tigloyl gomisin H - Moligand™,≥98% , CAS No.66069-55-4

CAS: 66069-55-4 Cat. No.: T664649 Molecular Weight: 500.58

GRADE & PURITY Moligand™, ≥98%

Synonyms

(2E)-2-Methyl-2-butenoic acid (6S,7S,12aR)-5,6,7,8-tetrahydro-7-hydroxy-2,3,10,11,12-pentamethoxy-6,7-dimethyldibenzo[a,c]cycloocten-1-yl ester

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Overview

Tigloylgomisin H is a lignan isolated from the fruits of S. chinensis, can induce quinone reductase (QR) activity in Hepa1c1c7 mouse hepatocarcinoma cells. Tigloylgomisin H functions as a monofunctional inducer that specifically upregulates phase II detoxification enzyme NQO1 through the NF-E2-related factor 2 (Nrf2)-ARE pathway, thus represents a potential liver cancer prevention agent.

Specifications

Synonyms

(2E)-2-Methyl-2-butenoic acid (6S, 7S, 12aR)-5, 6, 7, 8-tetrahydro-7-hydroxy-2, 3, 10, 11, 12-pentamethoxy-6, 7-dimethyldibenzo[a, c]cycloocten-1-yl ester

Specifications & Purity

Moligand™, ≥98%

Storage

Store at 2-8°C, Protected from light

Shipped In

Wet ice

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

Grade

Moligand™

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC=C(C)C(=O)OC1=C2C(=CC(=C1OC)OC)CC(C(CC3=CC(=C(C(=C32)OC)OC)OC)(C)O)C
• IUPAC Name: [(9S,10S)-10-hydroxy-4,5,14,15,16-pentamethoxy-9,10-dimethyl-3-tricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaenyl] (E)-2-methylbut-2-enoate
• InChIKey: ZSAUXCVJDYCLRS-QEEHVONISA-N
• INCHI: 1S/C28H36O8/c1-10-15(2)27(29)36-26-21-17(12-19(31-5)24(26)34-8)11-16(3)28(4,30)14-18-13-20(32-6)23(33-7)25(35-9)22(18)21/h10,12-13,16,30H,11,14H2,1-9H3/b15-10+/t16-,28-/m0/s1
• Isomeric SMILES: C/C=C(\C)/C(=O)OC1=C2C(=CC(=C1OC)OC)C[C@@H]([C@@](CC3=CC(=C(C(=C32)OC)OC)OC)(C)O)C
• Alternate CAS: 66069-55-4
• MeSH Entry Terms: tigloylgomisin H
• Molecular Weight: 500.58

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Tannins
      • Subclass Hydrolyzable tannins

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Tannins
• Subclass: Hydrolyzable tannins
• Intermediate Tree Nodes: Not available
• Direct Parent: Hydrolyzable tannins
• Alternative Parents: Dibenzocyclooctadiene lignans Anisoles Fatty acid esters Alkyl aryl ethers Tertiary alcohols Enoate esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Hydrolyzable tannin - Dibenzocyclooctane lignan - Anisole - Alkyl aryl ether - Fatty acid ester - Fatty acyl - Benzenoid - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Tertiary alcohol - Carboxylic acid ester - Ether - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organic oxygen compound - Alcohol - Hydrocarbon derivative - Carbonyl group - Organooxygen compound - Organic oxide - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.
• 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)

ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)

Discover Target: ALOX5

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

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

HL-60 (67320 Activities)

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SK-MEL (619 Activities)

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SK-OV-3 (52876 Activities)

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KB (17409 Activities)

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Associated Targets(non-human)

LLC-PK1 (2135 Activities)

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Vero (26788 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: light sensitive
• Molecular Weight: 500.600 g/mol
• XLogP3: 5.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 500.241 Da
• Monoisotopic Mass: 500.241 Da
• Topological Polar Surface Area: 92.700 Ų
• Heavy Atom Count: 36
• Formal Charge: 0
• Complexity: 771.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1