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

General Information of Drug (ID: DR2314)
Drug Name
ANW-32821
Synonyms
Cholest-5-en-3-beta-ol; Cholesterol; Cholest-5-en-3-ol (3beta)-; Cholest-5-en-3beta-ol; Cholesterin; Cholesterine; Cholesterol base H; Cholesteryl alcohol; Cholestrin; Cholestrol; Cordulan; Dastar; Dusoline; Dusoran; Dythol; Hydrocerin; Kathro; Lidinit; Lidinite; Nimco cholesterol base H; Provitamin D; Super hartolan; Tegolan; Tegolan (VAN); Wool alcohols B. P.; cholesterol; (-)-Cholesterol; (3beta)-cholest-5-en-3-ol; 3-beta-Hydroxycholest-5-ene; 3beta-Hydroxycholest-5-ene; 5-Cholesten-3beta-ol; 57-88-5; 5:6-Cholesten-3beta-ol; CCRIS 2834; Lanol
Indication Cone rod dystrophy [ICD11: 9B70] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 386.664 Topological Polar Surface Area 20.2
Heavy Atom Count 28 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
5997
PubChem SID
10318723 ; 10586602 ; 12159193 ; 14927473 ; 15054036 ; 2231 ; 24848759 ; 24852491 ; 24856217 ; 24856220 ; 24870712 ; 24892329 ; 24892335 ; 24892388 ; 24893064 ; 24893094 ; 24899653 ; 25621399 ; 26750557 ; 26754461 ; 29203946 ; 29215267 ; 29225011 ; 3132495 ; 3487 ; 4266362 ; 46393729 ; 47211564 ; 47722068 ; 48421907 ; 49684278 ; 49688267 ; 49786946 ; 49833611 ; 49854209 ; 49903086 ; 53787861 ; 56311936 ; 57323103 ; 57647874 ; 629186 ; 74414 ; 7847108 ; 7886645 ; 8025561 ; 8145005 ; 8153730 ; 825929 ; 827331 ; 841782
ChEBI ID
ChEBI:15372
CAS Number
17528-72-2
Formula
C27H46O
Canonical SMILES
CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
InChI
InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChIKey
HVYWMOMLDIMFJA-DPAQBDIFSA-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
24S-hydroxycholesterol DM006713
121948
Unclear 1 [2]
27-hydroxycholesterol DM006710
123976
Unclear 1 [2]
27-hydroxycholesterol DM006710
123976
Unclear 1 [3] , [4]
7alpha-hydroxycholesterol DM006711
107722
Unclear 1 [2]
Pregnenolone DM006712
8955
Unclear 1 [2]
Carboxylic acid DM002458 N. A. Unclear 2 [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007244 ANW-32821 27-hydroxycholesterol Unclear cyp125A1 ... [3], [4]
MR007246 ANW-32821 7alpha-hydroxycholesterol Unclear CYP7A1 [2]
MR007247 ANW-32821 Pregnenolone Unclear CYP11A1 [2]
MR007248 ANW-32821 24S-hydroxycholesterol Unclear CYP46A1 [2]
MR007245 27-hydroxycholesterol Carboxylic acid Unclear cyp124A1 ... [3], [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cholesterol 24-hydroxylase (CYP46A1) DME0028 Homo sapiens
CP46A_HUMAN
1.14.14.25
[2]
Cholesterol desmolase (CYP11A1) DME0099 Homo sapiens
CP11A_HUMAN
1.14.15.6
[2]
Cytochrome P450 124A1 (cyp124A1) DMEN359 Mycobacterium tuberculosis Not Available Not Available [3] , [4]
Cytochrome P450 125A1 (cyp125) DME1551 Mycobacterium tuberculosis
CP125_MYCTU
1.14.15.29
[4]
Cytochrome P450 125A3 (cyp125) DME1549 Mycolicibacterium smegmatis
CP125_MYCS2
1.14.15.29
[3]
Cytochrome P450 142A1 (cyp142) DME1552 Mycobacterium tuberculosis
CP142_MYCTU
1.14.15.28
[4]
Cytochrome P450 142A2 (cyp142) DME1550 Mycolicibacterium smegmatis
CP142_MYCS2
1.14.15.28
[3]
Cytochrome P450 7A1 (CYP7A1) DME0624 Homo sapiens
CP7A1_HUMAN
1.14.14.23
[2]
Steroid C26-monooxygenase (cyp125A1) DMEN355 Mycobacterium tuberculosis
CP125_MYCTU
1.14.15.29
[3] , [4]
Steroid C26-monooxygenase (cyp142A1) DMEN356 Mycobacterium tuberculosis
CP142_MYCTU
1.14.15.28
[3] , [4]
Unclear metabolic mechanism (DME-unclear) DME1548 Eubacterium coprostanoligenes Not Available Not Available [5]
Vitamin D(3) 25-hydroxylase (CYP27A1) DME0026 Homo sapiens
CP27A_HUMAN
1.14.15.15
[2]
⏷ Show the Full List of 12  DME(s)
References
1 ClinicalTrials.gov (NCT01773278) Cholesterol and Antioxidant Treatment in Patients With Smith-Lemli-Opitz Syndrome (SLOS)
2 Cholesterol-metabolizing cytochromes P450. Drug Metab Dispos. 2006 Apr;34(4):513-20.
3 Cholesterol ester oxidation by mycobacterial cytochrome P450. J Biol Chem. 2014 Oct 31;289(44):30417-25.
4 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.
5 Mechanism of cholesterol reduction to coprostanol by Eubacterium coprostanoligenes ATCC 51222. Steroids. 1996 Jan;61(1):33-40.

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