Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2667)
Drug Name
Obtusifoldienol
Synonyms
Ebericol; Eburicol; 24-Methylenedihydrolanosterol; Q27138657; SCHEMBL4169147; XJLZCPIILZRCPS-ANMPWZFDSA-N; ZINC5440303; (3beta)-24-methylidenelanost-8-en-3-ol; 24-Methylene-24,25-dihydrolanosterol; 24-Methylenelanost-8-en-3-ol #; 24-Methylenelanost-8-en-3beta-ol; 24-Methylenelanostenol; 24-methylene-24-dihydrolanosterol; 24-methylidenelanost-8-en-3beta-ol; 6890-88-6; CHEBI:70315; Lanost-8-en-3-ol, 24-methylene-, (3.beta.)-; Lanost-8-en-3.beta.-ol, 24-methylene-; W2396
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 440.7 Topological Polar Surface Area 20.2
Heavy Atom Count 32 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
9803310
ChEBI ID
CHEBI:70315
CAS Number
6890-88-6
Formula
C31H52O
Canonical SMILES
CC(C)C(=C)CCC(C)C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)O)C)C)C
InChI
1S/C31H52O/c1-20(2)21(3)10-11-22(4)23-14-18-31(9)25-12-13-26-28(5,6)27(32)16-17-29(26,7)24(25)15-19-30(23,31)8/h20,22-23,26-27,32H,3,10-19H2,1-2,4-9H3/t22-,23-,26+,27+,29-,30-,31+/m1/s1
InChIKey
XJLZCPIILZRCPS-ANMPWZFDSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
31-noreburicol DM004055 N. A. Unclear 1 [4]
Obtusifoldienol Metabolite C1 DM004064 N. A. Oxidation - 14alpha-demethylation 1 [5]
Obtusifoliol DM004062
65252
Unclear 1 [4]
14alpha-methyl fecosterol DM004063 N. A. Unclear 2 [4]
4alpha-methyl fecosterol DM004056 N. A. Unclear 2 [4]
Ergosterol DM004061
444679
Unclear 3 [4]
Fecosterol DM004057
440371
Unclear 3 [4]
Ergost-8-enol DM004058 N. A. Unclear 4 [4]
Ergost-7-enol DM004059
129679889
Unclear 5 [4]
Ergost-7,22-enol DM004060 N. A. Unclear 6 [4]
Ergosterol DM004061
444679
Unclear 7 [4]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012917 Obtusifoldienol 31-noreburicol Unclear Unclear [4]
MR012924 Obtusifoldienol Obtusifoliol Unclear Unclear [4]
MR012927 Obtusifoldienol Obtusifoldienol Metabolite C1 Oxidation - 14alpha-demethylation cyp51A [5]
MR012918 31-noreburicol 4alpha-methyl fecosterol Unclear Unclear [4]
MR012925 Obtusifoliol 14alpha-methyl fecosterol Unclear Unclear [4]
MR012926 14alpha-methyl fecosterol Ergosterol Unclear Unclear [4]
MR012919 4alpha-methyl fecosterol Fecosterol Unclear Unclear [4]
MR012920 Fecosterol Ergost-8-enol Unclear Unclear [4]
MR012921 Ergost-8-enol Ergost-7-enol Unclear Unclear [4]
MR012922 Ergost-7-enol Ergost-7,22-enol Unclear Unclear [4]
MR012923 Ergost-7,22-enol Ergosterol Unclear Unclear [4]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 monooxygenase 51A (cyp51A) DME1664 Aspergillus fumigatus
CP51A_ASPFU
1.14.14.154
[2] , [3]
References
1 24-Methylenedihydrolanosterol as a precursor of steroids and triterpenoids. Chemical Communications. 1968;1565-1738.
2 The fungal CYP51s: their functions, structures, related drug resistance, and inhibitors. Front Microbiol. 2019 Apr 24;10:691.
3 Lung colonization by Aspergillus fumigatus is controlled by ZNF77. Nat Commun. 2018 Sep 20;9(1):3835.
4 Sterol 24-C-methyltransferase: an enzymatic target for the disruption of ergosterol biosynthesis and homeostasis in Cryptococcus neoformans
5 Azole Antifungal Sensitivity of Sterol 14-Demethylase (CYP51) and CYP5218 from Malassezia globosa

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