Details of the Drug

General Information of Drug (ID: DMV8SUM)

Drug Name
desmosterol
Synonyms
DESMOSTEROL; 24-Dehydrocholesterol; 313-04-2; UNII-ANP93865R8; cholest-5,24-dien-3beta-ol; Cholesta-5,24-dien-3beta-ol; NSC 226126; CHEBI:17737; 3beta-cholesta-5,24-dien-3-ol; ANP93865R8; (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; Cholesta-5,24-dien-3-ol; desmesterol; EINECS 206-236-2; 24-dehydro Cholesterol; 24,25-Dehydrocholesterol; AC1L97ME; Cholesta-5,24-dien-3b-ol; 5,24-Cholestadien-3beta-ol; 5,24-Cholestadien-3
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) 384.6
Logarithm of the Partition Coefficient (xlogp) 8.3
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 1
Chemical Identifiers
Formula
C27H44O
IUPAC Name
(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylhept-5-en-2-yl]-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(C)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
InChI
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChIKey
AVSXSVCZWQODGV-DPAQBDIFSA-N
Cross-matching ID
PubChem CID
439577
ChEBI ID
CHEBI:17737
CAS Number
313-04-2
TTD ID
D01RNA
INTEDE ID
DR0437

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Farnesoid X-activated receptor (FXR) TTS4UGC NR1H4_HUMAN Agonist [2]
Oxysterols receptor LXR-alpha (NR1H3) TTECBXN NR1H3_HUMAN Agonist [3]
Oxysterols receptor LXR-beta (NR1H2) TTXA6PH NR1H2_HUMAN Agonist [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Delta(24)-sterol reductase (DHCR24) DEAXY04 DHC24_HUMAN Substrate [4]
Sterol Delta(7)-reductase (DHCR7) DEL7GFA DHCR7_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
C-type lectin domain family 4 member E (CLEC4E) OT7P8ICY CLC4E_HUMAN Gene/Protein Processing [6]
E3 ubiquitin-protein ligase MARCHF6 (MARCHF6) OTBTA03N MARH6_HUMAN Protein Interaction/Cellular Processes [7]
Sterol 26-hydroxylase, mitochondrial (CYP27A1) OT649C01 CP27A_HUMAN Regulation of Drug Effects [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Farnesoid X-activated receptor (FXR) DTT NR1H4 5.72E-01 0.39 1.68
Sterol Delta(7)-reductase (DHCR7) DME DHCR7 1.14E-01 2.27E-01 6.36E-01
Delta(24)-sterol reductase (DHCR24) DME DHCR24 9.64E-01 -1.44E-01 -5.66E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression 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: 2748).
2 Identification of farnesoid X receptor beta as a novel mammalian nuclear receptor sensing lanosterol. Mol Cell Biol. 2003 Feb;23(3):864-72.
3 Sterol intermediates from cholesterol biosynthetic pathway as liver X receptor ligands. J Biol Chem. 2006 Sep 22;281(38):27816-26.
4 Alzheimer's disease: brain desmosterol levels. J Alzheimers Dis. 2013;33(3):881-8.
5 Inhibitors of 7-dehydrocholesterol reductase: screening of a collection of pharmacologically active compounds in Neuro2a cells. Chem Res Toxicol. 2016 May 16;29(5):892-900.
6 Human Mincle Binds to Cholesterol Crystals and Triggers Innate Immune Responses. J Biol Chem. 2015 Oct 16;290(42):25322-32. doi: 10.1074/jbc.M115.645234. Epub 2015 Aug 20.
7 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.
8 Novel sterols synthesized via the CYP27A1 metabolic pathway. Arch Biochem Biophys. 2003 Dec 1;420(1):35-9. doi: 10.1016/j.abb.2003.09.028.