Ginkgetin

Details

• Internal ID: 853f008a-dd9f-44d3-aac2-0a4f63021fe4
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: 5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)OC)O)C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)OC)O)C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)O)O)O
• InChI: InChI=1S/C32H22O10/c1-39-18-10-20(34)30-23(37)13-27(41-28(30)11-18)16-5-8-25(40-2)19(9-16)29-21(35)12-22(36)31-24(38)14-26(42-32(29)31)15-3-6-17(33)7-4-15/h3-14,33-36H,1-2H3
• InChI Key: AIFCFBUSLAEIBR-UHFFFAOYSA-N
• Popularity: 203 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₂₂O₁₀
• Molecular Weight: 566.50 g/mol
• Exact Mass: 566.12129689 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 5.74
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 481-46-9
• 7,4'-Dimethylamentoflavone
• Amentoflavone 7,4'-dimethyl ether
• CHEBI:5353
• HY5EZW8269
• 5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)chromen-4-one
• 4H-1-Benzopyran-4-one, 5,7-dihydroxy-8-(5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl)-2-(4-hydroxyphenyl)-
• 4H-1-Benzopyran-4-one, 5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)-
• 5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• 5,7-dihydroxy-8-(5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl)-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• Spectrum_001932
• Spectrum2_000054
• Spectrum3_001727
• Spectrum4_001610
• Spectrum5_000339
• UNII-HY5EZW8269
• BSPBio_003374
• KBioGR_001959
• KBioSS_002476
• SCHEMBL888410
• SPBio_000207
• jm5b01461, Compound 89
• KBio2_002469
• KBio2_005037
• KBio2_007605
• KBio3_002594
• DTXSID70197416
• BDBM429271
• HY-N0889
• LMPK12040003
• MFCD09970948
• AKOS015896770
• CS-3727
• Ginkgetin 7''-O-beta-D-glucopyranoside
• 5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxo-chromen-2-yl)-2-methoxy-phenyl]-2-(4-hydroxyphenyl)chromen-4-one
• AC-35029
• MS-30254
• FT-0686623
• Q-100523
• BRD-K92123432-237-02-8
• Q27089352
• 3''',8-Biflavone, 4',5,5'',7-tetrahydroxy-4''',7''-dimethoxy-
• 4''',5,5'',7''-tetrahydroxy-4',7-dimethoxy-(3'->8'')-biflavone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9325	93.25%
Caco-2	-	0.8199	81.99%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8148	81.48%
OATP2B1 inhibitior	-	0.5669	56.69%
OATP1B1 inhibitior	-	0.6639	66.39%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9268	92.68%
P-glycoprotein inhibitior	+	0.8531	85.31%
P-glycoprotein substrate	-	0.5922	59.22%
CYP3A4 substrate	+	0.6242	62.42%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.5831	58.31%
CYP2C9 inhibition	+	0.6590	65.90%
CYP2C19 inhibition	+	0.6234	62.34%
CYP2D6 inhibition	-	0.7411	74.11%
CYP1A2 inhibition	+	0.6533	65.33%
CYP2C8 inhibition	+	0.8845	88.45%
CYP inhibitory promiscuity	+	0.6726	67.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6328	63.28%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.8503	85.03%
Skin irritation	-	0.7256	72.56%
Skin corrosion	-	0.9363	93.63%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3928	39.28%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.9458	94.58%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.4772	47.72%
Acute Oral Toxicity (c)	III	0.6505	65.05%
Estrogen receptor binding	+	0.8992	89.92%
Androgen receptor binding	+	0.9509	95.09%
Thyroid receptor binding	+	0.6512	65.12%
Glucocorticoid receptor binding	+	0.8414	84.14%
Aromatase binding	+	0.5534	55.34%
PPAR gamma	+	0.7182	71.82%
Honey bee toxicity	-	0.7523	75.23%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5649	56.49%
Fish aquatic toxicity	+	0.9066	90.66%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4822	P56817	Beta-secretase 1	4180 nM	IC50	PMID: 20598535

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL242	Q92731	Estrogen receptor beta	97.75%	98.35%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.50%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	96.56%	99.15%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.13%	91.11%
CHEMBL3194	P02766	Transthyretin	95.43%	90.71%
CHEMBL2581	P07339	Cathepsin D	95.26%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.64%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.38%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.24%	85.14%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.58%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.47%	86.33%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	89.11%	95.78%
CHEMBL308	P06493	Cyclin-dependent kinase 1	88.18%	91.73%
CHEMBL4208	P20618	Proteasome component C5	85.72%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.64%	86.92%
CHEMBL2535	P11166	Glucose transporter	83.47%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.46%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.66%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	82.55%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.36%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.20%	94.45%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.02%	91.71%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	81.89%	96.09%
CHEMBL1907	P15144	Aminopeptidase N	81.48%	93.31%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.46%	90.71%
CHEMBL5747	Q92793	CREB-binding protein	80.82%	95.12%
CHEMBL1951	P21397	Monoamine oxidase A	80.58%	91.49%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.40%	97.28%

Plants that contains it

• Afrocarpus gracilior
• Anemarrhena asphodeloides
• Cephalotaxus fortunei
• Cephalotaxus nana
• Cupressus nootkatensis
• Elateriospermum tapos
• Epimedium koreanum
• Equisetum hyemale
• Ginkgo biloba
• Metasequoia glyptostroboides
• Pinalia yunnanensis
• Piranhea mexicana
• Selaginella moellendorffii
• Selaginella sinensis
• Selaginella willdenowii
• Taxus baccata
• Taxus canadensis
• Taxus cuspidata
• Torreya nucifera

Cross-Links

• PubChem: 5271805
• NPASS: NPC265624
• ChEMBL: CHEMBL377324
• LOTUS: LTS0137798
• wikiData: Q27089352