Showing metabocard for 7-Dehydrodesmosterol (BMDB0003896)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:06:30 UTC
Update Date2020-05-21 16:27:04 UTC
BMDB IDBMDB0003896
Secondary Accession Numbers
  • BMDB03896
Metabolite Identification
Common Name7-Dehydrodesmosterol
Description7-Dehydrodesmosterol, also known as 24-dehydroprovitamin D3, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7-dehydrodesmosterol is considered to be a sterol. Based on a literature review a significant number of articles have been published on 7-Dehydrodesmosterol.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
24-Dehydroprovitamin D3ChEBI
Cholesta-5,7,24-trien-3beta-olChEBI
Cholesta-5,7,24-triene-3beta-olChEBI
Cholesta-5,7,24-trien-3b-olGenerator
Cholesta-5,7,24-trien-3β-olGenerator
Cholesta-5,7,24-triene-3b-olGenerator
Cholesta-5,7,24-triene-3β-olGenerator
Cholesta-5,7,24-trien-3 beta-olHMDB
Chemical FormulaC27H42O
Average Molecular Weight382.6218
Monoisotopic Molecular Weight382.323565966
IUPAC Name(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
Traditional Name(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
CAS Registry Number1715-86-2
SMILES
[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC=C(C)C
InChI Identifier
InChI=1S/C27H42O/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/h7,9-10,19,21,23-25,28H,6,8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1
InChI KeyRUSSPKPUXDSHNC-DDPQNLDTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol
  • Cholesterol-skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxy-delta-7-steroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • Delta-7-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.101Not Available
Predicted Properties
PropertyValueSource
logP7.46ALOGPS
logP6.3ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)18.27ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity122.32 m³·mol⁻¹ChemAxon
Polarizability48.87 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gi0-1019000000-873a0675c614937f5167View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-009l-3005900000-0215415f55ca045c8a21View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0019000000-efc1163570a7981b4304View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-067i-3149000000-7066d7865c8679b6ce89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4349000000-c831059d6c69b04010e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-3be597719610dcae03e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-2a8728016430bb3e3dd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-1019000000-aa1ecf0c3ee0da1fc01eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-334e990fc728bf944c79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-a497ed6306144dc39405View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0009000000-13938bbaae8b6325524cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0029000000-8e9727bf1d7dd88dd659View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zgi-5089000000-c68d3deb786943f988d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-9830000000-1416c39d793c0b990a13View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0003896
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030623
KNApSAcK IDC00055229
Chemspider ID389458
KEGG Compound IDC05107
BioCyc IDCPD-8646
BiGG ID45126
Wikipedia Link7-Dehydrodesmosterol
METLIN IDNot Available
PubChem Compound440558
PDB IDNot Available
ChEBI ID27910
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 24-dehydrocholesterol reductase
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
DHCR24
Uniprot ID:
A6QR14
Molecular weight:
60173.0
Reactions
7-Dehydrodesmosterol + NADPH → 7-Dehydrocholesterol + NADPdetails