Showing metabocard for 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol (BMDB0001286)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:43:37 UTC
Update Date2020-05-21 16:28:43 UTC
BMDB IDBMDB0001286
Secondary Accession Numbers
  • BMDB01286
Metabolite Identification
Common Name4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol
Description4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol, also known as 14-demethyllanosterol or 4,4-dimethyl-8,24-cholestadienol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-olHMDB
14-DemethyllanosterolHMDB
4,4-Dimethyl-5 alpha -cholesta-8,24-dien-3 beta -olHMDB
4,4-Dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-olHMDB
4,4-Dimethyl-5-alpha-cholesta-8,24-dien-3-beta-olHMDB
4,4-Dimethyl-5a-cholesta-8,24-dien-3b-olHMDB
4,4-Dimethyl-5alpha -cholesta-8,24-dien-3-beta -olHMDB
4,4-Dimethyl-5alpha-cholest-7-en-3beta-olHMDB
4,4-Dimethyl-5alpha-cholesta-8,24-dien-3beta-olHMDB
4,4-Dimethyl-8,24-cholestadienolHMDB
4,4-DimethylzymosterolHMDB
4,4-Dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol, (3beta)-isomerHMDB
Chemical FormulaC29H48O
Average Molecular Weight412.6908
Monoisotopic Molecular Weight412.370516158
IUPAC Name(2S,5S,7R,11R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Traditional Name(2S,5S,7R,11R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
CAS Registry Number7448-02-4
SMILES
[H][C@@]12CCC([C@H](C)CCC=C(C)C)[C@@]1(C)CCC1=C2CC[C@@]2([H])C(C)(C)[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C29H48O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,20,22-23,25-26,30H,8,10-18H2,1-7H3/t20-,22?,23+,25+,26+,28-,29-/m1/s1
InChI KeyCHGIKSSZNBCNDW-GKBRUXRCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.14ALOGPS
logP7.41ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity130.07 m³·mol⁻¹ChemAxon
Polarizability53.05 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001286
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022534
KNApSAcK IDNot Available
Chemspider ID25994967
KEGG Compound IDC05108
BioCyc IDNot Available
BiGG ID45128
Wikipedia LinkNot Available
METLIN ID6135
PubChem Compound50990081
PDB IDNot Available
ChEBI ID18364
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Delta(14)-sterol reductase TM7SF2
General function:
Involved in delta14-sterol reductase activity
Specific function:
Catalyzes the reduction of the C14-unsaturated bond of lanosterol, as part of the metabolic pathway leading to cholesterol biosynthesis.
Gene Name:
TM7SF2
Uniprot ID:
Q8WMV1
Molecular weight:
46751.0
Reactions
4,4-Dimethylcholesta-8,14,24-trienol + NADPH → 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADPdetails
Enzyme Details
2. 24-dehydrocholesterol reductase
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
DHCR24
Uniprot ID:
A6QR14
Molecular weight:
60173.0
Reactions
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADPH → 4,4-Dimethyl-5a-cholesta-8-en-3b-ol + NADPdetails
Enzyme Details
3. Methylsterol monooxygenase 1
General function:
Not Available
Specific function:
Not Available
Gene Name:
MSMO1
Uniprot ID:
A6H7G3
Molecular weight:
35061.0
Reactions
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + 3 NADPH + 3 Oxygen → 4a-Methylzymosterol-4-carboxylic acid +3 NADP +4 Waterdetails