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Showing NP-Card for cis-2-Methylaconitate (NP0087501)

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Record Information
Version2.0
Created at2022-05-11 16:51:25 UTC
Updated at2022-05-11 16:51:25 UTC
NP-MRD IDNP0087501
Secondary Accession NumbersNone
Natural Product 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. A tricarboxylic acid comprising (Z)-but-2-ene having the three carboxy groups at the 1-, 2- and 3-positions. Cis-2-Methylaconitate is a moderately acidic compound (based on its pKa). Cis-2-Methylaconitate exists in all living species, ranging from bacteria to humans. Outside of the human body, cis-2-Methylaconitate has been detected, but not quantified in, several different foods, such as quinoa, european chestnuts, black cabbages, okra, and banana. This could make cis-2-methylaconitate a potential biomarker for the consumption of these foods.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0087501 (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
Download

3D MOL for NP0087501 (cis-2-Methylaconitate)

     RDKit          3D

 21 20  0  0  0  0  0  0  0  0999 V2000
    0.7679   -1.7356    0.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9302   -0.2831    0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1135    0.3590    0.7503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9175   -0.3242    1.4762 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5125    1.6229    0.5055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0253    0.1931   -0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2084   -0.6968   -0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4735   -0.1803   -0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1563    0.6683   -0.8340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9106   -0.6542    0.9863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0088    1.5407   -0.9314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0198    1.8947   -1.6593 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9029    2.5371   -0.7740 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917   -2.0272    1.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8416   -2.4280   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1452   -1.8032    1.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4235    1.7773    0.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9855   -1.7141   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -0.7327   -1.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5139   -1.4870    0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130    3.4733   -0.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
  2  6  2  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  6 11  1  0
 11 13  1  0
 11 12  2  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 NP0087501 (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>
NP0087501

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
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3D-SDF for NP0087501 (cis-2-Methylaconitate)

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PDB for NP0087501 (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 NP0087501 (cis-2-Methylaconitate)
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SMILES for NP0087501 (cis-2-Methylaconitate)
C\C(C(O)=O)=C(/CC(O)=O)C(O)=O
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INCHI for NP0087501 (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 JSmol
Synonyms
ValueSource
(Z)-But-2-ene-1,2,3-tricarboxylateChEBI
alpha-Methyl-cis-aconitateChEBI
alpha-MethylaconitateChEBI
cis-2-Butene-1,2,3-tricarboxylic acidChEBI
(Z)-But-2-ene-1,2,3-tricarboxylic acidGenerator
a-Methyl-cis-aconitateGenerator
a-Methyl-cis-aconitic acidGenerator
alpha-Methyl-cis-aconitic acidGenerator
Α-methyl-cis-aconitateGenerator
Α-methyl-cis-aconitic acidGenerator
a-MethylaconitateGenerator
a-Methylaconitic acidGenerator
alpha-Methylaconitic acidGenerator
Α-methylaconitateGenerator
Α-methylaconitic acidGenerator
cis-2-Butene-1,2,3-tricarboxylateGenerator
cis-2-Methylaconitic acidGenerator
(2Z)-But-2-ene-1,2,3-tricarboxylic acidHMDB
(Z)-2-Butene-1,2,3-tricarboxylic acidHMDB
Chemical FormulaC7H8O6
Average Mass188.1348 Da
Monoisotopic Mass188.03209 Da
IUPAC Name(1Z)-1-methylprop-1-ene-1,2,3-tricarboxylic acid
Traditional Nameα-methylaconitate
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.33ALOGPS
logP-0.13ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.25ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity39.59 m³·mol⁻¹ChemAxon
Polarizability15.55 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0006357  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General References