Details of the Drug

General Information of Drug (ID: DMW2KI5)

Drug Name
24(S), 25-epoxycholesterol
Synonyms 24,25-epoxy-cholesterol
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 400.6
Logarithm of the Partition Coefficient (xlogp) 6.6
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C27H44O2
IUPAC Name
(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-4-[(2S)-3,3-dimethyloxiran-2-yl]butan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Canonical SMILES
C[C@H](CC[C@H]1C(O1)(C)C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O)C)C
InChI
InChI=1S/C27H44O2/c1-17(6-11-24-25(2,3)29-24)21-9-10-22-20-8-7-18-16-19(28)12-14-26(18,4)23(20)13-15-27(21,22)5/h7,17,19-24,28H,6,8-16H2,1-5H3/t17-,19+,20+,21-,22+,23+,24+,26+,27-/m1/s1
InChIKey
OSENKJZWYQXHBN-XVYZBDJZSA-N
Cross-matching ID
PubChem CID
3247059
ChEBI ID
CHEMBL434302
CAS Number
77058-74-3
TTD ID
D0Q2RP
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Oxysterols receptor LXR-alpha (NR1H3) TTECBXN NR1H3_HUMAN Agonist [2]
Oxysterols receptor LXR-beta (NR1H2) TTXA6PH NR1H2_HUMAN Agonist [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [3]
Phospholipid-transporting ATPase ABCA1 (ABCA1) OT94G6BQ ABCA1_HUMAN Gene/Protein Processing [3]
T-lymphocyte activation antigen CD80 (CD80) OTJBLUQE CD80_HUMAN Gene/Protein Processing [4]
Tumor necrosis factor ligand superfamily member 15 (TNFSF15) OTNGA2BW TNF15_HUMAN Gene/Protein Processing [3]
Vascular cell adhesion protein 1 OTP74K37 VCAM1_HUMAN Gene/Protein Processing [3]
Molecular Interaction Atlas (MIA) 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: 2751).
2 Brain endogenous liver X receptor ligands selectively promote midbrain neurogenesis. Nat Chem Biol. 2013 Feb;9(2):126-33.
3 LXR-activating oxysterols induce the expression of inflammatory markers in endothelial cells through LXR-independent mechanisms. Atherosclerosis. 2009 Nov;207(1):38-44.
4 9-cis-Retinoic acid (9cRA), a retinoid X receptor (RXR) ligand, exerts immunosuppressive effects on dendritic cells by RXR-dependent activation: inhibition of peroxisome proliferator-activated receptor gamma blocks some of the 9cRA activities, and precludes them to mature phenotype development. J Immunol. 2007 May 15;178(10):6130-9. doi: 10.4049/jimmunol.178.10.6130.