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]
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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: CHEBI:42977
CAS Number: 2140-46-7
DrugBank ID: DB04705
TTD ID: D06OVX

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]

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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]
Acyl-CoA (FADS1)	OTUYOYHX	FADS1_HUMAN	Gene/Protein Processing	[5]
Adiponectin receptor protein 1 (ADIPOR1)	OT65ZFZN	PAQR1_HUMAN	Gene/Protein Processing	[6]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[7]
Cytochrome P450 7A1 (CYP7A1)	OT8Z5KLD	CP7A1_HUMAN	Regulation of Drug Effects	[8]
E3 ubiquitin-protein ligase MARCHF6 (MARCHF6)	OTBTA03N	MARH6_HUMAN	Protein Interaction/Cellular Processes	[9]
Interleukin-1 beta (IL1B)	OT0DWXXB	IL1B_HUMAN	Gene/Protein Processing	[10]
Interleukin-6 (IL6)	OTUOSCCU	IL6_HUMAN	Protein Interaction/Cellular Processes	[10]
Interleukin-8 (CXCL8)	OTS7T5VH	IL8_HUMAN	Gene/Protein Processing	[11]
Lipoprotein lipase (LPL)	OTTW0267	LIPL_HUMAN	Gene/Protein Processing	[12]

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Molecular Interaction Atlas (MIA)

MIA Detail

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: 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	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	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.
6	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.
7	Quercetin-3-O-(2-galloyl)--L-rhamnopyranoside attenuates cholesterol oxidation product-induced apoptosis by suppressing NF-B-mediated cell death process in differentiated PC12 cells. Naunyn Schmiedebergs Arch Pharmacol. 2015 Aug;388(8):869-81. doi: 10.1007/s00210-015-1120-7. Epub 2015 Apr 7.
8	Oxysterol 7 alpha-hydroxylase activity by cholesterol 7 alpha-hydroxylase (CYP7A). J Biol Chem. 2000 Nov 3;275(44):34046-53. doi: 10.1074/jbc.M002663200.
9	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.
10	Oxysterols induce interleukin-1beta production in human macrophages. Eur J Clin Invest. 2002 Jan;32(1):35-42. doi: 10.1046/j.1365-2362.2002.00931.x.
11	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.
12	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.