Geniposidic acid - ≥99% , CAS No.27741-01-1

CAS: 27741-01-1 Cat. No.: G129326 Molecular Weight: 374.34 EC Number: 683-161-5

GRADE & PURITY ≥99%

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 2-8°C

Shipped In

Wet ice

Specifications

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

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

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 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 488189808
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488189808
• Canonical Smiles: 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
• Isomeric 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
• Molecular Weight: 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
    • Class Prenol lipids
      • Subclass Terpene glycosides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: 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
• Description: 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

Associated Targets(Human)

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

Discover Target: PTGS1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

Discover Target: PTGS2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

XDH Tclin Xanthine dehydrogenase (1038 Activities)

Discover Target: XDH

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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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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

pol Human immunodeficiency virus type 1 integrase (9041 Activities)

Discover Target: pol

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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)

Discover Target: rep

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO 16 mg/mL Water <1 mg/mL Ethanol 2 mg/mL
• Molecular Weight: 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

References

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]