Lipoamide

HCID 863CAS 3206-73-3
Substructure searchFind similar structures

Basic information

Standard SMILES
NC(=O)CCCCC1CCSS1
InChIKey
FCCDDURTIIUXBY-UHFFFAOYSA-N
Molecular formula
C8H15NOS2
Average molar mass
205.3 g/mol
Monoisotopic mass
205.0595061

Overview

Lipoamide is a monocarboxylic acid amide resulting from the formal condensation of the carboxy group of lipoic acid with ammonia. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a human metabolite. It is a monocarboxylic acid amide and a member of dithiolanes. It is functionally related to a lipoic acid.

Names & identifiers

Preferred name
Lipoamide
IUPAC
5-(dithiolan-3-yl)pentanamide
English name
DL-5-(1,2-Dithiolan-3-yl)valeramide
Molecular formula
C8H15NOS2
Molecular weight
205.34

Names & synonyms

lipoamide940-69-2Thioctamide5-(1,2-Dithiolan-3-yl)pentanamidethioctic acid amideLipoacindl-6,8-ThioctamideDL-lipoamideLipamideVitamin NLipoamidLipoicin
Show more names
DL-a-LipoamideDL-α-LipoamideDL-THIOCTAMIDETHIOCTIC AMIDEDL-α-LipoamideALPHA-LIPOAMIDE6-THIOCTIC AMIDEDL-thioctic amide
Pathoclon1,2-Dithiolane-3-pentanamideThioctamidThiotominThioamiTicolinLypoaranalpha-Lipoic acid amide

Database identifiers

CAS
3206-73-3、940-69-2
PubChem CID
863
DTXSID
DTXSID2046541
ChEMBL
CHEMBL1403899
ChEBI
CHEBI:17460
UNII
Q1GT04827L
EC Number
213-375-2、221-710-9
Nikkaji
J25.390A

Properties

Computed structural properties

XLogP
1
Topological polar surface area
93.7 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
5
Heavy atoms
12

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Amides, Other
LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> Primary amides [FA0801]
Melting Point126.0 - 129.0 °C
Physical Description · 2 items

Yellow solid; [Alfa Aesar MSDS]

Solid

Collision Cross Section · 5 items

146.29 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

150.4 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

150.5 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

139.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

150.6 Ų [M+Na]+

Physicochemical properties

Melting point
127 · 127-129 °C(lit.)
storage temp.
2 · 2-8°C
InChI
InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)
InChIKey
FCCDDURTIIUXBY-UHFFFAOYSA-N
SMILES
C(N)(=O)CCCCC1CCSS1
CAS DataBase Reference
3206 · 3206-73-3(CAS DataBase Reference)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazards SummaryHarmful by ingestion; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

wgk
3
rtecs
JP1185000
safety_code
22-24/25

Chemistry & industry

Pharmacology

Tissue LocationsPlacenta
Cellular LocationsMembrane
Metabolite Pathways2-aminoadipic 2-oxoadipic aciduria

Applications

Useshepatoprotectant

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
苏州申拓医药科技有限公司13911244683 18151949202
天津长江化学有限公司19129375004; 15321929114 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Lipoamide is a monocarboxylic acid amide resulting from the formal condensation of the carboxy group of lipoic acid with ammonia. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a member of dithiolanes and a monocarboxylic acid amide. It is functionally related to a lipoic acid.

Related reactions

8 records
New reaction record

Linked notes

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