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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 Date2020-04-23 20:52:32 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
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 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
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
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