Details of the Drug

General Information of Drug (ID: DM6N4PR)

Drug Name

Cerulenin

Synonyms

Helicocerin; Cerulenin, Cephalosporium caerulens; Oxiranecarboxamide, 3-(1-oxo-4,7-nonadienyl)-, (2R-(2-alpha,3-alpha(4E,7E)))-(9CI); (2R,3S)-2,3-Epoxy-4-oxo-7E,10E-dodecadienamide; (2R,3S)-3-((4E,7E)-Nona-4,7-dienoyl)-oxirane-2-carboxylic acid amide; (2R,3S)-3-((4E,7E)-nona-4,7-dienoyl)oxirane-2-carboxamide; (2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide; (2R,3S)-3-nona-4,7-dienoyloxirane-2-carboxamide; (2R,3S,E,E)-2,3-Epoxy-4-oxo-7,10-dodecadienamide; (2R-(2alpha,3alpha(4E,7E)))-3-(1-Oxonona-4,7-dienyl)oxirane-2-carboxamide; (2S)(3R)-2,3-Epoxy-4-oxo-7,10-dodecadienoylamide; (2S,3R)-2,3-epoxy-4-oxy-7,10-dodecadienoylamide; (2r,3s)-3-(nona-4,7-dienoyl)oxirane-2-carboxamide; 2,3-Epoxy-4-oxo-7,10-dodecadienamide; 2,3-Epoxy-4-oxo-7,10-dodecadienoylamide; 3-(1-Oxo-4,7-nonadienyl)oxiranecarboxamide; 3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide; 3-nona-4,7-dienoyloxirane-2-carboxamide

Indication

Disease Entry	ICD 11	Status	REF
Weight loss	MG43.5	Approved	[1]

Therapeutic Class

Antiinfective Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

223.27

Topological Polar Surface Area (xlogp)

0.8

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C12H17NO3
IUPAC Name: (2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide
Canonical SMILES: C/C=C/C/C=C/CCC(=O)[C@@H]1[C@@H](O1)C(=O)N
InChI: InChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+/t10-,11-/m1/s1
InChIKey: GVEZIHKRYBHEFX-NQQPLRFYSA-N

Cross-matching ID

PubChem CID: 5282054
ChEBI ID: CHEBI:171741
CAS Number: 17397-89-6
DrugBank ID: DB01034
TTD ID: D03ZFG

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Fatty acid synthase (FASN)	TT7AOUD	FAS_HUMAN	Inhibitor	[2], [3], [4]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Novel agents in the management of Mycobacterium tuberculosis disease. Curr Med Chem. 2007;14(18):2000-8.
2	Inhibition of fatty acid biosynthesis prevents adipocyte lipotoxicity on human osteoblasts in vitro. J Cell Mol Med. 2010 Apr;14(4):982-91.
3	Proliferation inhibition and apoptosis induction of K562 cells by fatty acid synthase inhibitor--cerulenin. Zhonghua Xue Ye Xue Za Zhi. 2000 May;21(5):244-6.
4	The antibiotic cerulenin, a novel tool for biochemistry as an inhibitor of fatty acid synthesis. Bacteriol Rev. 1976 Sep;40(3):681-97.
5	Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids. J Med Chem. 2006 Jun 1;49(11):3345-53.
6	Imidazopyridine-Based Fatty Acid Synthase Inhibitors That Show Anti-HCV Activity and in Vivo Target Modulation. ACS Med Chem Lett. 2013 January 10; 4(1): 113-117.
7	Fatty Acid Synthase Inhibitor TVB-2640 Reduces Hepatic de Novo Lipogenesis in Males With Metabolic Abnormalities. Hepatology. 2020 Jul;72(1):103-118.
8	Novel antifungal agents, targets or therapeutic strategies for the treatment of invasive fungal diseases: a review of the literature (2005-2009). Rev Iberoam Micol. 2009 Mar 31;26(1):15-22.
9	2-Hexadecynoic acid inhibits plasmodial FAS-II enzymes and arrests erythrocytic and liver stage Plasmodium infections. Bioorg Med Chem. 2010 Nov 1;18(21):7475-85.