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1357003-01-0 molecular structure
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(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-{[(2S)-3-phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanoyl]oxy}oxane-2-carboxylic acid

ChemBase ID: 175027
Molecular Formular: C25H35NO9
Molecular Mass: 493.5467
Monoisotopic Mass: 493.23118171
SMILES and InChIs

SMILES:
C([C@H](NC(=O)[C@@H]1CC[C@H](CC1)C(C)C)C(=O)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)c1ccccc1
Canonical SMILES:
CC([C@@H]1CC[C@H](CC1)C(=O)N[C@H](C(=O)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)Cc1ccccc1)C
InChI:
InChI=1S/C25H35NO9/c1-13(2)15-8-10-16(11-9-15)22(30)26-17(12-14-6-4-3-5-7-14)24(33)35-25-20(29)18(27)19(28)21(34-25)23(31)32/h3-7,13,15-21,25,27-29H,8-12H2,1-2H3,(H,26,30)(H,31,32)/t15-,16-,17-,18+,19+,20-,21+,25+/m0/s1
InChIKey:
YTIRWNSTJVSCRW-GUJLTLOXSA-N

Cite this record

CBID:175027 http://www.chembase.cn/molecule-175027.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-{[(2S)-3-phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanoyl]oxy}oxane-2-carboxylic acid
IUPAC Traditional name
(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-{[(2S)-3-phenyl-2-{[(1r,4r)-4-isopropylcyclohexyl]formamido}propanoyl]oxy}oxane-2-carboxylic acid
Synonyms
N-[[trans-4-(1-Methylethyl)cyclohexyl]carbonyl]-L-phenylalanine β-D-Glucopyranuronic Acid
L-Nateglinide Acyl Glucuronide
ent-Nateglinide Acyl-β-D-glucuronide
CAS Number
1357003-01-0
PubChem SID
164230937
PubChem CID
71750956

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC N379385 external link Add to cart
PubChem 71750956 external link
Data Source Data ID Price
TRC
N379385 external link Add to cart Please log in.
Data Source Data ID
PubChem 71750956 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.171759  H Acceptors
H Donor LogD (pH = 5.5) -0.2231105 
LogD (pH = 7.4) -1.3695333  Log P 2.0807772 
Molar Refractivity 121.7591 cm3 Polarizability 49.041466 Å3
Polar Surface Area 162.62 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 - N379385 external link
Potential metabolite of Nateglinide impurity, a novel D-phenylalanine-derivative hypoglycemic agent.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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