6alpha-hydroxy-alpha-toxicarol - Compound Card

6alpha-hydroxy-alpha-toxicarol

Select a section from the left sidebar

6alpha-hydroxy-alpha-toxicarol

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Rotenoid
Canonical Smiles COc1cc2O[C@@H](O)[C@@H]3[C@H](c2cc1OC)C(=O)c1c(O3)c2C=CC(Oc2cc1O)(C)C
InChI InChI=1S/C23H22O8/c1-23(2)6-5-10-14(31-23)8-12(24)18-19(25)17-11-7-15(27-3)16(28-4)9-13(11)29-22(26)21(17)30-20(10)18/h5-9,17,21-22,24,26H,1-4H3/t17-,21+,22-/m1/s1
InChIKey BODIYHGGDLTKIS-VOQZNFBZSA-N
Formula C23H22O8
HBA 8
HBD 2
MW 426.42
Rotatable Bonds 2
TPSA 103.68
LogP 3.03
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 426.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tephrosia villosa Leguminosae/Fabaceae Plantae 62125

Showing of synonyms

  • Muiva-Mutisya L, Macharia B, et al. (2014). 6α-Hydroxy-α-toxicarol and (+)-tephrodin with antiplasmodial activities from Tephrosia species.. Phytochemistry Letters,2014,10,179-183. [View] [PubMed]
Pubchem: 101892987

No compound-protein relationship available.

Structure

SMILES: C1=CCOc2ccc(c3c12)C(=O)C4c5c(OCC4O3)cccc5

Level: 0

Mol. Weight: 426.42 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.88
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.750
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.210
Plasma Protein Binding
81.38
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.120
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.030
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.660
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.990
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-52.830
Rat (Acute)
2.760
Rat (Chronic Oral)
2.270
Fathead Minnow
4.740
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
495.880
Hydration Free Energy
-4.020
Log(D) at pH=7.4
3.160
Log(P)
3.48
Log S
-5.37
Log(Vapor Pressure)
-9.17
Melting Point
233.31
pKa Acid
7.47
pKa Basic
2.71
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8853
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8853
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8652
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8652
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8377
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8377
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7804
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7804
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7791
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7791
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7757
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7757
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7538
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7538
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7464
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7464
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7435
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7435
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7334
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7334
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7270
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7270
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7198
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7198
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7171
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7171
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7067
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7067
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7025
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7025

Download SDF