5,7-diihydroxy-3,8,3',4',5'-pentamethoxyflavone - Compound Card

5,7-diihydroxy-3,8,3',4',5'-pentamethoxyflavone

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5,7-diihydroxy-3,8,3',4',5'-pentamethoxyflavone

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles COc1cc(cc(c1OC)OC)c1oc2c(OC)c(O)cc(c2c(=O)c1OC)O
InChI InChI=1S/C20H20O9/c1-24-12-6-9(7-13(25-2)18(12)27-4)16-20(28-5)15(23)14-10(21)8-11(22)17(26-3)19(14)29-16/h6-8,21-22H,1-5H3
InChIKey WFUOMXZWZFSZEM-UHFFFAOYSA-N
Formula C20H20O9
HBA 9
HBD 2
MW 404.37
Rotatable Bonds 6
TPSA 116.82
LogP 2.91
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 404.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Conyza pyrrhopappa Asteraceae Plantae 72919

Showing of synonyms

  • Bitchagno GTM, Schüffler A, et al. (2021). Neo-clerodane diterpenoids from Conyza pyrrhopappa Sch.Bip. ex A.Rich.. Nat Prod Res. 2021, 35(19),3210-3219. [View] [PubMed]
Pubchem: 13916282
Nmrshiftdb2: 60065738

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 404.37 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 404.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 404.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.91
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.910
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.97

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.260
Plasma Protein Binding
75.32
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.120
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.840
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.210
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.310
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
-11.810
Rat (Acute)
2.280
Rat (Chronic Oral)
2.620
Fathead Minnow
5.100
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
485.260
Hydration Free Energy
-7.840
Log(D) at pH=7.4
3.420
Log(P)
3.05
Log S
-4.29
Log(Vapor Pressure)
-7.8
Melting Point
180.91
pKa Acid
7.8
pKa Basic
0.64
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9394
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9022
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8978
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8937
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8900
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8873
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8742
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8719
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8677
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8667
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8624
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8622
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8607
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8567
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8555
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8542
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8532
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8526
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 6 0.8525
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8512
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8480
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8470
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8467
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8466
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8465
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8460
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8458
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8442
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8441
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8431
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8419
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8385
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8353
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8297
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8295
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8278
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8269
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8244
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.8241
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8214
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8212
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8207
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8188
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8174
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.8138
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8136
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8134
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8108
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8080
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8072
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8062
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8049
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8040
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8003
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7998
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7998
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7955
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7953
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7947
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7932
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7929
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7926
BMP-2-inducible protein kinase Q9NSY1 BMP2K_HUMAN Homo sapiens 3 0.7911
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7897
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7888
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7888
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7882
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7841
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7837
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7821
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7798
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7789
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.7766
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7763
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7760
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7739
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7734
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7726
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7718
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7709
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7707
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7676
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7647
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7641
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7637
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7620
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7615
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7593
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7574
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7573
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7564
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7535
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7532
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7522
NADPH--cytochrome P450 reductase P00388 NCPR_RAT Rattus norvegicus 4 0.7521
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7511
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7511
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7509
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7491
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7487
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7476
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7435
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7414
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7395
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 5 0.7385
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 4 0.7369
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7366
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7329
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7319
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7309
NADPH--cytochrome P450 reductase P00388 NCPR_RAT Rattus norvegicus 4 0.7307
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7289
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7276
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7274
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 4 0.7268
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7267
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 6 0.7263
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7261
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7245
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7228
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7225
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7220
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7216
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7214
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7212
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7201
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7196
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7183
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7179
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7178
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7166
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7156
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7155
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7152
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7147
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7141
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7132
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7130
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7125
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7121
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7119
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7099
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7098
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7096
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7096
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7095
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7076
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 5 0.7073
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7069
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7065
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7061
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7059
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7059
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7037
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7026
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7020
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7008
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7005
TGF-beta-activated kinase 1 and MAP3K7-binding protein 1 Q15750 TAB1_HUMAN Homo sapiens 3 0.7000

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