Gossypol

PubChem CID	3503
Molecular Formula	C30H30O8
Structure
Synonyms	gossypol 303-45-7 (-)-Gossypol 90141-22-3 Pogosin (+)-Gossypol Tash 1 (R)-Gossypol (R)-(-)-Gossypol (+/-)-Gossypol No Fertil 20300-26-9 AT 101 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-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde BL 193 Gossypol, (R)- Gossypol, (S)- NSC56817 NSC-56817 XNA7DR63CQ NSC-624336 BRN 1917878 8DY2X8LXW4 CHEMBL51483 KAV15B369O DTXSID5023110 303-45-7 (free) 2,2'-bi[8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene] 2,2'-Bis(1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthalene) BL-193 MFCD00017352 NSC624336 NSC-726190 (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-, (+)- 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'-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-3,3'-dimethyl-5,5'-bis(1-methylethyl)-, (2R)- 4-08-00-03754 (Beilstein Handbook Reference) DTXCID803110 (+-)-Gossypol gosipol 1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde 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 CCRIS 2689 Gissypol, (R)- NSC-19048 Sodium Salt, Gossypol (S)-(+)-Gossypol Gossypol, (+)-Isomer Gossypol, (-)-Isomer SR-01000597521 C30H30O8 Gossypol Dipotassium Salt UNII-XNA7DR63CQ NSC 56817 Gossypol, (+-)-Isomer Dipotassium Salt, Gossypol UNII-8DY2X8LXW4 NSC 624336 ssypol UNII-KAV15B369O AI3-22957 HSDB 7872 Gossypol, 4 (S)-Gossypol GO3 Prestwick_1031 R-(-)-gossypol Pogosin; AT101 Spectrum_000359 Spectrum_001521 Tocris-1964 ST065835 SpecPlus_000602 GOSSYPOL [MI] GOSSYPOL [VANDF] GOSSYPOL, R- Prestwick0_000677 Prestwick1_000677 Prestwick2_000677 Prestwick3_000677 Spectrum2_001472 Spectrum2_001624 Spectrum3_001102 Spectrum3_001516 Spectrum4_000846 Spectrum4_001931 Spectrum5_000693 Spectrum5_001035 8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methyl-2,2'-bisnaphthalene 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 UPCMLD-DP103:001 UPCMLD-DP103:002 BDBM23223 BDBM46555 CHEBI:28584 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 Tox21_110434 Tox21_500847 CCG-35400 HB0304 NSC726190 NSC728875 s6852 STK063457 (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahyd AKOS002140475 Tox21_110434_1 AT25344 BCP9000332 CS-0966 DB13044 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- 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 A820340 Q411882 J-017920 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 ( inverted exclamation markA)-GOSSYPOL FROM COTTON SEEDS 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- (+)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'-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 1,1',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 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

Computed Descriptors

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
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
Canonical 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
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
InChIKey	QBKSWRVVCFFDOT-UHFFFAOYSA-N

Computed Properties

Molecular Weight	518.6 g/mol
XLogP3	6.9
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	5
Exact Mass	518.194
Monoisotopic Mass	518.194
Topological Polar Surface Area	156
Heavy Atom Count	38
Formal Charge	0
Complexity	780
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1

Annotation

C1907 - Drug, Natural Product|C274 - Antineoplastic Agent

C1931 - Antineoplastic Plant Product|C471 - Enzyme Inhibitor

C1404 - Protein Kinase Inhibitor

C61074 - Serine/Threonine Kinase Inhibitor|D012102 - Reproductive Control Agents

D003270 - Contraceptive Agents

6 pairs of Verified P450 and Gossypol

Insect	Gene Symbol	Validation	Reference
Aphis gossypii	CYP6DA2	R	Cytochrome P450 CYP6DA2 regulated by cap 'n' collar isoform C (CncC) is associated with gossypol tolerance in Aphis gossypii Glover Insect Molecular Biology 2016/8/1 \| 10.1111/imb.12230 \| WOS:000379613100010 PubMed Link
Helicoverpa armigera	CYP6AE14	R	Silencing a cotton bollworm P450 monooxygenase gene by plant-mediated RNAi impairs larval tolerance of gossypol Nature Biotechnology 2007/11/1 \| 10.1038/nbt1352 \| WOS:000251086500032 PubMed Link
Helicoverpa armigera	CYP6AE14	Y	Effect of a functional recombinant cytochrome P450 enzyme of Helicoverpa armigera on gossypol metabolism co-expressed with NADPH-cytochrome P450 reductase in Pichia pastoris Pesticide Biochemistry and Physiology 2019/4/5 \| 10.1016/j.pestbp.2019.01.003 \| WOS:000462265000003 PubMed Link
Helicoverpa armigera	CYP9A12	Y	Effect of a functional recombinant cytochrome P450 enzyme of Helicoverpa armigera on gossypol metabolism co-expressed with NADPH-cytochrome P450 reductase in Pichia pastoris Pesticide Biochemistry and Physiology 2019/4/5 \| 10.1016/j.pestbp.2019.01.003 \| WOS:000462265000003 PubMed Link
Helicoverpa armigera	CYP9A12	Y	Optimization of the process parameters for reduction of gossypol levels in cottonseed meal by functional recombinant NADPH-cytochrome P450 reductase and cytochrome P450 CYP9A12 of Helicoverpa armigera Amb Express 2019/8/2 \| 10.1186/s13568-019-0823-4 \| WOS:000476636600001 PubMed Link
Spodoptera litura	CYP6AB12	R	Knockdown of cytochrome P450 gene CYP6AB12 based on nanomaterial technology reduces the detoxification ability of Spodoptera litura to gossypol Pesticide Biochemistry and Physiology 2023/1/23 \| 10.1016/j.pestbp.2022.105284 \| WOS:000908320300004 PubMed Link

Gossypol

Computed Descriptors

Computed Properties

Annotation

6 pairs of Verified P450 and Gossypol Validation

6 pairs of Verified P450 and Gossypol