Eryvarin K - Compound Card

Eryvarin K

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Eryvarin K

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Pterocarpan
Canonical Smiles COc1cc2c(cc1O)O[C@@H]1[C@H]2COc2c1cc(c(c2)O)CC=C(C)C
InChI InChI=1S/C21H22O5/c1-11(2)4-5-12-6-14-18(8-16(12)22)25-10-15-13-7-20(24-3)17(23)9-19(13)26-21(14)15/h4,6-9,15,21-23H,5,10H2,1-3H3/t15-,21-/m0/s1
InChIKey CVUYVQZALVRDIK-BTYIYWSLSA-N
Formula C21H22O5
HBA 5
HBD 2
MW 354.4
Rotatable Bonds 3
TPSA 68.15
LogP 4.22
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 354.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Erythrina abyssinica Leguminosae/Fabaceae Plantae 1237573

Showing of synonyms

  • Nguyen PH, Le TV, et al. (2009). Cytotoxic and PTP1B inhibitory activities from Erythrina abyssinica. Bioorganic & medicinal chemistry letters,2009, 19(23), 6745-9. [View] [PubMed]
Pubchem: 11187348
Nmrshiftdb2: 60046406
Bindingdb: 50311575

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC3C2COc4c3cccc4

Level: 0

Mol. Weight: 354.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.680
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.72

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.060
Plasma Protein Binding
85.33
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
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.520
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.670
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.970
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.550
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-1.730
Rat (Acute)
1.810
Rat (Chronic Oral)
2.140
Fathead Minnow
4.880
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
448.760
Hydration Free Energy
-7.740
Log(D) at pH=7.4
3.770
Log(P)
3.8
Log S
-5.26
Log(Vapor Pressure)
-8.7
Melting Point
199.32
pKa Acid
9.71
pKa Basic
6.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9457
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.9337
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9317
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9270
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.9180
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9116
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8964
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8963
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.8938
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8781
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8748
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8718
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8712
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8686
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8677
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8675
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8637
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8441
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8363
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8350
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8302
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8267
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8235
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8203
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8178
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8129
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.8123
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8060
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8057
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8026
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8022
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7974
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.7968
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7944
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7918
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7908
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.7833
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7777
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7764
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7751
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7725
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7721
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7711
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7708
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7702
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7671
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7668
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7664
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7659
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7657
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7599
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7599
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7599
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7591
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7590
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7577
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7545
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7531
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7496
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7470
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7468
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7465
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7445
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7418
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7408
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7385
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7380
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7377
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7364
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7360
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7357
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7347
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7341
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7334
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7333
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7332
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7326
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7325
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7313
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7310
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7306
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7288
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7280
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7276
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7264
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7242
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7241
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7240
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7197
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7197
ADP-ribosylation factor-like protein 3 A8ISN6 ARL3_CHLRE Chlamydomonas reinhardtii 4 0.7173
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7169
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7169
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7138
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7124
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7102
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7101
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7098
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7096
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7084
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7077
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7071
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7070
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7065
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7063
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7061
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7051
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7044
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7044
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7031
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7022
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7018
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 3 0.7013
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7013
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7005
Histone-lysine N-methyltransferase 2C Q8NEZ4 KMT2C_HUMAN Homo sapiens 3 0.7004
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 2 0.7004

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