Compound: cholesterol
SMILES: O[C@@H]1CC2=CC[C@H]3[C@H]4[C@]([C@@H]([C@@H](CCCC(C)C)C)CC4)(C)CC[C@@H]3[C@@]2(C)CC1
InChIKey: HVYWMOMLDIMFJA-DPAQBDIFSA-N
Synonyms: cholesterol, 57-88-5, Cholesterin, Cholest-5-en-3beta-ol, Cholesteryl alcohol, Dythol, Cordulan, Dusoline, Dusoran, Cholesterine, Cholestrin, Cholestrol, Hydrocerin, Lidinite, Kathro, Lanol, Super hartolan, Lidinit, Cholesterol base H, Nimco cholesterol base H, (-)-Cholesterol, 3beta-Hydroxycholest-5-ene, Tegolan, (3beta)-cholest-5-en-3-ol, 5:6-Cholesten-3beta-ol, Provitamin-d, (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol, Cholest-5-en-3-ol (3beta)-, NSC 8798, 5-Cholesten-3B-ol, AI3-03112, NSC-8798, 97C5T2UQ7J, DTXSID3022401, CHEBI:16113, NSC8798, DTXCID402401, (3beta,14beta,17alpha)-cholest-5-en-3-ol, (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((2R)-6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthren-3-ol, 10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthren-3-ol, 10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol, Cholesterol 1551, RefChem:6411, (1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-((2R)-6-methylheptan-2-yl)tetracyclo(8.7.0.02,7.011,15)heptadec-7-en-5-ol, 200-353-2, Cholesterinum, Tegolan (VAN), Cholest-5-en-3-beta-ol, 3-beta-Hydroxycholest-5-ene, Cholest-5-en-3-ol (3.beta.)-, 5-Cholesten-3beta-ol, CCRIS 2834, Dastar, Cholest-5-en-3-ol, HSDB 7106, delta(sup 5)-Cholesten-3-beta-ol, Fancol CH, 3beta-Hydroxy-5-cholestene, 3h-cholesterol, MFCD00003646, Nimco cholesterol base No. 712, Cholesterol (Excipient), 5:6-Cholesten-3-ol, 5-Cholesten-3.beta.-ol, Cholest-5-en-3.beta.-ol, 5,6-Cholesten-3.beta.-ol, 3.beta.-Hydroxycholest-5-ene, (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol, 129111-15-5, C27H46O, NCGC00159351-02, (3.beta.)-cholest-5-en-3-ol, Cholesterol-t, (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-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-dimethylhexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol, CLR, (3H)-Cholesterol, Cholest-5-en-3-ol, (3beta)-, EINECS 200-353-2, epicholesterin, UNII-97C5T2UQ7J, Cholesterol [BAN:JAN:NF], Cholesterol?, .DELTA.5-Cholesten-3-.beta.-ol, Cholesterol CRS, 80356-14-5, 1zhy, Cholest-5-en-3-ol, (3.beta.)- #, 20-epi-cholesterol, 20-iso-cholesterol, Cholesterol, 94%, Liquid crystal CN/9, (+)-ent-Cholesterol, cholest-5-en-3b-ol, 5-Cholesten-3ss--ol, 5-cholestene-3beta-ol, Cholesterol (Standard), Cholesterol in Methanol, Cholesterol (>99%), Cholesterol, 99.0%, CHOLESTEROL [II], CHOLESTEROL [MI], ALF component cholesterol, CHOLESTEROL [JAN], Cholesterol (animal-free), Cholesterol (plant-based), ALFQ component cholesterol, Cholesterol (JP18/NF), 57-88-5(solution), CHOLESTEROL [HSDB], CHOLESTEROL [IARC], Phospholipon & Cholesterol, Cholesterol, Plant-Derived, Delta5-Cholesten-3beta-ol, Epitope ID:150761, CHOLESTEROL [VANDF], EC 200-353-2, 3beta-cholest-5-en-3-ol, 3ss--Hydroxy-5-cholestene, Cholesterol (for injection), SCHEMBL2156, ALF43 component cholesterol, CHOLESTERINUM [HPUS], CHOLESTEROL [MART.], BIDD:PXR0095, (3b)-cholest-5-en-3-ol, CHOLESTEROL [USP-RS], CHOLESTEROL [WHO-DD], 3beta-hydroxy-cholesta-5-ene, 5:6-Cholesten-3.beta.-ol, 20bFH-cholest-5-en-3b-ol, BIDD:ER0548, Cholest-5-en-3-ol (3beta)-, labeled with tritium, (3|A)-cholest-5-en-3-ol, CHEMBL112570, GTPL2718, orb1224601, orb1310316, orb3139450, SCHEMBL9501738, SCHEMBL22206715, SCHEMBL28302508, SCHEMBL31229441, BDBM20192, HY-N0322B, HY-N0322R, (20bFH)-cholest-5-en-3b-ol, CHEBI:140435, CHOLESTEROL [EP MONOGRAPH], Cholesterol, Sigma Grade, >=99%, HY-N0322, Cholesterol (formerly GBW09203b), Tox21_111595, CMC_13392, EBC-03865, LMST01010001, MSK000797, s4154, SBB058670, AKOS005267135, Cholest-5-en-3-ol, (3-.beta.)-, CS-5106, DB04540, FC28806, GS-6857, CAS-57-88-5, Cholesterol, NIST(R) SRM(R) 911c, SMP1_000069, NCGC00159351-03, (1R,3aS,3bS,7S,9aR,9bS,11aR)-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol, 22243-67-0, BP-26125, Cholesterol 10 microg/mL in Acetonitrile, Cholesterol, tested according to Ph.Eur., SY012864, C3624, Cholesterol, from lanolin, >=95.0% (GC), Cholesterol, from lanolin, >=99.0% (GC), CS-1096707, NS00005787, T0760, Army Liposome Formulation component cholesterol, C00187, D00040, EN300-323186, F70214, Q43656, AB00443913_03, Cholesterol, >=95% (GC), powder, Ash, free, Cholesterol, Vetec(TM) reagent grade, >=92.5%, F121530, Soya phospholipon & Cholesterol (2:1 molar ratio), 5BBA213B-ECF4-44AF-8AAF-8A0120F2F886, WLN: L E5 B666 LUTJ A1 E1 FY1&3Y1&1 OQ, Z2033589790, Cholesterol, powder, BioReagent, suitable for cell culture, >=99%, Cholesterol, United States Pharmacopeia (USP) Reference Standard, Cholesterol, Pharmaceutical Secondary Standard; Certified Reference Material, 14-((1R)-1,5-dimethylhexyl)(1S,5S,10S,11S,2R,14R,15R)-2,15-dimethyltetracyclo[ 8.7.0.0<2,7>.0<11,15>]heptadec-7-en-5-ol
Theoretical properties:
molecular_formula: C27H46O
molecular_weight: 386.7 g/mol
exact_mass: 386.354866087 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 5
heavy_atom_count: 28
topological_polar_surface_area: 20.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White or faintly yellow pearly granules or crystals
color: White or faintly yellow pearly granules or crystals
odor: Almost odorless
density: 1.067 @ 20 °C/4 °C
vapor_pressure: VP: 0.171 mm Hg at 149 °C
Descriptions:
pubchem: Cholesterol is a cholestanoid consisting of cholestane having a double bond at the 5,6-position as well as a 3beta-hydroxy group. It has a role as a mouse metabolite, a human metabolite, a Daphnia galeata metabolite and an algal metabolite. It is a C27-steroid, a 3beta-hydroxy-Delta(5)-steroid, a 3beta-sterol and a cholestanoid.
chebi: A cholestanoid consisting of cholestane having a double bond at the 5,6-position as well as a 3β-hydroxy group.
chembl: CHOLESTEROL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Cholesterol is the principal sterol of all animals, distributed in body tissues, especially the brain and spinal cord, and in animal fats and oils.
Cholesterol is biosynthesized by all animal cells and is an essential structural and signaling component of animal cell membranes. In vertebrates, hepatic cells typically produce the greatest amounts. In the brain, astrocytes produce cholesterol and transport it to neurons. It is absent among prokaryotes (bacteria and archaea), although there are some exceptions, such as Mycoplasma, which require cholesterol for growth. Cholesterol also serves as a precursor for the biosynthesis of steroid hormones, bile acid, and vitamin D.
Elevated levels of cholesterol in the blood, especially when bound to low-density lipoprotein (LDL, often referred to as "bad cholesterol"), may increase the risk of cardiovascular disease.
François Poulletier de la Salle first identified cholesterol in solid form in gallstones in 1769. In 1815, chemist Michel Eugène Chevreul named the compound "cholesterine".