Tricetin

Details

• Internal ID: 4321f678-0c95-4d66-8757-eff064b8f789
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones
• IUPAC Name: 5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1=C(C=C(C(=C1O)O)O)C2=CC(=O)C3=C(C=C(C=C3O2)O)O
• SMILES (Isomeric): C1=C(C=C(C(=C1O)O)O)C2=CC(=O)C3=C(C=C(C=C3O2)O)O
• InChI: InChI=1S/C15H10O7/c16-7-3-8(17)14-9(18)5-12(22-13(14)4-7)6-1-10(19)15(21)11(20)2-6/h1-5,16-17,19-21H
• InChI Key: ARSRJFRKVXALTF-UHFFFAOYSA-N
• Popularity: 67 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₇
• Molecular Weight: 302.23 g/mol
• Exact Mass: 302.04265265 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.99
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 1

Synonyms

• 520-31-0
• 5,7,3',4',5'-Pentahydroxyflavone
• Hieracin
• 5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
• 5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
• UNII-5627PY99ZO
• 5,7,3,4,5-pentahydroxyflavone
• CHEBI:507499
• C10192
• 5627PY99ZO
• 3',4',5,5',7-pentahydroxyflavone
• MYF
• Spectrum_001591
• SpecPlus_000826
• Spectrum2_000741
• Spectrum3_001617
• Spectrum4_001678
• Spectrum5_000615
• BSPBio_003253
• KBioGR_002235
• KBioSS_002071
• DivK1c_006922
• SCHEMBL158384
• SPECTRUM1504115
• SPBio_000722
• CHEMBL247484
• BDBM26656
• KBio1_001866
• KBio2_002071
• KBio2_004639
• KBio2_007207
• KBio3_002473
• DTXSID60199964
• 2o65
• ARSRJFRKVXALTF-UHFFFAOYSA-N
• 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-
• CCG-40135
• LMPK12110847
• AKOS024287743
• DB08230
• SDCCGMLS-0066804.P001
• NCGC00095682-01
• NCGC00095682-02
• NCGC00178184-01
• BP-10199
• MS-24353
• HY-131592
• CS-0137311
• AR-683/41530196
• SR-05000002560
• SR-05000002560-1
• BRD-K22585547-001-03-3
• Q15303946
• Z1980554244
• 5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one
• 5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one, 9CI
• 2-(3,4,5-TRIHYDROXYPHENYL)-5,7-DIHYDROXY-4H-1-BENZOPYRAN-4-ONE; PENTAHYDROXYFLAVONE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9071	90.71%
Caco-2	+	0.6658	66.58%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5892	58.92%
OATP2B1 inhibitior	+	0.5027	50.27%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.6600	66.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8681	86.81%
P-glycoprotein inhibitior	-	0.9005	90.05%
P-glycoprotein substrate	-	0.9159	91.59%
CYP3A4 substrate	-	0.5577	55.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8553	85.53%
CYP3A4 inhibition	+	0.6951	69.51%
CYP2C9 inhibition	-	0.5823	58.23%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9287	92.87%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	+	0.6452	64.52%
CYP inhibitory promiscuity	+	0.5822	58.22%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6750	67.50%
Eye corrosion	-	0.9905	99.05%
Eye irritation	+	0.9524	95.24%
Skin irritation	+	0.5835	58.35%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8174	81.74%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.7447	74.47%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.7676	76.76%
Acute Oral Toxicity (c)	II	0.7348	73.48%
Estrogen receptor binding	+	0.8503	85.03%
Androgen receptor binding	+	0.8615	86.15%
Thyroid receptor binding	+	0.6538	65.38%
Glucocorticoid receptor binding	+	0.8768	87.68%
Aromatase binding	+	0.8035	80.35%
PPAR gamma	+	0.8734	87.34%
Honey bee toxicity	-	0.8695	86.95%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9124	91.24%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	17782.8 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	2511.9 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	707.9 nM; 707.9 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL1293237	P54132	Bloom syndrome protein	25118.9 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	19952.6 nM; 19952.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	12589.3 nM	Potency	via CMAUP
CHEMBL1293257	P51570	Galactokinase	42128.5 nM	Potency	via CMAUP
CHEMBL4331	P68871	Hemoglobin beta chain	25118.9 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	10000 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	7943.3 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2396508	Q13332	Receptor-type tyrosine-protein phosphatase S	17500 nM	IC50	PMID: 26602279
CHEMBL2147	P11309	Serine/threonine-protein kinase PIM1	650 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.32%	91.11%
CHEMBL3194	P02766	Transthyretin	96.14%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.23%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.13%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	90.20%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.96%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.03%	95.56%
CHEMBL2581	P07339	Cathepsin D	86.00%	98.95%
CHEMBL3038469	P24941	CDK2/Cyclin A	85.81%	91.38%
CHEMBL3401	O75469	Pregnane X receptor	85.74%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.73%	90.71%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	82.98%	83.57%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.11%	94.42%
CHEMBL1929	P47989	Xanthine dehydrogenase	81.93%	96.12%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.22%	99.23%
CHEMBL2424	Q04760	Glyoxalase I	81.19%	91.67%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.82%	95.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.29%	86.33%

Plants that contains it

• Aglaia elaeagnoidea
• Aristolochia littoralis
• Astragalus gummifer
• Biebersteinia orphanidis
• Camellia sinensis
• Cardiospermum halicacabum
• Centaurea nigrescens
• Cirsium japonicum
• Coreopsis fasciculata
• Crepis foetida
• Crinum viviparum
• Cuphea carthagenensis
• Dioscoreophyllum cumminsii
• Dorstenia lindeniana
• Erigeron canadensis
• Euphorbia segetalis
• Ficus pumila
• Garcinia celebica
• Larix sibirica
• Lathyrus pratensis
• Ozoroa insignis
• Parastrephia lepidophylla
• Penstemon secundiflorus
• Phedimus kamtschaticus
• Phlogacanthus thyrsiformis
• Phytolacca acinosa
• Pilosella officinarum
• Piper arboreum
• Pouzolzia occidentalis
• Punica granatum
• Rhodiola quadrifida
• Ruta microcarpa
• Selinum carvifolium
• Sidastrum multiflorum
• Syncolostemon parviflorus
• Thuja plicata
• Triglochin maritima
• Urtica triangularis
• Zanthoxylum schreberi

Cross-Links

• PubChem: 5281701
• NPASS: NPC175013
• ChEMBL: CHEMBL247484
• LOTUS: LTS0163585
• wikiData: Q15303946