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Showing Compound 7-Dehydrocholesterol (FDB021882)

Record Information
Version1.0
Creation date2011-09-21 00:04:28 UTC
Update date2020-09-17 15:42:04 UTC
Primary IDFDB021882
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number434-16-2
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(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
(-)-7-dehydrocholesterolhmdb
(3β)-cholesta-5,7-dien-3-olGenerator
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
7-dehydro-cholesterolhmdb
7-Dehydrocholesterolhmdb
7,8-dehydro-cholesterolhmdb
cholesta-5,7-dien-3 beta -olhmdb
cholesta-5,7-dien-3b-olhmdb
delta5,7-Cholestadien-3beta-olhmdb
delta5,7-Cholesterolhmdb
delta7-Cholesterolhmdb
provitamin-D3hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
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
Chemical FormulaC27H44O
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
InChI IdentifierInChI=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
Isomeric SMILES[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])C2=CC=C2C[C@@H](O)CC[C@]12C
Average Molecular Weight384.6377
Monoisotopic Molecular Weight384.33921603
Classification
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:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
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
ChemSpider ID388534
ChEMBL IDCHEMBL1797131
KEGG Compound IDC01164
Pubchem Compound ID439423
Pubchem Substance IDNot Available
ChEBI ID17759
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00032
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36958
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID7-Dehydrocholesterol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
7-dehydrocholesterol reductaseDHCR7Q9UBM7
Hydroxymethylglutaryl-CoA synthase, mitochondrialHMGCS2P54868
Non-specific lipid-transfer proteinSCP2P22307
Pathways
NameSMPDB LinkKEGG Link
Steroid BiosynthesisSMP00023 map00100
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference