Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:47 UTC
HMDB IDHMDB00032
Secondary Accession NumbersNone
Metabolite Identification
Common Name7-Dehydrocholesterol
Description7-Dehydrocholesterol is a zoosterol (a sterol produced by animals rather than plants). It is a provitamin-D. The presence of this compound in skin enables humans to manufacture vitamin D3 from ultra-violet rays in the sun light, via an intermediate isomer provitamin D3. It is also found in breast milk.
Structure
Thumb
Synonyms
  1. (-)-7-dehydrocholesterol
  2. (3b)-Cholesta-5,7-dien-3-ol
  3. (3beta)-Cholesta-5,7-dien-3-ol
  4. 10,13-Dimethyl-17-(6-methylheptan-2-yl)-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
  5. 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-ol
  6. 5,7-Cholestadien-3-beta-ol
  7. 5,7-Cholestandien-3-ol
  8. 5,7-Cholestandien-3beta-ol
  9. 7,8-Dehydro-cholesterol
  10. 7,8-Didehydrocholesterol
  11. 7-Dehydro-cholesterol
  12. 7-Dehydrocholesterin
  13. 7-Dehydrocholesterol
  14. 7DHC
  15. Cholesta-5,7-dien-3 beta -ol
  16. Cholesta-5,7-dien-3-beta-ol
  17. Cholesta-5,7-dien-3-ol
  18. Cholesta-5,7-dien-3b-ol
  19. Cholesta-5,7-dien-3beta-ol
  20. Dehydrocholesterin
  21. Dehydrocholesterol
  22. Delta5,7-Cholestadien-3beta-ol
  23. Delta5,7-Cholesterol
  24. Delta7-Cholesterol
  25. Provitamin D3
  26. Provitamin-D3
Chemical FormulaC27H44O
Average Molecular Weight384.6377
Monoisotopic Molecular Weight384.33921603
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 IUPAC Name7-dehydrocholesterol
CAS Registry Number434-16-2
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
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
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassCholesterols and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Cholesterol and derivatives(Lipidmaps)
Substituents
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Secondary Alcohol
  • Sesterterpene
Direct ParentCholesterols and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
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
water solubility1.480E-04 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 area20.23ChemAxon
rotatable bond count5ChemAxon
refractivity121.47ChemAxon
polarizability49.94ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adrenal Gland
  • Brain
  • Fetus
  • Fibroblasts
  • Liver
  • Skin
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Steroid BiosynthesisSMP00023map00100
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified5.0 +/- 2.2 uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0 - 0.02 uMAdult (>18 years old)BothNormal
UrineDetected and Quantified0.029 (0.0068-0.051) umol/mmol creatinineAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified369.0 (46.0 - 1220.0) uMAdult (>18 years old)BothSmith-Lemli-Opitz syndrome
Cerebrospinal Fluid (CSF)Detected and Quantified0.3 +/- 0.2 (0.1 - 0.6) uMInfant (0-1 year old)BothSmith-Lemli-Opitz syndrome
Associated Disorders and Diseases
Disease References
Smith-Lemli-Opitz syndrome
  • 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
  • Johnson DW, ten Brink HJ, Jakobs C: A rapid screening procedure for cholesterol and dehydrocholesterol by electrospray ionization tandem mass spectrometry. J Lipid Res. 2001 Oct;42(10):1699-705. Pubmed: 11590227
Associated OMIM IDs
    270400 (Smith-Lemli-Opitz syndrome)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021882
KNApSAcK IDNot Available
Chemspider ID388534
KEGG Compound IDC01164
BioCyc ID7-DEHYDRO-CHOLESTEROL
BiGG ID36958
Wikipedia Link7-Dehydrocholesterol
NuGOwiki LinkHMDB00032
Metagene LinkHMDB00032
METLIN ID5101
PubChem Compound439423
PDB IDNot Available
ChEBI ID17759
References
Synthesis ReferenceWilliam G. Dauben, Jerome F. Eastham, and Robert A. Micheli A new method for the preparation of 7-dehydrocholesterol. Journal of the American Chemical Society (1951), 73 4496.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lehmann B, Genehr T, Knuschke P, Pietzsch J, Meurer M: UVB-induced conversion of 7-dehydrocholesterol to 1alpha,25-dihydroxyvitamin D3 in an in vitro human skin equivalent model. J Invest Dermatol. 2001 Nov;117(5):1179-85. Pubmed: 11710930
  2. Muzzin KB, Harper LF: Smith-Lemli-Opitz syndrome: a review, case report and dental implications. Spec Care Dentist. 2003;23(1):22-7. Pubmed: 12887150
  3. Paterson CR, Moody JP, Pennington CR: Skin content of 7-dehydrocholesterol in patients with malabsorption. Nutrition. 1997 Sep;13(9):771-3. Pubmed: 9290088
  4. Jira PE, Wevers RA, de Jong J, Rubio-Gozalbo E, Janssen-Zijlstra FS, van Heyst AF, Sengers RC, Smeitink JA: Simvastatin. A new therapeutic approach for Smith-Lemli-Opitz syndrome. J Lipid Res. 2000 Aug;41(8):1339-46. Pubmed: 10946022
  5. Johnson DW, ten Brink HJ, Jakobs C: A rapid screening procedure for cholesterol and dehydrocholesterol by electrospray ionization tandem mass spectrometry. J Lipid Res. 2001 Oct;42(10):1699-705. Pubmed: 11590227
  6. 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
  7. Andersson HC, Frentz J, Martinez JE, Tuck-Muller CM, Bellizaire J: Adrenal insufficiency in Smith-Lemli-Opitz syndrome. Am J Med Genet. 1999 Feb 19;82(5):382-4. Pubmed: 10069708
  8. GarciaFuentes E, icioso Recio MV, del Castillo Acedo Del Olmo E, atas Jurado MM, Arana Aguera M, Lopez Lopez J: [Biochemical diagnosis of Smith-Lemli-Opitz syndrome in a patient with congenital adrenal hyperplasia] An Esp Pediatr. 2000 Nov;53(5):482-7. Pubmed: 11141372
  9. Jezela-Stanek A, Malunowicz EM, Ciara E, Popowska E, Goryluk-Kozakiewicz B, Spodar K, Czerwiecka M, Jezuita J, Nowaczyk MJ, Krajewska-Walasek M: Maternal urinary steroid profiles in prenatal diagnosis of Smith-Lemli-Opitz syndrome: first patient series comparing biochemical and molecular studies. Clin Genet. 2006 Jan;69(1):77-85. Pubmed: 16451140
  10. Moody JP, Humphries CA, Allan SM, Paterson CR: Determination of 7-dehydrocholesterol in human skin by high-performance liquid chromatography. J Chromatogr. 1990 Aug 24;530(1):19-27. Pubmed: 2277111

Enzymes

Gene Name:
SC5DL
Uniprot ID:
O75845
Reactions
Lathosterol + NAD(P)H + Oxygen unknown 7-Dehydrocholesterol + NAD(P)(+) + Waterdetails
Lathosterol + NADH + Hydrogen Ion + Oxygen unknown 7-Dehydrocholesterol + NAD + Waterdetails
Lathosterol + NADPH + Hydrogen Ion + Oxygen unknown 7-Dehydrocholesterol + NADP + Waterdetails
Gene Name:
SCP2
Uniprot ID:
P22307
Gene Name:
DHCR7
Uniprot ID:
Q9UBM7
Reactions
Cholesterol + NADP unknown 7-Dehydrocholesterol + NADPHdetails
Cholesterol + NAD unknown 7-Dehydrocholesterol + NADH + Hydrogen Iondetails
Cholesterol + NADP unknown 7-Dehydrocholesterol + NADPH + Hydrogen Iondetails
Gene Name:
DHCR24
Uniprot ID:
Q15392
Reactions
7-Dehydrodesmosterol + NADPH + Hydrogen Ion unknown 7-Dehydrocholesterol + NADPdetails