Deguelin - Compound Card

Deguelin

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Deguelin

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Rotenoid
Canonical Smiles COc1cc2c(cc1OC)OC[C@@H]1[C@H]2C(=O)c2c(O1)c1C=CC(Oc1cc2)(C)C
InChI InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1
InChIKey ORDAZKGHSNRHTD-UXHICEINSA-N
Formula C23H22O6
HBA 6
HBD 0
MW 394.42
Rotatable Bonds 2
TPSA 63.22
LogP 4.01
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 394.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Millettia dura Leguminosae/Fabaceae Plantae 62119
2 Milletia dura Leguminosae/Fabaceae Plantae 1369122
3 Derris trifoliata Leguminosae/Fabaceae Plantae 185716
4 Derris trifoliata Leguminosae/Fabaceae Plantae 185716
5 Tephrosia villosa Leguminosae/Fabaceae Plantae 62125
6 Tephrosia vogelii Leguminosae/Fabaceae Plantae 1157238
7 Tephrosia elata Leguminosae/Fabaceae Plantae 1368159

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]
  • Yenesew A, Mushibe EK, et al. (2005). 7a-O-methyldeguelol, a modified rotenoid with an open ring-C, from the roots of Derris trifoliata.. Phytochemistry,2005,66(6),653-657. [View] [PubMed]
  • Yenesew AB, Twinomuhwezi H, et al. (2009). Antiplasmodial and larvicidal flavonoids from Derris trifoliata.. Bulletin of the Chemical Society of Ethiopia,2009,23(3),409-414. [View] [PubMed]
  • Muiva LM, Yenesew A, et al. (2009). Antiplasmodial β-hydroxydihydrochalcone from seedpods of Tephrosia elata. Phytochemistry Letters,2009,2(3),99-102. [View] [PubMed]
  • Stevenson PC, Kite GC, et al. (2012). Distinct chemotypes of Tephrosia vogelii and implications for their use in pest control and soil enrichment.. Phytochemistry,2012(78),135-146. [View] [PubMed]
  • Yenesew A, Derese S, et al. (2003). Effect of rotenoids from the seeds of Millettia dura on larvae of Aedes aegypti.. Pest Management Science,2003,59(10),1159-1161. [View] [PubMed]
  • Yenesew A, Kiplagat JT Mushibe EK Derese S, et al. (2005). Rotenoid derivatives from Kenyan Millettia and Derris species as larvicidal agents. Natural products and drug discovery, Proceedings of the 11th NAPRECA Symposium August 9-12, 2005, Hôtel Panorama, Antananarivo, Madagascar. [View] [PubMed]
Pubchem: 107935
Kegg Ligand: C10417
Chebi: 4357
Nmrshiftdb2: 60027676
Metabolights: MTBLC4357
Bindingdb: 50505204
CPRiL: 79392
Structure

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

Level: 0

Mol. Weight: 394.42 g/mol

Anti-plasmodial
Larvicidal

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.610
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.320
Plasma Protein Binding
84.48
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
Non-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
9.570
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.370
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.200
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.000
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
-22.660
Rat (Acute)
3.560
Rat (Chronic Oral)
1.560
Fathead Minnow
5.100
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
482.010
Hydration Free Energy
-5.640
Log(D) at pH=7.4
3.350
Log(P)
4.02
Log S
-5.56
Log(Vapor Pressure)
-8.21
Melting Point
177.11
pKa Acid
9.34
pKa Basic
3.66
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9604
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9604
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8985
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8985
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8470
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8470
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8236
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8236
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8235
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8235
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8006
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8006
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7889
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7889
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7836
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7836
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7662
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7662
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7570
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7570
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7519
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7519
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7493
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7493
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7459
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7459
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7357
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7357
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7356
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7356
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7347
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7347
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7325
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7325
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7317
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7317
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7309
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7309
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7299
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7299
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7298
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7298
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7287
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7287
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7241
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7241
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7204
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7204
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7202
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7202
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7167
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7167
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7161
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7161
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7112
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7112
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7061
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7061
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7032
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7032
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7019
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7019
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7015
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7015

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