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Human Metabolome Database Version 3.5

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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 | 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 Comments
Blood Detected and Quantified
Article_icon
5.0 +/- 2.2 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0 - 0.02 uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.029 (0.0068-0.051) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
369.0 (46.0 - 1220.0) uM Adult (>18 years old) Both Smith-Lemli-Opitz syndrome Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.3 +/- 0.2 (0.1 - 0.6) uM Infant (0-1 year old) Both Smith-Lemli-Opitz syndrome Not Available
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
    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:
    • acetyl-CoA + H2O + acetoacetyl-CoA = (S)-3-hydroxy-3-methylglutaryl-CoA + CoA [RN:R01978]
    Gene Name: HMGCS2
    Uniprot ID: P54868 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Lathosterol oxidase
    Reactions:
    • 5alpha-cholest-7-en-3beta-ol + NAD(P)H + H+ + O2 = cholesta-5,7-dien-3beta-ol + NAD(P)+ + 2 H2O [RN:R03310 R07215]
    Gene Name: SC5DL
    Uniprot ID: O75845 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Non-specific lipid-transfer protein
    Reactions:
    • 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl-CoA + propanoyl-CoA = CoA + 3alpha,7alpha,12alpha-trihydroxy-24-oxo-5beta-cholestanoyl-CoA [RN:R03719]
    Gene Name: SCP2
    Uniprot ID: P22307 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: 7-dehydrocholesterol reductase
    Reactions:
    • cholesterol + NADP+ = cholesta-5,7-dien-3beta-ol + NADPH + H+ [RN:R01456]
    Gene Name: DHCR7
    Uniprot ID: Q9UBM7 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Cholesterol side-chain cleavage enzyme, mitochondrial
    Reactions:
    • cholesterol + reduced adrenal ferredoxin + O2 = pregnenolone + 4-methylpentanal + oxidized adrenal ferredoxin + H2O [RN:R02724]
    Gene Name: CYP11A1
    Uniprot ID: P05108 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: 24-dehydrocholesterol reductase
    Reactions:
      Gene Name: DHCR24
      Uniprot ID: Q15392 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA