NP-MRD: Showing NP-Card for Lipoamide (NP0001201)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-17 15:44:31 UTC

NP-MRD ID

NP0001201

Natural Product DOI

https://doi.org/10.57994/2829

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lipoamide

Description

Lipoamide is a trivial name for 6,8-dithiooctanoic amide. It is 6,8-dithiooctanoic acid's functional form where the carboxyl group is attached to protein (or any other amine) by an amide linkage (containing -NH2) to an amino group. Lipoamide forms a thioester bond, oxidizing the disulfide bond, with acetaldehyde (pyruvate after it has been decarboxylated). It then transfers the acetaldehyde group to CoA which can then continue in the TCA cycle. Lipoamide is an intermediate in glycolysis/gluconeogenesis, citrate cycle (TCA cycle), alanine, aspartate and pyruvate metabolism, and valine, leucine and isoleucine degradation (KEGG:C00248). It is generated from dihydrolipoamide via the enzyme dihydrolipoamide dehydrogenase (EC:1.8.1.4) And then converted to S-glutaryl-dihydrolipoamide via the enzyme oxoglutarate dehydrogenase (EC:1.2.4.2).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  S   UNK     0      18.471 -12.711   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      16.931 -12.711   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      16.469 -11.249   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.701 -10.325   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.933 -11.249   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.242 -10.479   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.628 -11.249   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.937 -10.479   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.246 -11.249   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.632 -10.479   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      26.941 -11.249   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      25.632  -8.939   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    HMDB0000962
HETATM    1  N1  UNL     1       4.162   0.393   0.389  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.985  -0.387   0.308  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.477  -0.840   1.390  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.301  -0.718  -0.942  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.020  -1.459  -0.812  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.053  -0.726  -0.042  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.404   0.589  -0.687  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.458   1.361   0.039  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.711   0.561   0.102  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.734   1.315   0.918  1.00  0.00           C  
HETATM   11  S1  UNL     1      -2.960   1.526   2.578  1.00  0.00           S  
HETATM   12  S2  UNL     1      -0.941   1.607   1.792  1.00  0.00           S  
HETATM   13  H1  UNL     1       5.043   0.187  -0.121  1.00  0.00           H  
HETATM   14  H2  UNL     1       4.154   1.233   1.000  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.998  -1.390  -1.524  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.196   0.198  -1.594  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.235  -2.388  -0.213  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.611  -1.816  -1.778  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.958  -1.408  -0.077  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.224  -0.685   1.002  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.481   1.249  -0.797  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.719   0.352  -1.731  1.00  0.00           H  
HETATM   23  H11 UNL     1      -1.675   2.319  -0.428  1.00  0.00           H  
HETATM   24  H12 UNL     1      -3.113   0.460  -0.909  1.00  0.00           H  
HETATM   25  H13 UNL     1      -2.622  -0.448   0.530  1.00  0.00           H  
HETATM   26  H14 UNL     1      -3.942   2.319   0.549  1.00  0.00           H  
HETATM   27  H15 UNL     1      -4.599   0.664   1.056  1.00  0.00           H  
CONECT    1    2   13   14
CONECT    2    3    3    4
CONECT    4    5   15   16
CONECT    5    6   17   18
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9   12   23
CONECT    9   10   24   25
CONECT   10   11   26   27
CONECT   11   12
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
1,2-Dithiolane-3-pentanamide	ChEBI
alpha-Lipoic acid amide	ChEBI
Lipoacin	ChEBI
Thioctamide	ChEBI
Thioctic acid amide	ChEBI
Vitamin N	ChEBI
a-Lipoate amide	Generator
a-Lipoic acid amide	Generator
alpha-Lipoate amide	Generator
Α-lipoate amide	Generator
Α-lipoic acid amide	Generator
Thioctate amide	Generator
5-(1,2-Dithiolan-3-yl)-pentanamide	HMDB
5-(1,2-Dithiolan-3-yl)pentanamide	HMDB
5-(1,2-Dithiolan-3-yl)valeramide	HMDB
5-(Dithiolan-3-yl)valeramide	HMDB
alpha-Lipoate	HMDB
alpha-Lipoic acid	HMDB
DL-6-Thioctic amide	HMDB
DL-Lipoamide	HMDB
Lipamide	HMDB
Lipoamid	HMDB
Lipoicin	HMDB
Lipozyme	HMDB
Lypoaran	HMDB
Pathoclon	HMDB
Thioami	HMDB
Thioctamid	HMDB
Thiotomin	HMDB
Ticolin	HMDB
1,2-Dithiolane-3-valeramide	HMDB
6,8-Thioctic amide	HMDB
alpha-Lipoic amide	HMDB
Lipoamide, (+-)-isomer	HMDB

Chemical Formula

C₈H₁₅NOS₂

Average Mass

205.3410 Da

Monoisotopic Mass

205.05951 Da

IUPAC Name

5-(1,2-dithiolan-3-yl)pentanamide

Traditional Name

lipoamide

CAS Registry Number

940-69-2

SMILES

NC(=O)CCCCC1CCSS1

InChI Identifier

InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)

InChI Key

FCCDDURTIIUXBY-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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	¹³C NMR Spectrum (1D, 252 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	¹³C NMR Spectrum (1D, 75 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	¹³C NMR Spectrum (1D, 126 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	¹³C NMR Spectrum (1D, 176 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	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CDCl₃, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum

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
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Paraburkholderia phymatum	-	KNApSAcK
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 lipoamides. Lipoamides are compounds containing a lipoamide moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dithiolanes

Sub Class

Lipoamides

Direct Parent

Lipoamides

Alternative Parents

Substituents

Lipoamide
Fatty amide
Fatty acyl
1,2-dithiolane
Carboxamide group
Organic disulfide
Primary carboxylic acid amide
Carboxylic acid derivative
Carbonyl group
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:17460 )
dithiolanes (CHEBI:17460 )
Primary amides (LMFA08010006 )
a small molecule (LIPOAMIDE )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	126.0 - 129.0 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	2.3	ALOGPS
logP	1.31	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	16.45	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	56.19 m³·mol⁻¹	ChemAxon
Polarizability	22.38 Å³	ChemAxon
Number of Rings	1	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

HMDB0000962

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17460

Good Scents ID

Not Available

References

General References

Arner ES, Nordberg J, Holmgren A: Efficient reduction of lipoamide and lipoic acid by mammalian thioredoxin reductase. Biochem Biophys Res Commun. 1996 Aug 5;225(1):268-74. [PubMed:8769129 ]
Nordman T, Xia L, Bjorkhem-Bergman L, Damdimopoulos A, Nalvarte I, Arner ES, Spyrou G, Eriksson LC, Bjornstedt M, Olsson JM: Regeneration of the antioxidant ubiquinol by lipoamide dehydrogenase, thioredoxin reductase and glutathione reductase. Biofactors. 2003;18(1-4):45-50. [PubMed:14695919 ]
Oizumi J, Hayakawa K: Liberation of lipoate by human serum lipoamidase from bovine heart pyruvate dehydrogenase. Biochem Biophys Res Commun. 1989 Jul 31;162(2):658-63. [PubMed:2502979 ]
Nakai T, Nakagawa N, Maoka N, Masui R, Kuramitsu S, Kamiya N: Ligand-induced conformational changes and a reaction intermediate in branched-chain 2-oxo acid dehydrogenase (E1) from Thermus thermophilus HB8, as revealed by X-ray crystallography. J Mol Biol. 2004 Apr 2;337(4):1011-33. [PubMed:15033367 ]
Wynn RM, Machius M, Chuang JL, Li J, Tomchick DR, Chuang DT: Roles of His291-alpha and His146-beta' in the reductive acylation reaction catalyzed by human branched-chain alpha-ketoacid dehydrogenase: refined phosphorylation loop structure in the active site. J Biol Chem. 2003 Oct 31;278(44):43402-10. Epub 2003 Aug 5. [PubMed:12902323 ]
Panak KC, Ruiz OA, Giorgieri SA, Diaz LE: Direct determination of glutathione in human blood by micellar electrokinetic chromatography: simultaneous determination of lipoamide and lipoic acid. Electrophoresis. 1996 Oct;17(10):1613-6. [PubMed:8957191 ]

Showing NP-Card for Lipoamide (NP0001201)

MOL for NP0001201 (Lipoamide)

3D MOL for NP0001201 (Lipoamide)

3D SDF for NP0001201 (Lipoamide)

3D-SDF for NP0001201 (Lipoamide)

PDB for NP0001201 (Lipoamide)

3D PDB for NP0001201 (Lipoamide)

SMILES for NP0001201 (Lipoamide)

INCHI for NP0001201 (Lipoamide)

Structure for NP0001201 (Lipoamide)

3D Structure for NP0001201 (Lipoamide)