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Guttiferone G

CAT: 0804-HY-N9892Size: 1 EachDry Ice: NoHazardous: No
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CAT#:0804-HY-N9892Size:1 Each
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Description
Guttiferone G inhibits recombinant human SIRT1 and SIRT2 (IC50: 9 and 22 μM, respectively) . Guttiferone G is weakly cytotoxic in A2780 human ovarian cell line (IC50: 8.0 μg/mL) . Guttiferone G can be isolated from Garcinia macrophylla[1][2].
CAS Number
666174-75-0
UNSPSC
12352005
Target
Sirtuin
Type
Natural Products
Related Pathways
Cell Cycle/DNA Damage; Epigenetics
Applications
Cancer-programmed cell death
Field of Research
Others
Assay Protocol
https://www.medchemexpress.com/guttiferone-g.html
Solubility
10 mM in DMSO
Smiles
C/C(C)=C/C[C@](C([C@]12C/C=C(C)/C)=O)(C(C(C(C(C=C3)=CC(O)=C3O)=O)=C1O)=O)[C@](C)([C@@H](C2)C/C=C(C)/CC/C=C(C)/C)CC/C=C(C)/C
Molecular Formula
C43H58O6
Molecular Weight
670.92
References & Citations
[1]Williams RB, et al. A novel cytotoxic guttiferone analogue from Garcinia macrophylla from the Suriname rainforest. Planta Med. 2003 Sep;69 (9) :864-6.|[2]Gey C, et al. Phloroglucinol derivatives guttiferone G, aristoforin, and hyperforin: inhibitors of human sirtuins SIRT1 and SIRT2. Angew Chem Int Ed Engl. 2007;46 (27) :5219-22.
Shipping Conditions
Room temperature
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Guttiferone G

Guttiferone G has been reported in Garcinia macrophylla with data available.

CAS Number666174-75-0
PubChem CID132598259
IUPAC Name(1R,5R,6S,7R)-3-[(3,4-dihydroxyphenyl)-hydroxymethylidene]-7-[(2E)-3,7-dimethylocta-2,6-dienyl]-1,5,6-tris(3-methylbut-2-enyl)bicyclo[3.3.1]nonane-2,4,9-trione
Molecular FormulaC41H54O6
Molecular Weight642.9
XLogP11.3
Topological Polar Surface Area112
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count12
Heavy Atom Count47
Formal Charge0
Complexity1390
SMILES
CC(=CCC/C(=C/C[C@@H]1C[C@@]2(C(=O)C(=C(C3=CC(=C(C=C3)O)O)O)C(=O)[C@]([C@H]1CC=C(C)C)(C2=O)CC=C(C)C)CC=C(C)C)/C)C
InChI
InChI=1S/C41H54O6/c1-25(2)11-10-12-29(9)14-15-31-24-40(21-19-27(5)6)37(45)35(36(44)30-16-18-33(42)34(43)23-30)38(46)41(39(40)47,22-20-28(7)8)32(31)17-13-26(3)4/h11,13-14,16,18-20,23,31-32,42-44H,10,12,15,17,21-22,24H2,1-9H3/b29-14+,36-35?/t31-,32+,40-,41+/m1/s1
InChIKey
WVVJNGUTZLKXSY-FFNRHCHASA-N
Chemical Structure
2D Structure
2D structure of Guttiferone G
CAS: 666174-75-0
CID: 132598259
Formula: C41H54O6
MW: 642.9
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight642.9
XLogP311.3
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count12
Exact Mass642.39203944
Monoisotopic Mass642.39203944
Topological Polar Surface Area112 Ų
Heavy Atom Count47
Formal Charge0
Complexity1390
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count1
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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