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Bovine Metabolome Database



Showing metabocard for 7-Dehydrocholesterol (BMDB00032)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:38
Accession Number BMDB00032
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.
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-Didehydrocholesterol
  10. 7,8-dehydro-cholesterol
  11. 7-Dehydrocholesterin
  12. 7-Dehydrocholesterol
  13. 7-dehydro-cholesterol
  14. 7DHC
  15. Cholesta-5,7-dien-3-beta-ol
  16. Cholesta-5,7-dien-3-ol
  17. Cholesta-5,7-dien-3beta-ol
  18. Dehydrocholesterin
  19. Dehydrocholesterol
  20. Provitamin D3
  21. cholesta-5,7-dien-3 beta -ol
  22. cholesta-5,7-dien-3b-ol
  23. delta5,7-Cholestadien-3beta-ol
  24. delta5,7-Cholesterol
  25. delta7-Cholesterol
  26. provitamin-D3
Chemical IUPAC Name 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
Chemical Formula C27H44O
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Vitamin D3 derivatives
Family
  • Mammalian_Metabolite
Species
  • secondary alcohol; alkene
Biofunction
  • Hormones, Membrane component
Application
Source
  • Endogenous
Average Molecular Weight 384.638
Monoisotopic Molecular Weight 384.339203
Isomeric SMILES CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
Canonical SMILES CC(C)CCCC(C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C
KEGG Compound ID C01164 Link Image
BioCyc ID 7-DEHYDRO-CHOLESTEROL Link Image
BiGG ID 36958 Link Image
Wikipedia Link 7-Dehydrocholesterol Link Image
METLIN ID 5101 Link Image
PubChem Compound 439423 Link Image
PubChem Substance 3132652 Link Image
ChEBI ID 17759 Link Image
CAS Registry Number 434-16-2
InChI Identifier InChI=1/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
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.
Melting Point (Experimental) 150.5 oC
Experimental Water Solubility 1 mg/mL [HMP experimental] Source: PhysProp
Predicted Water Solubility 1.08e-07 mg/mL [MEYLAN,WM et al. (1996)]; 1.48e-04 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 7.30 [Predicted by ALOGPS]; 7.2 [Predicted by PubChem via XLOGP]; 8.65 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
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Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
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Medium Energy
Download File
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High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane
  • Cytoplasm
  • endoplasmic reticulum
Biofluid Location Not Available
Tissue Location
Tissue References
Adrenal Gland
Brain
Epidermis
Fetus
Fibroblasts
Liver
Skin
Testes
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Steroid Biosynthesis
HMDB Pathways
Name Steroid Biosynthesis
Image Show Link Image
KEGG Pathways
Name Steroid Biosynthesis
Image Show Link Image
SimCell Pathways
Name Steroid Biosynthesis
Image Show Link Image
Graph
SBML
General References
  1. Wikipedia Link Image
Metabolic Enzymes
  1. 7-dehydrocholesterol reductase
Enzyme 1 [top]
Enzyme 1 ID 910
Enzyme 1 Name 7-dehydrocholesterol reductase
Enzyme 1 Synonyms
  1. 7-DHC reductase
  2. Sterol Delta(7)-reductase
Enzyme 1 Gene Name DHCR7
Enzyme 1 Protein Sequence >7-dehydrocholesterol reductase
MAAKSQPSAPKTKSTSGLTNGNAAAQGQWGRAWEVDWFSLASVIFLLLFAPFIVYYFIMA
CDQYGCSLTVPVADLATGRARLADIWARTPPVTAKAAQIYTAWVTLQVLLYMLLPDFCHK
FLPGYVGGVQEGAVTPAGAVNKYEINGLQAWLLTHLLWFANAHLLGWFSPTIIFDNWIPL
LWCANILGYTVSTFAMVKGYLFPTDARECKFTGNFFYNYMMGVEFNPRIGKWFDFKLFFN
GRPGIVAWTLINLSFAAKQQELYGHVTNSMVLVNILQAIYVLDFFWNETWYLKTIDICHD
HFGWYLGWGDCVWLPYLYTLQGLYLVYHPVQLPTYYALGVLLLGLLGYYIFRMTNHQKDL
FRRTDGRCLIWGRKPKAIECSYTSADGQRHHSKLLVSGFWGVARHFNYTGDLMGSLAYCL
ACGGGHLLPYFYIIFMAILLTHRCLRDEHRCANKYGRDWEHYTAAVPYRLLPGIF
Enzyme 1 Number of Residues 475
Enzyme 1 Molecular Weight 54270.7
Enzyme 1 Theoretical pI 8.53
Enzyme 1 GO Classification
Function
Process
Component
Enzyme 1 General Function Involved in 7-dehydrocholesterol reductase activity
Enzyme 1 Specific Function Production of cholesterol by reduction of C7-C8 double bond of 7-dehydrocholesterol (7-DHC)
Enzyme 1 Pathways
  • Steroid biosynthesis
  • cholesterol biosynthesis
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • 40-60 151-173 178-200 266-286 306-326 331-351 420-440
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 59858215 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q5E9J5 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name DHCR7_BOVIN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1428 bp
ATGGCTGCGAAGTCCCAGCCCAGCGCCCCTAAAACCAAGAGCACCAGCGGCCTCACCAAC
GGCAACGCTGCAGCCCAAGGCCAGTGGGGCCGAGCCTGGGAGGTGGACTGGTTTTCCCTG
GCGAGCGTCATCTTCCTGCTGCTGTTTGCGCCCTTCATCGTGTACTACTTCATCATGGCC
TGCGACCAGTACGGCTGCTCCCTGACAGTGCCCGTGGCGGACCTCGCCACTGGGCGGGCT
CGGCTCGCCGACATCTGGGCCAGGACGCCGCCCGTGACCGCAAAGGCGGCCCAGATCTAC
ACAGCATGGGTCACGCTCCAGGTGCTTCTGTACATGCTGCTTCCTGACTTCTGCCACAAG
TTTCTTCCGGGCTACGTGGGGGGCGTTCAGGAGGGCGCCGTGACTCCCGCAGGAGCCGTC
AACAAGTATGAGATCAACGGCCTGCAGGCCTGGCTCCTCACGCACCTCCTGTGGTTCGCC
AACGCCCACCTCCTCGGCTGGTTCTCCCCCACCATCATTTTCGACAACTGGATCCCGCTG
CTCTGGTGTGCCAACATCCTGGGCTACACCGTCTCCACCTTCGCCATGGTCAAGGGCTAC
CTCTTCCCCACTGACGCCCGGGAATGCAAATTCACGGGCAATTTCTTTTACAACTACATG
ATGGGCGTTGAGTTTAACCCCCGAATTGGGAAGTGGTTTGACTTCAAGCTCTTCTTCAAT
GGACGCCCCGGGATCGTCGCCTGGACCCTCATCAACCTGTCCTTTGCAGCCAAGCAGCAG
GAGCTCTACGGCCACGTGACCAACTCCATGGTCTTGGTCAACATCCTGCAGGCCATCTAC
GTGCTGGACTTCTTCTGGAACGAAACCTGGTACCTGAAAACCATCGACATCTGCCACGAC
CACTTTGGGTGGTACCTGGGCTGGGGGGACTGCGTCTGGCTGCCATACCTGTACACGCTG
CAGGGCCTGTACCTGGTGTACCACCCCGTGCAGCTGCCCACCTACTACGCGCTGGGCGTC
CTGCTCCTGGGCCTGCTCGGCTACTACATCTTCCGGATGACCAACCACCAGAAGGACCTC
TTCCGCCGCACGGACGGGCGCTGCCTGATCTGGGGCAGGAAGCCCAAGGCCATCGAGTGC
TCCTACACATCAGCCGACGGGCAGAGACACCACAGCAAGCTGCTGGTCTCGGGCTTCTGG
GGCGTGGCCCGCCACTTCAACTACACGGGTGACCTGATGGGCAGCCTGGCGTACTGCCTG
GCCTGCGGCGGCGGCCACCTCCTGCCCTACTTCTACATCATCTTCATGGCCATCCTGCTG
ACCCACCGCTGCCTCCGGGACGAGCACCGCTGTGCCAACAAGTACGGCCGCGACTGGGAG
CACTACACGGCCGCCGTGCCGTACCGCCTGCTCCCTGGCATCTTCTAG
Enzyme 1 GenBank Gene ID BT020925 Link Image
Enzyme 1 GeneCard ID DHCR7 Link Image
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Chromosome:1
Enzyme 1 Locus 11q13.2-q13.5
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available