Villosinol - Compound Card

Villosinol

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Villosinol

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Rotenoid
Canonical Smiles COc1cc2OCC3C(c2cc1OC)(O)C(=O)c1c(O3)c2CC(Oc2cc1O)C(=C)C
InChI InChI=1S/C23H22O8/c1-10(2)14-5-11-15(30-14)7-13(24)20-21(11)31-19-9-29-16-8-18(28-4)17(27-3)6-12(16)23(19,26)22(20)25/h6-8,14,19,24,26H,1,5,9H2,2-4H3
InChIKey JCJPVNDLAAXNEX-UHFFFAOYSA-N
Formula C23H22O8
HBA 8
HBD 2
MW 426.42
Rotatable Bonds 3
TPSA 103.68
LogP 2.51
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: 14704458
Nmrshiftdb2: 70051781

No compound-protein relationship available.

Structure

SMILES: C1COc(c12)ccc3c2OC4C(C3=O)c5c(OC4)cccc5

Level: 0

Mol. Weight: 426.42 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-5.19
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.730
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.61

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.210
Plasma Protein Binding
39.26
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.130
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.150
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.580
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.900
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
-70.780
Rat (Acute)
2.550
Rat (Chronic Oral)
2.460
Fathead Minnow
5.030
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
459.670
Hydration Free Energy
-3.500
Log(D) at pH=7.4
2.840
Log(P)
3.26
Log S
-4.8
Log(Vapor Pressure)
-8.99
Melting Point
221.21
pKa Acid
7.27
pKa Basic
2.34
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9236
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9236
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8778
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8778
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7953
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7953
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7761
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7761
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7604
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7604
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7447
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7447
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7317
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7317
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7300
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7300
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7265
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7265
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7253
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7253
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7243
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7243
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7119
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7119
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7058
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7058
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7054
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7054
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7026
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7026

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