gossypol 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
1328 303-45-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • gossypol sodium
  • gossypol dipotassium
  • gossypol potassium
  • gosipol
  • gossypol
A dimeric sesquiterpene found in cottonseed (GOSSYPIUM). The (-) isomer is active as a male contraceptive (CONTRACEPTIVE AGENTS, MALE) whereas toxic symptoms are associated with the (+) isomer.
  • Molecular weight: 518.56
  • Formula: C30H30O8
  • CLOGP: 5.75
  • LIPINSKI: 3
  • HAC: 8
  • HDO: 6
  • TPSA: 155.52
  • ALOGS: -5.13
  • ROTB: 4

Drug dosage:

None

ADMET properties:

None

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 3.792 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 2.275 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 10.069 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 51.168 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 0.320 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 0.450 % High 1
herg hERG pIC50 4.679 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 55.208 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 6.427 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 0.790 % High 1
kinase-safety-class AAK1,ACVR1B,ACVR2A,ACVR2B,ACVRL1,AKT2,AKT3,ALK,AURKA,AURKB,AURKC,AXL,BLK,BMX,BRAF,BTK,CAMK2A,CAMK2B,CAMK2D,CAMK2G,CDK1,CDK14,CDK16,CDK19,CDK2,CDK3,CDK4,CDK5,CDK7,CDK9,CHUK,CLK4,CSF1R,DDR1,DYRK1B,DYRK3,EGFR,EIF2AK3,EPHA2,EPHB4,ERBB2,ERBB4,FGFR1,FLT1,FLT3,FLT4,FYN,GRK2,GRK3,GSK3A,GSK3B,HIPK2,IGF1R,INSR,IRAK1,ITK,JAK1,JAK2,JAK3,KDR,KIT,LYN,MAP2K4,MAP2K6,MAP3K1,MAP3K10,MAP3K11,MAP3K14,MAP3K2,MAP3K21,MAP3K3,MAP3K7,MAP4K1,MAP4K2,MAP4K3,MAP4K5,MAPK1,MAPK10,MAPK12,MAPK14,MAPK7,MAPK8,MAPK9,MAPKAPK2,MAPKAPK5,MARK2,MARK4,MELK,MET,MINK1,MTOR,NTRK1,NTRK2,PAK4,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIK3CD,PIK3CG,PIM1,PIM2,PIM3,PRKAA1,PRKCD,PRKCZ,PRKDC,PTK2,SGK1,SIK2,SIK3,SRC,STK10,STK17A,STK33,SYK,TBK1,TEK,TGFBR1,TNIK,TTK,UHMK1,ULK1,ULK2,YES1,ZAP70 128
kinase-selectivity-class ACVR2B,AURKC,AXL,BRAF,CAMK2B,CAMK2D,CDK16,CDK4,CDK9,DYRK1B,EIF2AK3,EPHB4,FGFR1,GRK2,GSK3A,JAK2,MAP2K4,MAP2K6,MAP3K14,MAPK1,MAPK12,MAPK7,MAPK8,MAPKAPK2,PDK1,PIK3CD,PIM3,PRKAA1,PRKDC,SIK2,STK10,STK33,SYK,TEK,TGFBR1,TYRO3,ZAP70 37
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 7.047 High 1
mh-clint Mouse hepatocyte intrinsic clearance 53.456 High 1
mppb Mouse plasma protein binding (% unbound) 0.500 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 2.805 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 0.810 % High 1
rh-clint Rat hepatocyte intrinsic clearance 62.661 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 4.060 % High 1
rppb Rat plasma protein binding (% unbound) 0.550 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 35.975 uM High 1

Approvals:

None

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

None

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
MeSH PA D003272 Contraceptive Agents, Male
MeSH PA D012102 Reproductive Control Agents
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:67079 anti-inflammatory agent
CHEBI has role CHEBI:76924 plant metabolite
CHEBI has role CHEBI:145047 antispermatogenic agent

Drug Use | Suggest Off label Use Form| |View source of the data|

None




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 5.11 acidic
pKa2 6.9 acidic
pKa3 7.29 acidic
pKa4 8.04 acidic
pKa5 11.44 acidic
pKa6 12.05 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Estrogen receptor Nuclear hormone receptor IC50 5.59 CHEMBL
Androgen receptor Nuclear hormone receptor IC50 5.14 CHEMBL
Aldose reductase Enzyme Ki 6.30 CHEMBL
Aspartyl/asparaginyl beta-hydroxylase Enzyme IC50 6.60 CHEMBL
Apoptosis regulator Bcl-2 Cytosolic other Ki 6.77 CHEMBL
Induced myeloid leukemia cell differentiation protein Mcl-1 Cytosolic other Ki 6.74 CHEMBL
Bcl-2-like protein 1 Cytosolic other Ki 6.32 CHEMBL
L-lactate dehydrogenase A chain Enzyme Ki 5.72 CHEMBL
Apoptosis regulator Bcl-W Cytosolic other Ki 4.75 CHEMBL
Kinesin-like protein 1 Enzyme IC50 4.97 CHEMBL
Solute carrier family 2, facilitated glucose transporter member 1 Transporter Ki 4.70 CHEMBL
DNA-3-methyladenine glycosylase Enzyme IC50 5.52 CHEMBL
L-lactate dehydrogenase B chain Enzyme Ki 5.85 CHEMBL
Bcl2-associated agonist of cell death Cytosolic other Ki 6.34 CHEMBL
Beta-lactamase Enzyme IC50 4.34 CHEMBL
Malate dehydrogenase, mitochondrial Enzyme IC50 5.55 CHEMBL
Lactate dehydrogenase Enzyme IC50 5.58 CHEMBL
Malate dehydrogenase Enzyme IC50 5.69 CHEMBL
Malate dehydrogenase, cytoplasmic Enzyme IC50 5.24 CHEMBL
Replicase polyprotein 1ab Enzyme IC50 4.85 CHEMBL
Inosine-5'-monophosphate dehydrogenase Enzyme IC50 6.05 CHEMBL

External reference:

IDSource
4021343 VANDF
C0018096 UMLSCUI
GO3 PDB_CHEM_ID
CHEMBL51483 ChEMBL_ID
D006072 MESH_DESCRIPTOR_UI
DB13044 DRUGBANK_ID
4204 IUPHAR_LIGAND_ID
KAV15B369O UNII
3503 PUBCHEM_CID
3757009 SNOMEDCT_US
CHEBI:28584 CHEBI

Pharmaceutical products:

None