Trihydroxymethoxy flavone - Compound Card

Trihydroxymethoxy flavone

Select a section from the left sidebar

Trihydroxymethoxy flavone

Structure
Zoomed Structure
  • Family: Plantae - Cyperaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonol
Canonical Smiles COc1c(oc2c(c1=O)c(O)c(c(c2)O)O)c1ccccc1
InChI InChI=1S/C16H12O6/c1-21-16-14(20)11-10(7-9(17)12(18)13(11)19)22-15(16)8-5-3-2-4-6-8/h2-7,17-19H,1H3
InChIKey KGHRUOOWABATNV-UHFFFAOYSA-N
Formula C16H12O6
HBA 6
HBD 3
MW 300.27
Rotatable Bonds 2
TPSA 100.13
LogP 2.59
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.06
Exact Mass 300.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cyperus alternifolius Cyperaceae Plantae 4611

Showing of synonyms

  • Farrag A.R.H, Abdallah H.M.I, et al. (2019). Antiulcer activity of Cyperus alternifolius in relation to its UPLC-MS metabolite fingerprint: A mechanistic study. Phytomedicine : international journal of phytotherapy and phytopharmacology, 2019, 62, 152970. [View] [PubMed]
Pubchem: 129636874

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 300.27 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 300.27 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 300.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.14
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.900
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.1

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.120
Plasma Protein Binding
97.51
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
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
6.440
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.970
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.600
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.260
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Toxic
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
3.910
Rat (Acute)
2.470
Rat (Chronic Oral)
3.070
Fathead Minnow
4.670
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
457.240
Hydration Free Energy
-13.060
Log(D) at pH=7.4
1.870
Log(P)
2.94
Log S
-3.99
Log(Vapor Pressure)
-8.33
Melting Point
205.82
pKa Acid
5.63
pKa Basic
5.01
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9694
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9504
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.9331
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.9213
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9173
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.9161
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9074
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8914
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8865
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8784
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8747
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8727
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8723
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8715
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8681
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8673
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8636
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8631
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8610
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8597
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8564
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8540
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8522
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.8516
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8472
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8458
Gag-Pol polyprotein O12158 POL_HV192 Human immunodeficiency virus type 1 group M subtype C 3 0.8426
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8421
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8419
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8410
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8404
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8393
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8382
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8373
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8357
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8310
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.8233
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8210
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 4 0.8209
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8206
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8203
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8201
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8191
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.8171
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8164
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8134
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8117
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8113
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8100
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8090
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8082
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8068
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.8038
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8002
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7991
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7954
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7952
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7857
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7826
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7824
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7813
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7810
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7799
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7780
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7776
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7767
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7749
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 5 0.7739
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7732
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7717
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7703
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7682
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7678
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7676
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7673
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7666
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 3 0.7651
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7623
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7621
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7619
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7613
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7578
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7564
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7564
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7562
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7557
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7552
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7552
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7550
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7523
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7512
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7510
Cystathionine gamma-synthase P56069 METB_HELPY Helicobacter pylori 3 0.7493
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7489
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7486
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7485
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7482
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7453
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7451
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7404
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7398
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 4 0.7392
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7387
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7379
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7376
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7372
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7346
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7324
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7323
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7321
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7311
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7305
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7302
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7267
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7260
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7251
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7234
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7224
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7206
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7202
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7179
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7177
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7172
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.7167
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7165
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial Q6NVY1 HIBCH_HUMAN Homo sapiens 3 0.7161
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7157
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7156
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7146
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7140
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7132
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7126
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7120
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7115
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7103
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7101
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7096
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7096
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7095
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7094
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7086
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7078
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7073
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7073
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7072
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7071
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7060
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7058
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7057
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7053
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7048
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7047
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7038
Glycylpeptide N-tetradecanoyltransferase A5K1A2 A5K1A2_PLAVS Plasmodium vivax 3 0.7027
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7026
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7023
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7011
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7010
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7007
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7002

Download SDF