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Tetrahydroxyflavone

Family: Plantae - Cyperaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol

Canonical Smiles	Oc1cc2oc(c3ccccc3)c(c(=O)c2c(c1O)O)O
InChI	InChI=1S/C15H10O6/c16-8-6-9-10(12(18)11(8)17)13(19)14(20)15(21-9)7-4-2-1-3-5-7/h1-6,16-18,20H
InChIKey	SDILYIBSLKZODH-UHFFFAOYSA-N
Formula	C₁₅H₁₀O₆
HBA	6
HBD	4
MW	286.24
Rotatable Bonds	1
TPSA	111.13
LogP	2.28
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.0
Exact Mass	286.05
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: 15233950

Cas: 142646-44-4

Nmrshiftdb2: 60029581

Comptox: DTXSID30570342

CPRiL: 426027

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

Level: 1

Mol. Weight: 286.24 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 286.24 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 286.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.35
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.090
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.22

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.900
Plasma Protein Binding: 103.9
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Non-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: 6.190
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.440
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.250
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.420
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: 3.440
Rat (Acute): 2.530
Rat (Chronic Oral): 3.520
Fathead Minnow: 4.140
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 467.980
Hydration Free Energy: -12.660
Log(D) at pH=7.4: 0.960
Log(P): 1.85
Log S: -2.85
Log(Vapor Pressure): -8.73
Melting Point: 260.73
pKa Acid: 4.99
pKa Basic: 6.31

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9699
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9476
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	5	0.9264
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.9205
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.9050
Cell division cycle 7-related protein kinase	O00311	CDC7_HUMAN	Homo sapiens	4	0.9046
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8887
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8852
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8808
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8704
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8682
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8662
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.8659
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.8620
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8537
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8535
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8507
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8491
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8488
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.8463
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8456
Protein polybromo-1	Q86U86	PB1_HUMAN	Homo sapiens	5	0.8446
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8435
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8430
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8415
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8408
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.8394
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8364
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8358
Quercetin 2,3-dioxygenase	Q7SIC2	QDOI_ASPJA	Aspergillus japonicus	4	0.8340
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.8323
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8298
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8256
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.8238
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8222
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8208
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	5	0.8206
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	4	0.8206
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8158
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.8144
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8133
Nucleoside permease	Q9KPL5	Q9KPL5_VIBCH	Vibrio cholerae serotype O1	4	0.8121
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.8115
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8106
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.8087
Gag-Pol polyprotein	O12158	POL_HV192	Human immunodeficiency virus type 1 group M subtype C	3	0.8085
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.8055
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7994
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7959
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.7953
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7953
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7926
Exotoxin A	P11439	TOXA_PSEAE	Pseudomonas aeruginosa	3	0.7912
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7903
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7902
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7874
Cyclin-dependent kinase 6	Q00534	CDK6_HUMAN	Homo sapiens	5	0.7867
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7861
Cyclin-dependent kinase 5	Q00535	CDK5_HUMAN	Homo sapiens	4	0.7855
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7849
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7822
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7818
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7795
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7791
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7790
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	5	0.7774
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7741
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7738
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	5	0.7731
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7714
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7710
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7698
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7690
Glycosyltransferase	A4F1R4	A4F1R4_CLITE	Clitoria ternatea	5	0.7674
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7666
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7665
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7654
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7652
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7645
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7635
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7631
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7629
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7623
Heat shock protein 75 kDa, mitochondrial	Q12931	TRAP1_HUMAN	Homo sapiens	3	0.7616
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7614
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7604
Putative secreted protein	C9Z6T8	C9Z6T8_STRSW	Streptomyces scabiei	4	0.7600
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7593
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	4	0.7563
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7559
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7532
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7497
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7496
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7491
Major strawberry allergen Fra a 1-3	D0E0C7	FRA13_FRAAN	Fragaria ananassa	4	0.7484
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	4	0.7483
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	3	0.7455
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7432
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7408
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7406
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7395
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7391
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7384
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7350
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.7346
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	5	0.7327
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7306
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7304
Cystathionine gamma-synthase	P56069	METB_HELPY	Helicobacter pylori	3	0.7299
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7296
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7294
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7288
Myosin heavy chain, striated muscle	P24733	MYS_ARGIR	Argopecten irradians	3	0.7263
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7251
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7240
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7200
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.7191
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	4	0.7168
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial	Q6NVY1	HIBCH_HUMAN	Homo sapiens	3	0.7168
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7158
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7156
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7152
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	5	0.7144
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7139
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7136
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7123
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7121
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	3	0.7113
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7101
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7092
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	4	0.7086
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7086
Histidine kinase 4	Q9C5U0	AHK4_ARATH	Arabidopsis thaliana	3	0.7081
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7076
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7069
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7064
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7058
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7052
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	3	0.7045
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7044
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7042
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7040
cGMP-dependent protein kinase, putative	A5K0N4	A5K0N4_PLAVS	Plasmodium vivax	3	0.7039
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7022
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7007
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7006
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7006
Glycylpeptide N-tetradecanoyltransferase	A5K1A2	A5K1A2_PLAVS	Plasmodium vivax	3	0.7005
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7005
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7004

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