Human Metabolome Database Version 3.5

Showing metabocard for 7-Dehydrocholesterol (HMDB00032)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:47 -0700
HMDB ID HMDB00032
Secondary Accession Numbers None
Metabolite Identification
Common Name 7-Dehydrocholesterol
Description 7-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C27H44O
Average Molecular Weight 384.6377
Monoisotopic Molecular Weight 384.33921603
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 Name 7-dehydrocholesterol
CAS Registry Number 434-16-2
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 Key UCTLRSWJYQTBFZ-DDPQNLDTSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Cholesterols and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Cholesterol and derivatives(Lipidmaps)
Substituents
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Secondary Alcohol
  • Sesterterpene
Direct Parent Cholesterols and Derivatives
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
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
Predicted Properties
Property Value Source
Water Solubility 1.480E-04 g/L ALOGPS
LogP 7.30 ALOGPS
LogP 6.71 ChemAxon
LogS -6.41 ALOGPS
pKa (strongest acidic) 18.27 ChemAxon
pKa (strongest basic) -1.4 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 121.47 ChemAxon
Polarizability 49.94 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Fibroblasts
  • Testes
  • Liver
  • Brain
  • Adrenal Gland
  • Fetus
  • Skin
Pathways
Name SMPDB Link KEGG Link
Steroid Biosynthesis SMP00023 map00100 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
5.0 +/- 2.2 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0 - 0.02 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.029 (0.0068-0.051) umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 369.0 (46.0 - 1220.0) uM Adult (>18 years old) Both Smith-Lemli-Opitz syndrome
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
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 Link_out
  • 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 Link_out
      Associated OMIM IDs
      • 270400 Link_out (Smith-Lemli-Opitz syndrome)
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB021882
      KNApSAcK ID Not Available
      Chemspider ID 388534 Link_out
      KEGG Compound ID C01164 Link_out
      BioCyc ID 7-DEHYDRO-CHOLESTEROL Link_out
      BiGG ID 36958 Link_out
      Wikipedia Link 7-Dehydrocholesterol Link_out
      NuGOwiki Link HMDB00032 Link_out
      Metagene Link HMDB00032 Link_out
      METLIN ID 5101 Link_out
      PubChem Compound 439423 Link_out
      PDB ID Not Available
      ChEBI ID 17759 Link_out
      References
      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.
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out

      Enzymes
      Name: Hydroxymethylglutaryl-CoA synthase, mitochondrial
      Reactions: Not Available
      Gene Name: HMGCS2
      Uniprot ID: P54868 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Lathosterol oxidase
      Reactions:
      Lathosterol + NAD(P)H + Oxygen unknown 7-Dehydrocholesterol + NAD(P)(+) + Water details
      Lathosterol + NADH + Hydrogen Ion + Oxygen unknown 7-Dehydrocholesterol + NAD + Water details
      Lathosterol + NADPH + Hydrogen Ion + Oxygen unknown 7-Dehydrocholesterol + NADP + Water details
      Gene Name: SC5DL
      Uniprot ID: O75845 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Non-specific lipid-transfer protein
      Reactions: Not Available
      Gene Name: SCP2
      Uniprot ID: P22307 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 7-dehydrocholesterol reductase
      Reactions:
      Cholesterol + NADP unknown 7-Dehydrocholesterol + NADPH details
      Cholesterol + NAD unknown 7-Dehydrocholesterol + NADH + Hydrogen Ion details
      Cholesterol + NADP unknown 7-Dehydrocholesterol + NADPH + Hydrogen Ion details
      Gene Name: DHCR7
      Uniprot ID: Q9UBM7 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cholesterol side-chain cleavage enzyme, mitochondrial
      Reactions: Not Available
      Gene Name: CYP11A1
      Uniprot ID: P05108 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Delta(24)-sterol reductase
      Reactions:
      7-Dehydrodesmosterol + NADPH + Hydrogen Ion unknown 7-Dehydrocholesterol + NADP details
      Gene Name: DHCR24
      Uniprot ID: Q15392 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA