Compound: gossypol
SMILES: O=Cc1c(O)c(O)c(C(C)C)c2c1c(O)c(-c3c(O)c4c(c(c(O)c(c4C=O)O)C(C)C)cc3C)c(C)c2
InChIKey: QBKSWRVVCFFDOT-UHFFFAOYSA-N
Synonyms: gossypol, 303-45-7, Pogosin, Tash 1, No Fertil, (+-)-Gossypol, 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, BL 193, CCRIS 2689, DTXSID5023110, NSC56817, NSC 56817, NSC-56817, NSC 624336, NSC-624336, BRN 1917878, KAV15B369O, AI3-22957, BL-193, NSC624336, DTXCID803110, CHEBI:28584, 8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methyl-2,2'-bisnaphthalene, (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)-, 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, Cottonseed Meal Toxin, RefChem:782655, 2,2'-bis(1,6,7-trihydroxy-4-methyl-5-isopropyl-8-aldehydonaphthalene), 2,2'-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene), (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6'7, 7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-, 1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3-3'-dimethyl(2,2'-binaphthalene)-8,8'-dicarboxaldehyde, 90141-22-3, (-)-Gossypol, (+)-Gossypol, (R)-Gossypol, (R)-(-)-Gossypol, AT 101, (+/-)-Gossypol, 20300-26-9, 1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2'-binaphthalene]-8,8'-dicarbaldehyde, (S)-Gossypol, Gossypol, (R)-, Gossypol, (S)-, MFCD00017352, XNA7DR63CQ, 8DY2X8LXW4, CHEMBL51483, 2,2'-Bis(1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthalene), NSC-726190, (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)-, (2R)-, 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, NCGC00016423-03, CAS-303-45-7, ST065835, racemic-Gossypol, 4-08-00-03754 (Beilstein Handbook Reference), 7-(8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methyl-2-naphthyl)-2,3,8-trihydroxy-4-isopropyl-6-methyl-naphthalene-1-carbaldehyde, gosipol, ( inverted exclamation markA)-GOSSYPOL FROM COTTON SEEDS, ;ssypol, 1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-di(propan-2-yl)[2,2'-binaphthalene]-8,8'-dicarbaldehyde, 7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(methylethyl)(2-naphthyl)]-2,3,8-trihy droxy-6-methyl-4-(methylethyl)naphthalenecarbaldehyde, Gossypol Sodium Salt, Gissypol, (R)-, Sodium Salt, Gossypol, (S)-(+)-Gossypol, Gossypol, (+)-Isomer, Gossypol, (-)-Isomer, SR-01000597521, C30H30O8, Gossypol Dipotassium Salt, UNII-XNA7DR63CQ, Gossypol, (+-)-Isomer, Dipotassium Salt, Gossypol, UNII-8DY2X8LXW4, ssypol, UNII-KAV15B369O, 303-45-7 (free), HSDB 7872, Gossypol, 4, GO3, Gossypol (Standard), Prestwick_1031, R-(-)-gossypol, Spectrum_000359, Spectrum_001521, Tocris-1964, SpecPlus_000602, GOSSYPOL [MI], GOSSYPOL [VANDF], GOSSYPOL, R-, 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, Prestwick0_000677, Prestwick1_000677, Prestwick2_000677, Prestwick3_000677, Spectrum2_001472, Spectrum2_001624, Spectrum3_001102, Spectrum3_001516, Spectrum4_000846, Spectrum4_001931, Spectrum5_000693, Spectrum5_001035, 2,2'-bi[8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene], GOSSYPOL [MART.], Gossypol from cotton seeds, UPCMLD-DP103, NCIMech_000271, cid_3503, SCHEMBL3939, BSPBio_000773, BSPBio_002804, BSPBio_003191, GOSSYPOL, (+)-, KBioGR_001451, KBioGR_002303, KBioSS_000839, KBioSS_002001, (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-, (-)-, MLS000028490, DivK1c_000173, DivK1c_006698, GOSSYPOL R-FORM [MI], GOSSYPOL S-FORM [MI], SPECTRUM1504019, SPBio_001423, SPBio_001687, SPBio_002694, BPBio1_000851, cid_227456, GTPL4204, orb1300699, orb3025494, AT 101 [WHO-DD], SCHEMBL29355719, SCHEMBL29798874, SCHEMBL30260519, UPCMLD-DP103:001, UPCMLD-DP103:002, BDBM23223, BDBM46555, KBio1_000173, KBio1_001642, KBio2_000839, KBio2_002001, KBio2_003407, KBio2_004569, KBio2_005975, KBio2_007137, KBio3_002024, KBio3_002691, EX-A068, MSK7506, NINDS_000173, GLXC-05080, HMS1570G15, HMS2097G15, HMS3262J15, HMS3268O22, HMS3413L10, HMS3651C18, HMS3677L10, HMS3868F13, HMS5086E08, (+/-)-Gossypol from cotton seeds, ALBB-033351, NEA58077, QDA14122, Tox21_110434, Tox21_500847, CCG-35400, HB0304, HY-13407R, NSC726190, NSC728875, s6852, SBB012338, STK063457, (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahyd, AKOS002140475, Tox21_110434_1, AT25344, CS-0966, DB13044, EBC-454694, FG41647, LMPR0103330002, LP00847, NSC 726190, NSC-728875, SB17342, SDCCGSBI-0051726.P004, IDI1_000173, SMP2_000170, NCGC00016423-01, NCGC00016423-02, NCGC00016423-04, NCGC00016423-05, NCGC00016423-06, NCGC00016423-07, NCGC00016423-08, NCGC00016423-09, NCGC00016423-10, NCGC00016423-12, NCGC00016423-14, NCGC00016423-15, NCGC00016423-17, NCGC00016423-34, NCGC00025331-01, NCGC00025331-02, NCGC00025331-03, NCGC00025331-04, NCGC00025331-06, NCGC00025331-07, NCGC00261532-01, (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-, AC-20251, AC-30274, AC-34521, AS-55885, BP-25397, HY-13407, HY-15464, NCI60_001588, NCI60_004391, SMR000058386, DB-047766, AB00052921, NS00069172, SW197103-2, C07667, Q411882, SR-01000597521-1, SR-01000597521-5, SR-01000597521-6, (+/-)-Gossypol from cotton seeds, >=95% (HPLC), BRD-K19295594-001-06-9, BRD-K19295594-001-10-1, BRD-K19295594-001-15-0, BRD-K19295594-001-16-8, BRD-K19295594-015-02-8, BRD-K19295594-015-12-7, BRD-K19295594-015-13-5, BRD-K19295594-015-14-3, 2,2'-bis[8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthyl], 8-Formyl-1,7-trihydroxy-5-isopropyl-3-methyl-2,2'-bisnaphthalene, 2,2'-bis[1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthyl], (+/-)-2,2'-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene), (-)-2,2'-Bis(1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthalene), (2,8'-dicarboxaldehyde, 1,1',6,6'7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-, (R)-2,2'-BIS(8-FORMYL-1,6,7-TRIHYDROXY-5-ISOPROPYL-3-METHYLNAPHTHALENE), [2,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-, ( inverted exclamation markA)-Gossypol; NSC 56817; NSC 624336; BL 193; Pogosin; 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'-dicarboxaldehyde, (-)-1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde, (2,2'-BINAPHTHALENE)-8,8'-DICARBOXALDEHYDE, 1,1',6,6',7,7'-HEXAHYDROXY-3,3'-DIMETHYL-5,5'-BIS(1-METHYLETHYL)-, (2S)-, (2,2'-BINAPHTHALENE)-8,8'-DICARBOXALDEHYDE, 1,1',6,6',7,7'-HEXAHYDROXY-3,3'-DIMETHYL-5,5'-BIS(1-METHYLETHYL)-, (S)-, [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)-, 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'-bis(propan-2-yl)-[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-3,3'-dimethyl-5,5'-diisopropyl[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, 1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-8,8'-dicarboxaldehyde, 7-(8-Formyl-1,6,7-trihydroxy-3-methyl-5-(methylethyl)(2-naphthyl))-2,3,8-trihydroxy-6-methyl-4-(methylethyl)naphthalenecarbaldehyde, 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, 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
Theoretical properties:
molecular_formula: C30H30O8
molecular_weight: 518.6 g/mol
exact_mass: 518.19406791 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 8
rotatable_bond_count: 5
heavy_atom_count: 38
topological_polar_surface_area: 156 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Yellow, crystalline pigment
color: Yellow, crystalline pigment
melting_point: 184 °C (from ether); 199 °C (from chloroform); 214 °C (from ligroin)
solubility: Very soluble in methanol, ethanol, cold dioxane, diethylene glucol, ether, ethyl acetate, acetone, carbon tetrachloride, pyridine, chloroform, DMF, lipds. Freely soluble (with slow desomposition) in dilute aqueous solutions of ammonia and sodium carbonate. Slightly soluble in glycerol, cyclohexane. Insoluble in water.
Descriptions:
pubchem: Gossypol is an aldehyde, a hydroxynaphthalene, a polyphenol and a hexol. It has a role as an antispermatogenic agent, an anti-inflammatory agent and a plant metabolite.
chembl: GOSSYPOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Gossypol () is a natural phenol derived from the cotton plant (genus Gossypium). Gossypol is a phenolic aldehyde that permeates cells and acts as an inhibitor for several dehydrogenase enzymes. It is a yellow pigment. The structure exhibits atropisomerism, with the two enantiomers having different biochemical properties.
Among other applications, it has been tested as a male oral contraceptive in China. In addition to its putative contraceptive properties, gossypol has also long been known to possess antimalarial properties.