5,7,4',5'-tetrahydroxy-3,6,2'-trimethoxyflavone - Compound Card

5,7,4',5'-tetrahydroxy-3,6,2'-trimethoxyflavone

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5,7,4',5'-tetrahydroxy-3,6,2'-trimethoxyflavone

Structure
Zoomed Structure
  • Family: Sapindaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles COc1cc(O)c(cc1c1oc2cc(O)c(c(c2c(=O)c1OC)O)OC)O
InChI InChI=1S/C18H16O9/c1-24-11-5-9(20)8(19)4-7(11)16-18(26-3)15(23)13-12(27-16)6-10(21)17(25-2)14(13)22/h4-6,19-22H,1-3H3
InChIKey NEEAZBRBEVXSIZ-UHFFFAOYSA-N
Formula C18H16O9
HBA 9
HBD 4
MW 376.32
Rotatable Bonds 4
TPSA 138.82
LogP 2.31
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.17
Exact Mass 376.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Dodonaea viscosa Sapindaceae Plantae 151065

Showing of synonyms

  • Kaigongi MM, Lukhoba CW, et al. (2020). LC-MS-Based Metabolomics for the Chemosystematics of Kenyan Dodonaea viscosa Jacq (Sapindaceae) Populations. Molecules. 2020, 25(18), 4130. [View] [PubMed]
Pubchem: 13942680
Chebi: 180422
Nmrshiftdb2: 60032855

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)
-6.08
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.190
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.69

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.090
Plasma Protein Binding
81.28
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-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
11.770
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.940
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.130
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.330
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
-0.720
Rat (Acute)
2.390
Rat (Chronic Oral)
3.120
Fathead Minnow
4.600
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
517.680
Hydration Free Energy
-10.050
Log(D) at pH=7.4
2.650
Log(P)
2.44
Log S
-5.18
Log(Vapor Pressure)
-7.97
Melting Point
221.61
pKa Acid
7.56
pKa Basic
3.42
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9373
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9248
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9160
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9028
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8957
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8909
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8880
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8875
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8873
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8817
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.8814
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8778
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8720
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8700
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8669
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8620
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8603
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8599
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8588
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8561
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8524
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8522
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8513
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8489
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8475
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8450
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8430
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8426
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8424
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8377
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8373
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.8330
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8312
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.8303
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8303
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8284
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8280
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8261
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8260
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8246
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8225
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8214
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8211
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8199
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8186
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8182
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8167
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8165
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 6 0.8149
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8142
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8139
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8132
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8128
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8106
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8103
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8085
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8068
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8058
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8037
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8027
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8013
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 4 0.8010
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8000
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 4 0.7995
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7995
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7994
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7991
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7983
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7974
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7973
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7916
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7910
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7899
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7890
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7873
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7846
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7845
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7844
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7839
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7817
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 5 0.7808
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7807
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7802
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7767
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 4 0.7766
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7757
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7737
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 5 0.7735
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 7 0.7686
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7672
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7671
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7657
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7647
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 4 0.7637
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7615
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7612
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7603
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7595
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7592
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7591
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7558
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7548
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7528
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7521
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7521
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7520
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7510
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7488
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7487
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7484
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7461
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7451
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7450
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7446
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7440
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7440
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7415
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7402
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7397
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7394
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7388
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7373
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7370
NADPH--cytochrome P450 reductase P00388 NCPR_RAT Rattus norvegicus 4 0.7369
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7366
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.7365
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7352
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7325
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7320
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7314
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7312
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7287
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7286
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7272
DNA gyrase subunit B Q839Z1 GYRB_ENTFA Enterococcus faecalis 3 0.7269
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7266
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7247
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 6 0.7233
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7226
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7223
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7219
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7204
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7186
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7182
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7162
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7159
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7152
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7140
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7127
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7117
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.7115
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7098
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7096
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7073
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7063
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7049
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7040
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7026
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7005
Ribosomal RNA large subunit methyltransferase J P37634 RLMJ_ECOLI Escherichia coli 4 0.7002
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7001

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