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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-11-09 23:11:40 UTC |
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HMDB ID | HMDB0000032 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 7-Dehydrocholesterol |
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Description | 7-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. |
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Structure | |
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Synonyms | Value | Source |
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(3beta)-Cholesta-5,7-dien-3-ol | ChEBI | 5,7-Cholestadien-3-beta-ol | ChEBI | 5,7-Cholestadien-3beta-ol | ChEBI | Provitamin D3 | ChEBI | Cholesta-5,7-dien-3beta-ol | Kegg | (3b)-Cholesta-5,7-dien-3-ol | Generator | (3Β)-cholesta-5,7-dien-3-ol | Generator | 5,7-Cholestadien-3-b-ol | Generator | 5,7-Cholestadien-3-β-ol | Generator | 5,7-Cholestadien-3b-ol | Generator | 5,7-Cholestadien-3β-ol | Generator | Cholesta-5,7-dien-3b-ol | Generator | Cholesta-5,7-dien-3β-ol | Generator | (-)-7-Dehydrocholesterol | HMDB | 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 | HMDB | 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 | HMDB | 5,7-Cholestandien-3-ol | HMDB | 5,7-Cholestandien-3beta-ol | HMDB | 7,8-dehydro-Cholesterol | HMDB | 7,8-Didehydrocholesterol | HMDB, MeSH | 7-dehydro-Cholesterol | HMDB | 7-Dehydrocholesterin | HMDB | 7DHC | HMDB | Cholesta-5,7-dien-3 beta -ol | HMDB | Cholesta-5,7-dien-3-beta-ol | HMDB | Cholesta-5,7-dien-3-ol | HMDB | Dehydrocholesterin | HMDB | Dehydrocholesterol | HMDB | Delta5,7-Cholestadien-3beta-ol | HMDB | Delta5,7-Cholesterol | HMDB | Delta7-Cholesterol | HMDB | Provitamin-D3 | HMDB | Provitamin D(3) | MeSH, HMDB | Cholesta-5,7-dien-3 beta-ol | MeSH, HMDB | 7-Dehydrocholesterol, (3beta,10alpha)-isomer | MeSH, HMDB | 7-Dehydrocholesterol, (3beta,9beta,10alpha)-isomer | MeSH, HMDB | 7-DHC | MeSH, HMDB | 7-Dehydrocholesterol, (3alpha)-isomer | MeSH, HMDB | 7-Dehydrocholesterol, (3beta,9beta)-isomer | MeSH, HMDB |
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Chemical Formula | C27H44O |
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Average Molecular Weight | 384.6377 |
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Monoisotopic Molecular Weight | 384.33921603 |
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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 |
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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 |
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CAS Registry Number | 434-16-2 |
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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 |
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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 |
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InChI Key | UCTLRSWJYQTBFZ-DDPQNLDTSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Cholestane steroids |
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Direct Parent | Cholesterols and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 150.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1 mg/mL | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0axr-1019000000-73894a6c7b7346b2d1b0 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-002f-3005900000-c63a75d6ed190e98a35b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-0009000000-124abe0c8995f883f002 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-05oa-4942000000-dbfe3e996983256b1e0c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-05o0-5900000000-8115f37d8da9a1d6f5d8 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - n/a 26V, negative | splash10-000i-0090000000-3645f0c0605ff7c97405 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014r-0019000000-d2b535e3c3ed257f2215 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ar9-3139000000-87132b4b12416fa4f01e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-5249000000-257a8915fd5fab2dfaaa | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0009000000-8ff4cced50a3c638abba | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0009000000-6d9a73d8f487e848e538 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ldi-1019000000-eb1f58f2c9df95716640 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
- Endoplasmic reticulum
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Urine
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Tissue Locations | - Adrenal Gland
- Brain
- Epidermis
- Fibroblasts
- Liver
- Testis
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | <0.65 uM | Children (1-13 years old) | Male | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 5.0 +/- 2.2 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0 - 0.02 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.029 (0.0068-0.051) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 0.21 uM | Children (1-13 years old) | Male | Lathosterolosis | | details | Blood | Detected and Quantified | 369.0 (46.0 - 1220.0) uM | Adult (>18 years old) | Both | Smith-Lemli-Opitz syndrome | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.3 +/- 0.2 (0.1 - 0.6) uM | Infant (0-1 year old) | Both | Smith-Lemli-Opitz syndrome | | details |
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Associated Disorders and Diseases |
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Disease References | Lathosterolosis |
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- 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 |
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- 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 ]
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Associated OMIM IDs | - 607330 (Lathosterolosis)
- 270400 (Smith-Lemli-Opitz syndrome)
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB021882 |
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KNApSAcK ID | C00023747 |
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Chemspider ID | Not Available |
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KEGG Compound ID | C01164 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | 7-Dehydrocholesterol |
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METLIN ID | Not Available |
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PubChem Compound | 439423 |
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PDB ID | Not Available |
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ChEBI ID | 17759 |
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Food Biomarker Ontology | Not Available |
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VMH ID | 7DHCHSTEROL |
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MarkerDB ID | |
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References |
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Synthesis Reference | William 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. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - 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 ]
- 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 ]
- Paterson CR, Moody JP, Pennington CR: Skin content of 7-dehydrocholesterol in patients with malabsorption. Nutrition. 1997 Sep;13(9):771-3. [PubMed:9290088 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
- Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..
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