Garcinol - Moligand™, ≥95% , Inhibitor of E1A binding protein p300;Inhibitor of lysine acetyltransferase 2B, CAS No.78824-30-3, Inhibitor of E1A binding protein p300;Inhibitor of lysine acetyltransferase 2B

CAS: 78824-30-3 Cat. No.: G275583 Molecular Weight: 602.8

GRADE & PURITY Moligand™, ≥95%

Synonyms

Garcinol | CHEBI:5276 | MFCD03700761 | (1R,5R,7R)-3-(3,4-Dihydroxybenzyol)-4-hydroxy-8,8-dimethyl-1,7-bis(3-methyl-2-buten-1-yl)-5-[(2S)-5-methyl-2-(1-methylethenyl)-4-hexen-1-yl]bicyclo[3.3.1]non-3-ene-2,9-dione | MS-30635 | C09929 | (1S,3Z,5R,7R)-3-[(3,

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Garcinol, a polyisoprenylated benzophenone harvested from Garcinia indica, exerts anti-cholinesterase properties towards acetyl cholinesterase (AChE) and butyrylcholinesterase (BChE) with IC50s of 0.66 μM and 7.39 μM, respectively. Garcinol also inhibits histone acetyltransferases (HATs, IC50= 7 μM) and p300/CPB-associated factor (PCAF, IC50 = 5 μM). Garcinol has anti-inflammatory and anti-cancer activity.

Specifications

Synonyms

Garcinol | CHEBI:5276 | MFCD03700761 | (1R, 5R, 7R)-3-(3, 4-Dihydroxybenzyol)-4-hydroxy-8, 8-dimethyl-1, 7-bis(3-methyl-2-buten-1-yl)-5-[(2S)-5-methyl-2-(1-methylethenyl)-4-hexen-1-yl]bicyclo[3.3.1]non-3-ene-2, 9-dione | MS-30635 | C09929 | (1S, 3Z, 5R, 7R)-3-[(3,

Specifications & Purity

Moligand™, ≥95%

Biochemical and Physiological Mechanisms

Potent histone acetyltransferase p300 and PCAF inhibitor (IC 50 values are 7 and 5 μM for p300 and PCAF respectively). Pleiotropic agent. Strongly inhibits chromatin transcription and induces apoptosis. Inhibits histone acetylation in vivo .

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Inhibitor of E1A binding protein p300;Inhibitor of lysine acetyltransferase 2B

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

≥95%

Names and Identifiers

• Canonical Smiles: CC(=CCC1CC2(C(=O)C(=C(C3=CC(=C(C=C3)O)O)O)C(=O)C(C2=O)(C1(C)C)CC=C(C)C)CC(CC=C(C)C)C(=C)C)C
• IUPAC Name: (1S,3Z,5R,7R)-3-[(3,4-dihydroxyphenyl)-hydroxymethylidene]-6,6-dimethyl-5,7-bis(3-methylbut-2-enyl)-1-[(2S)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]bicyclo[3.3.1]nonane-2,4,9-trione
• InChIKey: DTTONLKLWRTCAB-BZSUNBQASA-N
• INCHI: 1S/C38H50O6/c1-22(2)11-13-27(25(7)8)20-37-21-28(15-12-23(3)4)36(9,10)38(35(37)44,18-17-24(5)6)34(43)31(33(37)42)32(41)26-14-16-29(39)30(40)19-26/h11-12,14,16-17,19,27-28,39-41H,7,13,15,18,20-21H2,1-6,8-10H3/b32-31-/t27-,28+,37+,38-/m0/s1
• Isomeric SMILES: CC(=CC[C@@H]1C[C@@]2(C(=O)/C(=C(\C3=CC(=C(C=C3)O)O)/O)/C(=O)[C@@](C2=O)(C1(C)C)CC=C(C)C)C[C@H](CC=C(C)C)C(=C)C)C
• Molecular Weight: 602.8
• Reaxy-Rn: 31968658
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=31968658&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Monoterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Monoterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Bicyclic monoterpenoids
• Alternative Parents: Aromatic monoterpenoids Catechols 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Vinylogous acids Ketones Enols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Bicyclic monoterpenoid - Aromatic monoterpenoid - Catechol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Benzenoid - Monocyclic benzene moiety - Vinylogous acid - Ketone - Enol - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
• 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)

EP300 Tchem Histone acetyltransferase p300 (1 Activities)

Discover Target: EP300

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

KAT2B Tchem Histone acetyltransferase KAT2B (1 Activities)

Discover Target: KAT2B

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Solubility: Soluble in DMSO to 25 mM and in ethanol to 25 mM
• Sensitivity: Moisture sensitive
• Molecular Weight: 602.800 g/mol
• XLogP3: 10.300
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 602.361 Da
• Monoisotopic Mass: 602.361 Da
• Topological Polar Surface Area: 112.000 Ų
• Heavy Atom Count: 44
• Formal Charge: 0
• Complexity: 1300.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• 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