Obovatin methyl ether - Compound Card

Obovatin methyl ether

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Obovatin methyl ether

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Pyranoflavonoid
Canonical Smiles COc1cc2OC(C)(C)C=Cc2c2c1C(=O)CC(O2)c1ccccc1
InChI InChI=1S/C21H20O4/c1-21(2)10-9-14-17(25-21)12-18(23-3)19-15(22)11-16(24-20(14)19)13-7-5-4-6-8-13/h4-10,12,16H,11H2,1-3H3
InChIKey ITOTUSMHIQFNHJ-UHFFFAOYSA-N
Formula C21H20O4
HBA 4
HBD 0
MW 336.39
Rotatable Bonds 2
TPSA 44.76
LogP 4.59
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 336.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tephrosia purpurea Leguminosae/Fabaceae Plantae 228354
2 Tephrosia vogelii Leguminosae/Fabaceae Plantae 1157238
3 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]
  • 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]
Pubchem: 2729164
Chebi: 180256
Nmrshiftdb2: 70037833

No compound-protein relationship available.

Structure

SMILES: C1=CCOc2ccc(c3c12)C(=O)CC(O3)c4ccccc4

Level: 1

Mol. Weight: 336.39 g/mol

Structure

SMILES: O1CCC(=O)c(c1c23)ccc2OCC=C3

Level: 0

Mol. Weight: 336.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 336.39 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.590
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.84

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.520
Plasma Protein Binding
65.02
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
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
8.570
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.600
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.230
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.320
Micronucleos
Safe
NR-AhR
Toxic
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
1.840
Rat (Acute)
2.780
Rat (Chronic Oral)
1.780
Fathead Minnow
5.020
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
431.610
Hydration Free Energy
-7.060
Log(D) at pH=7.4
3.720
Log(P)
4.36
Log S
-5.49
Log(Vapor Pressure)
-7.21
Melting Point
117.29
pKa Acid
10.59
pKa Basic
4.76
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9215
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9215
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9076
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9076
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9013
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9013
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9008
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9008
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8915
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8915
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8822
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8822
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8731
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8731
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8715
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8715
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8703
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8703
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8681
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8681
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8560
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8560
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8546
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8546
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8447
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8447
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8361
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8361
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.8314
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.8314
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8205
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8205
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8175
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8175
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8127
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8127
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.8042
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.8042
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7986
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7986
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7918
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7918
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7855
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7855
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7838
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7838
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7783
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7783
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7779
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7779
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7706
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7706
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7648
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7648
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7631
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7631
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7630
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7630
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7580
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7580
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7541
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7541
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7534
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7534
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7534
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7534
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7513
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7513
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7494
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7494
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7489
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7489
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7473
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7473
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7445
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7445
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7418
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7418
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7413
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7413
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7412
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7412
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7409
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7409
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7408
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7408
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7352
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7352
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7311
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7311
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7301
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7301
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7278
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7278
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7275
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7275
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7272
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7272
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7250
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7250
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7232
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7232
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7229
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7229
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7225
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7225
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7211
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7211
Dipeptidyl peptidase 4 P22411 DPP4_PIG Sus scrofa 3 0.7200
Dipeptidyl peptidase 4 P22411 DPP4_PIG Sus scrofa 3 0.7200
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7172
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7172
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7158
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7158
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7154
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7154
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7147
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7147
Metallo-beta-lactamase type 2 P25910 BLAB_BACFG Bacteroides fragilis 3 0.7147
Metallo-beta-lactamase type 2 P25910 BLAB_BACFG Bacteroides fragilis 3 0.7147
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7146
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7146
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7144
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7144
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7135
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7135
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7126
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7126
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7108
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7108
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7103
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7103
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7102
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7102
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7096
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7096
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7074
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7074
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7034
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7034
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7023
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7023
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7002
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7002

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