ChemSpider 2D Image | Gossypol | C30H30O8

Gossypol

  • Molecular FormulaC30H30O8
  • Average mass518.554 Da
  • Monoisotopic mass518.194092 Da
  • ChemSpider ID3383

More details:

Featured data source
The Merck Index Online

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(-)-1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde
(-)-Gossypol
(+)-Gossypol
(±)-2,2'-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)
(±)-Gossypol from cotton seeds
[2,2'-Binaphthalene]-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)- [ACD/Index Name]
1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde
1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-2,2'-binaphthalene-8,8'-dicarbaldehyde
1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-di(propan-2-yl)-2,2'-binaphthalene-8,8'-dicarbaldehyde
1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl[2,2'-binaphthalene]-8,8'-dicarboxaldehyde
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

8DY2X8LXW4 [DBID]
DU3100000 [DBID]
KAV15B369O [DBID]
UNII:8DY2X8LXW4 [DBID]
UNII:KAV15B369O [DBID]
UNII:XNA7DR63CQ [DBID]
XNA7DR63CQ [DBID]
AI3-22957 [DBID]
AIDS000457 [DBID]
AIDS-000457 [DBID]
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  • Spectroscopy
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Ester; Food Toxin; Plant Toxin; Metabolite; Natural Compound Toxin, Toxin-Target Database T3D3081

    • Safety:

      22 40 LKT Labs [G5874]
      351 LKT Labs [G5874]
      None LKT Labs [G5874]
      Xn LKT Labs [G5874]

    • Chemical Class:

      aromatic Microsource [01504019]

    • Drug Status:

      experimental Microsource [01504019]

    • Compound Source:

      Gossypium raimondii PlantCyc CPD-9526
      Gossypium spp Microsource [01504019]
      gossypol biosynthesis PlantCyc CPD-9526, CPD-9526
      Linum usitatissimum PlantCyc CPD-9526

    • Bio Activity:

      2 hemigossypol + an oxidized electron acceptor -> gossypol + a reduced electron acceptor PlantCyc CPD-9526, CPD-9526
      Apoptosis Tocris Bioscience 3367, 1964
      Apoptosis MedChem Express HY-15464, HY-13407
      Apoptosis; MedChem Express HY-15464, HY-13407
      AT101, the R-(-) enantiomer of Gossypol acetic acid, binds with Bcl-2, Bcl-xL and Mcl-1 with Ki of 0.32 ?M, 0.48 ?M and 0.18 ?M.; IC50 Value: 0.32/0.48/0.18 uM for Bcl-2/Bcl-xL/Mcl-1; Target: Bcl-2; Bcl-xl; Mcl-1; AT-101 is orally bioavailable solvate of R-(-)-enantiomer of gossypol with potential antineoplastic activity. MedChem Express HY-15464, HY-13407
      Bcl-2 Family Tocris Bioscience 3367, 1964
      Bcl-2 Family MedChem Express HY-15464, HY-13407
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio HB0304
      Cell Biology Tocris Bioscience 3367, 1964
      Dehydrogenase enzyme inhibitor Hello Bio HB0304
      Dehydrogenase enzyme inhibitor. Bcl-2 homology 3 (BH3)-mimetic agent, binds to the BH3 domain of members of the B-cell lymphoma 2 (Bcl-2) family. Inhibits APE-1 (apurinic/apyrimidinic endonuclease 1) activity. Shows antioxidant, antiviral, antiparasitic, apoptotic and anticancer actions. Hello Bio HB0304
      Downregulates Bcl-2 and Mcl-1; pro-apoptotic Tocris Bioscience 3367
      Enzymes/Dehydrogenase Hello Bio HB0304
      Gossypol has been known to exert a potential for anti-cancer, anti-inflammatory and other important therapeutic activities, gossypol binds and antagonizes anti-apoptotic effect of Bcl-2 family protein s MedChem Express
      Gossypol has been known to exert a potential for anti-cancer, anti-inflammatory and other important therapeutic activities, gossypol binds and antagonizes anti-apoptotic effect of Bcl-2 family proteins ; IC50 value:; Target: Bcl-2; anticancer agent; The substance, a yellow pigment similar to flavonoids, is present in cottonseed oil. MedChem Express HY-15464, HY-13407
      Gossypol has been known to exert a potential for anti-cancer, anti-inflammatory and other important therapeutic activities, gossypol binds and antagonizes anti-apoptotic effect of Bcl-2 family proteins ;IC50 value:;Target: Bcl-2; anticancer agent;The substance, a yellow pigment similar to flavonoids, is present in cottonseed oil. In the plant, it acts as a natural defensive agent against predators, provoking infertility in insects. In most animals, gossypol provokes infertility, and in man it causes spermatogenesis arrest at relatively low doses.;In vitro: The natural product and putative BH3 mimetic gossypol enhanced the cytotoxicity of BRD4770 in a synergistic manner in p53-mutant PANC-1 cells but not in immortalized non-tumorigenic pancreatic cells. The combination of gossypol and BRD4770 increased LC3-II levels and the autophagosome number in PANC-1 cells, and the compound combination appears to act in a BNIP3 (B-cell lymphoma 2 19-kDa interacting protein)-dependent manner [1] MedChem Express HY-15464, HY-13407
      Lipophilic agent derived from cottonseed. Exhibits multiple biological effects including antifertility and anticancer activity. Proapoptotic; downregulates Bcl-2 and Bcl-XL. R-enantiomer also available. Tocris Bioscience 1964
      Lipophilic agent derived from cottonseed. Exhibits multiple biological effects including antifertility and anticancer activity. Proapoptotic; downregulates Bcl-2 and Bcl-XL. R-enantiomer available (Ca t. No. 3367). Tocris Bioscience 1964
      Lipophilic agent derived from cottonseed. Exhibits multiple biological effects including antifertility and anticancer activity. Proapoptotic; downregulates Bcl-2 and Bcl-XL. R-enantiomer available (Cat. No. 3367). Tocris Bioscience 1964
      Proapoptotic; downregulates Bcl-2 and Bcl-XL Tocris Bioscience 1964
      R-(-)-enantiomer of gossypol (Cat. No. 1964). Mimics the BH3 domains of Bcl-2, Bcl-XL and Mcl-1. Disrupts heterodimerization of Bcl-2 with proapoptotic family members. Induces apoptosis in vitro throu gh activation of caspase-9; cytotoxic to multiple myeloma and drug-resistant cell lines. Delays onset of androgen-independent growth of VCaP prostate cancer xenografts in vivo. Tocris Bioscience 3367
      R-(-)-enantiomer of gossypol (Cat. No. 1964). Mimics the BH3 domains of Bcl-2, Bcl-XL and Mcl-1. Disrupts heterodimerization of Bcl-2 with proapoptotic family members. Induces apoptosis in vitro through activation of caspase-9; cytotoxic to multiple myeloma and drug-resistant cell lines. Delays onset of androgen-independent growth of VCaP prostate cancer xenografts in vivo. Tocris Bioscience 3367

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.4±0.1 g/cm3
Boiling Point: 707.9±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.3 mmHg at 25°C
Enthalpy of Vaporization: 107.2±3.0 kJ/mol
Flash Point: 395.9±28.0 °C
Index of Refraction: 1.742
Molar Refractivity: 149.3±0.3 cm3
#H bond acceptors: 8
#H bond donors: 6
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 3
ACD/LogP: 6.16
ACD/LogD (pH 5.5): 5.77
ACD/BCF (pH 5.5): 14281.62
ACD/KOC (pH 5.5): 32483.58
ACD/LogD (pH 7.4): 5.16
ACD/BCF (pH 7.4): 3506.47
ACD/KOC (pH 7.4): 7975.47
Polar Surface Area: 156 Å2
Polarizability: 59.2±0.5 10-24cm3
Surface Tension: 71.3±3.0 dyne/cm
Molar Volume: 369.6±3.0 cm3

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