(1R,5R,7R)-3-(3,4-dihydroxybenzoyl)-4-hydroxy-8,8-dimethyl-5-[(2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione

• ChemBase ID: 153216
• Molecular Formular: C38H50O6
• Molecular Mass: 602.8
• Monoisotopic Mass: 602.36073932
• SMILES: CC(=CC[C@@H]1C[C@@]2(C(=C(C(=O)[C@@](C2=O)(C1(C)C)CC=C(C)C)C(=O)c1ccc(c(c1)O)O)O)C[C@H](CC=C(C)C)C(=C)C)C
• Canonical SMILES: CC(=CC[C@]12C(=O)C(=C([C@@](C1=O)(C[C@@H](C(=C)C)CC=C(C)C)C[C@H](C2(C)C)CC=C(C)C)O)C(=O)c1ccc(c(c1)O)O)C
• InChI: 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/h11-12,14,16-17,19,27-28,39-40,42H,7,13,15,18,20-21H2,1-6,8-10H3/t27-,28+,37+,38-/m0/s1
• InChIKey: QDKLRKZQSOQWJQ-SMDXAGPFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,5R,7R)-3-(3,4-dihydroxybenzoyl)-4-hydroxy-8,8-dimethyl-5-[(2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione
• IUPAC Traditional name: garcinol
• Synonyms: (1R,5R,7R)-3-(3,4-Dihydroxybenzoyl)-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; Camboginol; Garcinol

Database IDs

• CAS Number: 78824-30-3
• MDL Number: MFCD03700761
• PubChem SID: 162247355
• PubChem CID: 174159

CALCULATED PROPERTIES

• Acid pKa: 2.312387
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 6.11443
• LogD (pH = 7.4): 5.5304914
• Log P: 9.140703
• Molar Refractivity: 180.584 cm^3
• Polarizability: 68.62504 Å^3
• Polar Surface Area: 111.9 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: : >5 mg/mL
• Apperance: powder, yellow

Safety Information

• Storage Temperature: -20°C

Product Information

• Purity: ≥95%
• Empirical Formula (Hill Notation): C38H50O6

DETAILS

Sigma Aldrich - G5173

Biochem/physiol Actions
Garcinol is a HAT (histone acetyltransferase) inhibitor. Garcinol is anti-inflammatory and anti-carcinogenic. Histone acetyltransferases provide opposing enzymatic mechanisms for chromatin remodeling and epigenetic control of gene expression. HATs are involved in regulation of transformation, transcription, differentiation, apoptosis, embryonic development and oncogenesis. IC50 p300 = 7 mM; IC50 PCAF = 5 mM (similar to anacardic acid). Garcinol is highly toxic compared to LTK-14, and does not discriminate between p300 and PCAF.