CAS 24512-63-8|Geniposide|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|Genipo...

General Information

Structure

Molecular Formula

C₁₇H₂₄O₁₀

Molecular Mass

388.36646

Exact Mass

388.13694697

Charge

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

Canonic 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

Isomeric 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

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

Polarizability

35.61959

Polar Surface Area

155.14

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Synonyms

GeniposideGeniposideGenipin 1-glucosideJasminoidin

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

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

Names and Identifiers

Registration numbers

CAS Number

24512-63-8

PubChem CID

107848

PubChem SID

162038192

Registration numbers

Properties

Safety Information

Storage Condition

-20°C

Product Information

Pharmacology Properties

Glucagon-like peptide-1 (GLP-1) receptor agonist

Physical Property

Powder

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Selleck Chemicals

S2411

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

Molecule Details

References

PubChem Literature

From Data Sources

• Ma T et al. J Pharm Pharmacol. 2011 Apr; 63(4):587-93.

• 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.

• 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.

• Cancer Lett. 113 (1997), pp. 31?7.

• 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.

• 1. Hsua HY, Yangb JJ, Lina SY, Lin CC. Comparisons of geniposidic acid and previous termgeniposidenext term on antitumor and radioprotection after sublethal irradiation,

• 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.

• Neurochem Int. 2007 Nov-Dec;51(6-7):361-9. Epub 2007 May 6.

• Biol Pharm Bull. 2006 Jan;29(1):174-6.

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Commercial Catalog

Academic Data

Names and Identifiers

Synonyms

GeniposideGeniposideGenipin 1-glucosideJasminoidin

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

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

Registration numbers

CAS Number

PubChem CID

PubChem SID

Molecule Details

S2411

References

PubChem Literature

From Data Sources

• Ma T et al. J Pharm Pharmacol. 2011 Apr; 63(4):587-93.

• 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.

• 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.

• Cancer Lett. 113 (1997), pp. 31?7.

• 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.

• 1. Hsua HY, Yangb JJ, Lina SY, Lin CC. Comparisons of geniposidic acid and previous termgeniposidenext term on antitumor and radioprotection after sublethal irradiation,

• 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.

• Neurochem Int. 2007 Nov-Dec;51(6-7):361-9. Epub 2007 May 6.

• Biol Pharm Bull. 2006 Jan;29(1):174-6.

Bioactivity

PubChem BioAssay

Properties

Safety Information

Storage Condition

-20°C

Product Information

Pharmacology Properties

Glucagon-like peptide-1 (GLP-1) receptor agonist

Physical Property

Powder

Molecule

ID:73272