24-Methylenecholesterol
Basic information
- CAS
474-63-5- Standard SMILES
C=C(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C- InChIKey
INDVLXYUCBVVKW-PXBBAZSNSA-N- Molecular formula
- C28H46O
- Average molar mass
- 398.7 g/mol
- Monoisotopic mass
- 398.35486609
Overview
24-methylenecholesterol is a 3beta-sterol having the structure of cholesterol with a methylene group at C-24. It has a role as a mouse metabolite. It is a 3beta-hydroxy-Delta(5)-steroid and a 3beta-sterol. It is functionally related to a cholesterol.
Names & identifiers
- Preferred name
- 24-Methylenecholesterol
- IUPAC
- (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
- English name
- 5,24(28)-Cholestadien-24-methylen-3beta-ol
- Molecular formula
- C28H46O
- Molecular weight
- 398.66
Names & synonyms
24-MethylenecholesterolChalinasterolOstreasterol474-63-5SJ0718OYKX24-methylene-cholest-5-en-3beta-olCHEBI:19812DTXSID80963826NSC-232664(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((2R)-6-methyl-5-methylideneheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthren-3-olRefChem:910353
Show more names
Nsc 232664Ergosta-5,24(28)-dien-3β-olErgosta-5,24(28)-dien-3beta-ol5α-Ergosta-5,24(28)-dien-3β-olErgosta-5,24(28)-dien-3-ol, (3β)-Cholesterol 24-Methylene ImpurityErgosta-5,24(28)-dien-3beta-ol (8ci)24-Methylcholesta-5,24(28)-dien-3β-ol
DTXCID601837713ergosta-5,24(28)-dien-3 beta-ol24-methylencholesterol24-methylene-CholesterolCholesterol, 24-methylene-(3beta,14beta,17alpha)-ergosta-5,24(28)-dien-3-ol(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methyl-5-methyleneheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol24-Methylene cholesterol
Database identifiers
- CAS
474-63-5- PubChem CID
- 92113
- DTXSID
DTXSID80963826- ChEMBL
CHEMBL477971- ChEBI
CHEBI:19812- UNII
- SJ0718OYKX
- Nikkaji
- J12.062F
Properties
Computed structural properties
- XLogP
- 8.6
- Topological polar surface area
- 20.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 5
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 659
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Ergosterols and C24-methyl derivatives [ST0103]
Physical DescriptionSolid
Physicochemical properties
- storage temp.
- -20 °C · -20°C
- solubility
- Chloroform (Slightly), Methanol (Slightly, Heated)
- form
- Solid
- color
- White
- InChIKey
- INDVLXYUCBVVKW-PXBBAZSNSA-N
- SMILES
- CC1(CC[C@H](O)C2)C2=CCC3C1CCC4(C)C3CCC4C(CCC(C(C)C)=C)C
- FDA UNII
- 718 OYKX · SJ0718OYKX
- UNSPSC Code
- 12352211 · 12352211
- NACRES
- 25 · NA.25
- WGK Germany
- 3 · WGK 3
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
UsesOstreasterol is a marine steroid, and also a derivative compound of hydroxycholesterol (H918040), which functions as the main cholesterol elimination product of the brain and was found to be increased in serum of Alzheimer patients.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: A 3beta-sterol having the structure of cholesterol with a methylene group at C-24.
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