Np mrd loader

Showing NP-Card for 5-methoxy-1h-indole-2-carboxylic acid (NP0285855)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-09-09 14:12:12 UTC
Updated at2022-09-09 14:12:12 UTC
NP-MRD IDNP0285855
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-methoxy-1h-indole-2-carboxylic acid
Description5-Methoxyindole-2-carboxylic acid, also known as 5-methoxy-2-indolic acid or 5-methoxy-2-indolecarboxylate, belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole. 5-Methoxyindole-2-carboxylic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 5-methoxy-1h-indole-2-carboxylic acid is found in Solanum lycopersicum. 5-methoxy-1h-indole-2-carboxylic acid was first documented in 2012 (PMID: 22551394). Based on a literature review a significant number of articles have been published on 5-Methoxyindole-2-carboxylic acid (PMID: 32551363) (PMID: 31629836) (PMID: 29765243) (PMID: 29709515) (PMID: 29448100) (PMID: 29017857).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0285855 (5-methoxy-1h-indole-2-carboxylic acid)


  Mrv1652309092216122D          

 14 15  0  0  0  0            999 V2000
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   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  2  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 12  2  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
M  END
Download

3D MOL for NP0285855 (5-methoxy-1h-indole-2-carboxylic acid)

     RDKit          3D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -4.2049   -0.5460   -0.8147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9307   -0.8536   -1.3507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8265   -0.4038   -0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9277    0.3047    0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8415    0.7542    1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4192    0.4534    0.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6702    0.7174    1.1505 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5746    0.2119    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0329    0.2879    0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5687    0.8813    1.3597 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8636   -0.2760   -0.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8889   -0.4105   -0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5339   -0.2552   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886   -0.6865   -1.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2073   -0.9278    0.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0311   -0.9431   -1.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2681    0.5798   -0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9343    0.5148    0.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9090    1.3085    2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8904    1.2466    2.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4327    0.2231   -1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2582   -0.9323   -1.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4637   -1.2489   -2.0576 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8 12  2  0
 12 13  1  0
 13 14  2  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
 14  3  1  0
 13  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  5 19  1  0
  7 20  1  0
 12 22  1  0
 14 23  1  0
 11 21  1  0
M  END
Download

3D SDF for NP0285855 (5-methoxy-1h-indole-2-carboxylic acid)


  Mrv1652309092216122D          

 14 15  0  0  0  0            999 V2000
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   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  2  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 12  2  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0285855

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2NC(=CC2=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO3/c1-14-7-2-3-8-6(4-7)5-9(11-8)10(12)13/h2-5,11H,1H3,(H,12,13)

> <INCHI_KEY>
YEBJVSLNUMZXRJ-UHFFFAOYSA-N

> <FORMULA>
C10H9NO3

> <MOLECULAR_WEIGHT>
191.186

> <EXACT_MASS>
191.058243154

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
19.27440027530503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methoxy-1H-indole-2-carboxylic acid

> <JCHEM_LOGP>
1.491920575

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.890024309159852

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.108336039828466

> <JCHEM_PKA_STRONGEST_BASIC>
-4.830483466198215

> <JCHEM_POLAR_SURFACE_AREA>
62.32000000000001

> <JCHEM_REFRACTIVITY>
50.7414

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-methoxy-1H-indole-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0285855 (5-methoxy-1h-indole-2-carboxylic acid)

Download
PDB for NP0285855 (5-methoxy-1h-indole-2-carboxylic acid)
HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.090   1.509   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.090   4.177   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13    3                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

Download
3D PDB for NP0285855 (5-methoxy-1h-indole-2-carboxylic acid)
Download
SMILES for NP0285855 (5-methoxy-1h-indole-2-carboxylic acid)
COC1=CC=C2NC(=CC2=C1)C(O)=O
Download
INCHI for NP0285855 (5-methoxy-1h-indole-2-carboxylic acid)
InChI=1S/C10H9NO3/c1-14-7-2-3-8-6(4-7)5-9(11-8)10(12)13/h2-5,11H,1H3,(H,12,13)
Download
View in JSmol
Synonyms
ValueSource
5-Methoxy-2-indolecarboxylic acidChEBI
5-Methoxy-2-indolic acidChEBI
5-Methoxy-2-indolecarboxylateGenerator
5-Methoxy-2-indolateGenerator
5-Methoxyindole-2-carboxylateGenerator
Chemical FormulaC10H9NO3
Average Mass191.1860 Da
Monoisotopic Mass191.05824 Da
IUPAC Name5-methoxy-1H-indole-2-carboxylic acid
Traditional Name5-methoxy-1H-indole-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
COC1=CC=C2NC(=CC2=C1)C(O)=O
InChI Identifier
InChI=1S/C10H9NO3/c1-14-7-2-3-8-6(4-7)5-9(11-8)10(12)13/h2-5,11H,1H3,(H,12,13)
InChI KeyYEBJVSLNUMZXRJ-UHFFFAOYSA-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
Solanum lycopersicumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndolecarboxylic acids and derivatives  
Direct ParentIndolecarboxylic acids and derivatives  
Alternative Parents
Substituents
  • Indolecarboxylic acid derivative
    • 

  • Indole
    • 

  • Anisole
    • 

  • Pyrrole-2-carboxylic acid
    • 

  • Pyrrole-2-carboxylic acid or derivatives
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Substituted pyrrole
    • 

  • Heteroaromatic compound
    • 

  • Pyrrole
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Ether
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Azacycle
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic nitrogen compound
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP1.49ChemAxon
pKa (Strongest Acidic)5.11ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.74 m³·mol⁻¹ChemAxon
Polarizability19.27 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0246823  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID19216  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20401  
PDB IDNot Available
ChEBI ID133222  
Good Scents IDNot Available
References
General References
  1. Darwish HW, Attia MI: New spectrofluorimetric methods for determination of melatonin in the presence of N-2-[1-(3-[2-(acetylamino)ethyl]-5-methoxy-1H-indol-2-ylmethyl)-5-methoxy-1H-indol-3-yl]- ethylacetamide: a contaminant in commercial melatonin preparations. Chem Cent J. 2012 May 2;6(1):36. doi: 10.1186/1752-153X-6-36. [PubMed:22551394  ] 
  2. Li CY, Ma WX, Yan LJ: 5-Methoxyindole-2-Carboylic Acid (MICA) Fails to Retard Development and Progression of Type II Diabetes in ZSF1 Diabetic Rats. React Oxyg Species (Apex). 2020 May 1;9(27):144-147. [PubMed:32551363  ] 
  3. Sumien N, Huang R, Chen Z, Vann PH, Wong JM, Li W, Yang S, Forster MJ, Yan LJ: Effects of dietary 5-methoxyindole-2-carboxylic acid on brain functional recovery after ischemic stroke. Behav Brain Res. 2020 Jan 27;378:112278. doi: 10.1016/j.bbr.2019.112278. Epub  2019 Oct 17. [PubMed:31629836  ] 
  4. Yan LJ: Reexploring 5-methoxyindole-2-carboxylic acid (MICA) as a potential antidiabetic agent. Diabetes Metab Syndr Obes. 2018 May 4;11:183-186. doi: 10.2147/DMSO.S166485.  eCollection 2018. [PubMed:29765243  ] 
  5. Ahmad W, Ebert PR: 5-Methoxyindole-2-carboxylic acid (MICA) suppresses Abeta-mediated pathology in C. elegans. Exp Gerontol. 2018 Jul 15;108:215-225. doi: 10.1016/j.exger.2018.04.021. Epub  2018 Apr 27. [PubMed:29709515  ] 
  6. Wu J, Jin Z, Yang X, Yan LJ: Post-ischemic administration of 5-methoxyindole-2-carboxylic acid at the onset of reperfusion affords neuroprotection against stroke injury by preserving mitochondrial function and attenuating oxidative stress. Biochem Biophys Res Commun. 2018 Feb 26;497(1):444-450. doi:  10.1016/j.bbrc.2018.02.106. Epub 2018 Feb 12. [PubMed:29448100  ] 
  7. Wu J, Li R, Li W, Ren M, Thangthaeng N, Sumien N, Liu R, Yang S, Simpkins JW, Forster MJ, Yan LJ: Administration of 5-methoxyindole-2-carboxylic acid that potentially targets mitochondrial dihydrolipoamide dehydrogenase confers cerebral preconditioning against ischemic stroke injury. Free Radic Biol Med. 2017 Dec;113:244-254. doi:  10.1016/j.freeradbiomed.2017.10.008. Epub 2017 Oct 7. [PubMed:29017857  ] 
  8. Sun Z, Park SY, Hwang E, Zhang M, Seo SA, Lin P, Yi TH: Thymus vulgaris alleviates UVB irradiation induced skin damage via inhibition of MAPK/AP-1 and activation of Nrf2-ARE antioxidant system. J Cell Mol Med. 2017 Feb;21(2):336-348. doi: 10.1111/jcmm.12968. Epub 2016 Sep  19. [PubMed:27641753  ] 
  9. Cinar M, Karabacak M, Asiri AM: An experimental and density functional study on conformational and spectroscopic analysis of 5-methoxyindole-2-carboxylic acid. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Feb 25;137:670-6. doi:  10.1016/j.saa.2014.08.090. Epub 2014 Sep 4. [PubMed:25255480  ] 
  10. Siva AB, Panneerdoss S, Sailasree P, Singh DK, Kameshwari DB, Shivaji S: Inhibiting sperm pyruvate dehydrogenase complex and its E3 subunit, dihydrolipoamide dehydrogenase affects fertilization in Syrian hamsters. PLoS One. 2014 May 22;9(5):e97916. doi: 10.1371/journal.pone.0097916. eCollection  2014. [PubMed:24852961  ] 
  11. LOTUS database [Link]