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
Affected Organisms
Humans and other mammalsFungiBacteriaMycobacterium tuberculosis
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 223.27
Logarithm of the Partition Coefficient (xlogp) 0.8
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
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
CHEMBL45627
CAS Number
17397-89-6
UNII
MF286Y830Q
DrugBank ID
DB01034
TTD ID
D03ZFG
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

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]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Eukaryotic translation initiation factor 2A (EIF2A) OTWXELQP EIF2A_HUMAN Post-Translational Modifications [3]
Piezo-type mechanosensitive ion channel component 1 (PIEZO1) OTBG1FU4 PIEZ1_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) 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 Inhibition of fatty acid synthase induces endoplasmic reticulum stress in tumor cells. Cancer Res. 2007 Feb 1;67(3):1262-9. doi: 10.1158/0008-5472.CAN-06-1794.
4 Exposure to dietary fatty acids oleic and palmitic acid alters structure and mechanotransduction of intestinal cells in vitro. Arch Toxicol. 2023 Jun;97(6):1659-1675. doi: 10.1007/s00204-023-03495-3. Epub 2023 Apr 29.