Showing Compound Card for 7-Dehydrodesmosterol (CDB005348)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Created at2020-04-17 19:34:12 UTC
Updated at2020-12-07 19:12:00 UTC
CannabisDB IDCDB005348
Secondary Accession NumbersNot Available
Cannabis Compound 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 lipid molecule. 7-Dehydrodesmosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 7-Dehydrodesmosterol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight382.62
Monoisotopic Molecular Weight382.3236
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS7-Dehydrodesmosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0gi0-1019000000-873a0675c614937f5167Spectrum
Predicted GC-MS7-Dehydrodesmosterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-009l-3005900000-0215415f55ca045c8a21Spectrum
Predicted GC-MS7-Dehydrodesmosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Dehydrodesmosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0019000000-efc1163570a7981b43042017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-067i-3149000000-7066d7865c8679b6ce892017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4349000000-c831059d6c69b04010e52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-3be597719610dcae03e82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-2a8728016430bb3e3dd82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-1019000000-aa1ecf0c3ee0da1fc01e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-334e990fc728bf944c792021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-a497ed6306144dc394052021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0009000000-13938bbaae8b6325524c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0029000000-8e9727bf1d7dd88dd6592021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zgi-5089000000-c68d3deb786943f988d62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-9830000000-1416c39d793c0b990a132021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Delta(24)-sterol reductaseDHCR241p32.3Q15392 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0003896
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available

Enzymes

Enzyme Details
1. Delta(24)-sterol reductase
General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:
DHCR24
Uniprot ID:
Q15392
Molecular weight:
60100.805