Details of the Drug

General Information of Drug (ID: DMH6LD0)

Drug Name
7alpha-hydroxycholesterol
Synonyms 7-alpha-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) 7.4
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C27H46O2
IUPAC Name
(3S,7S,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]phenanthrene-3,7-diol
Canonical SMILES
C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C=C4[C@@]3(CC[C@@H](C4)O)C)O)C
InChI
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1
InChIKey
OYXZMSRRJOYLLO-RVOWOUOISA-N
Cross-matching ID
PubChem CID
107722
ChEBI ID
CHEBI:17500
CAS Number
566-26-7
TTD ID
D0K5QH

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]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [3]
C-C motif chemokine 3 (CCL3) OTW2H3ND CCL3_HUMAN Gene/Protein Processing [4]
C-C motif chemokine 4 (CCL4) OT6B8P25 CCL4_HUMAN Gene/Protein Processing [4]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [5]
Cholesterol 24-hydroxylase (CYP46A1) OTJ27FOX CP46A_HUMAN Biotransformations [6]
Integrin beta-1 (ITGB1) OT6G1IAR ITB1_HUMAN Gene/Protein Processing [3]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [7]
Lipoprotein lipase (LPL) OTTW0267 LIPL_HUMAN Gene/Protein Processing [8]
Matrix metalloproteinase-9 (MMP9) OTB2QDAV MMP9_HUMAN Gene/Protein Processing [3]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Gene/Protein Processing [9]
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: 4351).
2 Oxysterols direct B-cell migration through EBI2. Nature. 2011 Jul 27;475(7357):519-23.
3 Loading into nanoparticles improves quercetin's efficacy in preventing neuroinflammation induced by oxysterols. PLoS One. 2014 May 6;9(5):e96795.
4 27-Hydroxycholesterol and 7alpha-hydroxycholesterol trigger a sequence of events leading to migration of CCR5-expressing Th1 lymphocytes. Toxicol Appl Pharmacol. 2014 Feb 1;274(3):462-70. doi: 10.1016/j.taap.2013.12.007. Epub 2013 Dec 24.
5 Alpha-tocopherol prevents apoptosis of vascular endothelial cells via a mechanism exceeding that of mere antioxidation. Eur J Pharmacol. 2002 Dec 5;456(1-3):29-37. doi: 10.1016/s0014-2999(02)02639-0.
6 Broad substrate specificity of human cytochrome P450 46A1 which initiates cholesterol degradation in the brain. Biochemistry. 2003 Dec 9;42(48):14284-92.
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 Oxysterols present in atherosclerotic tissue decrease the expression of lipoprotein lipase messenger RNA in human monocyte-derived macrophages. J Clin Invest. 1996 Jan 15;97(2):461-8. doi: 10.1172/JCI118436.
9 7beta-hydroxycholesterol induces Ca(2+) oscillations, MAP kinase activation and apoptosis in human aortic smooth muscle cells. Atherosclerosis. 2000 Nov;153(1):23-35. doi: 10.1016/s0021-9150(00)00380-4.