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24512-63-8 molecular structure
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methyl (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-carboxylate

ChemBase ID: 73272
Molecular Formular: C17H24O10
Molecular Mass: 388.36646
Monoisotopic Mass: 388.13694697
SMILES and InChIs

SMILES:
[C@H]1([C@H](O[C@H]([C@@H]([C@H]1O)O)O[C@@H]1OC=C([C@@H]2[C@H]1C(=CC2)CO)C(=O)OC)CO)O
Canonical SMILES:
OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2C(=CC3)CO)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI:
InChI=1S/C17H24O10/c1-24-15(23)9-6-25-16(11-7(4-18)2-3-8(9)11)27-17-14(22)13(21)12(20)10(5-19)26-17/h2,6,8,10-14,16-22H,3-5H2,1H3/t8-,10-,11-,12-,13+,14-,16+,17+/m1/s1
InChIKey:
IBFYXTRXDNAPMM-BVTMAQQCSA-N

Cite this record

CBID:73272 http://www.chembase.cn/molecule-73272.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
methyl (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-carboxylate
IUPAC Traditional name
geniposide
methyl (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-carboxylate
Synonyms
Geniposide
Genipin 1-glucoside
Jasminoidin
Geniposide
CAS Number
24512-63-8
PubChem SID
162038192
PubChem CID
107848

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 107848 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.206515  H Acceptors
H Donor LogD (pH = 5.5) -2.2147315 
LogD (pH = 7.4) -2.2147381  Log P -2.2147312 
Molar Refractivity 88.5066 cm3 Polarizability 35.61959 Å3
Polar Surface Area 155.14 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Apperance
Powder expand Show data source
Storage Condition
-20°C expand Show data source
Mechanism of Action
Glucagon-like peptide-1 (GLP-1) receptor agonist expand Show data source
Salt Data
Free Base expand Show data source
Biological Source
Constit. of Gardenia jasminoides expand Show data source
Application(s)
Anti-angiogenic expand Show data source
Anti-inflammatory expand Show data source
Antithrombotic expand Show data source
Antitumor expand Show data source
Neuroprotective expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals
Selleck Chemicals - S2411 external link
Research Area: Cardiovascular Disease
Biological Activity:
Geniposide is an iridoid glycoside isolated from the fruit of Gardenia jasminoides Ellis. Geniposide is one of the biologically active ingredients of gardenia fruit. Geniposide is widely used in multi-component injection in the treatment of cerebrovascular and cardiovascular diseases in China for its anti-thrombotic and anti-inflammatory effects. Geniposide exerts protective effects against hepatic steatosis in rats fed with a high fat diet; the underlying mechanism may be associated with its antioxidant actions or regulation of adipocytokine release and expression of peroxisome proliferator-activated receptor-α. Geniposide (10-20 μM) inhibited high glucose (33 mM)-induced adhesion of monocytes to HUVECs in a dose-dependent manner. Geniposide (5-40 μM) also inhibited high glucose-induced expression of VCAM-1 and E-selectin at the gene and protein levels. Furthermore, geniposide (5-20 mM) decreased reactive oxygen species production and prevented IkappaB degradation in the cytoplasm and NF-kappaB translocation from the cytoplasm to the nucleus in HUVECs. [1][2][3]References on Geniposide[1] J Zhejiang Univ Sci B., 2011 Feb, 12(2):143-8[2] J Pharm Pharmacol., 2011 Apr, 63(4):587-93[3] Acta Pharmacol Sin., 2010 Aug, 31(8):953-62

REFERENCES

REFERENCES

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  • • Ma T et al. J Pharm Pharmacol. 2011 Apr; 63(4):587-93.
  • • 1. Hsua HY, Yangb JJ, Lina SY, Lin CC. Comparisons of geniposidic acid and previous termgeniposidenext term on antitumor and radioprotection after sublethal irradiation,
  • • Cancer Lett. 113 (1997), pp. 31?7.
  • • 2. Koo HJ, Lee S, Shin KH, Kim BC, Lim CJ, Park EH. Geniposide, an anti-angiogenic compound from the fruits of Gardenia jasminoides. Planta Med. 2004 May;70(5):467-9.
  • • 3. Koo HJ, Lim KH, Jung HJ, Park EH. Anti-inflammatory evaluation of gardenia extract, geniposide and genipin. J Ethnopharmacol. 2006 Feb 20;103(3):496-500. Epub 2005 Sep 19.
  • • 4. Suzuki Y, Kondo K, Ikeda Y, Umemura K. Antithrombotic effect of geniposide and genipin in the mouse thrombosis model. Planta Med. 2001 Dec;67(9):807-10.
  • • 5. Lee P, Lee J, Choi SY, Lee SE, Lee S, Son D. Geniposide from Gardenia jasminoides attenuates neuronal cell death in oxygen and glucose deprivation-exposed rat hippocampal slice culture.
  • • Biol Pharm Bull. 2006 Jan;29(1):174-6.
  • • 6. Liu J, Yin F, Zheng X, Jing J, Hu Y. Geniposide, a novel agonist for GLP-1 receptor, prevents PC12 cells from oxidative damage via MAP kinase pathway.
  • • Neurochem Int. 2007 Nov-Dec;51(6-7):361-9. Epub 2007 May 6.
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PATENTS

PATENTS

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INTERNET

INTERNET

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