Gossypetin

Details

• Internal ID: 1af15262-c52f-41ac-9ea9-18e4b35baed9
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > Flavonols
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-3,5,7,8-tetrahydroxychromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)O)O)O)O
• InChI: InChI=1S/C15H10O8/c16-6-2-1-5(3-7(6)17)14-13(22)12(21)10-8(18)4-9(19)11(20)15(10)23-14/h1-4,16-20,22H
• InChI Key: YRRAGUMVDQQZIY-UHFFFAOYSA-N
• Popularity: 312 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₈
• Molecular Weight: 318.23 g/mol
• Exact Mass: 318.03756727 g/mol
• Topological Polar Surface Area (TPSA): 148.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.69
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 1

Synonyms

• 489-35-0
• Articulatidin
• Equisporol
• 3,5,7,8,3',4'-Hexahydroxyflavone
• UNII-SET4M23ZTM
• 3,3',4',5,7,8-Hexahydroxyflavone
• SET4M23ZTM
• 2-(3,4-Dihydroxyphenyl)-3,5,7,8-tetrahydroxychromen-4-one
• 8-hydroxyquercetin
• 2-(3,4-Dihydroxyphenyl)-3,5,7,8-tetrahydroxy-4H-chromen-4-one
• CHEBI:16400
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,5,7,8-tetrahydroxy-
• CHEMBL253570
• DTXSID50197631
• 2-(3,4-dihydroxyphenyl)-3,5,7,8-tetrahydroxy-chromen-4-one
• 8-hydroxy-quercetin
• C.I.-75750
• FLAVONE, 3,3',4',5,7,8-HEXAHYDROXY-
• D0Z7EL
• BSPBio_002552
• SCHEMBL157033
• SPECTRUM1505143
• BDBM26655
• DTXCID10120122
• YRRAGUMVDQQZIY-UHFFFAOYSA-N
• LMPK12113231
• MFCD00017680
• AT33743
• CCG-231029
• NCGC00096031-01
• NCGC00096031-02
• NCGC00178604-01
• BP-10444
• MS-24692
• HY-119917
• CS-0078364
• FT-0632211
• C04109
• A827629
• SR-05000002577
• Q3036428
• SR-05000002577-1
• BRD-K06692906-001-01-6
• 2-(3,4-Dihydroxyphenyl)-3,5,7,8-tetrahydroxy-4H-chromen-4-one #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9071	90.71%
Caco-2	-	0.8144	81.44%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5892	58.92%
OATP2B1 inhibitior	+	0.5356	53.56%
OATP1B1 inhibitior	+	0.9518	95.18%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.6600	66.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8561	85.61%
P-glycoprotein inhibitior	-	0.9293	92.93%
P-glycoprotein substrate	-	0.9009	90.09%
CYP3A4 substrate	-	0.5461	54.61%
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	+	0.7578	75.78%
CYP inhibitory promiscuity	+	0.5822	58.22%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6750	67.50%
Eye corrosion	-	0.9905	99.05%
Eye irritation	+	0.9258	92.58%
Skin irritation	+	0.5835	58.35%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	+	0.7263	72.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.8462	84.62%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.7447	74.47%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8007	80.07%
Acute Oral Toxicity (c)	II	0.7348	73.48%
Estrogen receptor binding	+	0.7716	77.16%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	-	0.4925	49.25%
Glucocorticoid receptor binding	+	0.8948	89.48%
Aromatase binding	+	0.7232	72.32%
PPAR gamma	+	0.8740	87.40%
Honey bee toxicity	-	0.8951	89.51%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
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	35481.3 nM	Potency	via CMAUP
CHEMBL2524	P06280	Alpha-galactosidase A	28183.8 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	3981.1 nM	Potency	via CMAUP
CHEMBL2487	P05067	Beta amyloid A4 protein	< 3000 nM	IC50	PMID: 25086914
CHEMBL1978	P11511	Cytochrome P450 19A1	11000 nM	IC50	PMID: 18778944
CHEMBL2362978	P43351	DNA repair protein RAD52 homolog	913 nM	IC50	via Super-PRED
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	501.2 nM; 501.2 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	2818.4 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	< 3000 nM	IC50	PMID: 25086914

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.80%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.81%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.37%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	91.19%	91.49%
CHEMBL3194	P02766	Transthyretin	89.26%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.01%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.08%	86.33%
CHEMBL2581	P07339	Cathepsin D	86.94%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.90%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.34%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.03%	90.71%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	82.70%	98.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.60%	99.23%

Plants that contains it

• Abelmoschus manihot
• Askidiosperma andreaeanum
• Hibiscus sabdariffa
• Lotus corniculatus
• Millettia zechiana
• Phedimus kamtschaticus
• Pyrrosia lingua
• Rhodiola rosea
• Rhododendron dauricum
• Rhododendron intranervatum
• Rhododendron micranthum
• Rhododendron mucronatum
• Rhododendron mucronulatum
• Sedum album
• Sinocrassula indica
• Tetradium ruticarpum

Cross-Links

• PubChem: 5280647
• NPASS: NPC27208
• ChEMBL: CHEMBL253570
• LOTUS: LTS0000356
• wikiData: Q3036428