NP-MRD: Showing NP-Card for S-Acetyldihydrolipoamide (NP0086810)

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Record Information

Version

2.0

Created at

2022-05-11 16:31:39 UTC

Updated at

2022-05-11 16:31:39 UTC

NP-MRD ID

NP0086810

Secondary Accession Numbers

None

Natural Product Identification

Common Name

S-Acetyldihydrolipoamide

Description

S-Acetyldihydrolipoamide 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, S-acetyldihydrolipoamide is considered to be a fatty amide lipid molecule. The molecule is commonly conjugated to lysine residues. S-Acetyldihydrolipoamide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. S-Acetyldihydrolipoamide exists in all living organisms, ranging from bacteria to humans. In humans, S-acetyldihydrolipoamide is involved in pyruvate metabolism. Pyruvate dehydrogenase complex. The reaction is 2-(alpha-hydroxyethyl)-TPP + lipoamide => S-acetyldihydrolipoamide + TPP , occuring in mitochondrial matrix. Outside of the human body, S-Acetyldihydrolipoamide has been detected, but not quantified in, several different foods, such as parsnips, wild celeries, japanese chestnuts, american pokeweeds, and common walnuts. This could make S-acetyldihydrolipoamide a potential biomarker for the consumption of these foods. The structure shown is the free form of the molecule. S-Acetyldihydrolipoamide is a thio-acetylated form of dihydrolipoamide. It is then converted to acetyl-CoA via the enzyme pyruvate dehydrogenase E2 component (dihydrolipoamide acetyltransferase) (EC:2.3.1.12). S-Acetyldihydrolipoamide is an intermediate in alanine, aspartate and pyruvate metabolism and glycolysis/gluconeogenesis (KEGG:C01136). S-Acetyldihydrolipoamide is found in Apis cerana. S-Acetyldihydrolipoamide was first documented in 1975 (PMID: 1089667). It is converted from 2-hydroxyethyl-THPP and lipoamide via the enzyme pyruvate dehydrogenase (EC:1.2.4.1) (PMID: 3101735) (PMID: 6801041).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 33  0  0  0  0  0  0  0  0999 V2000
   -1.5003    3.2422    0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2802    1.8510   -0.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9746    1.6112   -1.4409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4532    0.4824    0.8410 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1450   -1.1099    0.1236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1293   -1.3901   -1.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5390   -1.3519   -0.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6947   -2.6114    0.8667 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2403   -1.4329   -0.3172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2892   -1.4341    0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5969   -0.1629    1.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1606    0.9321    0.5756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4697    0.6079   -0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0645    1.5203   -0.9559 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0597   -0.4597    0.2198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9684    3.8017   -0.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5196    3.7252    0.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1201    3.3080    1.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3790   -1.9060    0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0315   -0.6425   -1.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9899   -2.4028   -1.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7581   -0.3410    0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2584   -1.6188   -1.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6280   -3.5286    0.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1958   -2.4936   -0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5701   -0.8124   -1.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9789   -2.2446    1.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2331   -1.8323    0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7643    0.2326    2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4072   -0.4005    2.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4246    1.2597   -0.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3170    1.8079    1.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8007    2.5484   -0.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7965    1.2454   -1.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  1
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
M  END


  Mrv0541 02231219112D          

 15 14  0  0  0  0            999 V2000
   -1.1896   -0.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4793   -0.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1896    0.6378    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9033   -0.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2379   -0.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4793    1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6205   -0.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9551   -0.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2379    0.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4793    1.8722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6205    0.6378    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689   -0.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3826   -0.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0928   -0.1931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3826   -1.4309    0.0000 O   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
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  2  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0086810

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)SC(CCS)CCCCC(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H19NO2S2/c1-8(12)15-9(6-7-14)4-2-3-5-10(11)13/h9,14H,2-7H2,1H3,(H2,11,13)

> <INCHI_KEY>
ARGXEXVCHMNAQU-UHFFFAOYSA-N

> <FORMULA>
C10H19NO2S2

> <MOLECULAR_WEIGHT>
249.393

> <EXACT_MASS>
249.085720237

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.661351810788403

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(acetylsulfanyl)-8-sulfanyloctanamide

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
1.2364680790000007

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.552166740788277

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.190901379680659

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5791099252102924

> <JCHEM_POLAR_SURFACE_AREA>
60.160000000000004

> <JCHEM_REFRACTIVITY>
67.22659999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
S(6)-acetyldihydrolipoamide

> <JCHEM_VEBER_RULE>
0

$$$$

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      -2.221  -0.360   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.895  -1.133   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0      -2.221   1.191   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0      -3.553  -1.133   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.444  -0.360   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.895   1.957   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.892  -0.360   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.783  -1.133   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.444   1.191   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.895   3.495   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0      -4.892   1.191   0.000  0.00  0.00           S+0
HETATM   12  C   UNK     0       3.115  -0.360   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.448  -1.133   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.773  -0.360   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       4.448  -2.671   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    2    8                                                       
CONECT    6    3    9   10                                                  
CONECT    7    4   11                                                       
CONECT    8    5   12                                                       
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
6-S-Acetyldihydrolipoamide	ChEBI
6-Acetylsulfanyl-8-sulfanyl-octanamide	HMDB
S-[6-Amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioate	HMDB
S-[6-Amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioic acid	HMDB

Chemical Formula

C₁₀H₁₉NO₂S₂

Average Mass

249.3930 Da

Monoisotopic Mass

249.08572 Da

IUPAC Name

6-(acetylsulfanyl)-8-sulfanyloctanamide

Traditional Name

S(6)-acetyldihydrolipoamide

CAS Registry Number

Not Available

SMILES

CC(=O)SC(CCS)CCCCC(N)=O

InChI Identifier

InChI=1S/C10H19NO2S2/c1-8(12)15-9(6-7-14)4-2-3-5-10(11)13/h9,14H,2-7H2,1H3,(H2,11,13)

InChI Key

ARGXEXVCHMNAQU-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Apis cerana	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

Fatty amides

Alternative Parents

Substituents

Fatty amide
Carboxamide group
Primary carboxylic acid amide
Thiocarboxylic acid ester
Carbothioic s-ester
Sulfenyl compound
Thiocarboxylic acid or derivatives
Alkylthiol
Carboxylic acid derivative
Carbonyl group
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

S-substituted dihydrolipoamide (CHEBI:16807 )
a small molecule (S-ACETYLDIHYDROLIPOAMIDE )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.46	ALOGPS
logP	1.24	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	10.19	ChemAxon
pKa (Strongest Basic)	-0.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	60.16 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	67.23 m³·mol⁻¹	ChemAxon
Polarizability	27.66 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001526

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022671

KNApSAcK ID

Not Available

Chemspider ID

1046

KEGG Compound ID

C01136

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6299

PubChem Compound

1076

PDB ID

Not Available

ChEBI ID

16807

Good Scents ID

Not Available

References

General References

Yang YS, Frey PA: Dihydrolipoyl transacetylase of Escherichia coli. Formation of 8-S-acetyldihydrolipoamide. Biochemistry. 1986 Dec 16;25(25):8173-8. doi: 10.1021/bi00373a008. [PubMed:3101735 ]
Butterworth PJ, Tsai CS, Eley MH, Roche TE, Reed LJ: A kinetic study of dihydrolipoyl transacetylase from bovine kidney. J Biol Chem. 1975 Mar 10;250(5):1921-5. [PubMed:1089667 ]
O'Connor TP, Roche TE, Paukstelis JV: 13C nuclear magnetic resonance study of the pyruvate dehydrogenase-catalyzed acetylation of dihydrolipoamide. J Biol Chem. 1982 Mar 25;257(6):3110-2. [PubMed:6801041 ]

Showing NP-Card for S-Acetyldihydrolipoamide (NP0086810)

MOL for NP0086810 (S-Acetyldihydrolipoamide)

3D MOL for NP0086810 (S-Acetyldihydrolipoamide)

3D SDF for NP0086810 (S-Acetyldihydrolipoamide)

3D-SDF for NP0086810 (S-Acetyldihydrolipoamide)

PDB for NP0086810 (S-Acetyldihydrolipoamide)

3D PDB for NP0086810 (S-Acetyldihydrolipoamide)

SMILES for NP0086810 (S-Acetyldihydrolipoamide)

INCHI for NP0086810 (S-Acetyldihydrolipoamide)

Structure for NP0086810 (S-Acetyldihydrolipoamide)

3D Structure for NP0086810 (S-Acetyldihydrolipoamide)