GRADE & PURITY 10mM in DMSO

Synonyms

2-​Butenoic acid,4-​[(1R,​3aS,​5S,​12aS)​-​9-​[(2E)​-​3,​7-​dimethyl-​2,​6-​octadien-​1-​yl]​-​3a,​4,​5,​7-​tetrahydro-​8,​10-​dihydroxy-​3,​3-​dimethyl-​11-​(3-​methyl-​2-​buten-​1-​yl)​-​7,​13-​dioxo-​1,​5-​methano-​1H,​3H-​furo[3,​4-​d]​xanthen-​1-​yl

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Information

Gambogenic acid is an active ingredient in gamboge, with anticancer activity. Gambogenic acid acts as an effective inhibitor of EZH2, specifically and covalently binds to Cys668 within the EZH2-SET domain, and induces EZH2 ubiquitination.

Targets

FGFR ; EZH2

Gambogenic acid is an active ingredient in gamboge, with anticancer activity. Gambogenic acid acts as an effective inhibitor of EZH2, specifically and covalently binds to Cys668 within the EZH2-SET domain, and induces EZH2 ubiquitination.

Specifications

Synonyms

2-​Butenoic acid, 4-​[(1R, ​3aS, ​5S, ​12aS)​-​9-​[(2E)​-​3, ​7-​dimethyl-​2, ​6-​octadien-​1-​yl]​-​3a, ​4, ​5, ​7-​tetrahydro-​8, ​10-​dihydroxy-​3, ​3-​dimethyl-​11-​(3-​methyl-​2-​buten-​1-​yl)​-​7, ​13-​dioxo-​1, ​5-​methano-​1H, ​3H-​furo[3, ​4-​d]​xanthen-​1-​yl

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Gambogenic Acid, identified from Gamboge, is an inhibitor of the FGFR signaling pathway in erlotinib-resistant non-small-cell lung cancer (NSCLC) and exhibits anti-tumor effects. Gambogenic acid acts is also an effective inhibitor of EZH2 that specificall

Storage

Protected from light, 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.

Product Properties

• ALogP: 7.717
• HBD Count: 2
• Rotatable Bond: 10

Names and Identifiers

• Canonical Smiles: CC(=CCCC(=CCC1=C(C(=C2C(=C1O)C(=O)C3=CC4CC5C3(O2)C(C4=O)(OC5(C)C)CC=C(C)C(=O)O)CC=C(C)C)O)C)C
• IUPAC Name: (Z)-4-[(1S,2S,13S,15R)-7-[(2E)-3,7-dimethylocta-2,6-dienyl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-enyl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.02,11.02,15.04,9]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid
• InChIKey: RCWNBHCZYXWDOV-VSFMGBBVSA-N
• INCHI: 1S/C38H46O8/c1-20(2)10-9-11-22(5)13-15-25-30(39)26(14-12-21(3)4)33-29(31(25)40)32(41)27-18-24-19-28-36(7,8)46-37(34(24)42,38(27,28)45-33)17-16-23(6)35(43)44/h10,12-13,16,18,24,28,39-40H,9,11,14-15,17,19H2,1-8H3,(H,43,44)/b22-13+,23-16-/t24-,28+,37+,38-/m1/s1
• Isomeric SMILES: CC(=CCC/C(=C/CC1=C(C(=C2C(=C1O)C(=O)C3=C[C@@H]4C[C@@H]5[C@@]3(O2)[C@](C4=O)(OC5(C)C)C/C=C(/C)\C(=O)O)CC=C(C)C)O)/C)C
• PubChem CID: 10794070
• Molecular Weight: 630.77

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Benzopyrans
      • Subclass 1-benzopyrans
        • Level5 Dibenzopyrans
          • Level6 Xanthenes
            • Level7 Xanthones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Benzopyrans
• Subclass: 1-benzopyrans
• Intermediate Tree Nodes: Dibenzopyrans - Xanthenes
• Direct Parent: Xanthones
• Alternative Parents: Chromones Aromatic monoterpenoids Aryl ketones Phenols Oxepanes Cyclohexenones Alkyl aryl ethers Vinylogous acids Oxolanes Oxacyclic compounds Monocarboxylic acids and derivatives Dialkyl ethers Carboxylic acids Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Xanthone - Chromone - Aromatic monoterpenoid - Monoterpenoid - Aryl ketone - Alkyl aryl ether - Phenol - Oxepane - Cyclohexenone - Benzenoid - Vinylogous acid - Oxolane - Ketone - Oxacycle - Carboxylic acid derivative - Carboxylic acid - Dialkyl ether - Ether - Monocarboxylic acid or derivatives - Organic oxide - Carbonyl group - Hydrocarbon derivative - Organic oxygen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.
• External Descriptors: Not available

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)

U-251 (51189 Activities)

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

A549 (127892 Activities)

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

HepG2 (196354 Activities)

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

TXN Tchem Thioredoxin (111 Activities)

Discover Target: TXN

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

Associated Targets(non-human)

Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

Discover Target: Ptpn1

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

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: light sensitive
• DMSO(mg / mL) Max Solubility: 10
• DMSO(mM) Max Solubility: 15.8537135992394
• Molecular Weight: 630.800 g/mol
• XLogP3: 7.900
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 630.319 Da
• Monoisotopic Mass: 630.319 Da
• Topological Polar Surface Area: 130.000 Ų
• Heavy Atom Count: 46
• Formal Charge: 0
• Complexity: 1440.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1