Details of the Drug

General Information of Drug (ID: DMHN74V)

Drug Name

Lanosterol

Synonyms

lanosterol; 79-63-0; Lanosterin; Lanster; Botalan base 138; Lanosta-8,24-dienol; Lanosta-8,24-dien-3beta-ol; (3beta)-lanosta-8,24-dien-3-ol; UNII-1J05Z83K3M; NSC60677; Botalan base; CHEBI:16521; Lanosta-8,24-dien-3.beta.-ol; CAHGCLMLTWQZNJ-BQNIITSRSA-N; 1J05Z83K3M; MFCD00021108; Lanostadien-3-beta-ol; NSC 60677; Lanosta-8,24-dien-3-ol, (3beta)-; Lanosta-8,24-dien-3-ol; Lanosta-8,24-dien-3-ol, (3.beta.)-; Lanosta-8,24-dien-3-beta-ol; 4,4',14alpha-Trimethyl-5alpha-cholesta-8,24-dien-3beta-ol; EINECS 201-214-9

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

426.7

Topological Polar Surface Area (xlogp)

8.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C30H50O
IUPAC Name: (3S,5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
Canonical SMILES: C[C@H](CCC=C(C)C)[C@H]1CC[C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C
InChI: InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1
InChIKey: CAHGCLMLTWQZNJ-BQNIITSRSA-N

Cross-matching ID

PubChem CID: 246983
ChEBI ID: CHEBI:16521
CAS Number: 79-63-0
DrugBank ID: DB03696
TTD ID: D0P4PQ
INTEDE ID: DR2470

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Lanosterol synthase (LSS)	TT7O8ZA	ERG7_HUMAN	Inhibitor	[2]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 monooxygenase 51A (cyp51A)	DEVSF75	CP51A_ASPFU	Substrate	[3], [4]
Cytochrome P450 51B1 (cyp51)	DEZNP5G	B2HH81_MYCMM	Substrate	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2746).
2	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
3	The fungal CYP51s: their functions, structures, related drug resistance, and inhibitors. Front Microbiol. 2019 Apr 24;10:691.
4	Lung colonization by Aspergillus fumigatus is controlled by ZNF77. Nat Commun. 2018 Sep 20;9(1):3835.
5	Function, essentiality, and expression of cytochrome P450 enzymes and their cognate redox partners in Mycobacterium tuberculosis: are they drug targets? Appl Microbiol Biotechnol. 2019 May;103(9):3597-3614.
6	Toxicologic lesions associated with two related inhibitors of oxidosqualene cyclase in the dog and mouse. Toxicol Pathol. 2001 Mar-Apr;29(2):174-9.
7	Effects of a novel 2,3-oxidosqualene cyclase inhibitor on cholesterol biosynthesis and lipid metabolism in vivo. J Lipid Res. 1997 Mar;38(3):564-75.
8	Effects of a novel 2,3-oxidosqualene cyclase inhibitor on the regulation of cholesterol biosynthesis in HepG2 cells. J Lipid Res. 1996 Jan;37(1):148-58.
9	Cytotoxic effects of combination of oxidosqualene cyclase inhibitors with atorvastatin in human cancer cells. J Med Chem. 2012 Jun 14;55(11):4990-5002.
10	Synthesis and inhibition studies of sulfur-substituted squalene oxide analogues as mechanism-based inhibitors of 2,3-oxidosqualene-lanosterol cyclase. J Med Chem. 1997 Jan 17;40(2):201-9.