Details of the Drug

General Information of Drug (ID: DM2L6OZ)

Drug Name
27-hydroxycholesterol
Synonyms 27-OHC; 26-hydroxycholesterol
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) 7.1
Rotatable Bond Count (rotbonds) 6
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,6R)-7-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](CCC[C@@H](C)[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)CO
InChI
InChI=1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChIKey
FYHRJWMENCALJY-YSQMORBQSA-N
Cross-matching ID
PubChem CID
123976
ChEBI ID
CHEBI:76591
CAS Number
20380-11-4
TTD ID
D0H2YM

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]
Oxysterols receptor LXR-alpha (NR1H3) TTECBXN NR1H3_HUMAN Agonist [3]
Oxysterols receptor LXR-beta (NR1H2) TTXA6PH NR1H2_HUMAN Agonist [3]

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]
Actin, aortic smooth muscle (ACTA2) OTEDLG8E ACTA_HUMAN Gene/Protein Processing [5]
Alpha-synuclein (SNCA) OTPWC1MR SYUA_HUMAN Gene/Protein Processing [6]
Amyloid-beta precursor protein (APP) OTKFD7R4 A4_HUMAN Protein Interaction/Cellular Processes [7]
ATP-binding cassette sub-family G member 1 (ABCG1) OT5BG6MK ABCG1_HUMAN Gene/Protein Processing [8]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [9]
Beta-secretase 1 (BACE1) OTCA7B6A BACE1_HUMAN Gene/Protein Processing [10]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [11]
C-C motif chemokine 3 (CCL3) OTW2H3ND CCL3_HUMAN Gene/Protein Processing [12]
C-C motif chemokine 4 (CCL4) OT6B8P25 CCL4_HUMAN Gene/Protein Processing [12]
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: 2752).
2 Oxysterols direct B-cell migration through EBI2. Nature. 2011 Jul 27;475(7357):519-23.
3 27-hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells. J Biol Chem. 2001 Oct 19;276(42):38378-87.
4 Studies on the relationships between 7 alpha-hydroxylation and the ability of 25- and 27-hydroxycholesterol to suppress the activity of HMG-CoA reductase. Biochim Biophys Acta. 1997 Feb 18;1344(3):241-9.
5 The 14-3-3/GSK-3/-catenin complex regulates EndMT induced by 27-hydroxycholesterol in HUVECs and promotes the migration of breast cancer cells. Cell Biol Toxicol. 2021 Aug;37(4):515-529. doi: 10.1007/s10565-020-09564-y. Epub 2020 Nov 1.
6 Regulation of alpha-synuclein expression by liver X receptor ligands in vitro. Neuroreport. 2008 Nov 19;19(17):1685-9. doi: 10.1097/WNR.0b013e32831578b2.
7 Impact of 27-hydroxycholesterol on amyloid-beta peptide production and ATP-binding cassette transporter expression in primary human neurons. J Alzheimers Dis. 2009;16(1):121-31. doi: 10.3233/JAD-2009-0944.
8 PXR induces CYP27A1 and regulates cholesterol metabolism in the intestine. J Lipid Res. 2007 Feb;48(2):373-84.
9 27-Hydroxycholesterol is a specific factor in the neoplastic microenvironment of HCC that causes MDR via GRP75 regulation of the redox balance and metabolic reprogramming. Cell Biol Toxicol. 2022 Apr;38(2):311-324. doi: 10.1007/s10565-021-09607-y. Epub 2021 Apr 20.
10 Differential effects of 24-hydroxycholesterol and 27-hydroxycholesterol on beta-amyloid precursor protein levels and processing in human neuroblastoma SH-SY5Y cells. Mol Neurodegener. 2009 Jan 6;4:1. doi: 10.1186/1750-1326-4-1.
11 Loading into nanoparticles improves quercetin's efficacy in preventing neuroinflammation induced by oxysterols. PLoS One. 2014 May 6;9(5):e96795.
12 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.