Details of the Drug

General Information of Drug (ID: DMMJOZD)

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
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 386.664
Logarithm of the Partition Coefficient (xlogp) 8.7
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 1
Chemical Identifiers
Formula
C27H46O
IUPAC Name
(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Canonical SMILES
CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
InChI
HVYWMOMLDIMFJA-DPAQBDIFSA-N
InChIKey
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
Cross-matching ID
PubChem CID
5997
ChEBI ID
ChEBI:15372
CAS Number
17528-72-2
INTEDE ID
DR2314

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cholesterol desmolase (CYP11A1) DE98XPV CP11A_HUMAN Substrate [1]
Vitamin D(3) 25-hydroxylase (CYP27A1) DEBS639 CP27A_HUMAN Substrate [1]
Cholesterol 24-hydroxylase (CYP46A1) DEKP5HX CP46A_HUMAN Substrate [1]
Cytochrome P450 142A2 (cyp142) DEPUK4S CP142_MYCS2 Substrate [2]
Cytochrome P450 125A3 (cyp125) DE6ZDK4 CP125_MYCS2 Substrate [2]
Cytochrome P450 142A1 (cyp142) DEMQ20F CP142_MYCTU Substrate [3]
Cytochrome P450 125A1 (cyp125) DELIXR8 CP125_MYCTU Substrate [3]
Cytochrome P450 7A1 (CYP7A1) DEDZRQ1 CP7A1_HUMAN Substrate [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR) OTRT3F3U HMDH_HUMAN Gene/Protein Processing [4]
7-dehydrocholesterol reductase (DHCR7) OTLILBUI DHCR7_HUMAN Regulation of Drug Effects [5]
Advanced glycosylation end product-specific receptor (AGER) OTPY0IH7 RAGE_HUMAN Regulation of Drug Effects [6]
Amphiregulin (AREG) OTJFOR67 AREG_HUMAN Gene/Protein Processing [7]
Apolipoprotein A-I (APOA1) OT5THARI APOA1_HUMAN Regulation of Drug Effects [8]
Aquaporin-9 (AQP9) OTLGH5ZY AQP9_HUMAN Gene/Protein Processing [7]
ATP-binding cassette sub-family G member 5 (ABCG5) OT1OMY93 ABCG5_HUMAN Regulation of Drug Effects [9]
ATP-binding cassette sub-family G member 8 (ABCG8) OTIJ76XW ABCG8_HUMAN Regulation of Drug Effects [9]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [10]
C-C motif chemokine 1 (CCL1) OT23NON8 CCL1_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Cholesterol-metabolizing cytochromes P450. Drug Metab Dispos. 2006 Apr;34(4):513-20.
2 Cholesterol ester oxidation by mycobacterial cytochrome P450. J Biol Chem. 2014 Oct 31;289(44):30417-25.
3 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.
4 Compared effect of immunosuppressive drugs cyclosporine A and rapamycin on cholesterol homeostasis key enzymes CYP27A1 and HMG-CoA reductase. Basic Clin Pharmacol Toxicol. 2007 Jun;100(6):392-7.
5 Development and characterization of a hypomorphic Smith-Lemli-Opitz syndrome mouse model and efficacy of simvastatin therapy. Hum Mol Genet. 2006 Mar 15;15(6):839-51. doi: 10.1093/hmg/ddl003. Epub 2006 Jan 30.
6 Resveratrol prevents the impairment of advanced glycosylation end products (AGE) on macrophage lipid homeostasis by suppressing the receptor for AGE via peroxisome proliferator-activated receptor gamma activation. Int J Mol Med. 2010 May;25(5):729-34. doi: 10.3892/ijmm_00000398.
7 Human Mincle Binds to Cholesterol Crystals and Triggers Innate Immune Responses. J Biol Chem. 2015 Oct 16;290(42):25322-32. doi: 10.1074/jbc.M115.645234. Epub 2015 Aug 20.
8 Resveratrol mediates anti-atherogenic effects on cholesterol flux in human macrophages and endothelium via PPARgama and adenosine. Eur J Pharmacol. 2013 Jan 5;698(1-3):299-309.
9 Relevance of hereditary defects in lipid transport proteins for the pathogenesis of cholesterol gallstone disease. Scand J Gastroenterol Suppl. 2004;(241):60-9. doi: 10.1080/00855920410011022.
10 Functional characterization of rainbow trout (Oncorhynchus mykiss) Abcg2a (Bcrp) transporter. Comp Biochem Physiol C Toxicol Pharmacol. 2016 Dec;190:15-23. doi: 10.1016/j.cbpc.2016.07.005. Epub 2016 Jul 27.