lanosterol   

GtoPdb Ligand ID: 2746

Synonyms: (3β)-lanosta-8,24-dien-3-ol | (3β,20R)-lanosta-8,24-dien-3-ol | lanosterin
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 20.23
Molecular weight 426.39
XLogP 10.21
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CC(=CCCC(C1CCC2(C1(C)CCC1=C2CCC2C1(C)CCC(C2(C)C)O)C)C)C
Isomeric SMILES CC(=CCC[C@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@@H](C2(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
InChI Key CAHGCLMLTWQZNJ-BQNIITSRSA-N
References
1. Friggeri L, Hargrove TY, Wawrzak Z, Guengerich FP, Lepesheva GI. (2019)
Validation of Human Sterol 14α-Demethylase (CYP51) Druggability: Structure-Guided Design, Synthesis, and Evaluation of Stoichiometric, Functionally Irreversible Inhibitors.
J. Med. Chem., 62 (22): 10391-10401. [PMID:31663733]
2. Otte K, Kranz H, Kober I, Thompson P, Hoefer M, Haubold B, Remmel B, Voss H, Kaiser C, Albers M, Cheruvallath Z, Jackson D, Casari G, Koegl M, Pääbo S, Mous J, Kremoser C, Deuschle U. (2003)
Identification of farnesoid X receptor beta as a novel mammalian nuclear receptor sensing lanosterol.
Mol. Cell. Biol., 23 (3): 864-72. [PMID:12529392]