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32222-06-3 molecular structure
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(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol

ChemBase ID: 72693
Molecular Formular: C27H44O3
Molecular Mass: 416.63646
Monoisotopic Mass: 416.32904527
SMILES and InChIs

SMILES:
[C@@H]1(C[C@@H](C(=C)/C(=C\C=C/2\[C@H]3[C@](CCC2)([C@H](CC3)[C@@H](CCCC(C)(C)O)C)C)/C1)O)O
Canonical SMILES:
O[C@H]1C[C@H](O)C(=C)/C(=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](CCCC(O)(C)C)C)C)/C1
InChI:
InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1
InChIKey:
GMRQFYUYWCNGIN-NKMMMXOESA-N

Cite this record

CBID:72693 http://www.chembase.cn/molecule-72693.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
IUPAC Traditional name
calcitriol
Synonyms
(1R,3S,5Z)-4-Methylene-5-[(2E)-2-[(1R,3aS,7aS)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol
(1α,3β,5Z,7E)- 9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol,
1α,25-Dihydroxyvitamin D3
Dihydroxyvitamin D3
Panbonis
Ro 21-5535
Solbone P
Soltriol
Toptriol
1α,25-Dihydroxycholecalciferol
Calcitriol
1α,25-Dihydroxyvitamin D3
Calcijex
Silkis
Rocaltrol
Topitriol
Cholecalci
Calcitriol
CAS Number
32222-06-3
EC Number
250-963-8
MDL Number
MFCD00867079
Beilstein Number
7559394
PubChem SID
24893473
162037614
PubChem CID
5280453

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 5280453 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 14.392874  H Acceptors
H Donor LogD (pH = 5.5) 4.350741 
LogD (pH = 7.4) 4.350741  Log P 4.350741 
Molar Refractivity 126.5325 cm3 Polarizability 49.421616 Å3
Polar Surface Area 60.69 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO expand Show data source
Do you have solubility information on this product that you would like to share? expand Show data source
Ethanol expand Show data source
Ethyl Acetate expand Show data source
Methanol expand Show data source
Tetrahydrofuran, expand Show data source
Apperance
White Solid expand Show data source
Melting Point
119-121°C expand Show data source
Storage Condition
-20°C expand Show data source
Amber Vial, -20°C Freezer expand Show data source
RTECS
FZ4645000 expand Show data source
European Hazard Symbols
Highly toxic Highly toxic (T+) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
1 expand Show data source
Risk Statements
63-26/27/28 expand Show data source
Safety Statements
36/37/39-45 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H300-H310-H330-H361 expand Show data source
GHS Precautionary statements
P260-P264-P280-P284-P301 + P310-P302 + P350 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 1 expand Show data source
Storage Temperature
-20°C expand Show data source
Gene Information
human ... VDR(7421) expand Show data source
Purity
≥99% (HPLC) expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Quality Level
PREMIUM expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
Selleck Chemicals - S1466 external link
Research Area: Metabolic Disease
Biological Activity:
Calcitriol, also called 1,25-dihydroxycholecalciferol or 1,25-dihydroxyvitamin D3, is the hormonally active form of vitamin D with three hydroxyl groups (abbreviated 1,25-(OH)2D3 or simply 1,25(OH)2D). It increases the level of calcium (Ca2+) in the blood by increasing the uptake of calcium from the gut into the blood, decreasing the transfer of calcium from blood to the urine by the kidney, and increasing the release of calcium into the blood from bone. [1]
Sigma Aldrich - D1530 external link
Frequently Asked Questions
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Application
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Biochem/physiol Actions
Biologically active form of vitamin D3 in calcium absorption and deposition. 1α,25-Dihydroxyvitamin D3 has widespread effects on cellular differentiation and proliferation, and can modulate immune responsiveness, and central nervous system function. Recent studies suggest that 1α,25-dihydroxyvitamin D3 acts as a chemopreventive agent against several malignancies including cancers of the prostate and colon and shows synergy with other anticancer compounds.
Cholecalciferol is an inactive form of vitamin D3 which undergoes various levels of hydroxylation to form active vitamin D3 analogs. 1α-Hydroxyvitamin D3 (alfacalcidol is a synthetic analog that is metabolized to 1,25-dihydroxycholecalciferol, the biologically active form of vitamin D3 in calcium absorption and deposition. 1α,25-Dihydroxyvitamin D3 has widespread effects on cellular differentiation and proliferation, and can modulate immune responsiveness, and central nervous system function. Recent studies suggest that 1α,25-dihydroxyvitamin D3 acts as a chemopreventive agent against several malignancies including cancers of the prostate and colon and shows synergy with other anticancer compounds.
Toronto Research Chemicals - C144500 external link
The biologically active form of Vitamin D3. Calcium regulator; vitamin (antirachitic); antihyperparathyroid; antineoplastic; antipsoriatic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • •  http://en.wikipedia.org/wiki/Calcitriol
  • • Myrtle, J.F., et al.: J. Biol. Chem., 245, 1190 (1970)
  • • Lawson, D.E.M., et al.: Nature, 230, 228 (1970)
  • • Norman, A.W., et al.: Science, 173, 51 (1970)
  • • Suda, T., et al.: Vitamins, 45, 175 (1970)
  • • Muindi, J.R., et al.: Clin. Pharmacol. Ther., 72, 648 (2002
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PATENTS

PATENTS

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INTERNET

INTERNET

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