5,7-diihydroxy-3,6,8,3',4',5'-hexamethoxyflavone - Compound Card

5,7-diihydroxy-3,6,8,3',4',5'-hexamethoxyflavone

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5,7-diihydroxy-3,6,8,3',4',5'-hexamethoxyflavone

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles COc1c(OC)cc(cc1OC)c1oc2c(OC)c(O)c(c(c2c(=O)c1OC)O)OC
InChI InChI=1S/C21H22O10/c1-25-10-7-9(8-11(26-2)17(10)27-3)16-20(29-5)14(23)12-13(22)19(28-4)15(24)21(30-6)18(12)31-16/h7-8,22,24H,1-6H3
InChIKey QXRNWRWFNALYGH-UHFFFAOYSA-N
Formula C21H22O10
HBA 10
HBD 2
MW 434.4
Rotatable Bonds 7
TPSA 126.05
LogP 2.92
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 434.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Conyza pyrrhopappa Asteraceae-Compositae 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: 5386963
Chebi: 196628
Nmrshiftdb2: 60065739

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 222.24 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 146.14 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.23
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.950
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.240
Plasma Protein Binding
66.67
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-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
7.220
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.790
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.190
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.990
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
-37.420
Rat (Acute)
2.460
Rat (Chronic Oral)
2.780
Fathead Minnow
5.290
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
487.590
Hydration Free Energy
-4.950
Log(D) at pH=7.4
3.400
Log(P)
2.68
Log S
-3.8
Log(Vapor Pressure)
-7.78
Melting Point
174.56
pKa Acid
7.45
pKa Basic
-0.83
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 0.9458
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9419
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9233
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9150
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8992
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8955
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8936
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8859
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8846
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8759
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8751
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8711
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8678
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8642
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8637
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8595
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 4 0.8584
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8568
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8540
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8525
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 6 0.8508
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8498
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8473
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8469
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8436
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8391
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8380
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8376
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8360
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8355
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8350
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8318
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8301
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8288
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8286
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8211
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8182
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8150
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8141
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8134
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8088
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.8086
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.8081
BMP-2-inducible protein kinase Q9NSY1 BMP2K_HUMAN Homo sapiens 3 0.8061
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8037
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.8033
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8029
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.8024
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7986
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7959
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7945
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7935
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7920
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7871
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7836
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7821
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7803
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7798
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7785
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7772
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7751
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7740
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7706
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7700
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.7691
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7650
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7613
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7613
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7598
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7533
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7523
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7514
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 4 0.7510
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7501
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7495
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7490
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 4 0.7466
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7457
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7452
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7449
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7440
NADPH--cytochrome P450 reductase P00388 NCPR_RAT Rattus norvegicus 4 0.7434
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7430
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7408
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7401
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7398
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7384
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7375
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7361
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7358
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7349
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7289
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7289
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7285
Purine nucleoside phosphorylase Q8DTU4 Q8DTU4_STRMU Streptococcus mutans serotype c 4 0.7285
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7257
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7250
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7225
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7222
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7219
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7212
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7210
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7208
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7207
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7202
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7197
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7193
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 5 0.7187
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7155
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7142
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7142
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7128
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7107
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7104
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7099
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7097
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7096
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7095
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7082
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 6 0.7080
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7071
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.7070
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7059
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7046
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7041
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7035
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7029
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7006
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7001

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