Human Metabolome Database Version 3.5

Showing metabocard for 24-Methylenecholesterol (HMDB06849)

Record Information
Version 3.5
Creation Date 2008-08-13 07:39:23 -0600
Update Date 2013-02-08 17:15:26 -0700
Secondary Accession Numbers None
Metabolite Identification
Common Name 24-Methylenecholesterol
Description 24-Methylenecholesterol is involved in the biosynthesis of steroids. 24-Methylenecholesterol is converted from 5-Dehydroepisterol by 7-dehydrocholesterol reductase [EC:]. 24-Methylenecholesterol is converted to Campesterol by delta24-sterol reductase [EC:].
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
  1. (3b)-Ergosta-5,24(28)-dien-3-ol
  2. 24-Methylencholesterol
  3. 24-Methylene-Cholesterol
  4. Chalinasterol
  5. Ergosta-5, 24(28)-dien-3b-ol
  6. Ergosta-5,24(28)-dien-3-ol
  7. Ergosta-5,24(28)-dien-3b-ol
  8. Ostreasterol
Chemical Formula C28H46O
Average Molecular Weight 398.6642
Monoisotopic Molecular Weight 398.354866094
IUPAC Name (1S,2R,5S,11S,14R,15R)-2,15-dimethyl-14-[(2S)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[^{2,7}.0^{11,15}]heptadec-7-en-5-ol
Traditional IUPAC Name (1S,2R,5S,11S,14R,15R)-2,15-dimethyl-14-[(2S)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[^{2,7}.0^{11,15}]heptadec-7-en-5-ol
CAS Registry Number 474-63-5
SMILES [H][C@@]1(CC[C@@]2([H])C3CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@@H](C)CCC(=C)C(C)C
InChI Identifier InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18,20,22-26,29H,3,7-8,10-17H2,1-2,4-6H3/t20-,22-,23?,24+,25-,26-,27-,28+/m0/s1
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Ergosterols and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Triterpenes
  • a steroid(Cyc)
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Isoprene
  • Secondary Alcohol
Direct Parent Ergosterols and Derivatives
Status Expected and Not Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.900E-04 g/L ALOGPS
LogP 6.61 ALOGPS
LogP 7.05 ChemAxon
LogS -6.32 ALOGPS
pKa (strongest acidic) 18.2 ChemAxon
pKa (strongest basic) -1.4 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 124.94 ChemAxon
Polarizability 51.06 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB001361
KNApSAcK ID C00007271 Link_out
Chemspider ID Not Available
KEGG Compound ID C15781 Link_out
BioCyc ID CPD-706 Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06849 Link_out
Metagene Link HMDB06849 Link_out
METLIN ID Not Available
PubChem Compound 53477901 Link_out
PDB ID Not Available
ChEBI ID 19812 Link_out
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Name: 7-dehydrocholesterol reductase
5-Dehydroepisterol unknown 24-Methylenecholesterol details
Gene Name: DHCR7
Uniprot ID: Q9UBM7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Delta(24)-sterol reductase
24-Methylenecholesterol + NADPH + Hydrogen Ion unknown Campesterol + NADP details
Gene Name: DHCR24
Uniprot ID: Q15392 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA