Gentiopicroside - 10mM in DMSO , CAS No.20831-76-9

CAS: 20831-76-9 Cat. No.: G422524 Molecular Weight: 356.33 EC Number: 244-070-2

GRADE & PURITY 10mM in DMSO

Synonyms

(3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one | Q27106718 | (5R,6S)-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-vinyl-5,6-dihydropyr

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Gentiopicroside (GPS) is a secoiridoid glycoside sourced from the dried roots of Gentiana rigescens.

Application：

Gentiopicroside has been used as a reference standard for the quantification of iridoid glycoside in six Caucasian Gentians herb samples using high-performance liquid chromatography with diode array detection (HPLC-DAD) technique.

Specifications

Synonyms

(3S, 4R)-4-ethenyl-3-[(2S, 3R, 4S, 5S, 6R)-3, 4, 5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4, 6-dihydro-3H-pyrano[3, 4-c]pyran-8-one | Q27106718 | (5R, 6S)-6-(((2S, 3R, 4S, 5S, 6R)-3, 4, 5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-vinyl-5, 6-dihydropyr

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Anticonvulsant agent. Downregulates GluN2B-containing NMDA receptors in the NAc. Antiaddiction, anticonvulsant and anxiolytic effects in vivo. Orally active.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Names and Identifiers

• Canonical Smiles: C=C[C@H]1[C@H](O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C3C(OCC=C31)=O
• IUPAC Name: (3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one
• InChIKey: DUAGQYUORDTXOR-GPQRQXLASA-N
• INCHI: 1S/C16H20O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2-3,6-7,10-13,15-20H,1,4-5H2/t7-,10-,11-,12+,13-,15+,16+/m1/s1
• Isomeric SMILES: C=C[C@H]1[C@@H](OC=C2C1=CCOC2=O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• Molecular Weight: 356.33
• Reaxy-Rn: 53772
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=53772&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 O-glycosyl compounds

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: O-glycosyl compounds
• Alternative Parents: Hexoses Dihydropyranones Oxanes Vinylogous esters Enoate esters Secondary alcohols Lactones Polyols Oxacyclic compounds Monocarboxylic acids and derivatives Acetals Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Hexose monosaccharide - O-glycosyl compound - Dihydropyranone - Monosaccharide - Oxane - Pyran - Enoate ester - Vinylogous ester - Alpha,beta-unsaturated carboxylic ester - Secondary alcohol - Carboxylic acid ester - Lactone - Organoheterocyclic compound - Carboxylic acid derivative - Polyol - Monocarboxylic acid or derivatives - Acetal - Oxacycle - Organic oxide - Hydrocarbon derivative - Alcohol - Carbonyl group - Primary alcohol - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
• External Descriptors: Iridoid, 10-alkyliridoid and secoiridoid monoterpenoids

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)

SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)

Discover Target: SMAD3

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Plasmodium falciparum (966862 Activities)

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Mus musculus (284745 Activities)

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Hepatitis C virus (23859 Activities)

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3T3-L1 (3664 Activities)

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CHO (4503 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 191°C
• Molecular Weight: 356.320 g/mol
• XLogP3: -1.200
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 356.111 Da
• Monoisotopic Mass: 356.111 Da
• Topological Polar Surface Area: 135.000 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 598.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 7
• 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. Bo Zou, Yue Fu, Chaofan Cao, Dianzhu Pan, Wei Wang, Lingfei Kong.  (2021)  Gentiopicroside ameliorates ovalbumin-induced airway inflammation in a mouse model of allergic asthma via regulating SIRT1/NF-κB signaling pathway.  PULMONARY PHARMACOLOGY & THERAPEUTICS,      [PMID:33887491] [10.1016/j.pupt.2021.102034]

2. Lili Dai, Yi Geng, Xiaofeng Ding, Zhikun Zhang, Chenhuan Lai, Daihui Zhang, Changlei Xia, Yongxian Lai.  (2025)  Highly stretchable, self-adhesive, and biocompatible cellulose/chitosan based double network hydrogel for wound dressing.  CARBOHYDRATE POLYMERS,      [PMID:40733801] [10.1016/j.carbpol.2025.123869]