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Showing metabocard for 7-Dehydrocholesterol (HMDB0000032)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
enzymes (6) Show 6 proteins
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-11-09 23:11:40 UTC
HMDB IDHMDB0000032
Secondary Accession Numbers
  • HMDB00032
Metabolite Identification
Common Name7-Dehydrocholesterol
Description7-Dehydrocholesterol, also known as provitamin D3 or 5,7-cholestadien-3-b-ol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7-dehydrocholesterol is considered to be a sterol lipid molecule. 7-Dehydrocholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 7-Dehydrocholesterol is a potentially toxic compound.
Structure
Data?1582752108
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3beta)-Cholesta-5,7-dien-3-olChEBI
5,7-Cholestadien-3-beta-olChEBI
5,7-Cholestadien-3beta-olChEBI
Provitamin D3ChEBI
Cholesta-5,7-dien-3beta-olKegg
(3b)-Cholesta-5,7-dien-3-olGenerator
(3Β)-cholesta-5,7-dien-3-olGenerator
5,7-Cholestadien-3-b-olGenerator
5,7-Cholestadien-3-β-olGenerator
5,7-Cholestadien-3b-olGenerator
5,7-Cholestadien-3β-olGenerator
Cholesta-5,7-dien-3b-olGenerator
Cholesta-5,7-dien-3β-olGenerator
(-)-7-DehydrocholesterolHMDB
10,13-Dimethyl-17-(6-methylheptan-2-yl)-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-olHMDB
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-olHMDB
5,7-Cholestandien-3-olHMDB
5,7-Cholestandien-3beta-olHMDB
7,8-dehydro-CholesterolHMDB
7,8-DidehydrocholesterolHMDB, MeSH
7-dehydro-CholesterolHMDB
7-DehydrocholesterinHMDB
7DHCHMDB
Cholesta-5,7-dien-3 beta -olHMDB
Cholesta-5,7-dien-3-beta-olHMDB
Cholesta-5,7-dien-3-olHMDB
DehydrocholesterinHMDB
DehydrocholesterolHMDB
Delta5,7-Cholestadien-3beta-olHMDB
Delta5,7-CholesterolHMDB
Delta7-CholesterolHMDB
Provitamin-D3HMDB
Provitamin D(3)MeSH, HMDB
Cholesta-5,7-dien-3 beta-olMeSH, HMDB
7-Dehydrocholesterol, (3beta,10alpha)-isomerMeSH, HMDB
7-Dehydrocholesterol, (3beta,9beta,10alpha)-isomerMeSH, HMDB
7-DHCMeSH, HMDB
7-Dehydrocholesterol, (3alpha)-isomerMeSH, HMDB
7-Dehydrocholesterol, (3beta,9beta)-isomerMeSH, HMDB
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 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
CAS Registry Number434-16-2
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)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/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1
InChI KeyUCTLRSWJYQTBFZ-DDPQNLDTSA-N
Chemical Taxonomy
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

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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 Solubility0.00015 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 Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.47 m³·mol⁻¹ChemAxon
Polarizability50.01 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0axr-1019000000-73894a6c7b7346b2d1b0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-002f-3005900000-c63a75d6ed190e98a35bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0009000000-124abe0c8995f883f002Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05oa-4942000000-dbfe3e996983256b1e0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05o0-5900000000-8115f37d8da9a1d6f5d8Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 26V, negativesplash10-000i-0090000000-3645f0c0605ff7c97405Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0019000000-d2b535e3c3ed257f2215Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar9-3139000000-87132b4b12416fa4f01eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5249000000-257a8915fd5fab2dfaaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-8ff4cced50a3c638abbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-6d9a73d8f487e848e538Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ldi-1019000000-eb1f58f2c9df95716640Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Adrenal Gland
  • Brain
  • Epidermis
  • Fibroblasts
  • Liver
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.65 uMChildren (1-13 years old)MaleNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
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 but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.029 (0.0068-0.051) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.21 uMChildren (1-13 years old)MaleLathosterolosis details
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
Lathosterolosis
  1. Ho AC, Fung CW, Siu TS, Ma OC, Lam CW, Tam S, Wong VC: Lathosterolosis: a disorder of cholesterol biosynthesis resembling smith-lemli-opitz syndrome. JIMD Rep. 2014;12:129-34. doi: 10.1007/8904_2013_255. Epub 2013 Oct 20. [PubMed:24142275 ]
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. 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
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021882
KNApSAcK IDC00023747
Chemspider IDNot Available
KEGG Compound IDC01164
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link7-Dehydrocholesterol
METLIN IDNot Available
PubChem Compound439423
PDB IDNot Available
ChEBI ID17759
Food Biomarker OntologyNot Available
VMH ID7DHCHSTEROL
MarkerDB ID
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)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. [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 ]
  11. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  12. Dietschy JM, Turley SD: Thematic review series: brain Lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal. J Lipid Res. 2004 Aug;45(8):1375-97. [PubMed:15254070 ]
  13. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  14. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  15. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  16. O'Byrne SM, Blaner WS: Retinol and retinyl esters: biochemistry and physiology. J Lipid Res. 2013 Jul;54(7):1731-43. doi: 10.1194/jlr.R037648. Epub 2013 Apr 26. [PubMed:23625372 ]
  17. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  18. Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..

Enzymes

Enzyme Details
1. Hydroxymethylglutaryl-CoA synthase, mitochondrial
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:
HMGCS2
Uniprot ID:
P54868
Molecular weight:
52481.065
References
  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. [PubMed:9548596 ]
Enzyme Details
2. Lathosterol oxidase
General function:
Involved in iron ion binding
Specific function:
Catalyzes a dehydrogenation to introduce C5-6 double bond into lathosterol.
Gene Name:
SC5DL
Uniprot ID:
O75845
Molecular weight:
35300.55
Reactions
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
References
  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. [PubMed:11731337 ]
Enzyme Details
3. Non-specific lipid-transfer protein
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:
SCP2
Uniprot ID:
P22307
Molecular weight:
34974.505
References
  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. [PubMed:7121212 ]
Enzyme Details
4. 7-dehydrocholesterol reductase
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:
DHCR7
Uniprot ID:
Q9UBM7
Molecular weight:
54488.98
Reactions
Cholesterol + NADP → 7-Dehydrocholesterol + NADPHdetails
Cholesterol + NAD → 7-Dehydrocholesterol + NADH + Hydrogen Iondetails
Cholesterol + NADP → 7-Dehydrocholesterol + NADPH + Hydrogen Iondetails
References
  1. Porter FD: Smith-Lemli-Opitz syndrome: pathogenesis, diagnosis and management. Eur J Hum Genet. 2008 May;16(5):535-41. doi: 10.1038/ejhg.2008.10. Epub 2008 Feb 20. [PubMed:18285838 ]
Enzyme Details
5. Cholesterol side-chain cleavage enzyme, mitochondrial
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:
CYP11A1
Uniprot ID:
P05108
Molecular weight:
60101.87
References
  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. [PubMed:14657394 ]
Enzyme Details
6. Delta(24)-sterol reductase
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