(E)-5-hydroxytephrostachin - Compound Card

(E)-5-hydroxytephrostachin

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(E)-5-hydroxytephrostachin

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles COc1cc(O)c2c(c1/C=C/C(O)(C)C)oc(cc2=O)c1ccccc1
InChI InChI=1S/C21H20O5/c1-21(2,24)10-9-14-18(25-3)12-16(23)19-15(22)11-17(26-20(14)19)13-7-5-4-6-8-13/h4-12,23-24H,1-3H3/b10-9+
InChIKey KPCRJDYZHRVZFS-MDZDMXLPSA-N
Formula C21H20O5
HBA 5
HBD 2
MW 352.39
Rotatable Bonds 4
TPSA 79.9
LogP 3.96
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.19
Exact Mass 352.13
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: 352.39 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 352.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 352.39 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.650
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.09

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.490
Plasma Protein Binding
89.83
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.180
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
2.230
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.900
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.600
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
0.620
Rat (Acute)
2.430
Rat (Chronic Oral)
2.440
Fathead Minnow
5.340
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
452.950
Hydration Free Energy
-10.700
Log(D) at pH=7.4
3.560
Log(P)
4.08
Log S
-5.34
Log(Vapor Pressure)
-8.33
Melting Point
190.93
pKa Acid
7.85
pKa Basic
5.69
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9470
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.9355
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9249
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.9190
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9057
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8940
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8920
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8915
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8901
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8894
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8784
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8740
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8652
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8618
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8617
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8601
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8553
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8528
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.8430
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8372
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8275
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8213
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8197
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.8194
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8187
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8061
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.8018
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8017
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8014
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7957
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7954
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7914
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7913
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7906
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7898
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7885
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7879
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7874
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7843
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7820
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7802
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7801
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7800
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7798
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7787
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7746
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7724
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7718
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7711
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7695
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7651
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7646
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7617
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7597
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7592
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7565
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7561
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7528
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7521
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7480
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7435
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7423
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7416
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7411
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7409
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7388
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7388
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7387
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7378
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7373
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7372
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7344
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7343
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7328
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7321
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7317
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7316
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7308
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7307
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7304
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7275
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7271
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7269
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7266
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7265
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7261
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7253
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7224
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7223
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7209
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7189
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7174
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7162
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7135
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7125
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7121
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7112
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7107
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7092
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7086
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7083
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7072
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7061
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7055
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7048
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7033
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7018
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7016
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7015
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7008
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7006

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