Geniposidic acid - 10mM in DMSO , CAS No.27741-01-1

CAS: 27741-01-1 Cat. No.: G422973 Summenformel: C₁₆H₂₂O₁₀ Molekulargewicht: 374.34 EG-Nummer: 683-161-5

GRADE & PURITY 10mM in DMSO

Synonyms

Q5533206 | NCGC00346663-03 | (1S,4aS,7aS)-7-(hydroxymethyl)-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid | Cyclopenta[c]pyran-4-carboxylic acid, 1-(beta-D-gluco

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Specifications

Synonyme

Q5533206 | NCGC00346663-03 | (1S,4aS,7aS)-7-(hydroxymethyl)-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid | Cyclopenta[c]pyran-4-carboxylic acid, 1-(beta-D-gluco

Spezifikationen & Reinheit

10mM in DMSO

Biochemische und physiologische Mechanismen

Anti-inflammatory and anticancer agent. Moderate COX inhibitor and Heat shock factor 1 inducer. Promotes collagen synthesis and shows antitumor effects in vivo. Orally active.

Storage

Store at -80°C

Verschickt in

Dry ice packs + Cold packs

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Namen und Kennungen

• Pubchem Sid: 528764747
• Kanonisches Lächeln: C1C=C(C2C1C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)O)CO
• IUPAC Name: (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
• InChIKey: ZJDOESGVOWAULF-OGJQONSISA-N
• 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
• Isomere SMILES: C1C=C([C@@H]2[C@H]1C(=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)O)CO
• Molekulargewicht: 374.34
• Reaxy-Rn: 37967573
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=37967573&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Klasse Prenol lipids
      • Subclass Terpene glycosides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Klasse: Prenol lipids
• Subclass: Terpene glycosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Iridoid O-glycosides
• Alternative Parents: Hexoses O-glycosyl compounds Iridoids and derivatives Bicyclic monoterpenoids Oxanes Vinylogous esters Secondary alcohols Polyols Oxacyclic compounds Acetals Monocarboxylic acids and derivatives Carboxylic acids Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Iridoid o-glycoside - Hexose monosaccharide - Glycosyl compound - Iridoid-skeleton - O-glycosyl compound - Bicyclic monoterpenoid - Monoterpenoid - Monosaccharide - Oxane - Vinylogous ester - Secondary alcohol - Acetal - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Oxacycle - Carboxylic acid - Carboxylic acid derivative - Polyol - Primary alcohol - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organic oxygen compound - Alcohol - Aliphatic heteropolycyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.
• External Descriptors: Iridoids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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XDH Tclin Xanthine dehydrogenase (1038 Activities)

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Raji (5516 Activities)

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dsDNA (365 Activities)

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quadruplex DNA (2700 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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pol Human immunodeficiency virus type 1 integrase (9041 Activities)

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Mus musculus (284745 Activities)

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Enterovirus A71 (1246 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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SARS-CoV-2 (38078 Activities)

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Wirkungsmechanismen

Chemische und physikalische Eigenschaften

• Molekulargewicht: 374.340 g/mol
• XLogP3: -2.700
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 374.121 Da
• Monoisotopic Mass: 374.121 Da
• Topological Polar Surface Area: 166.000 Ų
• Heavy Atom Count: 26
• Formal Charge: 0
• Complexity: 602.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referenzen

1. Yingya Zhou, Meng Feng, Hongyan Hai, Xinmeng Teng, Xinxin Zhou, Yong Gao, Yanhua Zhong, Changhui Liu.  (2025)  Geniposidic acid alleviated metabolic dysfunction-associated steatotic liver disease by exciting SIRT6 signaling.  PHYTOMEDICINE,      [PMID:40782762] [10.1016/j.phymed.2025.157140]