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Showing NP-Card for (2e)-2-(phenylmethylidene)butanedioic acid (NP0212610)

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Record Information
Version2.0
Created at2022-09-05 11:19:48 UTC
Updated at2022-09-05 11:19:48 UTC
NP-MRD IDNP0212610
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2e)-2-(phenylmethylidene)butanedioic acid
Description2-Benzylidenesuccinic acid belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. (2e)-2-(phenylmethylidene)butanedioic acid is found in Artemisia argyi. (2e)-2-(phenylmethylidene)butanedioic acid was first documented in 2005 (PMID: 16496677). Based on a literature review very few articles have been published on 2-benzylidenesuccinic acid.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0212610 ((2e)-2-(phenylmethylidene)butanedioic acid)


  Mrv1652309052213192D          

 15 15  0  0  0  0            999 V2000
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
Download

3D MOL for NP0212610 ((2e)-2-(phenylmethylidene)butanedioic acid)

     RDKit          3D

 25 25  0  0  0  0  0  0  0  0999 V2000
    2.4351   -1.5109    0.3760 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5293   -0.3039    0.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6814    0.2867    1.0998 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3071    0.5666    0.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9949    0.4553   -0.9975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2084    0.1202   -1.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2908   -0.1510   -0.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6749    0.6572    0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6975    0.3810    1.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3969   -0.7986    1.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0742   -1.6626    0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0442   -1.3281   -0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0690    0.7264   -1.9569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8346    0.6354   -3.1682 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3096    1.0734   -1.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6295    0.0497    0.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5346    1.5706    0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5543    0.0844    1.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3814    0.0450   -2.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1383    1.5899    0.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9196    1.0814    2.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2117   -1.0143    1.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6522   -2.5765    0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7821   -1.9925   -1.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5925    2.0151   -1.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  5 13  1  0
 13 15  1  0
 13 14  2  0
 12  7  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  6 19  1  0
  8 20  1  0
  9 21  1  0
 10 22  1  0
 11 23  1  0
 12 24  1  0
 15 25  1  0
M  END
Download

3D SDF for NP0212610 ((2e)-2-(phenylmethylidene)butanedioic acid)


  Mrv1652309052213192D          

 15 15  0  0  0  0            999 V2000
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0212610

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C\C(=C/C1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O4/c12-10(13)7-9(11(14)15)6-8-4-2-1-3-5-8/h1-6H,7H2,(H,12,13)(H,14,15)/b9-6+

> <INCHI_KEY>
KYILORDWJFEQBS-RMKNXTFCSA-N

> <FORMULA>
C11H10O4

> <MOLECULAR_WEIGHT>
206.197

> <EXACT_MASS>
206.057908802

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.832145470402047

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-2-(phenylmethylidene)butanedioic acid

> <JCHEM_LOGP>
1.6559636493333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.553323327849819

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7911598926056818

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
53.683400000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-2-(phenylmethylidene)butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0212610 ((2e)-2-(phenylmethylidene)butanedioic acid)

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PDB for NP0212610 ((2e)-2-(phenylmethylidene)butanedioic acid)
HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    5   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

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3D PDB for NP0212610 ((2e)-2-(phenylmethylidene)butanedioic acid)
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SMILES for NP0212610 ((2e)-2-(phenylmethylidene)butanedioic acid)
OC(=O)C\C(=C/C1=CC=CC=C1)C(O)=O
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INCHI for NP0212610 ((2e)-2-(phenylmethylidene)butanedioic acid)
InChI=1S/C11H10O4/c12-10(13)7-9(11(14)15)6-8-4-2-1-3-5-8/h1-6H,7H2,(H,12,13)(H,14,15)/b9-6+
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View in JSmol
Synonyms
ValueSource
2-BenzylidenesuccinateGenerator
Chemical FormulaC11H10O4
Average Mass206.1970 Da
Monoisotopic Mass206.05791 Da
IUPAC Name(2E)-2-(phenylmethylidene)butanedioic acid
Traditional Name(2E)-2-(phenylmethylidene)butanedioic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C\C(=C/C1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C11H10O4/c12-10(13)7-9(11(14)15)6-8-4-2-1-3-5-8/h1-6H,7H2,(H,12,13)(H,14,15)/b9-6+
InChI KeyKYILORDWJFEQBS-RMKNXTFCSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artemisia argyiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCinnamic acids and derivatives  
Sub ClassCinnamic acids  
Direct ParentCinnamic acids  
Alternative Parents
Substituents
  • Cinnamic acid
    • 

  • Benzenoid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Monocyclic benzene moiety
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
logP1.66ChemAxon
pKa (Strongest Acidic)3.79ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.68 m³·mol⁻¹ChemAxon
Polarizability19.83 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID716985  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound820629  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Gao LM, Yang P, Song DQ: [Synthesis and insulinotropic activity of 2-benzylidenesuccinic acid derivatives]. Yao Xue Xue Bao. 2005 Dec;40(12):1122-6. [PubMed:16496677  ] 
  2. LOTUS database [Link]