Details of the Drug

General Information of Drug (ID: DMCHAQ7)

Drug Name
25-hydroxycholesterol
Synonyms 25-OHC
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) 402.7
Logarithm of the Partition Coefficient (xlogp) 6.8
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C27H46O2
IUPAC Name
(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-6-hydroxy-6-methylheptan-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](CCCC(C)(C)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
InChI
InChI=1S/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1
InChIKey
INBGSXNNRGWLJU-ZHHJOTBYSA-N
Cross-matching ID
PubChem CID
65094
ChEBI ID
CHEMBL169046
CAS Number
2140-46-7
UNII
767JTD2N31
DrugBank ID
DB04705
TTD ID
D06OVX
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
EBV-induced G-protein coupled receptor 2 (GPR183) TTME5YJ GP183_HUMAN Agonist [2]
Nuclear receptor ROR-gamma (RORG) TTGV6LY RORG_HUMAN Agonist [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Acyl-CoA (FADS1) OTUYOYHX FADS1_HUMAN Gene/Protein Processing [4]
Adiponectin receptor protein 1 (ADIPOR1) OT65ZFZN PAQR1_HUMAN Gene/Protein Processing [5]
E3 ubiquitin-protein ligase MARCHF6 (MARCHF6) OTBTA03N MARH6_HUMAN Protein Interaction/Cellular Processes [6]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [7]
Stearoyl-CoA desaturase (SCD) OTB1073G SCD_HUMAN Gene/Protein Processing [8]
Steroidogenic factor 1 (NR5A1) OTOULYR4 STF1_HUMAN Gene/Protein Processing [9]
Sterol regulatory element-binding protein 2 (SREBF2) OTBXUNPL SRBP2_HUMAN Gene/Protein Processing [10]
Tumor necrosis factor ligand superfamily member 15 (TNFSF15) OTNGA2BW TNF15_HUMAN Gene/Protein Processing [11]
Vascular cell adhesion protein 1 OTP74K37 VCAM1_HUMAN Gene/Protein Processing [11]
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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: 2885).
2 Oxysterols direct B-cell migration through EBI2. Nature. 2011 Jul 27;475(7357):519-23.
3 Structural basis for hydroxycholesterols as natural ligands of orphan nuclear receptor RORgamma. Mol Endocrinol. 2010 May;24(5):923-9.
4 Delta5 desaturase mRNA levels are increased by simvastatin via SREBP-1 at early stages, not via PPARalpha, in THP-1 cells. Eur J Pharmacol. 2007 Oct 1;571(2-3):97-105.
5 Regulation of adiponectin receptor 1 in human hepatocytes by agonists of nuclear receptors. Biochem Biophys Res Commun. 2005 Sep 2;334(3):924-9. doi: 10.1016/j.bbrc.2005.06.187.
6 Cholesterol increases protein levels of the E3 ligase MARCH6 and thereby stimulates protein degradation. J Biol Chem. 2019 Feb 15;294(7):2436-2448. doi: 10.1074/jbc.RA118.005069. Epub 2018 Dec 13.
7 Comparison of the cytotoxic, pro-oxidant and pro-inflammatory characteristics of different oxysterols. Cell Biol Toxicol. 2005 Mar;21(2):97-114. doi: 10.1007/s10565-005-0141-2.
8 Inhibition of SREBP increases gefitinib sensitivity in non-small cell lung cancer cells. Oncotarget. 2016 Aug 9;7(32):52392-52403.
9 Activation of the orphan nuclear receptor steroidogenic factor 1 by oxysterols. Proc Natl Acad Sci U S A. 1997 May 13;94(10):4895-900. doi: 10.1073/pnas.94.10.4895.
10 Drug-induced activation of SREBP-controlled lipogenic gene expression in CNS-related cell lines: marked differences between various antipsychotic drugs. BMC Neurosci. 2006 Oct 20;7:69.
11 LXR-activating oxysterols induce the expression of inflammatory markers in endothelial cells through LXR-independent mechanisms. Atherosclerosis. 2009 Nov;207(1):38-44.