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

ChemBase ID: 144411
Molecular Formular: C27H44O3
Molecular Mass: 416.63646
Monoisotopic Mass: 416.32904527
SMILES and InChIs

SMILES:
C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]2[C@@]1(CCC/C/2=C\C=C\1/C[C@H](C[C@@H](C1=C)O)O)C
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/t18-,22-,23-,24+,25+,27-/m1/s1
InChIKey:
GMRQFYUYWCNGIN-ZVUFCXRFSA-N

Cite this record

CBID:144411 http://www.chembase.cn/molecule-144411.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,3S)-5-{2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
(1R,3S,5E)-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 oral solution
1,25-dihydroxycholecalciferol
Synonyms
1α,25-Dihydroxycalciferol solution
1α,25-Dihydroxyvitamin D2 solution
1α,25-Dihydroxycholecalciferol
Calcitriol
1α,25-Dihydroxyvitamin D3
(1R,3S,5E)-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,5E,7E)- 9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol
1,25-Dihydroxy-5,6-trans-vitamin D3
1α,25-Dihydroxy-5,6-trans-vitamin D3
5,6-trans-1α,25-Dihydroxyvitamin D3
5,6-trans-Calcitriol
CAS Number
32222-06-3
73837-24-8
EC Number
250-963-8
200-578-6
MDL Number
MFCD00867079
Beilstein Number
7559394
PubChem SID
24850808
162238626
PubChem CID
5283740

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 5283740 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)
Flash Point
14 °C expand Show data source
57.2 °F expand Show data source
RTECS
FZ4645000 expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Highly toxic Highly toxic (T+) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
1 expand Show data source
Risk Statements
11 expand Show data source
63-26/27/28 expand Show data source
Safety Statements
36/37/39-45 expand Show data source
7-16 expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H225 expand Show data source
H300-H310-H330-H361 expand Show data source
GHS Precautionary statements
P210 expand Show data source
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
-70°C expand Show data source
Gene Information
human ... VDR(7421) expand Show data source
Purity
≥97.0% (HPLC) expand Show data source
95% (CP) expand Show data source
98% (CP) expand Show data source
Concentration
100 μg/mL in ethanol expand Show data source
5 μg/mL in ethanol expand Show data source
50 μg/mL in ethanol expand Show data source
Certificate of Analysis
Download expand Show data source
Shelf Life
3 mo. at -20 °C (Please inquire with isosales@sial.com for a batch specific expiration date) expand Show data source
Empirical Formula (Hill Notation)
C27H44O3 expand Show data source
C28H44O3 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - 17936 external link
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.
Toronto Research Chemicals - C144510 external link
An impurity of Calcitriol (C144500). The trans isomer of Calcitriol.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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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