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152154-28-4 molecular structure
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(2R,3R,4R,5S,6S)-6-{2-[(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

ChemBase ID: 166718
Molecular Formular: C28H37FO11
Molecular Mass: 568.5851832
Monoisotopic Mass: 568.23199022
SMILES and InChIs

SMILES:
O1[C@@H]([C@H](O)[C@@H]([C@H]([C@H]1C(=O)O)O)O)OCC(=O)[C@@]1([C@@]2([C@H]([C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C2)O)F)C)C[C@H]1C)C)O
Canonical SMILES:
O=C1C=C[C@]2(C(=C1)CC[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1C[C@H]([C@]2(O)C(=O)CO[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)C)C)C
InChI:
InChI=1S/C28H37FO11/c1-12-8-16-15-5-4-13-9-14(30)6-7-25(13,2)27(15,29)17(31)10-26(16,3)28(12,38)18(32)11-39-24-21(35)19(33)20(34)22(40-24)23(36)37/h6-7,9,12,15-17,19-22,24,31,33-35,38H,4-5,8,10-11H2,1-3H3,(H,36,37)/t12-,15+,16+,17+,19-,20-,21+,22-,24+,25+,26+,27+,28+/m1/s1
InChIKey:
UBHXMSIBGRGDSX-DCSHZXMSSA-N

Cite this record

CBID:166718 http://www.chembase.cn/molecule-166718.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R,3R,4R,5S,6S)-6-{2-[(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
IUPAC Traditional name
(2R,3R,4R,5S,6S)-6-{2-[(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Synonyms
(11β,16α)-9-fluoro-11,17-dihydroxy-16-methyl-3,20-dioxopregna-1,4-dien-21-yl β-D-Glucopyranosiduronic Acid
Dexamethasone β-D-Glucuronide
CAS Number
152154-28-4
PubChem SID
162260851
PubChem CID
71315851

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC D298810 external link Add to cart
PubChem 71315851 external link
Data Source Data ID Price
TRC
D298810 external link Add to cart Please log in.
Data Source Data ID
PubChem 71315851 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.0697167  H Acceptors 11 
H Donor LogD (pH = 5.5) -2.1676288 
LogD (pH = 7.4) -3.2347093  Log P 0.23100857 
Molar Refractivity 134.7736 cm3 Polarizability 53.34473 Å3
Polar Surface Area 191.05 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
MSDS Link
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Certificate of Analysis
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DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - D298810 external link
It is a potential prodrug for colonic delivery of the antiinflammatory corticosteroid Dexamethasone.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Fotsis, T., et al.: J. Steroid Biochem., 14, 457 (1981)
  • • Choi, M., et al.: Steroids, 65, 54 (1981)
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PATENTS

PATENTS

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INTERNET

INTERNET

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