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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:32 UTC
Update Date2022-03-07 02:49:12 UTC
HMDB IDHMDB0002027
Secondary Accession Numbers
  • HMDB02027
Metabolite Identification
Common Name8-Dehydrocholesterol
Description8-Dehydrocholesterol (8-DHC) elevated concentration is one of the diagnostic biochemical hallmarks of classical Smith-Lemli-Opitz syndrome (SLOS). Plasma 8-DHC could be only marginally elevated. (PMID: 16435228 ). Smith-Lemli-Opitz syndrome (SLOS) is an autosomal recessive condition caused by a defect in cholesterol synthesis (caused by a deficit of 3beta-hydroxysterol-Delta7 reductase). Affected children often have malformations and mental retardation. Autistic behaviors also are evident. In children, the baseline cholesterol, 8-DHC levels, and cholesterol levels following supplementation does not correlate with the presence or severity of autistic symptoms. (PMID: 16761297 ). Accumulation of 8-dehydrocholesterol in Amniotic fluid is diagnostic for SLOS. (PMID 16231320 ).
Structure
Data?1582752224
Synonyms
ValueSource
3b-Cholesta-5,8-dien-3-olHMDB
Cholesta-5,8-dien-3 beta-olMeSH, HMDB
Chemical FormulaC27H44O
Average Molecular Weight384.6377
Monoisotopic Molecular Weight384.33921603
IUPAC Name(2S,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),7-dien-5-ol
Traditional Name8-dehydrocholesterol
CAS Registry Number70741-38-7
SMILES
[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3)[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/h9,18-19,21,23-24,28H,6-8,10-17H2,1-5H3/t19-,21+,23-,24+,26+,27-/m1/s1
InChI KeyVUKORTMHZDZZFR-BXAZICILSA-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-skeleton
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00091 g/LALOGPS
logP6.91ALOGPS
logP6.66ChemAxon
logS-5.6ALOGPS
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
Refractivity121.2 m³·mol⁻¹ChemAxon
Polarizability50.14 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]+195.27331661259
DarkChem[M-H]-194.14231661259
DeepCCS[M-2H]-243.22930932474
DeepCCS[M+Na]+217.90630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-Dehydrocholesterol[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3)[C@H](C)CCCC(C)C2541.0Standard polar33892256
8-Dehydrocholesterol[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3)[C@H](C)CCCC(C)C3146.1Standard non polar33892256
8-Dehydrocholesterol[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3)[C@H](C)CCCC(C)C3087.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-Dehydrocholesterol,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)CC1=CC33211.4Semi standard non polar33892256
8-Dehydrocholesterol,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)CC1=CC33424.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-Dehydrocholesterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ar0-1019000000-8455a6c27493f97ebe562017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Dehydrocholesterol GC-MS (1 TMS) - 70eV, Positivesplash10-002f-3104900000-efe703ec411e4c08c1ab2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Dehydrocholesterol 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 - 8-Dehydrocholesterol 10V, Positive-QTOFsplash10-014r-0009000000-8f5b8c3c66952dc51dc02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 20V, Positive-QTOFsplash10-05p9-3239000000-83a847e9f50d75c56b642016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 40V, Positive-QTOFsplash10-0a4i-5249000000-d434b4187b0bc28431c42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 10V, Negative-QTOFsplash10-001i-0009000000-e7c8524cf153f94d39132016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 20V, Negative-QTOFsplash10-001i-0009000000-484d145862cff531746a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 40V, Negative-QTOFsplash10-0gb9-1009000000-9618317ed2447b79a2522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 10V, Negative-QTOFsplash10-001i-0009000000-4d7a5f3b63c0fb62f1d72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 20V, Negative-QTOFsplash10-001i-0009000000-4d7a5f3b63c0fb62f1d72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 40V, Negative-QTOFsplash10-001i-0009000000-5f56c8ce69939caba8132021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 10V, Positive-QTOFsplash10-00kr-0009000000-76127d016864d5ef3d222021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 20V, Positive-QTOFsplash10-05g0-8469000000-301b48e0bb654ed1e2262021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Dehydrocholesterol 40V, Positive-QTOFsplash10-0a4l-9860000000-09ecca53ca89272c952c2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.65 (0.0-1.3) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified<0.000260 uMChildren (1-13 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified312.0 +/- 52.0 uMAdult (>18 years old)BothSmith-Lemli-Opitz syndrome details
BloodDetected and Quantified0.0754 uMChildren (1-13 years old)MaleChondrodysplasia punctata, X-linked dominant details
Cerebrospinal Fluid (CSF)Detected and Quantified0.3 +/- 0.1 (0.2 - 0.5) uMInfant (0-1 year old)Not SpecifiedSmith-Lemli-Opitz syndrome details
Associated Disorders and Diseases
Disease References
Chondrodysplasia punctata, X-linked dominant
  1. Aughton DJ, Kelley RI, Metzenberg A, Pureza V, Pauli RM: X-linked dominant chondrodysplasia punctata (CDPX2) caused by single gene mosaicism in a male. Am J Med Genet A. 2003 Jan 30;116A(3):255-60. doi: 10.1002/ajmg.a.10852. [PubMed:12503102 ]
Smith-Lemli-Opitz syndrome
  1. van Rooij A, Nijenhuis AA, Wijburg FA, Schutgens RB: Highly increased CSF concentrations of cholesterol precursors in Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 1997 Aug;20(4):578-80. [PubMed:9266395 ]
  2. Honda M, Tint GS, Honda A, Salen G, Shefer S, Batta AK, Matsuzaki Y, Tanaka N: Regulation of cholesterol biosynthetic pathway in patients with the Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 2000 Jul;23(5):464-74. [PubMed:10947201 ]
Associated OMIM IDs
  • 302960 (Chondrodysplasia punctata, X-linked dominant)
  • 270400 (Smith-Lemli-Opitz syndrome)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022805
KNApSAcK IDNot Available
Chemspider ID114943
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound129846
PDB IDNot Available
ChEBI ID89982
Food Biomarker OntologyNot Available
VMH IDCE1297
MarkerDB IDMDB00000367
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. van Rooij A, Nijenhuis AA, Wijburg FA, Schutgens RB: Highly increased CSF concentrations of cholesterol precursors in Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 1997 Aug;20(4):578-80. [PubMed:9266395 ]
  2. Haas D, Armbrust S, Haas JP, Zschocke J, Muhlmann K, Fusch C, Neumann LM: Smith-Lemli-Opitz syndrome with a classical phenotype, oesophageal achalasia and borderline plasma sterol concentrations. J Inherit Metab Dis. 2005;28(6):1191-6. [PubMed:16435228 ]
  3. Sikora DM, Pettit-Kekel K, Penfield J, Merkens LS, Steiner RD: The near universal presence of autism spectrum disorders in children with Smith-Lemli-Opitz syndrome. Am J Med Genet A. 2006 Jul 15;140(14):1511-8. [PubMed:16761297 ]
  4. Chevy F, Humbert L, Wolf C: Sterol profiling of amniotic fluid: a routine method for the detection of distal cholesterol synthesis deficit. Prenat Diagn. 2005 Nov;25(11):1000-6. [PubMed:16231320 ]