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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-13 02:06:58 UTC
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.
  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[²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol
Traditional Namedehydrocholesterol
CAS Registry Number434-16-2
InChI Identifier
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
  • Cholesterol-skeleton
  • Cholesterol
  • 3-beta-hydroxy-delta-7-steroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • 3-hydroxy-delta-5-steroid
  • Delta-7-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
StatusDetected and Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Physical Properties
Experimental Properties
Melting Point150.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.000148 mg/mLALOGPS
pKa (Strongest Acidic)18.27ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.47 m3·mol-1ChemAxon
Polarizability49.94 Å3ChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-002z000000-124abe0c8995f883f002View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-hzi8000000-dbfe3e996983256b1e0cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-mz20000000-8115f37d8da9a1d6f5d8View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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
Alendronate pathwaySMP00095Not Available
Atorvastatin PathwaySMP00131Not Available
Cerivastatin PathwaySMP00111Not Available
CHILD SyndromeSMP00387Not Available
Cholesteryl ester storage diseaseSMP00508Not Available
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)SMP00388Not Available
DesmosterolosisSMP00386Not Available
Fluvastatin PathwaySMP00119Not Available
Hyper-IgD syndromeSMP00509Not Available
HypercholesterolemiaSMP00209Not Available
Ibandronate PathwaySMP00079Not Available
Lovastatin PathwaySMP00099Not Available
Lysosomal Acid Lipase Deficiency (Wolman Disease)SMP00319Not Available
Mevalonic aciduriaSMP00510Not Available
Pamidronate PathwaySMP00117Not Available
Pravastatin PathwaySMP00089Not Available
Risedronate PathwaySMP00112Not Available
Rosuvastatin PathwaySMP00092Not Available
Simvastatin Action PathwaySMP00082Not Available
Smith-Lemli-Opitz Syndrome (SLOS)SMP00389Not Available
Steroid BiosynthesisSMP00023map00100
Wolman diseaseSMP00511Not Available
Zoledronate PathwaySMP00107Not Available
Normal Concentrations
BloodDetected and Quantified5.0 +/- 2.2 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0 - 0.02 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.029 (0.0068-0.051) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BloodDetected and Quantified369.0 (46.0 - 1220.0) uMAdult (>18 years old)BothSmith-Lemli-Opitz syndrome details
Cerebrospinal Fluid (CSF)Detected and Quantified0.3 +/- 0.2 (0.1 - 0.6) uMInfant (0-1 year old)BothSmith-Lemli-Opitz syndrome details
Associated Disorders and Diseases
Disease References
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. [9266395 ]
  2. 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. [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
BiGG ID36958
Wikipedia Link7-Dehydrocholesterol
NuGOwiki LinkHMDB00032
Metagene LinkHMDB00032
PubChem Compound439423
PDB IDNot Available
ChEBI ID17759
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)Download (PDF)
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. [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. [12887150 ]
  3. Paterson CR, Moody JP, Pennington CR: Skin content of 7-dehydrocholesterol in patients with malabsorption. Nutrition. 1997 Sep;13(9):771-3. [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. [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. [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. [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. [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. [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. [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. [2277111 ]


General function:
Involved in hydroxymethylglutaryl-CoA synthase activity
Specific function:
This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
Gene Name:
Uniprot ID:
Molecular weight:
  1. Honda M, Tint GS, Honda A, Nguyen LB, Chen TS, Shefer S: 7-Dehydrocholesterol down-regulates cholesterol biosynthesis in cultured Smith-Lemli-Opitz syndrome skin fibroblasts. J Lipid Res. 1998 Mar;39(3):647-57. [9548596 ]
General function:
Involved in iron ion binding
Specific function:
Catalyzes a dehydrogenation to introduce C5-6 double bond into lathosterol.
Gene Name:
Uniprot ID:
Molecular weight:
Lathosterol + NAD(P)H + Oxygen → 7-Dehydrocholesterol + NAD(P)(+) + Waterdetails
Lathosterol + NADH + Hydrogen Ion + Oxygen → 7-Dehydrocholesterol + NAD + Waterdetails
Lathosterol + NADPH + Hydrogen Ion + Oxygen → 7-Dehydrocholesterol + NADP + Waterdetails
  1. Sugawara T, Fujimoto Y, Ishibashi T: Molecular cloning and structural analysis of human sterol C5 desaturase. Biochim Biophys Acta. 2001 Oct 31;1533(3):277-84. [11731337 ]
General function:
Involved in oxidoreductase activity
Specific function:
Mediates in vitro the transfer of all common phospholipids, cholesterol and gangliosides between membranes. May play a role in regulating steroidogenesis.
Gene Name:
Uniprot ID:
Molecular weight:
  1. Morin RJ, Brun MJ, Srikantaiah MV: Effect of age and cholestyramine feeding on rat liver 3-hydroxy-3-methyl glutaryl CoA reductase, sterol carrier protein 1 and sterol carrier protein 2 activities. Lipids. 1982 Jul;17(7):507-10. [7121212 ]
General function:
Involved in 7-dehydrocholesterol reductase activity
Specific function:
Production of cholesterol by reduction of C7-C8 double bond of 7-dehydrocholesterol (7-DHC).
Gene Name:
Uniprot ID:
Molecular weight:
Cholesterol + NADP → 7-Dehydrocholesterol + NADPHdetails
Cholesterol + NAD → 7-Dehydrocholesterol + NADH + Hydrogen Iondetails
Cholesterol + NADP → 7-Dehydrocholesterol + NADPH + Hydrogen Iondetails
  1. Porter FD: Smith-Lemli-Opitz syndrome: pathogenesis, diagnosis and management. Eur J Hum Genet. 2008 May;16(5):535-41. Epub 2008 Feb 20. [18285838 ]
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:
Uniprot ID:
Molecular weight:
  1. Guryev O, Carvalho RA, Usanov S, Gilep A, Estabrook RW: A pathway for the metabolism of vitamin D3: unique hydroxylated metabolites formed during catalysis with cytochrome P450scc (CYP11A1). Proc Natl Acad Sci U S A. 2003 Dec 9;100(25):14754-9. Epub 2003 Dec 1. [14657394 ]
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:
Uniprot ID:
Molecular weight:
7-Dehydrodesmosterol + NADPH + Hydrogen Ion → 7-Dehydrocholesterol + NADPdetails