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64480-66-6 molecular structure
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2-[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanamido]acetic acid

ChemBase ID: 154701
Molecular Formular: C26H43NO5
Molecular Mass: 449.62332
Monoisotopic Mass: 449.31412348
SMILES and InChIs

SMILES:
C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]1[C@H]2[C@H](C[C@H]2[C@@]1(CC[C@H](C2)O)C)O)C
Canonical SMILES:
O[C@@H]1CC[C@]2([C@@H](C1)C[C@@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)NCC(=O)O)C)C)O)C
InChI:
InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21+,24+,25+,26-/m1/s1
InChIKey:
GHCZAUBVMUEKKP-XROMFQGDSA-N

Cite this record

CBID:154701 http://www.chembase.cn/molecule-154701.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanamido]acetic acid
IUPAC Traditional name
glycoursodeoxycholic acid
Synonyms
N-[(3.alpha.,5.beta.,7.beta.)-3,7-dihydroxy-24-oxocholan-24-yl]Glycine
3.alpha.,7.beta.-Dihydroxy-5.beta.-cholanoylglycine
N-(3.alpha.,7.beta.-Dihydroxy-5.beta.-cholan-24-oyl)glycine
Glycoursodeoxycholic Acid
N-(3α,7β-Dihydroxy-5β-cholan-24-oyl)glycine
N-[(3α,5β,7β)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine
GUDCA
Glycylursodeoxycholic acid
Ursodeoxycholylglycine
Glycoursodeoxycholic acid
CAS Number
64480-66-6
MDL Number
MFCD00137427
PubChem SID
162248839
PubChem CID
12310288

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 12310288 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.7733076  H Acceptors
H Donor LogD (pH = 5.5) 0.8800022 
LogD (pH = 7.4) -0.66643345  Log P 2.6080222 
Molar Refractivity 122.0773 cm3 Polarizability 48.680336 Å3
Polar Surface Area 106.86 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Ethanol expand Show data source
Methanol expand Show data source
Apperance
White to Off-White Solid expand Show data source
Melting Point
226-228°C expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Purity
≥96.0% (TLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C26H43NO5 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - 06863 external link
Biochem/physiol Actions
Secondary bile acid derived from acyl glycine. Glycoursodeoxycholic Acid (GUDCA) is reported to have cytoprotective and anti-inflammatory effects.
Toronto Research Chemicals - G679550 external link
A metabolite of Ursodeoxycholic Acid, which is used as an anticholelithogenic.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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