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1147403-03-9 molecular structure
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(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1s,3r,5R,7S)-3-({2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl}amino)adamantan-1-yl]oxy}oxane-2-carboxylic acid

ChemBase ID: 179497
Molecular Formular: C23H33N3O8
Molecular Mass: 479.52342
Monoisotopic Mass: 479.22676503
SMILES and InChIs

SMILES:
C1[C@]2(C[C@]3(C[C@@H]1C[C@@H](C2)C3)NCC(=O)N1CCC[C@H]1C#N)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
Canonical SMILES:
N#C[C@@H]1CCCN1C(=O)CN[C@]12C[C@@H]3C[C@H](C1)C[C@](C2)(C3)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
InChI:
InChI=1S/C23H33N3O8/c24-9-14-2-1-3-26(14)15(27)10-25-22-5-12-4-13(6-22)8-23(7-12,11-22)34-21-18(30)16(28)17(29)19(33-21)20(31)32/h12-14,16-19,21,25,28-30H,1-8,10-11H2,(H,31,32)/t12-,13+,14-,16-,17-,18+,19-,21-,22+,23-/m0/s1
InChIKey:
PSIDBGKCTWXOHS-VUHWNEFDSA-N

Cite this record

CBID:179497 http://www.chembase.cn/molecule-179497.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1s,3r,5R,7S)-3-({2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl}amino)adamantan-1-yl]oxy}oxane-2-carboxylic acid
IUPAC Traditional name
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1s,3r,5R,7S)-3-({2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl}amino)adamantan-1-yl]oxy}oxane-2-carboxylic acid
Synonyms
(2S)-1-[2-[(3-Hydroxytricyclo[3.3.1.13,7]dec-1-yl)amino]acetyl]-2-pyrrolidinecarbonitrileO-β-D-Glucopyranosiduronic Acid
Vildagliptin O-Glucuronide
Vildagliptin β-D-Glucuronide
CAS Number
1147403-03-9
PubChem SID
164235407
PubChem CID
71752941

DATA SOURCES

DATA SOURCES

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Data Source Data ID
TRC V305020 external link Add to cart
PubChem 71752941 external link
Data Source Data ID Price
TRC
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Data Source Data ID
PubChem 71752941 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.346729  H Acceptors 10 
H Donor LogD (pH = 5.5) -4.1418943 
LogD (pH = 7.4) -4.143939  Log P -4.1402965 
Molar Refractivity 114.2798 cm3 Polarizability 46.017567 Å3
Polar Surface Area 172.58 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

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 - V305020 external link
A metabolite of Vildagliptin.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Reimer, M.K., et al.: Eur. J. Endocrinol., 146, 717 (2002)
  • • Villhauer, E.B., et al.: J. Med. Chem., 46, 2774 (2002)
  • • Ahren, B., et al.: J. Clin. Endocrinol. Metab., 85, 2078 (2002)
  • • He, H., et al.: Drug Metab. Dispos., 37, 545 (2002)
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PATENTS

PATENTS

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INTERNET

INTERNET

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