12a-hydroxy-alpha-toxicarol - Compound Card

12a-hydroxy-alpha-toxicarol

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12a-hydroxy-alpha-toxicarol

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Rotenoid
Canonical Smiles COc1cc2OC[C@@H]3[C@@](c2cc1OC)(O)C(=O)c1c(O3)c2C=CC(Oc2cc1O)(C)C
InChI InChI=1S/C23H22O8/c1-22(2)6-5-11-14(31-22)8-13(24)19-20(11)30-18-10-29-15-9-17(28-4)16(27-3)7-12(15)23(18,26)21(19)25/h5-9,18,24,26H,10H2,1-4H3/t18-,23-/m1/s1
InChIKey OFLCPNIRDVOOEZ-WZONZLPQSA-N
Formula C23H22O8
HBA 8
HBD 2
MW 426.42
Rotatable Bonds 2
TPSA 103.68
LogP 2.82
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]
CPRiL: 428796
Structure

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

Level: 0

Mol. Weight: 426.42 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.98
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.720
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.73

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.200
Plasma Protein Binding
74.78
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
12.820
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.090
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.460
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.710
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
-50.690
Rat (Acute)
2.600
Rat (Chronic Oral)
2.330
Fathead Minnow
4.820
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
470.940
Hydration Free Energy
-3.920
Log(D) at pH=7.4
3.290
Log(P)
3.19
Log S
-5.48
Log(Vapor Pressure)
-8.97
Melting Point
224.39
pKa Acid
7.47
pKa Basic
2.85
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8866
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8866
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8836
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8836
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8154
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8154
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7824
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7824
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7752
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7752
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7721
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7721
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7699
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7699
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7687
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7687
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7609
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7609
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7551
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7551
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7513
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7513
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7457
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7457
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7456
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7456
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7374
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7374
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7325
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7325
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7245
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7245
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7236
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7236
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7212
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7212
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7189
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7189
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7151
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7151
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7112
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7112
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7073
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7073
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7071
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7071
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7056
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7056
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7048
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7048

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