Showing Compound Card for 7-Dehydrocholesterol (CDB005347)

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Record Information
Version1.0
Created at2020-04-17 19:34:06 UTC
Updated at2020-12-07 19:12:00 UTC
CannabisDB IDCDB005347
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name7-Dehydrocholesterol
Description7-Dehydrocholesterol, also known as 5,7-cholestadien-3-b-ol or provitamin 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-dehydrocholesterol is considered to be a sterol lipid molecule. 7-Dehydrocholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 7-Dehydrocholesterol is a potentially toxic compound. 7-Dehydrocholesterol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3beta)-Cholesta-5,7-dien-3-olChEBI
5,7-Cholestadien-3-beta-olChEBI
5,7-Cholestadien-3beta-olChEBI
Provitamin D3ChEBI
Cholesta-5,7-dien-3beta-olKegg
(3b)-Cholesta-5,7-dien-3-olGenerator
(3Β)-cholesta-5,7-dien-3-olGenerator
5,7-Cholestadien-3-b-olGenerator
5,7-Cholestadien-3-β-olGenerator
5,7-Cholestadien-3b-olGenerator
5,7-Cholestadien-3β-olGenerator
Cholesta-5,7-dien-3b-olGenerator
Cholesta-5,7-dien-3β-olGenerator
(-)-7-DehydrocholesterolHMDB
10,13-Dimethyl-17-(6-methylheptan-2-yl)-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-olHMDB
17-(1,5-Dimethylhexyl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-olHMDB
5,7-Cholestandien-3-olHMDB
5,7-Cholestandien-3beta-olHMDB
7,8-Dehydro-cholesterolHMDB
7,8-DidehydrocholesterolHMDB
7-Dehydro-cholesterolHMDB
7-DehydrocholesterinHMDB
7DHCHMDB
Cholesta-5,7-dien-3 beta -olHMDB
Cholesta-5,7-dien-3-beta-olHMDB
Cholesta-5,7-dien-3-olHMDB
DehydrocholesterinHMDB
DehydrocholesterolHMDB
Delta5,7-Cholestadien-3beta-olHMDB
Delta5,7-CholesterolHMDB
Delta7-CholesterolHMDB
Provitamin-D3HMDB
Provitamin D(3)HMDB
Cholesta-5,7-dien-3 beta-olHMDB
7-Dehydrocholesterol, (3beta,10alpha)-isomerHMDB
7-Dehydrocholesterol, (3beta,9beta,10alpha)-isomerHMDB
7-DHCHMDB
7-Dehydrocholesterol, (3alpha)-isomerHMDB
7-Dehydrocholesterol, (3beta,9beta)-isomerHMDB
Chemical FormulaC27H44O
Average Molecular Weight384.64
Monoisotopic Molecular Weight384.3392
IUPAC Name(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-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-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
CAS Registry Number434-16-2
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)CCCC(C)C
InChI Identifier
InChI=1S/C27H44O/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/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1
InChI KeyUCTLRSWJYQTBFZ-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 Point150.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.3ALOGPS
logP6.71ChemAxon
logS-6.4ALOGPS
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 Count5ChemAxon
Refractivity121.47 m³·mol⁻¹ChemAxon
Polarizability50.01 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-Dehydrocholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0axr-1019000000-73894a6c7b7346b2d1b0Spectrum
Predicted GC-MS7-Dehydrocholesterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002f-3005900000-c63a75d6ed190e98a35bSpectrum
Predicted GC-MS7-Dehydrocholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Dehydrocholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Dehydrocholesterol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0009000000-124abe0c8995f883f0022012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05oa-4942000000-dbfe3e996983256b1e0c2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05o0-5900000000-8115f37d8da9a1d6f5d82012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 26V, negativesplash10-000i-0090000000-3645f0c0605ff7c974052020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0019000000-d2b535e3c3ed257f22152017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar9-3139000000-87132b4b12416fa4f01e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5249000000-257a8915fd5fab2dfaaa2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-8ff4cced50a3c638abba2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-6d9a73d8f487e848e5382017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ldi-1019000000-eb1f58f2c9df957166402017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-5cafb4a46516e1c4ca5a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ktr-9168000000-27f4addc4e70c9e3fc882021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9510000000-fce215a9f0a5b16bb81c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-4d7a5f3b63c0fb62f1d72021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-4d7a5f3b63c0fb62f1d72021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0009000000-cf419f92ab7dfef8f2f82021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Hydroxymethylglutaryl-CoA synthase, mitochondrialHMGCS21p13-p12P54868 details
Lathosterol oxidaseSC5DL11q23.3O75845 details
Non-specific lipid-transfer proteinSCP21p32P22307 details
7-dehydrocholesterol reductaseDHCR711q13.4Q9UBM7 details
Delta(24)-sterol reductaseDHCR241p32.3Q15392 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Non-specific lipid-transfer proteinSCP21p32P22307 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Lathosterol oxidaseSC5DL11q23.3O75845 details
Cholesterol side-chain cleavage enzyme, mitochondrialCYP11A115q23-q24P05108 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000032
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021882
KNApSAcK IDC00023747
Chemspider IDNot Available
KEGG Compound IDC01164
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link7-Dehydrocholesterol
METLIN IDNot Available
PubChem Compound439423
PDB IDNot Available
ChEBI ID17759
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Hydroxymethylglutaryl-CoA synthase, mitochondrial
General function:
Involved in hydroxymethylglutaryl-CoA synthase activity
Specific function:
This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
Gene Name:
HMGCS2
Uniprot ID:
P54868
Molecular weight:
52481.065
Enzyme Details
2. Lathosterol oxidase
General function:
Involved in iron ion binding
Specific function:
Catalyzes a dehydrogenation to introduce C5-6 double bond into lathosterol.
Gene Name:
SC5DL
Uniprot ID:
O75845
Molecular weight:
35300.55
Enzyme Details
3. Non-specific lipid-transfer protein
General function:
Involved in oxidoreductase activity
Specific function:
Mediates in vitro the transfer of all common phospholipids, cholesterol and gangliosides between membranes. May play a role in regulating steroidogenesis.
Gene Name:
SCP2
Uniprot ID:
P22307
Molecular weight:
34974.505
Enzyme Details
4. 7-dehydrocholesterol reductase
General function:
Involved in 7-dehydrocholesterol reductase activity
Specific function:
Production of cholesterol by reduction of C7-C8 double bond of 7-dehydrocholesterol (7-DHC).
Gene Name:
DHCR7
Uniprot ID:
Q9UBM7
Molecular weight:
54488.98
Enzyme Details
5. 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

Transporters

Enzyme Details
1. Non-specific lipid-transfer protein
General function:
Involved in oxidoreductase activity
Specific function:
Mediates in vitro the transfer of all common phospholipids, cholesterol and gangliosides between membranes. May play a role in regulating steroidogenesis.
Gene Name:
SCP2
Uniprot ID:
P22307
Molecular weight:
34974.505