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Showing metabocard for 3-Chloro-2-methylmaleylacetate (HMDB0060369)

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enzymes (1) Show 1 protein
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:56:55 UTC
Update Date2023-02-21 17:29:56 UTC
HMDB IDHMDB0060369
Secondary Accession Numbers
  • HMDB60369
Metabolite Identification
Common Name3-Chloro-2-methylmaleylacetate
Description3-Chloro-2-methylmaleylacetate belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. 3-Chloro-2-methylmaleylacetate is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Chloro-2-methylmaleylacetate exists in all living organisms, ranging from bacteria to humans. These are keto acids with a 6 to 12 carbon atoms long side chain.
Structure
Data?1677000596
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0060369 (3-Chloro-2-methylmaleylacetate)


  Mrv1652302122020142D          

 13 12  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
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 Cl  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
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  2  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
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3D MOL for HMDB0060369 (3-Chloro-2-methylmaleylacetate)

HMDB0060369
     RDKit          3D
3-Chloro-2-methylmaleylacetate
 20 19  0  0  0  0  0  0  0  0999 V2000
   -2.9555    0.8141   -0.5595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204    0.2390    0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8925   -0.3533    1.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1226   -0.3098    1.8733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9886   -0.9379    2.2688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5612    0.3090   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6269    1.0965   -2.0536 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7215   -0.1582    0.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9119   -0.7235    1.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493    0.0311   -0.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1101   -0.5549   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1007   -1.6766    0.4845 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3307    0.1596   -0.1077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4128    0.0637   -1.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6130    1.7273   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6442    1.0893    0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0243   -1.9105    2.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7461   -0.6285   -1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1283    1.0711   -1.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5634    0.6524   -0.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
 10 18  1  0
 10 19  1  0
 13 20  1  0
M  END
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3D SDF for HMDB0060369 (3-Chloro-2-methylmaleylacetate)


  Mrv1652302122020142D          

 13 12  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
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 Cl  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
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  2  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060369

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(C(O)=O)=C(/Cl)C(=O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H7ClO5/c1-3(7(12)13)6(8)4(9)2-5(10)11/h2H2,1H3,(H,10,11)(H,12,13)/b6-3+

> <INCHI_KEY>
YXWGPDFKFBYCFE-ZZXKWVIFSA-N

> <FORMULA>
C7H7ClO5

> <MOLECULAR_WEIGHT>
206.58

> <EXACT_MASS>
205.998201041

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.89332439539171

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-chloro-2-methyl-4-oxohex-2-enedioic acid

> <ALOGPS_LOGP>
0.45

> <JCHEM_LOGP>
0.9654424433333333

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.6989562597725345

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.494976717093442

> <JCHEM_PKA_STRONGEST_BASIC>
-8.535485248663083

> <JCHEM_POLAR_SURFACE_AREA>
91.66999999999999

> <JCHEM_REFRACTIVITY>
43.65060000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-chloro-2-methyl-4-oxohex-2-enedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0060369 (3-Chloro-2-methylmaleylacetate)

HMDB0060369
     RDKit          3D
3-Chloro-2-methylmaleylacetate
 20 19  0  0  0  0  0  0  0  0999 V2000
   -2.9555    0.8141   -0.5595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204    0.2390    0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8925   -0.3533    1.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1226   -0.3098    1.8733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9886   -0.9379    2.2688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5612    0.3090   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6269    1.0965   -2.0536 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7215   -0.1582    0.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9119   -0.7235    1.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493    0.0311   -0.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1101   -0.5549   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1007   -1.6766    0.4845 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3307    0.1596   -0.1077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4128    0.0637   -1.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6130    1.7273   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6442    1.0893    0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0243   -1.9105    2.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7461   -0.6285   -1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1283    1.0711   -1.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5634    0.6524   -0.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
 10 18  1  0
 10 19  1  0
 13 20  1  0
M  END
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PDB for HMDB0060369 (3-Chloro-2-methylmaleylacetate)

HEADER    PROTEIN                                 12-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-FEB-20         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       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0      -0.770   1.334   0.000  0.00  0.00          Cl+0
HETATM    8  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.770  -4.001   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000  -5.335   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.310  -4.001   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for HMDB0060369 (3-Chloro-2-methylmaleylacetate)

COMPND    HMDB0060369
HETATM    1  C1  UNL     1      -2.955   0.814  -0.560  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.720   0.239   0.159  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.893  -0.353   1.445  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.123  -0.310   1.873  1.00  0.00           O  
HETATM    5  O2  UNL     1      -0.989  -0.938   2.269  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.561   0.309  -0.438  1.00  0.00           C  
HETATM    7 CL1  UNL     1      -0.627   1.097  -2.054  1.00  0.00          CL  
HETATM    8  C5  UNL     1       0.721  -0.158   0.038  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.912  -0.724   1.117  1.00  0.00           O  
HETATM   10  C6  UNL     1       1.949   0.031  -0.803  1.00  0.00           C  
HETATM   11  C7  UNL     1       3.110  -0.555  -0.118  1.00  0.00           C  
HETATM   12  O4  UNL     1       3.101  -1.677   0.484  1.00  0.00           O  
HETATM   13  O5  UNL     1       4.331   0.160  -0.108  1.00  0.00           O  
HETATM   14  H1  UNL     1      -3.413   0.064  -1.204  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.613   1.727  -1.067  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.644   1.089   0.262  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.024  -1.910   2.602  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.746  -0.628  -1.704  1.00  0.00           H  
HETATM   19  H6  UNL     1       2.128   1.071  -1.086  1.00  0.00           H  
HETATM   20  H7  UNL     1       4.563   0.652  -0.932  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    6    6
CONECT    3    4    4    5
CONECT    5   17
CONECT    6    7    8
CONECT    8    9    9   10
CONECT   10   11   18   19
CONECT   11   12   12   13
CONECT   13   20
END
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SMILES for HMDB0060369 (3-Chloro-2-methylmaleylacetate)

C\C(C(O)=O)=C(/Cl)C(=O)CC(O)=O
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INCHI for HMDB0060369 (3-Chloro-2-methylmaleylacetate)

InChI=1S/C7H7ClO5/c1-3(7(12)13)6(8)4(9)2-5(10)11/h2H2,1H3,(H,10,11)(H,12,13)/b6-3+
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-Chloro-2-methylmaleylacetic acidGenerator
(2E)-3-Chloro-2-methyl-4-oxohex-2-enedioateGenerator
Chemical FormulaC7H7ClO5
Average Molecular Weight206.58
Monoisotopic Molecular Weight205.998201041
IUPAC Name(2E)-3-chloro-2-methyl-4-oxohex-2-enedioic acid
Traditional Name(2E)-3-chloro-2-methyl-4-oxohex-2-enedioic acid
CAS Registry NumberNot Available
SMILES
C\C(C(O)=O)=C(/Cl)C(=O)CC(O)=O
InChI Identifier
InChI=1S/C7H7ClO5/c1-3(7(12)13)6(8)4(9)2-5(10)11/h2H2,1H3,(H,10,11)(H,12,13)/b6-3+
InChI KeyYXWGPDFKFBYCFE-ZZXKWVIFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassMedium-chain keto acids and derivatives
Direct ParentMedium-chain keto acids and derivatives
Alternative Parents
Substituents
  • Medium-chain keto acid
  • Beta-keto acid
  • Branched fatty acid
  • Halogenated fatty acid
  • Methyl-branched fatty acid
  • B'-hydroxy-alpha,beta-unsaturated-ketone
  • Beta-hydroxy ketone
  • Dicarboxylic acid or derivatives
  • Unsaturated fatty acid
  • 1,3-dicarbonyl compound
  • Fatty acyl
  • Alpha-branched alpha,beta-unsaturated-ketone
  • Acryloyl-group
  • Alpha-haloketone
  • Vinylogous halide
  • Alpha-chloroketone
  • Alpha,beta-unsaturated ketone
  • Enone
  • Ketone
  • Chloroalkene
  • Vinyl halide
  • Vinyl chloride
  • Haloalkene
  • Carboxylic acid derivative
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Organohalogen compound
  • Carbonyl group
  • Organochloride
  • 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
PropertyValueSource
Water Solubility2.31 g/LALOGPS
logP0.45ALOGPS
logP0.97ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)2.49ChemAxon
pKa (Strongest Basic)-8.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity43.65 m³·mol⁻¹ChemAxon
Polarizability16.89 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+143.4530932474
DeepCCS[M-H]-140.3930932474
DeepCCS[M-2H]-176.3530932474
DeepCCS[M+Na]+152.01630932474
AllCCS[M+H]+142.932859911
AllCCS[M+H-H2O]+139.232859911
AllCCS[M+NH4]+146.432859911
AllCCS[M+Na]+147.432859911
AllCCS[M-H]-137.932859911
AllCCS[M+Na-2H]-139.232859911
AllCCS[M+HCOO]-140.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.5.0 minutes32390414
Predicted by Siyang on May 30, 202210.1295 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.11 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1161.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid325.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid82.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid191.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid57.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid277.1 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid346.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)115.1 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid675.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid257.5 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid958.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid227.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid266.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate626.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA250.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water286.4 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Chloro-2-methylmaleylacetateC\C(C(O)=O)=C(/Cl)C(=O)CC(O)=O2669.8Standard polar33892256
3-Chloro-2-methylmaleylacetateC\C(C(O)=O)=C(/Cl)C(=O)CC(O)=O1367.4Standard non polar33892256
3-Chloro-2-methylmaleylacetateC\C(C(O)=O)=C(/Cl)C(=O)CC(O)=O1784.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Chloro-2-methylmaleylacetate,1TMS,isomer #1C/C(C(=O)O[Si](C)(C)C)=C(\Cl)C(=O)CC(=O)O1612.7Semi standard non polar33892256
3-Chloro-2-methylmaleylacetate,1TMS,isomer #2C/C(C(=O)O)=C(\Cl)C(=O)CC(=O)O[Si](C)(C)C1646.5Semi standard non polar33892256
3-Chloro-2-methylmaleylacetate,1TMS,isomer #3C/C(C(=O)O)=C(\Cl)C(=CC(=O)O)O[Si](C)(C)C1811.6Semi standard non polar33892256
3-Chloro-2-methylmaleylacetate,2TMS,isomer #1C/C(C(=O)O[Si](C)(C)C)=C(\Cl)C(=O)CC(=O)O[Si](C)(C)C1704.0Semi standard non polar33892256
3-Chloro-2-methylmaleylacetate,2TMS,isomer #2C/C(C(=O)O[Si](C)(C)C)=C(\Cl)C(=CC(=O)O)O[Si](C)(C)C1819.4Semi standard non polar33892256
3-Chloro-2-methylmaleylacetate,2TMS,isomer #3C/C(C(=O)O)=C(\Cl)C(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1865.4Semi standard non polar33892256
3-Chloro-2-methylmaleylacetate,3TMS,isomer #1C/C(C(=O)O[Si](C)(C)C)=C(\Cl)C(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1878.6Semi standard non polar33892256
3-Chloro-2-methylmaleylacetate,3TMS,isomer #1C/C(C(=O)O[Si](C)(C)C)=C(\Cl)C(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1744.0Standard non polar33892256
3-Chloro-2-methylmaleylacetate,3TMS,isomer #1C/C(C(=O)O[Si](C)(C)C)=C(\Cl)C(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1938.7Standard polar33892256
3-Chloro-2-methylmaleylacetate,1TBDMS,isomer #1C/C(C(=O)O[Si](C)(C)C(C)(C)C)=C(\Cl)C(=O)CC(=O)O1863.3Semi standard non polar33892256
3-Chloro-2-methylmaleylacetate,1TBDMS,isomer #2C/C(C(=O)O)=C(\Cl)C(=O)CC(=O)O[Si](C)(C)C(C)(C)C1885.1Semi standard non polar33892256
3-Chloro-2-methylmaleylacetate,1TBDMS,isomer #3C/C(C(=O)O)=C(\Cl)C(=CC(=O)O)O[Si](C)(C)C(C)(C)C2052.6Semi standard non polar33892256
3-Chloro-2-methylmaleylacetate,2TBDMS,isomer #1C/C(C(=O)O[Si](C)(C)C(C)(C)C)=C(\Cl)C(=O)CC(=O)O[Si](C)(C)C(C)(C)C2171.3Semi standard non polar33892256
3-Chloro-2-methylmaleylacetate,2TBDMS,isomer #2C/C(C(=O)O[Si](C)(C)C(C)(C)C)=C(\Cl)C(=CC(=O)O)O[Si](C)(C)C(C)(C)C2294.0Semi standard non polar33892256
3-Chloro-2-methylmaleylacetate,2TBDMS,isomer #3C/C(C(=O)O)=C(\Cl)C(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2312.2Semi standard non polar33892256
3-Chloro-2-methylmaleylacetate,3TBDMS,isomer #1C/C(C(=O)O[Si](C)(C)C(C)(C)C)=C(\Cl)C(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2519.1Semi standard non polar33892256
3-Chloro-2-methylmaleylacetate,3TBDMS,isomer #1C/C(C(=O)O[Si](C)(C)C(C)(C)C)=C(\Cl)C(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2358.8Standard non polar33892256
3-Chloro-2-methylmaleylacetate,3TBDMS,isomer #1C/C(C(=O)O[Si](C)(C)C(C)(C)C)=C(\Cl)C(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2338.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Chloro-2-methylmaleylacetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9500000000-b1c400518cf87144eb232017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Chloro-2-methylmaleylacetate GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-9242000000-e9322c8d8ea452018ea72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Chloro-2-methylmaleylacetate 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 - 3-Chloro-2-methylmaleylacetate 10V, Positive-QTOFsplash10-000i-0910000000-27f1220752f28d030e642017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Chloro-2-methylmaleylacetate 20V, Positive-QTOFsplash10-01p9-1900000000-db2aad19b8c16d7d7c782017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Chloro-2-methylmaleylacetate 40V, Positive-QTOFsplash10-05fu-9200000000-7c2163173d547a1091742017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Chloro-2-methylmaleylacetate 10V, Negative-QTOFsplash10-0w29-2960000000-45aa65d0a5716c7384e42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Chloro-2-methylmaleylacetate 20V, Negative-QTOFsplash10-08fu-3900000000-23afe582e9d0c960278d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Chloro-2-methylmaleylacetate 40V, Negative-QTOFsplash10-066u-8900000000-83d2d47e18a0d22f4a082017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Chloro-2-methylmaleylacetate 10V, Positive-QTOFsplash10-0002-0900000000-9edc065ed86225a740fa2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Chloro-2-methylmaleylacetate 20V, Positive-QTOFsplash10-0udi-3900000000-9fe0a7211dec80a3c5e62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Chloro-2-methylmaleylacetate 40V, Positive-QTOFsplash10-0uk9-8900000000-1171197aa95b436bffdf2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Chloro-2-methylmaleylacetate 10V, Negative-QTOFsplash10-02t9-1920000000-8a0cd89ec33b4ded6ea92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Chloro-2-methylmaleylacetate 20V, Negative-QTOFsplash10-02or-9700000000-1be2c413639f5e6a879a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Chloro-2-methylmaleylacetate 40V, Negative-QTOFsplash10-009x-9200000000-8cf06af6af98a1722c432021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart 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 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 IDC18310
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543305
PDB IDNot Available
ChEBI ID81661
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
3-Chloro-2-methyldienelactone + Water → 3-Chloro-2-methylmaleylacetatedetails