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Showing metabocard for cis-2-Methylaconitate (HMDB0006357)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-05-23 01:47:26 UTC
Update Date2023-02-21 17:17:18 UTC
HMDB IDHMDB0006357
Secondary Accession Numbers
  • HMDB06357
Metabolite Identification
Common Namecis-2-Methylaconitate
Descriptioncis-2-Methylaconitate, also known as alpha-methylaconitate or a-methylaconitic acid, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. cis-2-Methylaconitate exists in all living species, ranging from bacteria to plants to humans. cis-2-Methylaconitate has been detected, but not quantified in, several different foods, such as green tea, allia (Allium), wheats (Triticum), yellow bell peppers (Capsicum annuum), and ceylon cinnamons (Cinnamomum verum). This could make cis-2-methylaconitate a potential biomarker for the consumption of these foods. cis-2-Methylaconitate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on cis-2-Methylaconitate.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006357 (cis-2-Methylaconitate)

  Mrv0541 02231220382D          

 13 12  0  0  0  0            999 V2000
   16.1042   -5.0778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8188   -7.1405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9622   -3.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8188   -3.8403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1042   -5.9028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5332   -3.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5332   -5.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5332   -5.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2478   -4.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9622   -5.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8188   -4.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8188   -6.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2478   -3.8403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2 12  1  0  0  0  0
  3 13  1  0  0  0  0
  4 11  2  0  0  0  0
  5 12  2  0  0  0  0
  6 13  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
M  END
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3D MOL for HMDB0006357 (cis-2-Methylaconitate)

HMDB0006357
     RDKit          3D
cis-2-Methylaconitate
 21 20  0  0  0  0  0  0  0  0999 V2000
   -0.7361   -1.6688   -0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918   -0.2207   -0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3792    0.1819   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1797   -0.7695   -0.5221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0256    1.3138    0.1802 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0580    0.4695    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4539    0.0651    0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9581   -1.2255    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8490   -2.1916    0.8139 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6319   -1.5215   -1.1786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353    1.8952    0.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2286    2.4335    0.5833 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917    2.6629    0.9732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6875   -2.0069   -1.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7248   -2.3126    0.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0180   -1.7550   -1.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8454    1.4580    0.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9972    0.7888   -0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8676    0.4824    1.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5994   -1.2059   -1.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5092    3.1270    0.2634 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
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 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
  7 18  1  0
  7 19  1  0
 10 20  1  0
 13 21  1  0
M  END
Download

3D SDF for HMDB0006357 (cis-2-Methylaconitate)

  Mrv0541 02231220382D          

 13 12  0  0  0  0            999 V2000
   16.1042   -5.0778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8188   -7.1405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9622   -3.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8188   -3.8403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1042   -5.9028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5332   -3.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5332   -5.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5332   -5.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2478   -4.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9622   -5.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8188   -4.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8188   -6.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2478   -3.8403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2 12  1  0  0  0  0
  3 13  1  0  0  0  0
  4 11  2  0  0  0  0
  5 12  2  0  0  0  0
  6 13  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006357

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O6/c1-3(6(10)11)4(7(12)13)2-5(8)9/h2H2,1H3,(H,8,9)(H,10,11)(H,12,13)/b4-3-

> <INCHI_KEY>
NUZLRKBHOBPTQV-ARJAWSKDSA-N

> <FORMULA>
C7H8O6

> <MOLECULAR_WEIGHT>
188.1348

> <EXACT_MASS>
188.032087988

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
15.548107198906383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1Z)-1-methylprop-1-ene-1,2,3-tricarboxylic acid

> <ALOGPS_LOGP>
-0.33

> <JCHEM_LOGP>
-0.12548645266666678

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.8670232852737367

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2458676878407497

> <JCHEM_POLAR_SURFACE_AREA>
111.89999999999998

> <JCHEM_REFRACTIVITY>
39.58760000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-methylaconitate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0006357 (cis-2-Methylaconitate)

HMDB0006357
     RDKit          3D
cis-2-Methylaconitate
 21 20  0  0  0  0  0  0  0  0999 V2000
   -0.7361   -1.6688   -0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918   -0.2207   -0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3792    0.1819   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1797   -0.7695   -0.5221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0256    1.3138    0.1802 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0580    0.4695    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4539    0.0651    0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9581   -1.2255    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8490   -2.1916    0.8139 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6319   -1.5215   -1.1786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353    1.8952    0.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2286    2.4335    0.5833 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917    2.6629    0.9732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6875   -2.0069   -1.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7248   -2.3126    0.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0180   -1.7550   -1.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8454    1.4580    0.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9972    0.7888   -0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8676    0.4824    1.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5994   -1.2059   -1.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5092    3.1270    0.2634 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
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 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
  7 18  1  0
  7 19  1  0
 10 20  1  0
 13 21  1  0
M  END
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PDB for HMDB0006357 (cis-2-Methylaconitate)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      30.061  -9.479   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      31.395 -13.329   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      35.396  -6.399   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      31.395  -7.169   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      30.061 -11.019   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      32.729  -6.399   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      32.729  -9.479   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.729 -11.019   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      34.063  -8.709   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      35.396  -9.479   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.395  -8.709   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.395 -11.789   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.063  -7.169   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   11                                                            
CONECT    5   12                                                            
CONECT    6   13                                                            
CONECT    7    8    9   11                                                  
CONECT    8    7   12                                                       
CONECT    9    7   10   13                                                  
CONECT   10    9                                                            
CONECT   11    1    4    7                                                  
CONECT   12    2    5    8                                                  
CONECT   13    3    6    9                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for HMDB0006357 (cis-2-Methylaconitate)

COMPND    HMDB0006357
HETATM    1  C1  UNL     1      -0.736  -1.669  -0.485  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.992  -0.221  -0.092  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.379   0.182  -0.119  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.180  -0.770  -0.522  1.00  0.00           O  
HETATM    5  O2  UNL     1      -3.026   1.314   0.180  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.058   0.470   0.242  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.454   0.065   0.305  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.958  -1.225   0.024  1.00  0.00           C  
HETATM    9  O3  UNL     1       1.849  -2.192   0.814  1.00  0.00           O  
HETATM   10  O4  UNL     1       2.632  -1.522  -1.179  1.00  0.00           O  
HETATM   11  C7  UNL     1      -0.135   1.895   0.600  1.00  0.00           C  
HETATM   12  O5  UNL     1      -1.229   2.433   0.583  1.00  0.00           O  
HETATM   13  O6  UNL     1       0.992   2.663   0.973  1.00  0.00           O  
HETATM   14  H1  UNL     1      -1.687  -2.007  -1.043  1.00  0.00           H  
HETATM   15  H2  UNL     1      -0.725  -2.313   0.383  1.00  0.00           H  
HETATM   16  H3  UNL     1       0.018  -1.755  -1.251  1.00  0.00           H  
HETATM   17  H4  UNL     1      -3.845   1.458   0.720  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.997   0.789  -0.417  1.00  0.00           H  
HETATM   19  H6  UNL     1       1.868   0.482   1.304  1.00  0.00           H  
HETATM   20  H7  UNL     1       3.599  -1.206  -1.284  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.509   3.127   0.263  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   11
CONECT    7    8   18   19
CONECT    8    9    9   10
CONECT   10   20
CONECT   11   12   12   13
CONECT   13   21
END
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SMILES for HMDB0006357 (cis-2-Methylaconitate)

C\C(C(O)=O)=C(/CC(O)=O)C(O)=O
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INCHI for HMDB0006357 (cis-2-Methylaconitate)

InChI=1S/C7H8O6/c1-3(6(10)11)4(7(12)13)2-5(8)9/h2H2,1H3,(H,8,9)(H,10,11)(H,12,13)/b4-3-
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC7H8O6
Average Molecular Weight188.1348
Monoisotopic Molecular Weight188.032087988
IUPAC Name(1Z)-1-methylprop-1-ene-1,2,3-tricarboxylic acid
Traditional Nameα-methylaconitate
CAS Registry Number6061-93-4
SMILES
C\C(C(O)=O)=C(/CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H8O6/c1-3(6(10)11)4(7(12)13)2-5(8)9/h2H2,1H3,(H,8,9)(H,10,11)(H,12,13)/b4-3-
InChI KeyNUZLRKBHOBPTQV-ARJAWSKDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility56440 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023904
KNApSAcK IDNot Available
Chemspider ID2338376
KEGG Compound IDC04225
BioCyc IDCPD-1136
BiGG ID43396
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3080625
PDB IDNot Available
ChEBI ID16717
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1533181
References
Synthesis ReferenceTabuchi, Takeshi; Uchiyama, Hiroo. Methylcitrate condensing and methylisocitrate cleaving enzymes. Evidence for the pathway of oxidation of propionyl-CoA to pyruvate via C7-tricarboxylic acids. Agricultural and Biological Chemistry (1975), 39(10), 2035-42.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Garvey GS, Rocco CJ, Escalante-Semerena JC, Rayment I: The three-dimensional crystal structure of the PrpF protein of Shewanella oneidensis complexed with trans-aconitate: insights into its biological function. Protein Sci. 2007 Jul;16(7):1274-84. Epub 2007 Jun 13. [PubMed:17567742 ]