Tephrinone - Compound Card

Tephrinone

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Tephrinone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavanone
Canonical Smiles COc1cc(O)c2c(c1CC=C(C)C)OC(CC2=O)c1ccccc1
InChI InChI=1S/C21H22O4/c1-13(2)9-10-15-19(24-3)12-17(23)20-16(22)11-18(25-21(15)20)14-7-5-4-6-8-14/h4-9,12,18,23H,10-11H2,1-3H3
InChIKey NISHDQWTPMJBJI-UHFFFAOYSA-N
Formula C21H22O4
HBA 4
HBD 1
MW 338.4
Rotatable Bonds 4
TPSA 55.76
LogP 4.62
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 338.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tephrosia rhodesica Leguminosae/Fabaceae Plantae 556521

Showing of synonyms

  • Atilaw Y, Muiva-Mutisya L, et al. (2020). Prenylated Flavonoids from the Roots of Tephrosia rhodesica. Journal of natural products, 2020, 83(8), 2390–2398. [View]
Pubchem: 156589
Chebi: 187002
Nmrshiftdb2: 60069194

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 338.4 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 338.4 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 338.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.78
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
-2.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.160
Plasma Protein Binding
65.73
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.400
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.320
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.370
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
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
2.210
Rat (Acute)
1.970
Rat (Chronic Oral)
2.250
Fathead Minnow
5.040
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
415.540
Hydration Free Energy
-8.330
Log(D) at pH=7.4
3.660
Log(P)
5.14
Log S
-5.71
Log(Vapor Pressure)
-7.43
Melting Point
113.1
pKa Acid
8.6
pKa Basic
6.13
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9621
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9490
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.9382
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9351
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9245
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9179
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.9142
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.9079
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8952
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8943
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.8909
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8867
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8787
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8786
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8742
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8728
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8669
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8657
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8641
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8591
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8581
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8539
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8510
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8484
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.8399
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8375
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8365
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8341
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.8340
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8307
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.8292
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8278
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8248
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8223
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8191
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8160
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8145
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8133
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.8131
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8130
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8128
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8092
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8077
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8042
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8012
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8010
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7993
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7954
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7893
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7884
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7867
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7844
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7811
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7792
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7791
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7763
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7729
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7715
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7701
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7700
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7699
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7697
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7696
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7686
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7675
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7673
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7657
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7655
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7637
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7633
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7632
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7624
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7582
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7572
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 4 0.7561
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7553
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7552
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7536
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7519
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7513
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7492
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7488
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7472
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7471
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7460
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7453
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7448
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7439
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7438
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7433
Heat shock protein 83 P12861 HSP83_TRYBB Trypanosoma brucei brucei 3 0.7432
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7424
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7402
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7400
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7366
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7366
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7356
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7355
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7355
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7353
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7343
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7338
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7334
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7329
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7328
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7323
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7322
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 4 0.7320
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7319
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7317
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7317
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7311
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7310
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7310
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7287
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7282
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7276
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7272
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7268
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7263
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7259
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7259
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7253
Capsid scaffolding protein P88911 P88911_HHV8 Human herpesvirus 8 type M 3 0.7252
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.7250
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7240
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7232
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7230
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7228
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7220
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7220
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7218
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7216
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7185
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7172
Phosphatidylinositol 3-kinase catalytic subunit type 3 Q8NEB9 PK3C3_HUMAN Homo sapiens 3 0.7159
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7148
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7143
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7135
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 3 0.7132
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7131
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7129
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7129
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7121
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7117
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7113
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7111
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7101
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7099
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7094
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7083
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7065
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7054
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7052
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 2 0.7052
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7049
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7047
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7045
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7044
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7042
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7039
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7037
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 2 0.7029
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7022
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7019
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7010
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7010
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7002

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