4',5-dihydroxy-3',5',6,7,8-pentamethoxyflavone - Compound Card

4',5-dihydroxy-3',5',6,7,8-pentamethoxyflavone

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4',5-dihydroxy-3',5',6,7,8-pentamethoxyflavone

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles COc1cc(cc(c1O)OC)c1cc(=O)c2c(o1)c(OC)c(c(c2O)OC)OC
InChI InChI=1S/C20H20O9/c1-24-12-6-9(7-13(25-2)15(12)22)11-8-10(21)14-16(23)18(26-3)20(28-5)19(27-4)17(14)29-11/h6-8,22-23H,1-5H3
InChIKey GSQDOAHDMWDTMG-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 Crassocephalum bauchiense Asteraceae-Compositae Plantae 189210

Showing of synonyms

  • Parthasarathy R, Sathiyabama M (2015). Lovastatin-producing endophytic fungus isolated from a medicinal plant Solanum xanthocarpum. Nat Prod Res. 2015, 29(24), 2282-2286. [View] [PubMed]
Pubchem: 10386481
Nmrshiftdb2: 70002980

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)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.970
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.23

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.340
Plasma Protein Binding
71.89
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
8.740
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.860
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.450
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.630
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
-11.870
Rat (Acute)
2.350
Rat (Chronic Oral)
2.920
Fathead Minnow
5.170
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
482.460
Hydration Free Energy
-8.230
Log(D) at pH=7.4
3.090
Log(P)
2.42
Log S
-4.88
Log(Vapor Pressure)
-7.71
Melting Point
176.65
pKa Acid
7.64
pKa Basic
1.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9720
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9646
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9595
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9531
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9359
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9255
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9225
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9207
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.9110
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9057
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.9053
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9033
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8978
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8906
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8837
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8694
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8693
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8686
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8684
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8684
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8609
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8603
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8592
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8580
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8577
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 4 0.8525
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8497
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8495
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8486
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8456
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.8456
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8423
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8421
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8389
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8385
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8331
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8319
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8259
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8239
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8236
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8225
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8224
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8220
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8184
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8172
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8150
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.8114
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8044
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8037
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8001
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7959
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7944
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7927
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7923
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7923
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7908
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7900
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7845
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7835
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7824
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7802
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7799
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.7746
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7741
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7740
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7736
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7727
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7719
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7709
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7692
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7692
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7688
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.7667
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7667
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7656
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7642
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7639
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7616
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7616
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7616
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7614
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7613
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7607
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7596
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7576
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7571
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7554
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7554
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7554
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 5 0.7543
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7541
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7531
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7529
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7527
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7507
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7503
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7499
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7488
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7476
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7465
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7452
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7441
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7439
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7431
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7400
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7396
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7391
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7376
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7356
Gag-Pol polyprotein O12158 POL_HV192 Human immunodeficiency virus type 1 group M subtype C 3 0.7354
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7345
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7331
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7318
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7309
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7292
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7260
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7256
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7255
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7254
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7230
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7208
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7188
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7182
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7163
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 5 0.7161
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7151
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7146
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 6 0.7142
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7110
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7108
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7088
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7085
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7078
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7077
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7075
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7074
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 5 0.7072
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7068
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7067
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7066
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7062
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.7059
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7054
BMP-2-inducible protein kinase Q9NSY1 BMP2K_HUMAN Homo sapiens 3 0.7050
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 5 0.7048
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 5 0.7046
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7037
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7031
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7025
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7025
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7021
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7020
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7019
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7012
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7012
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7004
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7004

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