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Showing metabocard for cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide (HMDB0060455)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:22:03 UTC
Update Date2022-03-07 03:17:45 UTC
HMDB IDHMDB0060455
Secondary Accession Numbers
  • HMDB60455
Metabolite Identification
Common Namecis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide
Descriptioncis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide is an extremely weak basic (essentially neutral) compound (based on its pKa). These are dihydrofurans with a carbonyk group at the C2 carbon atom.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

Structure #1
  Mrv0541 02241207012D          

 11 11  0  0  0  0            999 V2000
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6212    0.0172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7706   -1.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  3  2  0  0  0  0
  2  5  1  4  0  0  0
  3 11  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  2  0  0  0  0
  6 11  1  0  0  0  0
M  END
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3D MOL for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

HMDB0060455
     RDKit          3D
cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide
 14 14  0  0  0  0  0  0  0  0999 V2000
    3.5363   -0.3518    0.0783 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3650    0.0936    0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995    1.4490    0.3862 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2528   -0.8151   -0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0005   -0.3603   -0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387   -1.1003   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2903   -0.3096   -0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9756   -0.7857   -0.1749 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7527    1.0190    0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4467    2.0528    0.3934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3683    0.9475    0.2332 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180    2.1806   -0.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4610   -1.8553   -0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608   -2.1644   -0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11  5  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
M  END
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3D SDF for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

Structure #1
  Mrv0541 02241207012D          

 11 11  0  0  0  0            999 V2000
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6212    0.0172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7706   -1.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  3  2  0  0  0  0
  2  5  1  4  0  0  0
  3 11  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  2  0  0  0  0
  6 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060455

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C=C1OC(=O)C(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H3ClO4/c7-4-1-3(2-5(8)9)11-6(4)10/h1-2H,(H,8,9)

> <INCHI_KEY>
ADSGHWJRPOXXTD-UHFFFAOYSA-N

> <FORMULA>
C6H3ClO4

> <MOLECULAR_WEIGHT>
174.539

> <EXACT_MASS>
173.971986291

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
14.127827275316989

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-chloro-5-oxo-2,5-dihydrofuran-2-ylidene)acetic acid

> <ALOGPS_LOGP>
1.05

> <JCHEM_LOGP>
0.5719121033333332

> <ALOGPS_LOGS>
-1.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6842205271850617

> <JCHEM_PKA_STRONGEST_BASIC>
-7.334826519314273

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
38.117000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
C6H3ClO4

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

HMDB0060455
     RDKit          3D
cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide
 14 14  0  0  0  0  0  0  0  0999 V2000
    3.5363   -0.3518    0.0783 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3650    0.0936    0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995    1.4490    0.3862 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2528   -0.8151   -0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0005   -0.3603   -0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387   -1.1003   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2903   -0.3096   -0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9756   -0.7857   -0.1749 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7527    1.0190    0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4467    2.0528    0.3934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3683    0.9475    0.2332 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180    2.1806   -0.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4610   -1.8553   -0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608   -2.1644   -0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11  5  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
M  END
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PDB for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.267  -1.375   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0       1.060   3.620   0.000  0.00  0.00          Cl+0
HETATM    8  O   UNK     0       4.893   0.032   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.172  -2.621   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.290  -0.290   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    3    5                                                       
CONECT    3    1    2   11                                                  
CONECT    4    1    6    7                                                  
CONECT    5    2    8    9                                                  
CONECT    6    4   10   11                                                  
CONECT    7    4                                                            
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    3    6                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

COMPND    HMDB0060455
HETATM    1  O1  UNL     1       3.536  -0.352   0.078  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.365   0.094   0.135  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.200   1.449   0.386  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.253  -0.815  -0.061  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.000  -0.360  -0.004  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.239  -1.100  -0.171  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.290  -0.310  -0.047  1.00  0.00           C  
HETATM    8 CL1  UNL     1      -3.976  -0.786  -0.175  1.00  0.00          CL  
HETATM    9  C6  UNL     1      -1.753   1.019   0.215  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.447   2.053   0.393  1.00  0.00           O  
HETATM   11  O4  UNL     1      -0.368   0.947   0.233  1.00  0.00           O  
HETATM   12  H1  UNL     1       2.518   2.181  -0.242  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.461  -1.855  -0.252  1.00  0.00           H  
HETATM   14  H3  UNL     1      -1.261  -2.164  -0.372  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5    5   13
CONECT    5    6   11
CONECT    6    7    7   14
CONECT    7    8    9
CONECT    9   10   10   11
END
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SMILES for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

OC(=O)C=C1OC(=O)C(Cl)=C1
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INCHI for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

InChI=1S/C6H3ClO4/c7-4-1-3(2-5(8)9)11-6(4)10/h1-2H,(H,8,9)
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View in JSmolView NMR AssignmentsView Stereo Labels
SynonymsNot Available
Chemical FormulaC6H3ClO4
Average Molecular Weight174.539
Monoisotopic Molecular Weight173.971986291
IUPAC Name2-(4-chloro-5-oxo-2,5-dihydrofuran-2-ylidene)acetic acid
Traditional NameC6H3ClO4
CAS Registry NumberNot Available
SMILES
OC(=O)C=C1OC(=O)C(Cl)=C1
InChI Identifier
InChI=1S/C6H3ClO4/c7-4-1-3(2-5(8)9)11-6(4)10/h1-2H,(H,8,9)
InChI KeyADSGHWJRPOXXTD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentButenolides
Alternative Parents
Substituents
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • Enol ester
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Chloroalkene
  • Vinyl chloride
  • Vinyl halide
  • Haloalkene
  • Carbonyl group
  • Organohalogen compound
  • Organochloride
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound190225
PDB IDNot Available
ChEBI ID38122
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
cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide + Water → 2-Chloromaleylacetatedetails