Showing metabocard for 3-chloro-cis,cis-muconic acid (MMDBc0054217)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-05 22:59:38 UTC
Update Date2022-09-01 02:27:52 UTC
Metabolite IDMMDBc0054217
Metabolite Identification
Common Name3-chloro-cis,cis-muconic acid
Description3-chloro-cis,cis-muconic acid, also known as (e,Z)-3-chloro-2,4-hexadienedioate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 3-chloro-cis,cis-muconic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f9223aa4f58>

 
  Mrv1533006041517122D          
 
 11 10  0  0  0  0            999 V2000
   16.9632   -9.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9632  -10.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6758   -9.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2507   -9.1415    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.2507  -10.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3921   -9.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5344  -10.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3883  -10.3772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1047   -9.1415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5382   -9.5547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8218  -10.7940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  1  0  0  0  0
  7 11  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f9223aa4f58>

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3D SDF for #<Metabolite:0x00007f9223aa4f58>
 
  Mrv1533006041517122D          
 
 11 10  0  0  0  0            999 V2000
   16.9632   -9.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9632  -10.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6758   -9.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2507   -9.1415    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.2507  -10.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3921   -9.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5344  -10.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3883  -10.3772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1047   -9.1415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5382   -9.5547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8218  -10.7940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  1  0  0  0  0
  7 11  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054217

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H5ClO4/c7-4(3-6(10)11)1-2-5(8)9/h1-3H,(H,8,9)(H,10,11)/b2-1-,4-3+

> <INCHI_KEY>
ICMVYBXQDUXEEE-BXTBVDPRSA-N

> <FORMULA>
C6H5ClO4

> <MOLECULAR_WEIGHT>
176.55

> <EXACT_MASS>
175.9876363

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
14.201514688240945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,4E)-4-chlorohexa-2,4-dienedioic acid

> <ALOGPS_LOGP>
1.20

> <JCHEM_LOGP>
0.723064441

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.226480972223682

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.474123571016081

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
39.6418

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-chloro-cis,cis-muconic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f9223aa4f58>
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PDB for #<Metabolite:0x00007f9223aa4f58>
HEADER    PROTEIN                                 04-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-15         0                                  
HETATM    1  C   UNK     0      31.665 -17.835   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      31.665 -19.378   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.995 -17.064   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0      30.335 -17.064   0.000  0.00  0.00          Cl+0
HETATM    5  C   UNK     0      30.335 -20.142   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      34.332 -17.835   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.997 -19.378   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      34.325 -19.371   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      35.662 -17.064   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      29.005 -17.835   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      27.667 -20.149   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1                                                            
CONECT    5    2    7                                                       
CONECT    6    3    8    9                                                  
CONECT    7    5   10   11                                                  
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for #<Metabolite:0x00007f9223aa4f58>
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SMILES for #<Metabolite:0x00007f9223aa4f58>
OC(=O)\C=C/C(/Cl)=C\C(O)=O
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INCHI for #<Metabolite:0x00007f9223aa4f58>
InChI=1S/C6H5ClO4/c7-4(3-6(10)11)1-2-5(8)9/h1-3H,(H,8,9)(H,10,11)/b2-1-,4-3+
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Synonyms
ValueSource
(e,Z)-3-Chloro-2,4-hexadienedioic acidChEBI
3-Chloro-cis,cis-muconateChEBI
(2E,4Z)-3-Chlorohexa-2,4-dienedioateKegg
(e,Z)-3-Chloro-2,4-hexadienedioateGenerator
(2E,4Z)-3-Chlorohexa-2,4-dienedioic acidGenerator
3-chloro-MuconateMeSH
Molecular FormulaC6H5ClO4
Average Mass176.55
Monoisotopic Mass175.9876363
IUPAC Name(2Z,4E)-4-chlorohexa-2,4-dienedioic acid
Traditional Name3-chloro-cis,cis-muconic acid
CAS Registry NumberNot Available
SMILES
OC(=O)\C=C/C(/Cl)=C\C(O)=O
InChI Identifier
InChI=1S/C6H5ClO4/c7-4(3-6(10)11)1-2-5(8)9/h1-3H,(H,8,9)(H,10,11)/b2-1-,4-3+
InChI KeyICMVYBXQDUXEEE-BXTBVDPRSA-N