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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles COc1cc(cc(c1O)OC)c1oc2c(OC)c(OC)cc(c2c(=O)c1OC)O
InChI InChI=1S/C20H20O9/c1-24-11-6-9(7-12(25-2)15(11)22)17-20(28-5)16(23)14-10(21)8-13(26-3)18(27-4)19(14)29-17/h6-8,21-22H,1-5H3
InChIKey UMYVSLCFNRCAHY-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: 129711279

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)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.930
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.88

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.320
Plasma Protein Binding
70.11
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-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
8.790
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.080
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.540
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.730
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
-11.610
Rat (Acute)
2.260
Rat (Chronic Oral)
2.830
Fathead Minnow
5.080
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
486.360
Hydration Free Energy
-8.260
Log(D) at pH=7.4
3.200
Log(P)
2.54
Log S
-4.68
Log(Vapor Pressure)
-7.58
Melting Point
179.17
pKa Acid
7.44
pKa Basic
1.27
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9232
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9225
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9224
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9158
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.9158
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9153
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.9077
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.9021
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8860
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8808
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8772
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8702
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8693
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8679
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8674
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8660
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8655
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8634
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8618
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8608
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8588
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8569
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8545
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8510
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8486
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8475
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8473
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8457
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8452
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8378
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8356
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.8341
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8287
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8283
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8234
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.8218
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8197
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8191
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8188
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8185
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8150
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8142
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8134
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8131
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8122
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8119
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8092
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8090
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.8089
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8076
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8062
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8044
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7979
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7949
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7938
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7914
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7911
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7907
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7855
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7838
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7814
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7811
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7804
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7802
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7799
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7784
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7771
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7768
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7767
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 4 0.7761
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7760
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7750
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7737
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7735
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7735
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7707
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7705
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7677
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7658
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7657
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7649
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7640
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 4 0.7638
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7617
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.7610
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7609
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7597
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7587
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7567
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 5 0.7556
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7554
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7550
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7536
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7530
NADPH--cytochrome P450 reductase P00388 NCPR_RAT Rattus norvegicus 4 0.7527
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7506
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7501
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7498
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.7490
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7489
NADPH--cytochrome P450 reductase P00388 NCPR_RAT Rattus norvegicus 4 0.7478
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.7470
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7432
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7420
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7411
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7408
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7393
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7367
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7326
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7316
Gag-Pol polyprotein O12158 POL_HV192 Human immunodeficiency virus type 1 group M subtype C 3 0.7314
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7290
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 5 0.7277
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7277
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7263
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7255
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7252
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7252
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7235
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7233
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7209
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7202
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7189
TGF-beta-activated kinase 1 and MAP3K7-binding protein 1 Q15750 TAB1_HUMAN Homo sapiens 3 0.7189
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7188
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7186
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 3 0.7182
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7179
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7162
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 5 0.7159
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7155
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 6 0.7131
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7116
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7110
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7109
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7103
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7102
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7090
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7086
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7081
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 5 0.7073
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7069
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7060
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7053
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7047
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7038
Maltokinase A1TH50 MAK_MYCVP Mycolicibacterium vanbaalenii 3 0.7036
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7031
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7024
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7018
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7017
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7014
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7011
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7008
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7004
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7002

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