                  
CONECT    6    4                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    2                                                            
CONECT   10    3                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0060461 (cis-Acetylacrylate)

COMPND    HMDB0060461
HETATM    1  C1  UNL     1      -2.362  -0.122  -0.160  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.839  -0.255  -0.138  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.452  -1.411  -0.355  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.062   0.923   0.120  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.243   0.948   0.167  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.137  -0.140  -0.020  1.00  0.00           C  
HETATM    7  O2  UNL     1       3.392   0.103   0.068  1.00  0.00           O  
HETATM    8  O3  UNL     1       1.808  -1.440  -0.288  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.788  -0.981   0.371  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.723  -0.113  -1.207  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.636   0.807   0.379  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.585   1.898   0.296  1.00  0.00           H  
HETATM   13  H5  UNL     1       1.744   1.929   0.377  1.00  0.00           H  
HETATM   14  H6  UNL     1       2.124  -2.147   0.392  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    4
CONECT    4    5    5   12
CONECT    5    6   13
CONECT    6    7    7    8
CONECT    8   14
END
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SMILES for HMDB0060461 (cis-Acetylacrylate)

[H]\C(=C(/[H])C(O)=O)C(C)=O
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INCHI for HMDB0060461 (cis-Acetylacrylate)

InChI=1S/C5H6O3/c1-4(6)2-3-5(7)8/h2-3H,1H3,(H,7,8)/b3-2-
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(Z)-Acetylacrylic acidChEBI
cis-4-Oxopent-2-enoic acidChEBI
(Z)-AcetylacrylateGenerator
cis-4-Oxopent-2-enoateGenerator
cis-Acetylacrylic acidGenerator
cis-AcetylacrylateGenerator
Chemical FormulaC5H6O3
Average Molecular Weight114.0993
Monoisotopic Molecular Weight114.031694058
IUPAC Name(2Z)-4-oxopent-2-enoic acid
Traditional Namecis-acetylacrylic acid
CAS Registry NumberNot Available
SMILES
[H]\C(=C(/[H])C(O)=O)C(C)=O
InChI Identifier
InChI=1S/C5H6O3/c1-4(6)2-3-5(7)8/h2-3H,1H3,(H,7,8)/b3-2-
InChI KeyXGTKSWVCNVUVHG-IHWYPQMZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Short-chain keto acid
  • Fatty acyl
  • Unsaturated fatty acid
  • Acryloyl-group
  • Enone
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC07091
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281015
PDB IDNot Available
ChEBI ID28993
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details
1. Carboxymethylenebutenolidase homolog
General function:
Involved in hydrolase activity
Specific function:
Cysteine hydrolase. Can convert the prodrug olmesartan medoxomil into its pharmacologically active metabolite olmerstatan, an angiotensin receptor blocker, in liver and intestine. May also activate beta-lactam antibiotics faropenem medoxomil and lenampicillin.
Gene Name:
CMBL
Uniprot ID:
Q96DG6
Molecular weight:
Not Available
Reactions
Protoanemonin + Water → cis-Acetylacrylatedetails