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: CHEMBL353882
CAS Number: 20380-11-4
TTD ID: D0H2YM

Drug-Molecule Activity Atlas (DMA)^NEW

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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]
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
Actin, aortic smooth muscle (ACTA2)	OTEDLG8E	ACTA_HUMAN	Gene/Protein Processing	[4]
Alpha-synuclein (SNCA)	OTPWC1MR	SYUA_HUMAN	Gene/Protein Processing	[5]
Amyloid-beta precursor protein (APP)	OTKFD7R4	A4_HUMAN	Protein Interaction/Cellular Processes	[6]
ATP-dependent translocase ABCB1 (ABCB1)	OTEJROBO	MDR1_HUMAN	Gene/Protein Processing	[7]
C-C motif chemokine 2 (CCL2)	OTAD2HEL	CCL2_HUMAN	Gene/Protein Processing	[8]
C-C motif chemokine 3 (CCL3)	OTW2H3ND	CCL3_HUMAN	Gene/Protein Processing	[9]
C-C motif chemokine 4 (CCL4)	OT6B8P25	CCL4_HUMAN	Gene/Protein Processing	[9]
Cadherin-5 (CDH5)	OTVX0E1Q	CADH5_HUMAN	Gene/Protein Processing	[4]
Catenin beta-1 (CTNNB1)	OTZ932A3	CTNB1_HUMAN	Gene/Protein Processing	[4]
CCN family member 5 (CCN5)	OTADU8JJ	CCN5_HUMAN	Gene/Protein Processing	[10]

Molecular Interaction Atlas (MIA)

MIA Detail

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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: 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	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.
5	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.
6	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.
7	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.
8	Loading into nanoparticles improves quercetin's efficacy in preventing neuroinflammation induced by oxysterols. PLoS One. 2014 May 6;9(5):e96795.
9	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.
10	27-hydroxycholesterol is an endogenous selective estrogen receptor modulator. Mol Endocrinol. 2008 Jan;22(1):65-77. doi: 10.1210/me.2007-0383. Epub 2007 Sep 13.