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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 06:55:06 UTC
Update Date2017-12-07 01:52:46 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
Thumb
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-olMeSH
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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol
Traditional Name7-dehydrodesmosterol
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
DescriptionThis compound belongs to the class of organic compounds known as cholesterols and derivatives. These 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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Multicellular process:

Role

Industrial application:

Biological role:

  Molecular messenger:

Physiological effect

Health effect:

  Health condition:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.101Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00064 g/LALOGPS
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
Polarizability48.9 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
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 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
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Alendronate pathwayPw000137Pw000137 greyscalePw000137 simpleNot Available
Atorvastatin PathwayPw000275Pw000275 greyscalePw000275 simpleNot Available
CHILD SyndromePw000096Pw000096 greyscalePw000096 simpleNot Available
Cerivastatin PathwayPw000271Pw000271 greyscalePw000271 simpleNot Available
Cholesteryl ester storage diseasePw000484Pw000484 greyscalePw000484 simpleNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012781
KNApSAcK IDNot Available
Chemspider ID389458
KEGG Compound IDC05107
BioCyc IDNot Available
BiGG ID45126
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440558
PDB IDNot Available
ChEBI ID27910
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