Entadanin - Compound Card

Entadanin

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Entadanin

Structure
Zoomed Structure
  • Family: Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Peltogynoid
Canonical Smiles COc1c2COc3c(c2cc(c1O)O)oc1c(c3=O)c(O)cc(c1)O
InChI InChI=1S/C17H12O8/c1-23-15-8-5-24-17-14(22)12-9(19)2-6(18)3-11(12)25-16(17)7(8)4-10(20)13(15)21/h2-4,18-21H,5H2,1H3
InChIKey IOYOFCWDKCNXJP-UHFFFAOYSA-N
Formula C17H12O8
HBA 8
HBD 4
MW 344.28
Rotatable Bonds 1
TPSA 129.59
LogP 2.18
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 344.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Entada abyssinica Leguminosae/Fabaceae Plantae 204973

Showing of synonyms

  • Melong R, Kapche D, et al. (2014). A New Aggreceride Analogue and a Peltogynoid Isolated from the Stem Bark of Entada abyssinica (Fabaceae). Natural Product Communications, 2014, 9(10), 1499-1502. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc3c4c(cccc4)COc3c2=O

Level: 0

Mol. Weight: 250.25 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.01
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.12
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.32

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.09
Plasma Protein Binding
88.51
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
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.26
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.89
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.97
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.87
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
2.4
Rat (Acute)
2.47
Rat (Chronic Oral)
2.83
Fathead Minnow
4.43
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
520.84
Hydration Free Energy
-9.0
Log(D) at pH=7.4
1.94
Log(P)
2.18
Log S
-4.93
Log(Vapor Pressure)
-8.53
Melting Point
304.23
pKa Acid
8.43
pKa Basic
4.27
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9709
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9578
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9268
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9243
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9068
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.8929
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8919
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8897
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 6 0.8878
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8869
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8769
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8749
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8741
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8698
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8625
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8608
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.8605
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8601
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8574
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8568
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8548
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8541
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.8539
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8533
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8503
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8482
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.8470
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8432
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8375
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8372
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8370
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8365
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8356
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8313
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.8304
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8284
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8256
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8233
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8232
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8225
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8217
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8203
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8155
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 7 0.8140
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8135
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8107
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8091
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8070
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8052
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8049
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8045
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8039
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8027
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8016
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7985
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7966
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7966
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7965
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7960
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7945
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7930
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7922
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7909
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 4 0.7899
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7868
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7864
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7856
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7830
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7830
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7801
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7782
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7751
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7726
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7725
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7725
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7701
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7701
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7629
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7610
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 5 0.7607
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7605
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7594
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7576
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7574
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7568
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7566
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7544
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7529
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7513
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7513
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7503
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7501
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7493
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7487
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7484
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7458
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7435
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7398
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7382
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7382
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7382
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7380
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7374
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7366
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7361
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7350
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7334
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7325
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7324
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7324
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7318
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7304
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7288
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7284
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7277
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7277
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7267
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7266
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7246
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7229
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7227
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7218
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7215
Quercetin 2,3-dioxygenase Q7SIC2 QDOI_ASPJA Aspergillus japonicus 4 0.7214
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7206
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 4 0.7201
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7195
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7184
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 5 0.7172
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7172
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7169
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7151
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7148
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7143
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7132
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7127
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7115
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7114
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7112
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7111
Gag-Pol polyprotein O12158 POL_HV192 Human immunodeficiency virus type 1 group M subtype C 3 0.7110
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7105
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7105
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7101
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7097
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7095
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 4 0.7092
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7083
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7075
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7073
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7072
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7068
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7065
Ribosomal protein S6 kinase alpha-1 Q15418 KS6A1_HUMAN Homo sapiens 3 0.7062
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7058
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7053
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7052
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7045
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7037
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7032
Maltokinase A1TH50 MAK_MYCVP Mycolicibacterium vanbaalenii 3 0.7026
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7024
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7014
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7013
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7012

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