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Showing metabocard for 2-chloro-trans-dienelactone (HMDB0304065)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 06:51:29 UTC
Update Date2021-09-24 06:51:29 UTC
HMDB IDHMDB0304065
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-chloro-trans-dienelactone
Description2-chloro-trans-dienelactone, also known as cis-2-chloro-4-carboxymethylenebut-2-en-1,4-olide, is a member of the class of compounds known as butenolides. Butenolides are dihydrofurans with a carbonyl group at the C2 carbon atom. 2-chloro-trans-dienelactone is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 2-chloro-trans-dienelactone can be found in a number of food items such as giant butterbur, soy bean, common persimmon, and salmonberry, which makes 2-chloro-trans-dienelactone a potential biomarker for the consumption of these food products.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0304065 (2-chloro-trans-dienelactone)


  Mrv1533007131514082D          

 12 12  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
    0.5678    1.9393    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
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  1  2  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  3  1  0  0  0  0
 11  6  1  0  0  0  0
 12  2  1  0  0  0  0
M  CHG  1   9  -1
M  END
Download

3D MOL for HMDB0304065 (2-chloro-trans-dienelactone)

HMDB0304065
     RDKit          3D
2-chloro-trans-dienelactone
 13 13  0  0  0  0  0  0  0  0999 V2000
   -3.7298   -0.2206   -0.0241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5750    0.2658   -0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3650    1.6298   -0.1545 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4525   -0.6547    0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2140   -0.1827    0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0230   -0.9553    0.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0726   -0.1516    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7658   -0.6004    0.0891 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5713    1.2066   -0.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    2.2636   -0.1532 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1698    1.1661   -0.0899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5957   -1.7204    0.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0881   -2.0464    0.1731 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  0
  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
  4 12  1  0
  6 13  1  0
M  CHG  1   3  -1
M  END
Download

3D SDF for HMDB0304065 (2-chloro-trans-dienelactone)


  Mrv1533007131514082D          

 12 12  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
    0.5678    1.9393    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
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  1  2  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  3  1  0  0  0  0
 11  6  1  0  0  0  0
 12  2  1  0  0  0  0
M  CHG  1   9  -1
M  END
> <DATABASE_ID>
HMDB0304065

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(C([O-])=O)=C1\OC(=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)/p-1/b3-2-

> <INCHI_KEY>
ADSGHWJRPOXXTD-IHWYPQMZSA-M

> <FORMULA>
C6H2ClO4

> <MOLECULAR_WEIGHT>
173.53

> <EXACT_MASS>
172.9647098

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
13.739491995982428

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2Z)-4-chloro-5-oxo-2,5-dihydrofuran-2-ylidene]acetate

> <ALOGPS_LOGP>
1.05

> <JCHEM_LOGP>
0.5719121033333332

> <ALOGPS_LOGS>
-1.36

> <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>
66.42999999999999

> <JCHEM_REFRACTIVITY>
48.954100000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2Z)-4-chloro-5-oxofuran-2-ylidene]acetate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0304065 (2-chloro-trans-dienelactone)

HMDB0304065
     RDKit          3D
2-chloro-trans-dienelactone
 13 13  0  0  0  0  0  0  0  0999 V2000
   -3.7298   -0.2206   -0.0241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5750    0.2658   -0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3650    1.6298   -0.1545 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4525   -0.6547    0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2140   -0.1827    0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0230   -0.9553    0.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0726   -0.1516    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7658   -0.6004    0.0891 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5713    1.2066   -0.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    2.2636   -0.1532 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1698    1.1661   -0.0899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5957   -1.7204    0.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0881   -2.0464    0.1731 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  0
  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
  4 12  1  0
  6 13  1  0
M  CHG  1   3  -1
M  END
Download

PDB for HMDB0304065 (2-chloro-trans-dienelactone)

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0       2.735  -1.536   0.000  0.00  0.00          Cl+0
HETATM    8  O   UNK     0      -1.608   3.620   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.274   5.930   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0       2.393   4.390   0.000  0.00  0.00           H+0
CONECT    1    3    4                                                       
CONECT    2    3    5   12                                                  
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                                                       
CONECT   12    2                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0304065 (2-chloro-trans-dienelactone)

COMPND    HMDB0304065
HETATM    1  O1  UNL     1      -3.730  -0.221  -0.024  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.575   0.266  -0.050  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.365   1.630  -0.155  1.00  0.00           O1-
HETATM    4  C2  UNL     1      -1.453  -0.655   0.035  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.214  -0.183   0.012  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.023  -0.955   0.087  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.073  -0.152   0.035  1.00  0.00           C  
HETATM    8 CL1  UNL     1       3.766  -0.600   0.089  1.00  0.00          CL  
HETATM    9  C6  UNL     1       1.571   1.207  -0.077  1.00  0.00           C  
HETATM   10  O3  UNL     1       2.241   2.264  -0.153  1.00  0.00           O  
HETATM   11  O4  UNL     1       0.170   1.166  -0.090  1.00  0.00           O  
HETATM   12  H1  UNL     1      -1.596  -1.720   0.118  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.088  -2.046   0.173  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5    5   12
CONECT    5    6   11
CONECT    6    7    7   13
CONECT    7    8    9
CONECT    9   10   10   11
END
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SMILES for HMDB0304065 (2-chloro-trans-dienelactone)

[H]\C(C([O-])=O)=C1\OC(=O)C(Cl)=C1
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INCHI for HMDB0304065 (2-chloro-trans-dienelactone)

InChI=1S/C6H3ClO4/c7-4-1-3(2-5(8)9)11-6(4)10/h1-2H,(H,8,9)/p-1/b3-2-
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View in JSmolView Stereo Labels
Synonyms
ValueSource
trans-2-Chloro-4-carboxylatomethylenebut-2-en-1,4-olideChEBI
trans-2-Chloro-4-carboxylatomethylenebut-2-en-1,4-olide anionChEBI
trans-2-Chloro-4-carboxymethylenebut-2-en-1,4-olideChEBI
Chemical FormulaC6H2ClO4
Average Molecular Weight173.53
Monoisotopic Molecular Weight172.9647098
IUPAC Name2-[(2Z)-4-chloro-5-oxo-2,5-dihydrofuran-2-ylidene]acetate
Traditional Name2-[(2Z)-4-chloro-5-oxofuran-2-ylidene]acetate
CAS Registry NumberNot Available
SMILES
[H]\C(C([O-])=O)=C1\OC(=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)/p-1/b3-2-
InChI KeyADSGHWJRPOXXTD-IHWYPQMZSA-M
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
  • Organic anion
  • 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
PropertyValueSource
logP1.05ALOGPS
logP0.57ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.68ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.95 m³·mol⁻¹ChemAxon
Polarizability13.74 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+134.95332859911
AllCCS[M+H-H2O]+130.56532859911
AllCCS[M+Na]+140.22332859911
AllCCS[M+NH4]+139.04332859911
AllCCS[M-H]-126.30132859911
AllCCS[M+Na-2H]-127.50332859911
AllCCS[M+HCOO]-128.88332859911
DeepCCS[M+H]+132.7730932474
DeepCCS[M-H]-130.36930932474
DeepCCS[M-2H]-163.41430932474
DeepCCS[M+Na]+138.67730932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-chloro-trans-dienelactone 10V, Negative-QTOFsplash10-004i-1900000000-11155b679defef5dea3d2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-chloro-trans-dienelactone 20V, Negative-QTOFsplash10-004i-0900000000-1f9229e5438470eddfc22019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-chloro-trans-dienelactone 40V, Negative-QTOFsplash10-001i-9300000000-db4d4644aa9b2a94d4952019-02-23Wishart LabView Spectrum
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 IDFDB030329
KNApSAcK IDNot Available
Chemspider ID7822202
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID57891
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 ReferencesNot Available