(-)-6-methoxygossypol - Compound Card

(-)-6-methoxygossypol

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(-)-6-methoxygossypol

Structure
Zoomed Structure
  • Family: Plantae - Malvaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpenoid
Canonical Smiles O=Cc1c(O)c(OC)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/C31H32O8/c1-12(2)20-16-8-14(5)22(28(36)24(16)18(10-32)26(34)30(20)38)23-15(6)9-17-21(13(3)4)31(39-7)27(35)19(11-33)25(17)29(23)37/h8-13,34-38H,1-7H3
InChIKey QSEHQWFPCMNMPH-UHFFFAOYSA-N
Formula C31H32O8
HBA 8
HBD 5
MW 532.59
Rotatable Bonds 6
TPSA 144.52
LogP 6.69
Number Rings 4
Number Aromatic Rings 4
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 532.21
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Thespesia garckeana Malvaceae Plantae 1833803

Showing of synonyms

  • Masila VM, Midiwo JO, et al. (2015). Anti-vancomycin-resistant Enterococcus faecium and E. faecalis activities of (-)-gossypol and derivatives from Thespesia garckeana.. Natural Product Communications,2015,10(4),613-616. [View] [PubMed]
Pubchem: 3085061

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)ccc(c2)-c(c3)ccc(c34)cccc4

Level: 1

Mol. Weight: 532.59 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 532.59 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-5.3
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.1
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
2.12

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.76
Plasma Protein Binding
74.78
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
Inhibitor

Excretion

Clearance
8.94
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.37
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.82
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.81
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
-1362.14
Rat (Acute)
2.23
Rat (Chronic Oral)
3.75
Fathead Minnow
8.59
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
544.91
Hydration Free Energy
-3.04
Log(D) at pH=7.4
4.75
Log(P)
6.74
Log S
-6.59
Log(Vapor Pressure)
-7.8
Melting Point
223.8
pKa Acid
9.4
pKa Basic
5.23
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7459
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7459
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7238
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7238
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.7207
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.7207
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7154
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7154
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7141
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7141
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7107
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7107
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7046
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7046

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