(1S,4aS,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid

• ChemBase ID: 73273
• Molecular Formular: C16H22O10
• Molecular Mass: 374.33988
• Monoisotopic Mass: 374.1212969
• SMILES: C1=C([C@@H]2[C@H]([C@@H](O1)O[C@@H]1O[C@@H]([C@H]([C@@H]([C@H]1O)O)O)CO)C(=CC2)CO)C(=O)O
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2C(=CC3)CO)C(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H22O10/c17-3-6-1-2-7-8(14(22)23)5-24-15(10(6)7)26-16-13(21)12(20)11(19)9(4-18)25-16/h1,5,7,9-13,15-21H,2-4H2,(H,22,23)/t7-,9-,10-,11-,12+,13-,15+,16+/m1/s1
• InChIKey: ZJDOESGVOWAULF-OGJQONSISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4aS,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid
• IUPAC Traditional name: geniposidic acid
• Synonyms: Geniposidic acid; Geniposidic acid

Database IDs

• CAS Number: 27741-01-1
• PubChem SID: 162038193
• PubChem CID: 443354
• CHEMBL: 460031
• Chemspider ID: 391590
• Wikipedia Title: Geniposidic_acid

CALCULATED PROPERTIES

• Acid pKa: 4.222503
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -3.8913703
• LogD (pH = 7.4): -5.6119847
• Log P: -2.5939586
• Molar Refractivity: 83.7375 cm^3
• Polarizability: 33.57636 Å^3
• Polar Surface Area: 166.14 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2413

Research Area: Cancer
Biological Activity:
Geniposidic acid is an effective anticancer and radioprotection agent. Geniposidic acid might be a more potent tumor growth inhibitor than geniposide (GP) when combined with the X-irradiation, though there was no significant synergetic effect on their combined antitumor activity. In a study, collagen synthesis was stimulated by the administration of a hot water extract from the leaves of Eucommia ulmoides OLIVER, Eucommiaceae (Du-Zhong leaves) in false aged model rats. The administration of geniposidic acid stimulated collagen synthesis in aged model rats. [1][2]References on Geniposidic acid[1] Cancer Lett., 1997 Feb 26, 113(1-2):31-7[2] Biol Pharm Bull., 1998 Dec, 21(12):1306-10

REFERENCES

• Li Y et al. Biol Pharm Bull. 1998 Dec; 21(12):1306-10.