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(-)-gossypol
- Family: Plantae - Malvaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpenoid
| Canonical Smiles | O=Cc1c(O)c(O)c(c2c1c(O)c(c(c2)C)c1c(C)cc2c(c1O)c(C=O)c(c(c2C(C)C)O)O)C(C)C |
|---|---|
| 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 |
| Formula | C30H30O8 |
| HBA | 8 |
| HBD | 6 |
| MW | 518.56 |
| Rotatable Bonds | 5 |
| TPSA | 155.52 |
| LogP | 6.38 |
| Number Rings | 4 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 38 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.27 |
| Exact Mass | 518.19 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Thespesia garckeana | Malvaceae | Plantae | 1833803 |
Showing of synonyms
(-)-gossypol
Gossypol
303-45-7
Pogosin
Tash 1
No Fertil
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
NSC56817
NSC 56817
NSC-56817
NSC 624336
NSC-624336
BRN 1917878
KAV15B369O
DTXSID5023110
AI3-22957
HSDB 7872
GOSSYPOL [MI]
GOSSYPOL [VANDF]
BL-193
NSC624336
GOSSYPOL [MART.]
2,2'-Bis(1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthalene)
DTXCID803110
CHEBI:28584
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]
(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'-hexahyd
GOSSYPOL (MART.)
(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-3,3'-dimethyl-5,5'-bis(1-methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde
(+-)-Gossypol
1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl[2,2'-binaphthalene]-8,8'-dicarbaldehyde
2,2'-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)
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
Cottonseed Meal Toxin
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'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6'7, 7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-
636-899-7
90141-22-3
(+)-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
Gossypol, (R)-
Gossypol, (S)-
MFCD00017352
XNA7DR63CQ
8DY2X8LXW4
CHEMBL51483
303-45-7 (free)
Gossypol-d2
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)-, (2R)-
4-08-00-03754 (Beilstein Handbook Reference)
113580-77-1
Gosipol
( inverted exclamation markA)-GOSSYPOL FROM COTTON SEEDS
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
Gossypol Dipotassium Salt
UNII-XNA7DR63CQ
Gossypol, (+-)-Isomer
Dipotassium Salt, Gossypol
UNII-8DY2X8LXW4
Ssypol
UNII-KAV15B369O
Gossypol, 4
(S)-Gossypol
GO3
Gossypol (Standard)
Prestwick_1031
R-(-)-gossypol
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
2,2'-bi[8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene]
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
GLXC-05080
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-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
1,6,7,1',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
Pubchem:
3503
Cas:
303-45-7
Gnps:
CCMSLIB00006562543
Zinc:
ZINC000003775575
Kegg Ligand:
C07667
Nmrshiftdb2:
60059370
Chembl:
CHEMBL51483
Comptox:
DTXSID5023110
Drugbank:
DB13044
Pdb Ligand:
GO3
Bindingdb:
23223
Selleck:
Gossypol
CPRiL:
2580
SMILES: c1cccc(c12)ccc(c2)-c(c3)ccc(c34)cccc4
Level: 1
Mol. Weight: 518.56 g/mol
SMILES: c1cccc(c12)cccc2
Level: 0
Mol. Weight: 518.56 g/mol
Antibacterial
Absorption
- Caco-2 (logPapp)
- -5.42
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.28
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 2.54
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.83
- Plasma Protein Binding
- 74.5
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.64
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.49
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.99
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.83
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -803.63
- Rat (Acute)
- 2.38
- Rat (Chronic Oral)
- 3.63
- Fathead Minnow
- 6.96
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 590.77
- Hydration Free Energy
- -3.15
- Log(D) at pH=7.4
- 2.66
- Log(P)
- 6.4
- Log S
- -5.99
- Log(Vapor Pressure)
- -9.17
- Melting Point
- 257.9
- pKa Acid
- 4.99
- pKa Basic
- 6.97
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.7594 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.7594 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.7315 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.7315 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 4 | 0.7033 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 4 | 0.7033 |