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Showing NP-Card for Dihydrolipoamide (NP0086679)

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Record Information
Version2.0
Created at2022-05-11 16:27:57 UTC
Updated at2022-05-11 16:27:57 UTC
NP-MRD IDNP0086679
Secondary Accession NumbersNone
Natural Product Identification
Common NameDihydrolipoamide
DescriptionDihydrolipoamide belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine. Thus, dihydrolipoamide is considered to be a fatty amide lipid molecule. Dihydrolipoamide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Dihydrolipoamide exists in all living species, ranging from bacteria to humans. Within humans, dihydrolipoamide participates in a number of enzymatic reactions. In particular, dihydrolipoamide can be converted into lipoamide through its interaction with the enzyme dihydrolipoyl dehydrogenase E3. In addition, dihydrolipoamide can be biosynthesized from S-(3-methylbutanoyl)-dihydrolipoamide-e through its interaction with the enzyme lipoamide acyltransferase component OF branched-chain alpha-keto acid dehydrogenase complex, mitochondrial. In humans, dihydrolipoamide is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway. Outside of the human body, Dihydrolipoamide has been detected, but not quantified in, several different foods, such as pistachio, other soy products, cardoons, orange mints, and alaska wild rhubarbs. This could make dihydrolipoamide a potential biomarker for the consumption of these foods. Dihydrolipoamide is found in Apis cerana. Dihydrolipoamide was first documented in 2005 (PMID: 15946682). Dihydrolipoamide is a molecule produced by the action of dihydrolipoyl dehydrogenase upon lipoamide (PMID: 15826505) (PMID: 15612914) (PMID: 15613977).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086679 (Dihydrolipoamide)


  Mrv0541 02231218512D          

 12 11  0  0  0  0            999 V2000
   12.3989   -8.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9864   -9.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2239   -8.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1614   -9.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2239   -7.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3989   -7.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6364   -8.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7489  -10.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9239  -10.3196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1614  -11.0341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9864   -6.7473    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.4614   -8.1762    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
Download

3D MOL for NP0086679 (Dihydrolipoamide)

     RDKit          3D

 29 28  0  0  0  0  0  0  0  0999 V2000
    2.2722    1.6090   -0.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9975    1.3199    0.4119 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3847    0.1632    0.7448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4338    0.1476    1.6976 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9198   -1.1390    0.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6879   -1.1984   -0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4334   -0.7085    0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6767   -0.8609   -0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0059   -0.3947   -0.3725 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5386   -1.2954    1.0836 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9893    1.1018   -0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3350    1.5967    0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2248    3.3946    0.5446 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3404   -0.2159    1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8164   -1.8664    1.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7438   -1.5668   -0.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5205   -2.2906   -0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8470   -0.7342   -1.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1163   -1.3905    0.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911    0.2957    0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7739   -1.9260   -1.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4039   -0.2905   -1.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7905   -0.5823   -1.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1906   -2.5074    0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8954    1.5501   -1.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1942    1.4277    0.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1478    1.3045   -0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5543    1.0920    1.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836    3.9646   -0.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  2  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
  4 14  1  0
  2  1  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  6
 10 24  1  0
 11 25  1  0
 11 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
M  END
Download

3D SDF for NP0086679 (Dihydrolipoamide)


  Mrv0541 02231218512D          

 12 11  0  0  0  0            999 V2000
   12.3989   -8.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9864   -9.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2239   -8.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1614   -9.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2239   -7.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3989   -7.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6364   -8.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7489  -10.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9239  -10.3196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1614  -11.0341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9864   -6.7473    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.4614   -8.1762    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086679

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=N)CCCCC(S)CCS

> <INCHI_IDENTIFIER>
InChI=1S/C8H17NOS2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H2,9,10)

> <INCHI_KEY>
VLYUGYAKYZETRF-UHFFFAOYSA-N

> <FORMULA>
C8H17NOS2

> <MOLECULAR_WEIGHT>
207.357

> <EXACT_MASS>
207.075155551

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.767533674169556

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,8-disulfanyloctanimidic acid

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
1.438392507588704

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.850896014465793

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.676732176319095

> <JCHEM_PKA_STRONGEST_BASIC>
8.781980224833603

> <JCHEM_POLAR_SURFACE_AREA>
44.08

> <JCHEM_REFRACTIVITY>
68.6954

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydrothioctamide

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0086679 (Dihydrolipoamide)

Download
PDB for NP0086679 (Dihydrolipoamide)
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  C   UNK     0      23.145 -16.596   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.375 -17.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.685 -16.596   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.835 -17.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.685 -13.929   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.145 -13.929   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.455 -15.262   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.065 -19.263   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      18.525 -19.263   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      20.835 -20.597   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0      22.375 -12.595   0.000  0.00  0.00           S+0
HETATM   12  S   UNK     0      26.995 -15.262   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    7    6                                                       
CONECT    6    5   11                                                       
CONECT    7    3    5   12                                                  
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0086679 (Dihydrolipoamide)
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SMILES for NP0086679 (Dihydrolipoamide)
OC(=N)CCCCC(S)CCS
Download
INCHI for NP0086679 (Dihydrolipoamide)
InChI=1S/C8H17NOS2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H2,9,10)
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Synonyms
ValueSource
6,8-DimercaptooctanamideChEBI
DihydrothioctamideChEBI
6,8-Bis-sulfanyloctanamideHMDB
6,8-Dimercapto-octanamideHMDB
6,8-DisulfanyloctanamideHMDB
Dihydrolipoamide, (+-)-isomerHMDB
Chemical FormulaC8H17NOS2
Average Mass207.3570 Da
Monoisotopic Mass207.07516 Da
IUPAC Name6,8-disulfanyloctanimidic acid
Traditional Namedihydrothioctamide
CAS Registry NumberNot Available
SMILES
OC(=N)CCCCC(S)CCS
InChI Identifier
InChI=1S/C8H17NOS2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H2,9,10)
InChI KeyVLYUGYAKYZETRF-UHFFFAOYSA-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
Apis ceranaLOTUS Database
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 fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty amides  
Direct ParentFatty amides  
Alternative Parents
Substituents
  • Fatty amide
    • 

  • Primary carboxylic acid amide
    • 

  • Carboxamide group
    • 

  • Carboxylic acid derivative
    • 

  • Alkylthiol
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organosulfur compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen 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
logP2.22ALOGPS
logP1.44ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.68ChemAxon
pKa (Strongest Basic)8.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area44.08 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity68.7 m³·mol⁻¹ChemAxon
Polarizability23.77 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000985  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022352  
KNApSAcK IDNot Available
Chemspider ID643  
KEGG Compound IDC00579  
BioCyc IDNot Available
BiGG ID35406  
Wikipedia LinkDihydrolipoamide  
METLIN ID5920  
PubChem Compound663  
PDB IDNot Available
ChEBI ID17694  
Good Scents IDNot Available
References
General References
  1. Brautigam CA, Chuang JL, Tomchick DR, Machius M, Chuang DT: Crystal structure of human dihydrolipoamide dehydrogenase: NAD+/NADH binding and the structural basis of disease-causing mutations. J Mol Biol. 2005 Jul 15;350(3):543-52. [PubMed:15946682  ] 
  2. Kim H: Asparagine-473 residue is important to the efficient function of human dihydrolipoamide dehydrogenase. J Biochem Mol Biol. 2005 Mar 31;38(2):248-52. doi: 10.5483/bmbrep.2005.38.2.248. [PubMed:15826505  ] 
  3. McMillan PJ, Stimmler LM, Foth BJ, McFadden GI, Muller S: The human malaria parasite Plasmodium falciparum possesses two distinct dihydrolipoamide dehydrogenases. Mol Microbiol. 2005 Jan;55(1):27-38. doi: 10.1111/j.1365-2958.2004.04398.x. [PubMed:15612914  ] 
  4. Deres P, Halmosi R, Toth A, Kovacs K, Palfi A, Habon T, Czopf L, Kalai T, Hideg K, Sumegi B, Toth K: Prevention of doxorubicin-induced acute cardiotoxicity by an experimental antioxidant compound. J Cardiovasc Pharmacol. 2005 Jan;45(1):36-43. doi: 10.1097/00005344-200501000-00007. [PubMed:15613977  ]