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Drug

D0268 | Gossypol

Molecular Formula C30H30O8
Molecular Weight 518.6
Structure

Toxicity Dose Time Species Model Method Action Positive criterion Reference
MEMBRANE POTENTIAL 1 µM 30 mins mouse liver mitochondria Rh123 fluorescence (excitation 485 nm, emission 535 nm) are recorded using a fluorescence multi-well plate reader (mCICCP (20 µM) treatments was considered as the 100% baseline for ΔΨm loss) decrease EC20 36
RESPIRATION 30.3 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. decrease EC20 36
RESPIRATION ND 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. Negative EC20 36
SWELLING > 10 µM 30 mins mouse liver mitochondria swelling assay: Absorbance at 545 nm using a fluorescence multi-well plate reader (CaCl2 (50 µM) was considered as the 100% baseline for the swelling ) increase EC20 36

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase 30.3 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. inhibit EC20 36
Succinate dehydrogenase ND 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. Negative EC20 36
Cytochrome c > 10 µM 30 mins mouse liver mitochondria Cytochrome c release was evaluated using ELISA kit ( 20 µg/ml Alamethicin was used as 100% baseline) release EC20 36

Pictogram Signal Statements Precautionary Statement Codes
Warning

Aggregated GHS information provided by 193 companies from 3 notifications to the ECHA C&L Inventory.


H351 (99.48%): Suspected of causing cancer [Warning Carcinogenicity]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P201, P202, P281, P308+P313, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism Test type Route Dose (normalized dose) Effect Source
rat LD50 oral 2315mg/kg (2315mg/kg) Journal of the American Oil Chemists' Society. Vol. 37, Pg. 40, 1960.
pig LD50 oral 550mg/kg (550mg/kg) Journal of the American Oil Chemists' Society. Vol. 40, Pg. 571, 1963.


  • (+)-Gossypol (+)1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde (+-)-Gossypol
    (+/-)-2,2'-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene) (+/-)-Gossypol (+/-)-Gossypol from cotton seeds, >=95% (HPLC)
    (-)-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'-dicarboxaldehyde (-)-2,2'-Bis(1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthalene)
    (-)-Gossypol (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahyd (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'-dicarboxaldehyde, 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-5,5'-diisopropyl-3,3'-dimethyl- (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-, (+)-
    (2,2-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-, (+-)- (2,8'-dicarboxaldehyde, 1,1',6,6'7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl- (R)-(-)-Gossypol
    (R)-Gossypol 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'-dicarboxaldehyde
    1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2'-binaphthalene]-8,8'-dicarbaldehyde 1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl[2,2'-binaphthalene]-8,8'-dicarbaldehyde 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'-dicarbaldehyde 1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthyl-8,8'-dicarbaldehyde
    1,1',6,6'-Tetrahydroxy-3,3'-dimethyl-5,5'-diisopropyl-8,8'-bis(hydroxymethylene)-2,2'-binaphthalene-7,7'(8H,8'H)-dione 156767-EP2284178A2 156767-EP2284179A2
    2,2'-Bis(1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthalene) 2,2'-bi[8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene] 20300-26-9
    303-45-7 303G457 4-08-00-03754 (Beilstein Handbook Reference)
    4CA-0193 7-(8-Formyl-1,6,7-trihydroxy-3-methyl-5-(methylethyl)(2-naphthyl))-2,3,8-trihydroxy-6-methyl-4-(methylethyl)naphthalenecarbaldehyde 7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde
    7-(8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methyl-2-naphthyl)-2,3,8-trihydroxy-4-isopropyl-6-methyl-naphthalene-1-carbaldehyde 7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(methylethyl)(2-naphthyl)]-2,3,8-trihy droxy-6-methyl-4-(methylethyl)naphthalenecarbaldehyde 7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(propan-2-yl)naphthalen-2-yl]-2,3,8-trihydroxy-6-methyl-4-(propan-2-yl)naphthalene-1-carbaldehyde
    8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methyl-2,2'-bisnaphthalene 8-Formyl-1,7-trihydroxy-5-isopropyl-3-methyl-2,2'-bisnaphthalene 8DY2X8LXW4
    90141-22-3 A15004 AB00052921
    AC-20251 AC-30274 AI3-22957
    AK148510 AKOS002140475 AS-55885
    AT-101/GOSSYPOL AT101 AT101
    BCP03607 BCP0726000183 BCP9000332
    BDBM23223 BDBM46555 BL 193
    BN0226 BPBio1_000851 BRD-K19295594-001-06-9
    BRD-K19295594-001-10-1 BRD-K19295594-015-02-8 BRN 1917878
    BSPBio_000773 BSPBio_002804 BSPBio_003191
    C-23051 C07667 C30H30O8
    CAS-303-45-7 CCG-35400 CCRIS 2689
    CHEMBL51483 CS-2106 CTK8G0094
    DB-047766 DB13044 DSSTox_CID_3110
    DSSTox_GSID_23110 DSSTox_RID_76879 DTXSID5023110
    Dipotassium Salt, Gossypol DivK1c_000173 DivK1c_006698
    EX-A068 FT-0631917 GTPL4204
    Gissypol, (R)- Gossyol Gossypol Dipotassium Salt
    Gossypol Sodium Salt Gossypol acetate Gossypol from cotton seeds
    Gossypol, (+)-Isomer Gossypol, (+-)-Isomer Gossypol, (-)-Isomer
    Gossypol, (R)- Gossypol, (S)- Gossypol, 4
    HMS1570G15 HMS2097G15 HMS3262J15
    HMS3268O22 HMS3413L10 HMS3651C18
    HMS3677L10 HSDB 7872 HY-13407
    IDI1_000173 J-017920 KAV15B369O
    KBio1_000173 KBio1_001642 KBio2_000839
    KBio2_002001 KBio2_003407 KBio2_004569
    KBio2_005975 KBio2_007137 KBio3_002024
    KBio3_002691 KBioGR_001451 KBioGR_002303
    KBioSS_000839 KBioSS_002001 KS-0000183E
    LMPR0103330002 LP00847 LS-43993
    LS-43994 LS-43996 LS-43997
    MCULE-2539927675 MFCD00017352 MLS000028490
    N2135 NCGC00016423-01 NCGC00016423-02
    NCGC00016423-03 NCGC00016423-04 NCGC00016423-05
    NCGC00016423-06 NCGC00016423-07 NCGC00016423-08
    NCGC00016423-09 NCGC00016423-10 NCGC00016423-14
    NCGC00016423-15 NCGC00025331-01 NCGC00025331-02
    NCGC00025331-03 NCGC00025331-04 NCGC00025331-06
    NCGC00025331-07 NCGC00261532-01 NCI60_001588
    NCI60_004391 NCIMech_000271 NINDS_000173
    NSC 56817 NSC 624336 NSC-19048
    NSC-56817 NSC-624336 NSC-726190
    NSC-728875 NSC56817 NSC624336
    NSC726190 NSC728875 No Fertil
    PXT0004725 Pogosin Pogosin
    Pogosin|||AT-101|||7-(8-Formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde Prestwick0_000677 Prestwick1_000677
    Prestwick2_000677 Prestwick3_000677 Prestwick_1031
    Q411882 QBKSWRVVCFFDOT-UHFFFAOYSA-N S-7805
    SB17342 SBB012338 SC-79036
    SCHEMBL3939 SMP2_000170 SMR000058386
    SPBio_001423 SPBio_001687 SPBio_002694
    SPECTRUM1504019 SR-01000597521 SR-01000597521-1
    SR-01000597521-5 SR-01000597521-6 ST065835
    ST24036539 STK063457 SW197103-2
    Sodium Salt, Gossypol SpecPlus_000602 Spectrum2_001472
    Spectrum2_001624 Spectrum3_001102 Spectrum3_001516
    Spectrum4_000846 Spectrum4_001931 Spectrum5_000693
    Spectrum5_001035 Spectrum_000359 Spectrum_001521
    Tash 1 Tocris-1964 Tox21_110434
    Tox21_110434_1 Tox21_500847 UNII-8DY2X8LXW4
    UNII-KAV15B369O UNII-XNA7DR63CQ UPCMLD-DP103
    UPCMLD-DP103:001 UPCMLD-DP103:002 V0195
    XNA7DR63CQ ZINC3775575 [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'-dicarboxaldehyde,1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-, (2R)- [2,8'-dicarboxaldehyde, 1,1',6,6',7,7'- hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-, (2R)- [2,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1- methylethyl)-
    [2,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)- [2,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl- acetic acid;7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-yl-2-naphthalenyl)-2,3,8-trihydroxy-6-methyl-4-propan-2-yl-1-naphthalenecarboxaldehyde
    acetic acid;7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde acetic acid;7-(8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methyl-2-naphthyl)-2,3,8-trihydroxy-4-isopropyl-6-methyl-naphthalene-1-carbaldehyde cid_227456
    cid_3503 ethanoic acid;7-[8-methanoyl-3-methyl-1,6,7-tris(oxidanyl)-5-propan-2-yl-naphthalen-2-yl]-6-methyl-2,3,8-tris(oxidanyl)-4-propan-2-yl-naphthalene-1-carbaldehyde gossypol
    racemic-Gossypol ssypol

    DrugBank Name Gossypol
    DrugBank DB13044
    CAS Number 1189561-66-7, 12542-36-8, 20300-26-9, 303-45-7, 40112-23-0, 5453-04-3, 866541-93-7, 90141-22-3, 96-24-2
    PubChem Compound 3503
    KEGG Compound ID C07667
    PubChem.Substance 347829175
    ChemSpider 3383
    BindingDB 23223.0
    Wikipedia Gossypol