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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 06:55:06 UTC
Update Date2021-09-14 15:19:03 UTC
HMDB IDHMDB0003896
Secondary Accession Numbers
  • HMDB03896
Metabolite Identification
Common Name7-Dehydrodesmosterol
Description7-Dehydrodesmosterol is a sterol intermediate in the biosynthesis of steroids. 7-Dehydrodesmosterol is a substrate of the enzyme 24-dehydrocholesterol reductase (EC:1.3.1.72), an important enzyme in the biosynthesis of Cholesterol. Cholesterol is synthesized from either Lathosterol, 7-Dehydrocholesterol, Desmosterol or Cholestenol by the enzyme 3beta-hydroxysterol delta7 reductase (EC 1.3.1.21, Dhcr7). The Smith-Lemli-Opitz syndrome (SLOS, OMIM 270400 ) is caused by a genetic defect in cholesterol biosynthesis; mutations in the enzyme 3beta-hydroxysterol delta7 reductase lead to a failure of cholesterol synthesis, with an accumulation of precursor sterols, such as 7-Dehydrodesmosterol. SLOS results in craniofacial, limb as well as major organ defects, including the brain. In individuals with this syndrome, mental retardation, as well as other CNS dysfunction, is almost 100% prevalent. (PMID: 15862627 , 17197219 ).
Structure
Data?1589313623
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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.101Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00064 g/LALOGPS
logP10(7.46) g/LALOGPS
logP10(6.3) g/LChemAxon
logS10(-5.8) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+190.49531661259
DarkChem[M-H]-187.29831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
7-Dehydrodesmosterol[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)C3030.8Standard polar33892256
7-Dehydrodesmosterol[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)C3150.9Standard non polar33892256
7-Dehydrodesmosterol[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)C3147.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7-Dehydrodesmosterol,1TMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3283.1Semi standard non polar33892256
7-Dehydrodesmosterol,1TBDMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3517.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7-Dehydrodesmosterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gi0-1019000000-873a0675c614937f51672017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-Dehydrodesmosterol GC-MS (1 TMS) - 70eV, Positivesplash10-009l-3005900000-0215415f55ca045c8a212017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-Dehydrodesmosterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-Dehydrodesmosterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydrodesmosterol 10V, Positive-QTOFsplash10-0159-0019000000-efc1163570a7981b43042017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydrodesmosterol 20V, Positive-QTOFsplash10-067i-3149000000-7066d7865c8679b6ce892017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydrodesmosterol 40V, Positive-QTOFsplash10-0a4i-4349000000-c831059d6c69b04010e52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydrodesmosterol 10V, Negative-QTOFsplash10-001i-0009000000-3be597719610dcae03e82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydrodesmosterol 20V, Negative-QTOFsplash10-001i-0009000000-2a8728016430bb3e3dd82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydrodesmosterol 40V, Negative-QTOFsplash10-014j-1019000000-aa1ecf0c3ee0da1fc01e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydrodesmosterol 10V, Negative-QTOFsplash10-001i-0009000000-334e990fc728bf944c792021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydrodesmosterol 20V, Negative-QTOFsplash10-001i-0009000000-a497ed6306144dc394052021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydrodesmosterol 40V, Negative-QTOFsplash10-004i-0009000000-13938bbaae8b6325524c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydrodesmosterol 10V, Positive-QTOFsplash10-001i-0029000000-8e9727bf1d7dd88dd6592021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydrodesmosterol 20V, Positive-QTOFsplash10-0zgi-5089000000-c68d3deb786943f988d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydrodesmosterol 40V, Positive-QTOFsplash10-0a4m-9830000000-1416c39d793c0b990a132021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDDDSMSTEROL
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yu H, Wessels A, Tint GS, Patel SB: Partial rescue of neonatal lethality of Dhcr7 null mice by a nestin promoter-driven DHCR7 transgene expression. Brain Res Dev Brain Res. 2005 Apr 21;156(1):46-60. [PubMed:15862627 ]
  2. Solca C, Pandit B, Yu H, Tint GS, Patel SB: Loss of apolipoprotein E exacerbates the neonatal lethality of the Smith-Lemli-Opitz syndrome mouse. Mol Genet Metab. 2007 May;91(1):7-14. Epub 2007 Jan 2. [PubMed:17197219 ]

Enzymes

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
Reactions
7-Dehydrodesmosterol + NADPH + Hydrogen Ion → 7-Dehydrocholesterol + NADPdetails