ContaminantDB: alpha-Lipoic acid amide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 05:47:53 UTC

Update Date

2016-11-09 01:15:55 UTC

Accession Number

CHEM019072

Identification

Common Name

alpha-Lipoic acid amide

Class

Small Molecule

Description

Lipoamidee, also known as lipoamidee or lipoamidee, belongs to the class of organic compounds known as lipoamidees. Lipoamidees are compounds containing a lipoamidee moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring. Thus, lipoamidee is considered to be a fatty amide lipid molecule. Lipoamidee exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Lipoamidee exists in all living species, ranging from bacteria to humans. In cattle, lipoamidee is involved in the metabolic pathway called the citric Acid cycle pathway.

Contaminant Sources

FooDB Chemicals
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

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 Molecular Mass

205.341 g/mol

Monoisotopic Mass

205.060 g/mol

CAS Registry Number

940-69-2

IUPAC Name

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

Traditional Name

lipoamide

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

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-014i-6963000000-7e1887d53c2801b09961	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-017l-3920000000-a3a7a08acf06d41c9b73	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-6963000000-7e1887d53c2801b09961	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-017l-3920000000-a3a7a08acf06d41c9b73	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1910000000-b6ee336856e354af8114	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-3900000000-60cad9dd198c3ad64ed7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f96-9800000000-ac967ad86beefc26c983	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0900000000-24fca44fc025dbd6be18	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0ziu-9700000000-7dfd23f450bdfd581100	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-056u-9000000000-13583c4eb6b06a56c392	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-052r-2920000000-a4fb7176abf63e581f5e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-2900000000-10a079a84f024494ae23	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0zfr-9800000000-b01332176d6829b1eaa1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0udl-9400000000-7a03c741edae36dff9cf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0a5c-9100000000-7b44dfbfcbb0cc516254	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000i-0900000000-50512172ce038bce2995	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-03di-0900000000-7652a33c17a37b6914aa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0udi-0900000000-0df59a6540bede8a4a79	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-052r-2920000000-a4fb7176abf63e581f5e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-2900000000-158c946037c5d7bb3e50	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0zfr-9800000000-b01332176d6829b1eaa1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udl-9400000000-7a03c741edae36dff9cf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a5c-9100000000-7b44dfbfcbb0cc516254	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-000i-0900000000-fa779b1c88469a732321	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-1900000000-9e4b6873b24c66cf9f69	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01p9-0900000000-b37ce6b25b9feef09b96	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0940000000-d79e1aa52057e567d71f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-3900000000-abd8148048c5f282d889	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0adr-9500000000-9769c619660ab6af46d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zml-1920000000-79d57d488cb8fbc804a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fdo-4910000000-d264eaf6e242c36bc563	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-289d2f20046f7819a7ca	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum