Gossypol
PubChem CID: 3503
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| Compound Synonyms | gossypol, 303-45-7, 90141-22-3, (-)-Gossypol, Pogosin, Tash 1, (+)-Gossypol, (R)-Gossypol, (R)-(-)-Gossypol, No Fertil, (+/-)-Gossypol, AT 101, 20300-26-9, 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, 1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2'-binaphthalene]-8,8'-dicarbaldehyde, BL 193, CCRIS 2689, NSC56817, NSC 56817, NSC-56817, NSC 624336, NSC-624336, BRN 1917878, KAV15B369O, Gossypol, (R)-, Gossypol, (S)-, DTXSID5023110, AI3-22957, HSDB 7872, GOSSYPOL [MI], GOSSYPOL [VANDF], BL-193, MFCD00017352, NSC624336, GOSSYPOL [MART.], XNA7DR63CQ, 8DY2X8LXW4, 2,2'-Bis(1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthalene), CHEMBL51483, DTXCID803110, 303-45-7 (free), CHEBI:28584, 2,2'-bi[8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene], 8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methyl-2,2'-bisnaphthalene, 2,2'-bis[8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene], Gossypol-d2, NSC-726190, (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-3,3'-dimethyl-5,5'-bis(1-methylethyl)-, 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, racemic-Gossypol, (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahyd, GOSSYPOL (MART.), (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)-, 1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde, 4-08-00-03754 (Beilstein Handbook Reference), (+-)-Gossypol, gosipol, ( inverted exclamation markA)-GOSSYPOL FROM COTTON SEEDS, 1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl[2,2'-binaphthalene]-8,8'-dicarbaldehyde, 7-(8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methyl-2-naphthyl)-2,3,8-trihydroxy-4-isopropyl-6-methyl-naphthalene-1-carbaldehyde, 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, 2,2'-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene), Gossypol, 4, (S)-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-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'-dicarboxaldehyde, 1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3-3'-dimethyl[2,2'-binaphthalene]-8,8'-dicarboxaldehyde, GO3, Gossypol (Standard), Prestwick_1031, R-(-)-gossypol, Cottonseed Meal Toxin, 113580-77-1, Pogosin, AT101, Spectrum_000359, Spectrum_001521, Tocris-1964, ST065835, SpecPlus_000602, GOSSYPOL, R-, 1189561-66-7, Prestwick0_000677, Prestwick1_000677, Prestwick2_000677, Prestwick3_000677, Spectrum2_001472, Spectrum2_001624, Spectrum3_001102, Spectrum3_001516, Spectrum4_000846, Spectrum4_001931, Spectrum5_000693, Spectrum5_001035, 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, 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, NINDS_000173, HMS1570G15, HMS2097G15, HMS3262J15, HMS3268O22, HMS3413L10, HMS3651C18, HMS3677L10, HMS3868F13, (+/-)-Gossypol from cotton seeds, ALBB-033351, BCP03607, NEA58077, QDA14122, Tox21_110434, Tox21_500847, CCG-35400, HB0304, HY-13407R, NSC726190, NSC728875, s6852, STK063457, AKOS002140475, Tox21_110434_1, AT25344, BCP9000332, CS-0966, DB13044, 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, 7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(methylethyl)(2-naphthyl)]-2,3,8-trihy droxy-6-methyl-4-(methylethyl)naphthalenecarbaldehyde, AC-20251, AC-30274, AC-34521, AS-55885, BP-25397, HY-13407, HY-15464, NCI60_001588, NCI60_004391, SMR000058386, BCP0726000183, 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-aldehydonaphthalene, 2,2'-bis(1,6,7-trihydroxy-4-methyl-5-isopropyl-8-aldehydonaphthalene), 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-, (+)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)-, (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6'7, 7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-, [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'-di(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'-binaphthyl-8,8'-dicarbaldehyde, 1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-8,8'-dicarboxaldehyde, 636-899-7, 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, 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, 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 |
|---|---|
| Ghose Rule | False |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 156.0 |
| Hydrogen Bond Donor Count | 6.0 |
| Pfizer 3 75 Rule | False |
| Scaffold Graph Level | C1CCC2CC(C3CCC4CCCCC4C3)CCC2C1 |
| Np Classifier Class | Cadinane sesquiterpenoids |
| Deep Smiles | O=CccO)cO)ccc6cO)ccc6)C))ccC)cccc6O))cC=O))ccc6CC)C)))O))O))))))))))))CC)C |
| Heavy Atom Count | 38.0 |
| Classyfire Class | Prenol lipids |
| Description | Gossypol, also known as gossypol, (+)-isomer or (-)-gossypol, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Thus, gossypol is considered to be an isoprenoid lipid molecule. Gossypol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Gossypol can be found in cottonseed, okra, soy bean, and sunflower, which makes gossypol a potential biomarker for the consumption of these food products. Gossypol is a non-carcinogenic (not listed by IARC) potentially toxic compound. Among other things, 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. Other researchers are investigating the anticancer properties of gossypol . Gossypol may cause apoptosis via the regulation of Bax and Bcl-2 proteins. It is also an inhibitor of calcineurin and protein kinases C, and has been shown to bind calmodulin (L1239) (T3DB). |
| Scaffold Graph Node Level | C1CCC2CC(C3CCC4CCCCC4C3)CCC2C1 |
| Classyfire Subclass | Sesquiterpenoids |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 780.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Uniprot Id | Q07817, P15121, P10415, Q07820, P00811, Q0PJ46, Q6VVP7, P00346, P11708, Q92843, P52732, P14061, P37059, n.a., O75604, P02545, P10828, P46063, P51570, Q99714, B2RXH2, P42858, P29466, P55210, P51151, Q16637, P42345, Q9NUW8, P10636, P25779, P33261, P51450, Q16665, P00352, Q962Y6, Q9F4F7, P97697, P16050, P28482, P18054, P03372, Q03164, O97447, P15917, O15118, P15428, P04637, P54132, O81014, P10253, Q6W5P4, P10635, P08684, P06746, P11712, Q16236, Q4Q090, P21728, Q92830, Q99549, O89049, P63073, Q96QE3, P13267, Q96KQ7, O15648, P07378, P83916, Q9UIF8, O15296, Q13526, Q13951, P39748, P05177, P11473, Q99700, P10275, Q96RI1, P04150, Q9UNA4, Q9UBT6, Q03181, P49798, P37231, P84022, O94782, P19793, P02768, Q72547, P11021, P08659, P19838, O94925, O75496, Q9R1A7, Q07869, O42275, P81908, P37840, Q9NPD5, Q9Y6L6, P07947, Q9NR56, P15289, P27695, P29372, P00338, P07195, Q00987, P11166, Q7BGE6, Q9HXM5, P0DTD1, Q12797, P43351, P04792, P05412 |
| Iupac Name | 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 |
| Prediction Hob | 0.0 |
| Class | Prenol lipids |
| Veber Rule | False |
| Classyfire Superclass | Lipids and lipid-like molecules |
| Target Id | NPT2796, NPT41, NPT980, NPT57, NPT3720, NPT832, NPT45, NPT483, NPT46, NPT47, NPT1619, NPT149, NPT48, NPT1197, NPT277, NPT1226, NPT537, NPT93, NPT940, NPT50, NPT51, NPT213, NPT211, NPT94, NPT792, NPT282, NPT1119, NPT108, NPT538, NPT151, NPT539, NPT58, NPT60, NPT1416, NPT110, NPT109, NPT59, NPT212, NPT208, NPT72, NPT73, NPT1670, NPT644, NPT3727, NPT942, NPT1274 |
| Xlogp | 6.9 |
| Superclass | Lipids and lipid-like molecules |
| Subclass | Sesquiterpenoids |
| Gsk 4 400 Rule | False |
| Molecular Formula | C30H30O8 |
| Scaffold Graph Node Bond Level | c1ccc2cc(-c3ccc4ccccc4c3)ccc2c1 |
| Prediction Swissadme | 0.0 |
| Inchi Key | QBKSWRVVCFFDOT-UHFFFAOYSA-N |
| Silicos It Class | Poorly soluble |
| Fcsp3 | 0.2666666666666666 |
| Logs | -3.554 |
| Rotatable Bond Count | 5.0 |
| State | Solid |
| Logd | 2.647 |
| Synonyms | 1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-[2,2'-binaphthalene]-8,8'-dicarboxaldehyde, 9CI, Thespesin, (-)-gossypol, (+-)-gossypol, (+)-gossypol, (+/-)-gossypol, (r)-(-)-gossypol, (r)-gossypol, Dipotassium salt, gossypol, Gossypol, Gossypol dipotassium salt, Gossypol from cotton seeds, Gossypol sodium salt, Gossypol, (-)-isomer, Gossypol, (+-)-isomer, Gossypol, (+)-isomer, Pogosin, Racemic-gossypol, Sodium salt, gossypol, Tash 1, (+)-Gossypol, (+-)-Gossypol, (R)-(-)-Gossypol, (R)-Gossypol, (+)-gossypol, gossoypol, gossypol, gossypol,(-)- |
| Substituent Name | Sesquiterpenoid, Cadinane sesquiterpenoid, 1-naphthol, 2-naphthol, Naphthalene, Nitrotoluene, Cumene, M-cresol, 1,2-diphenol, Benzoyl, Aryl-aldehyde, Benzenoid, Vinylogous acid, Polyol, Hydrocarbon derivative, Organooxygen compound, Carbonyl group, Aldehyde, Aromatic homopolycyclic compound |
| Esol Class | Poorly soluble |
| Functional Groups | cC=O, cO |
| Compound Name | Gossypol |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 518.194 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 518.194 |
| Hydrogen Bond Acceptor Count | 8.0 |
| Molecular Weight | 518.6 |
| Gi Absorption | False |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 0.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aromatic homopolycyclic compounds |
| Lipinski Rule Of 5 | False |
| Esol | -7.480458084210527 |
| Inchi | InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3 |
| Smiles | CC1=CC2=C(C(=C(C(=C2C(C)C)O)O)C=O)C(=C1C3=C(C4=C(C=C3C)C(=C(C(=C4C=O)O)O)C(C)C)O)O |
| Nring | 4.0 |
| Np Classifier Biosynthetic Pathway | Terpenoids |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | False |
| Taxonomy Direct Parent | Sesquiterpenoids |
| Np Classifier Superclass | Sesquiterpenoids |
- 1. Outgoing r'ship
FOUND_INto/from Abelmoschus Esculentus (Plant) Rel Props:Source_db:fooddb_chem_all - 2. Outgoing r'ship
FOUND_INto/from Abutilon Theophrasti (Plant) Rel Props:Reference:ISBN:9788172362089 - 3. Outgoing r'ship
FOUND_INto/from Azanza Lampas (Plant) Rel Props:Reference:ISBN:9788172360481 - 4. Outgoing r'ship
FOUND_INto/from Ceiba Pentandra (Plant) Rel Props:Reference:https://doi.org/10.15482/usda.adc/1239279 - 5. Outgoing r'ship
FOUND_INto/from Getonia Floribunda (Plant) Rel Props:Reference:ISBN:9788185042084 - 6. Outgoing r'ship
FOUND_INto/from Glycine Max (Plant) Rel Props:Source_db:fooddb_chem_all - 7. Outgoing r'ship
FOUND_INto/from Gossypium Arboreum (Plant) Rel Props:Reference:ISBN:9780387706375 - 8. Outgoing r'ship
FOUND_INto/from Gossypium Barbadense (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/22837586 - 9. Outgoing r'ship
FOUND_INto/from Gossypium Herbaceum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 10. Outgoing r'ship
FOUND_INto/from Gossypium Hirsutum (Plant) Rel Props:Reference:ISBN:9788172362300; ISBN:9788185042145 - 11. Outgoing r'ship
FOUND_INto/from Helianthus Annuus (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all - 12. Outgoing r'ship
FOUND_INto/from Hibiscus Tilliaceus (Plant) Rel Props:Reference:ISBN:9788172360481 - 13. Outgoing r'ship
FOUND_INto/from Kerria Japonica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 14. Outgoing r'ship
FOUND_INto/from Sida Cordata (Plant) Rel Props:Reference:ISBN:9780387706375; ISBN:9788172363178 - 15. Outgoing r'ship
FOUND_INto/from Thespesia Populnea (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all