(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-(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
PubChem CID: 9401
Connections displayed (default: 10).
Loading graph...
| Compound Synonyms | SCHEMBL26641636, AKOS030241244 |
|---|---|
| Topological Polar Surface Area | 20.2 |
| Hydrogen Bond Donor Count | 1.0 |
| Inchi Key | AVSXSVCZWQODGV-XWPGJHTNSA-N |
| Rotatable Bond Count | 4.0 |
| State | Solid |
| Substituent Name | Cholesterol-skeleton, Cholesterol, 3-beta-hydroxysteroid, 3-beta-hydroxy-delta-5-steroid, Hydroxysteroid, 3-hydroxysteroid, 3-hydroxy-delta-5-steroid, Delta-5-steroid, Cyclic alcohol, Secondary alcohol, Hydrocarbon derivative, Organooxygen compound, Alcohol, Aliphatic homopolycyclic compound |
| Synonyms | 24-dehydrocholesterol, 3b-Cholesta-5,24-dien-3-ol, 3beta-cholesta-5,24-dien-3-ol, 3beta-Hydroxy-5,24-cholestadiene, 3β-cholesta-5,24-dien-3-ol, 5,24-Cholestadien-3beta-ol, cholest-5,24-dien-3beta-ol, Cholesta-5,24-dien-3-ol, Cholesta-5,24-dien-3-ol, (3&beta, )-, Cholesta-5,24-dien-3&beta, -ol, Cholesta-5,24-dien-3b-ol, cholesta-5,24-dien-3beta-ol, Cholesta-5,24-dien-3β-ol, Delta5,24-cholestadien-3-beta-ol, Desmesterol, Desmosterol, Desmosterol-CPD |
| Heavy Atom Count | 28.0 |
| Pathway Kegg Map Id | map00100 |
| Compound Name | (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-(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 |
| Kingdom | Organic compounds |
| Description | Desmosterol is an intermediate in the synthesis of cholesterol. Desmosterolosis is a rare autosomal recessive inborn errors of cholesterol synthesis that is caused by defective activity of desmosterol reductase which results in an accumulation of demosterol (DHCR24, EC 1.3.1.72), combines a severe osteosclerotic skeletal dysplasia and includes 2-3 toe syndactyly with Smith-Lemli-Opitz syndrome (SLOS, the biochemical block in SLOS results in decreased cholesterol levels and increased 7-dehydrocholesterol levels). Desmosterolosis is caused by mutation of the 24-dehydrocholesterol reductase gene (DHCR24). Many of the malformations in SLOS and desmosterolosis are consistent with impaired hedgehog function. The hedgehog proteins include Sonic hedgehog (SHH), which plays a major role in midline patterning and limb development. Desmosterolosis, caused by defective activity of desmosterol reductase, combines a severe osteosclerotic skeletal dysplasia. 7-dehydrocholesterol reductase (DHCR7, EC 1.3.1.21) reduces the C7-C8 double bond in the sterol B ring to form cholesterol or desmosterol depending upon the precursor. Desmosterol can be converted to cholesterol by DHCR24. Therefore, SLOS and Desmosterolosis patients invariably have elevated levels of cholesterol precursor's 7-dehydrocholesterol (and its spontaneous isomer 8-dehydrocholesterol) and absent desmosterol. (PMID: 14631207, 16207203). Desmosterol is found in many foods, some of which are fig, sago palm, mexican groundcherry, and pepper (c. frutescens). |
| Exact Mass | 384.339 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 384.339 |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 641.0 |
| Hydrogen Bond Acceptor Count | 1.0 |
| Molecular Weight | 384.6 |
| Database Name | fooddb_chem_all;pubchem |
| Covalent Unit Count | 1.0 |
| Defined Atom Stereocenter Count | 7.0 |
| Iupac Name | (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-(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 |
| Total Atom Stereocenter Count | 8.0 |
| Total Bond Stereocenter Count | 0.0 |
| Class | Steroids and steroid derivatives |
| 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+/m0/s1 |
| Smiles | CC(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 |
| Xlogp | 8.3 |
| Superclass | Lipids and lipid-like molecules |
| Defined Bond Stereocenter Count | 0.0 |
| Subclass | Cholestane steroids |
| Molecular Formula | C27H44O |
- 1. Outgoing r'ship
FOUND_INto/from Elettaria Cardamomum (Plant) Rel Props:Source_db:fooddb_chem_all - 2. Outgoing r'ship
FOUND_INto/from Glycine Max (Plant) Rel Props:Source_db:fooddb_chem_all