Compound: DESMOSTEROL
SMILES: O[C@@H]1CC2=CC[C@H]3[C@H]4[C@]([C@@H]([C@@H](CCC=C(C)C)C)CC4)(C)CC[C@@H]3[C@@]2(C)CC1
InChIKey: AVSXSVCZWQODGV-DPAQBDIFSA-N
Synonyms: DESMOSTEROL, 313-04-2, 24-Dehydrocholesterol, desmesterol, cholest-5,24-dien-3beta-ol, CHEBI:17737, DTXSID10878676, ANP93865R8, Cholesta-5,24-dien-3-ol, (3beta)-, (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, NSC-226126, Demosterol, 24 Dehydrocholesterol, (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, RefChem:132268, DTXCID501016718, 206-236-2, 5,24-Cholestadien-3beta-ol, 3beta-cholesta-5,24-dien-3-ol, (3beta)-Cholesta-5,24-dien-3-ol, Cholesta-5,24-dien-3-ol, (3.beta.)-, Cholesta-5,24-dien-3-ol, NSC 226126, 3b-Cholesta-5,24-dien-3-ol, UNII-ANP93865R8, 3|A-Hydroxy-5,24-cholestadiene, MHQ, EINECS 206-236-2, (3|A)-Cholesta-5,24-dien-3-ol, DESMOSTEROL [MI], Cholesterol EP Impurity B, Cholesta-5,24-dien-3b-ol, SCHEMBL156561, Desmosterol, >=84% (GC), CHEMBL455876, GTPL2748, orb1705996, Cholesta-5,24-dien-3-beta-ol, Delta5,24-cholestadien-3-beta-ol, BDBM50280402, LMST01010016, MFCD00056432, AKOS025146947, EBC-618355, FD21370, MSK170595-100M, (1R,3aS,3bS,7S,9aR,9bS,11aR)-9a,11a-dimethyl-1-[(2R)-6-methylhept-5-en-2-yl]-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol, HY-113224, CS-0059348, NS00005490, (3.BETA.)-CHOLESTA-5,24-DIEN-3-OL, C01802, F87896, Q3024529, (3beta)-Cholesta-5,24-dien-3-ol Solution in Methanol, 100ug/mL, (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylhept-5-en-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol, (3S,8S,9S,10R,13R,14S,17R)-17-[(1R)-1,5-dimethylhex-4-enyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Theoretical properties:
molecular_formula: C27H44O
molecular_weight: 384.6 g/mol
exact_mass: 384.339216023 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 4
heavy_atom_count: 28
topological_polar_surface_area: 20.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 121.5 °C
Descriptions:
pubchem: Desmosterol is a cholestanoid that is cholesta-5,24-diene substituted by a beta-hydroxy group at position 3. It is an intermediate metabolite obtained during the synthesis of cholesterol. It has a role as a mouse metabolite and a human metabolite. It is a C27-steroid, a 3beta-hydroxy-Delta(5)-steroid, a 3beta-sterol and a cholestanoid.
chebi: A cholestanoid that is cholesta-5,24-diene substituted by a β-hydroxy group at position 3. It is an intermediate metabolite obtained during the synthesis of cholesterol.
chembl: DESMOSTEROL is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Desmosterol (cholesta-5,24-dien-3β-ol) is a lipid present in the membrane of phytoplankton and an intermediate product in cholesterol synthesis in mammal cells. Structurally, desmosterol has a similar backbone to cholesterol, with the exception of an additional double bond in the structure of desmosterol.
The similarity can be seen biologically through the synthesis of cholesterol in the human body, as desmosterol is the immediate precursor to cholesterol in the Bloch pathway. Desmosterol is accumulated in desmosterolosis and undergoes reduction with the enzyme 24-dehydrocholesterol reductase to form cholesterol.
In 2014, desmosterol was named the Molecule of the Year 2012 by the International Society for Molecular and Cell Biology and Biotechnology Protocols and Researches (ISMCBBPR).