(E)-5,7-dihydroxy-8-methoxy-3-(4’-methoxybenzylidene)-4-chromanone - Compound Card

(E)-5,7-dihydroxy-8-methoxy-3-(4’-methoxybenzylidene)-4-chromanone

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(E)-5,7-dihydroxy-8-methoxy-3-(4’-methoxybenzylidene)-4-chromanone

Structure
Zoomed Structure
  • Family: Plantae - Hyacinthaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Homoisoflavonoid
Canonical Smiles COc1ccc(cc1)/C=C/1\COc2c(C1=O)c(O)cc(c2OC)O
InChI InChI=1S/C18H16O6/c1-22-12-5-3-10(4-6-12)7-11-9-24-18-15(16(11)21)13(19)8-14(20)17(18)23-2/h3-8,19-20H,9H2,1-2H3/b11-7+
InChIKey ZQTVKHLRTZRJSM-YRNVUSSQSA-N
Formula C18H16O6
HBA 6
HBD 2
MW 328.32
Rotatable Bonds 3
TPSA 85.22
LogP 2.77
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.17
Exact Mass 328.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Eucomis zambesiaca Hyacinthaceae Plantae 208122

Showing of synonyms

  • Sihra JK, Thumser AE, et al. (2015). Constituents of Bulbs of three Species of the Hyacinthaceae (Hyacinthoideae): Eucomis vandermerwei, E. zambesiaca and Resnova humifusa. Natural Product Communications, 2015,10 (7), 1207-1209. [View]
Pubchem: 102116624
Nmrshiftdb2: 70092302

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=C(C2=O)COc(c23)cccc3

Level: 1

Mol. Weight: 328.32 g/mol

Structure

SMILES: O=C1C(=C)COc(c12)cccc2

Level: 0

Mol. Weight: 328.32 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 328.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.5
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.790
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.0

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.220
Plasma Protein Binding
72.63
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.650
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.130
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
Safe
Daphnia Maga
6.220
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
Toxic
T. Pyriformis
3.360
Rat (Acute)
2.220
Rat (Chronic Oral)
2.950
Fathead Minnow
4.970
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
432.060
Hydration Free Energy
-9.160
Log(D) at pH=7.4
3.470
Log(P)
3.29
Log S
-6.28
Log(Vapor Pressure)
-7.42
Melting Point
182.2
pKa Acid
6.73
pKa Basic
3.59
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9319
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9315
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8806
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.8631
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 3 0.8572
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8542
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.8463
Decaprenylphosphoryl-beta-D-ribose oxidase I6X8C4 I6X8C4_MYCTU Mycobacterium tuberculosis 3 0.8460
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.8365
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8346
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8267
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8262
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8238
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8201
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8182
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8166
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.8081
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.8068
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8034
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7886
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7865
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7842
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7825
Bis(5'-adenosyl)-triphosphatase P49789 FHIT_HUMAN Homo sapiens 3 0.7823
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7764
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7733
Cyclin-G-associated kinase O14976 GAK_HUMAN Homo sapiens 4 0.7730
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7707
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7640
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7617
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7581
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7551
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7524
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7522
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7481
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7481
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7466
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7465
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7454
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 3 0.7453
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7453
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7449
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7447
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7437
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7425
Succinyl-CoA:acetate CoA-transferase B3EY95 SCACT_ACEAC Acetobacter aceti 3 0.7425
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7402
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 3 0.7398
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7397
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7390
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7380
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 4 0.7379
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7375
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7373
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7371
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7366
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7350
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7347
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 2 0.7312
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7307
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7305
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7304
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7300
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7294
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7293
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7282
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7277
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 3 0.7262
Endoplasmic reticulum aminopeptidase 2 Q6P179 ERAP2_HUMAN Homo sapiens 2 0.7257
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7236
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7236
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7221
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7206
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7203
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7193
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7173
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7166
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.7146
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7134
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7121
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7116
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 4 0.7115
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7101
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7099
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 2 0.7092
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7084
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 2 0.7082
Cyclin-dependent kinase 6 Q00534 CDK6_HUMAN Homo sapiens 4 0.7078
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7078
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7057
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7036
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7030
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7027
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7022

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