(E)-5-hydroxyanhydrotephrostachin - Compound Card

(E)-5-hydroxyanhydrotephrostachin

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(E)-5-hydroxyanhydrotephrostachin

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles COc1cc(O)c2c(c1/C=C/C(=C)C)oc(cc2=O)c1ccccc1
InChI InChI=1S/C21H18O4/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/h4-12,23H,1H2,2-3H3/b10-9+
InChIKey YZVDBUYFRIYKGH-MDZDMXLPSA-N
Formula C21H18O4
HBA 4
HBD 1
MW 334.37
Rotatable Bonds 4
TPSA 59.67
LogP 4.76
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.1
Exact Mass 334.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tephrosia purpurea Leguminosae/Fabaceae Plantae 228354

Showing of synonyms

  • Atilaw Y, Muiva-Mutisya L, et al. (2017). Four Prenylflavone Derivatives with Antiplasmodial Activities from the Stem of Tephrosia purpurea subsp. Leptostachya. Molecules, 2017, 22(9), 1514. [View]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 334.37 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 334.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 334.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.430
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.520
Plasma Protein Binding
87.44
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.730
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
2.100
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.050
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.500
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
3.260
Rat (Acute)
2.220
Rat (Chronic Oral)
2.230
Fathead Minnow
5.390
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
444.620
Hydration Free Energy
-9.700
Log(D) at pH=7.4
4.380
Log(P)
5.24
Log S
-6.13
Log(Vapor Pressure)
-8.13
Melting Point
175.46
pKa Acid
8.63
pKa Basic
4.74
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.9722
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9651
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9506
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.9253
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.9221
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9215
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.9195
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.9176
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9134
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.9060
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8985
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8955
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8928
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8913
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8810
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8767
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8756
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8685
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8670
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8654
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8611
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8600
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8579
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.8560
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8542
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8533
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8455
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8448
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8407
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8391
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8374
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8284
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.8228
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8204
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8204
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.8145
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8138
TGF-beta-activated kinase 1 and MAP3K7-binding protein 1 Q15750 TAB1_HUMAN Homo sapiens 3 0.8111
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8107
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8106
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8062
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8049
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8043
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8035
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.8014
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8001
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7981
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7979
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7954
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7950
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7943
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7891
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7890
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7872
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7861
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7854
Phosphatidylinositol 3-kinase catalytic subunit type 3 Q8NEB9 PK3C3_HUMAN Homo sapiens 3 0.7843
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7762
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7757
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7750
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7709
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7698
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7664
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7655
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7651
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7643
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7631
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7626
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7626
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7623
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7611
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7598
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7596
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7566
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7543
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7543
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7523
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7523
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7520
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7518
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7497
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7491
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7483
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7477
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7477
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7460
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7458
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7455
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7427
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7413
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7410
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7402
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7402
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7401
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7399
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7398
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7389
Flavonoid 3-O-glucosyltransferase A6XNC6 UGFGT_MEDTR Medicago truncatula 2 0.7388
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7387
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7383
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7367
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7361
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7350
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7323
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7321
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7297
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7296
Choline kinase alpha P35790 CHKA_HUMAN Homo sapiens 3 0.7284
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7273
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7273
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7268
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7249
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7249
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7243
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7241
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7228
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 2 0.7220
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7220
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7210
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7203
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7201
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7196
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7194
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7191
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7188
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7188
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7184
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7177
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 3 0.7160
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7152
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7117
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7116
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7091
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7088
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7077
Glutamate receptor 2 P42262 GRIA2_HUMAN Homo sapiens 3 0.7073
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7070
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7069
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7056
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7056
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7055
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7052
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7049
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7046
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7041
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7034
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7032
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7028
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7025
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7022
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7022
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7017
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7012

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