Structure Database (LMSD)

Common Name
lipoamide
Systematic Name
5-(1,2-dithiolan-3-yl)pentanamide
Synonyms
  • Lipoamide
  • Thioctamide
  • Thioctic acid amide
  • alpha-lipoic acid amide
  • lipoamide
  • vitamin N
LM ID
LMFA08010006
Formula
C8H15NOS2
Exact Mass
Calculate m/z
205.059508
Status
Curated
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Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty amides [FA08]
Primary amides [FA0801]
Fatty Acids and Conjugates [FA01]
Thia fatty acids [FA0113]
Carbocyclic fatty acids [FA0114]

Biological Context

2-Chloro-N-methyl-N-(4-nitrophenyl)acetamide is a synthetic intermediate.1 It has been used in the synthesis of maternal embryonic leucine zipper kinase (MELK) inhibitors with anticancer activity.

This information has been provided by Cayman Chemical

References

1. Edupuganti, R., Taliaferro, J.M., Wang, Q., et al. Discovery of a potent inhibitor of MELK that inhibits expression of the anti-apoptotic protein Mcl-1 and TNBC cell growth. Bioorg. Med. Chem. 25(9), 2609-2616 (2017).

String Representations

InChiKey (Click to copy)
FCCDDURTIIUXBY-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)
SMILES (Click to copy)
C1CSSC1CCCCC(=O)N

Other Databases

KEGG ID
C00248
HMDB ID
HMDB0000962
CHEBI ID
17460
PubChem CID
863
Cayman ID
35336

Calculated Physicochemical Properties

Heavy Atoms 12
Rings 1
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 188.77
Topological Polar Surface Area 43.09
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 2.76
Molar Refractivity 57.12

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Updated at
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