Isoginkgetin

Details

• Internal ID: e7328a14-4094-4a04-8df2-6693d017684e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: 8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxyphenyl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4=C(C=CC(=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)OC
• SMILES (Isomeric): COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4=C(C=CC(=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)OC
• InChI: InChI=1S/C32H22O10/c1-39-18-6-3-15(4-7-18)26-14-24(38)31-22(36)12-21(35)29(32(31)42-26)19-9-16(5-8-25(19)40-2)27-13-23(37)30-20(34)10-17(33)11-28(30)41-27/h3-14,33-36H,1-2H3
• InChI Key: HUOOMAOYXQFIDQ-UHFFFAOYSA-N
• Popularity: 35 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

• 548-19-6
• iso-ginkgetin
• 4',4'''-Dimethylamentoflavone
• 8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxyphenyl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one
• CHEBI:79087
• 3''',8-Biflavone, 5,5'',7,7''-tetrahydroxy-4',4'''-dimethoxy-
• 8-(5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-methoxyphenyl)-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one
• 8-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-methoxyphenyl]-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one
• Spectrum_000406
• SpecPlus_000433
• Spectrum2_000302
• Spectrum3_001112
• Spectrum4_001945
• Spectrum5_000819
• BSPBio_002844
• KBioGR_002352
• KBioSS_000886
• DivK1c_006529
• SPBio_000264
• SCHEMBL22459983
• KBio1_001473
• KBio2_000886
• KBio2_003454
• KBio2_006022
• KBio3_002064
• DTXSID00203271
• HUOOMAOYXQFIDQ-UHFFFAOYSA-N
• BCP22629
• HY-N2117
• CCG-38579
• MFCD00597035
• AKOS032948383
• CS-5763
• SDCCGMLS-0066448.P001
• NCGC00094722-01
• NCGC00094722-02
• NCGC00178438-01
• AC-35025
• BS-17123
• FT-0706639
• A870346
• BRD-K72661036-001-02-1
• Q27148149
• B0005-464617
• 2-(4-Methoxyphenyl)-5,7-dihydroxy-8-[2-methoxy-5-(4-oxo-5,7-dihydroxy-4H-1-benzopyran-2-yl)phenyl]-4H-1-benzopyran-4-one
• 4H-1-Benzopyran-4-one, 8-(5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl)-5,7-dihydroxy-2-(4-methoxyphenyl)-
• 8-[5-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl]-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
• IgG

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9325	93.25%
Caco-2	-	0.7616	76.16%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8148	81.48%
OATP2B1 inhibitior	-	0.5684	56.84%
OATP1B1 inhibitior	-	0.7738	77.38%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9141	91.41%
P-glycoprotein inhibitior	+	0.8666	86.66%
P-glycoprotein substrate	-	0.6036	60.36%
CYP3A4 substrate	+	0.6481	64.81%
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	+	0.8891	88.91%
CYP inhibitory promiscuity	+	0.6726	67.26%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6328	63.28%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.8638	86.38%
Skin irritation	-	0.7256	72.56%
Skin corrosion	-	0.9363	93.63%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7081	70.81%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.9458	94.58%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.4557	45.57%
Acute Oral Toxicity (c)	III	0.6505	65.05%
Estrogen receptor binding	+	0.8835	88.35%
Androgen receptor binding	+	0.9423	94.23%
Thyroid receptor binding	+	0.6267	62.67%
Glucocorticoid receptor binding	+	0.8491	84.91%
Aromatase binding	-	0.5432	54.32%
PPAR gamma	+	0.7267	72.67%
Honey bee toxicity	-	0.7648	76.48%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5849	58.49%
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	3010 nM	IC50	PMID: 20598535
CHEMBL4096	P04637	Cellular tumor antigen p53	31622.8 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	3981.1 nM; 3981.1 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM	Potency	via CMAUP
CHEMBL4331	P68871	Hemoglobin beta chain	19952.6 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	17782.8 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	19952.6 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.84%	94.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.33%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	96.35%	99.15%
CHEMBL3194	P02766	Transthyretin	96.21%	90.71%
CHEMBL2581	P07339	Cathepsin D	95.17%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.16%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.89%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	92.20%	91.49%
CHEMBL4208	P20618	Proteasome component C5	91.65%	90.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.46%	96.21%
CHEMBL308	P06493	Cyclin-dependent kinase 1	90.48%	91.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.33%	86.33%
CHEMBL242	Q92731	Estrogen receptor beta	90.10%	98.35%
CHEMBL1907	P15144	Aminopeptidase N	89.33%	93.31%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.27%	86.92%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.40%	95.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.24%	99.17%
CHEMBL1929	P47989	Xanthine dehydrogenase	84.98%	96.12%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.71%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.45%	95.50%
CHEMBL2535	P11166	Glucose transporter	82.74%	98.75%
CHEMBL5747	Q92793	CREB-binding protein	82.16%	95.12%
CHEMBL3401	O75469	Pregnane X receptor	81.36%	94.73%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	81.01%	83.57%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.29%	97.14%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	80.23%	89.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.23%	90.71%

Plants that contains it

• Cupressus nootkatensis
• Cycas circinalis
• Dysoxylum lenticellare
• Epimedium koreanum
• Ginkgo biloba
• Nageia nagi
• Podocarpus macrophyllus
• Zingiber officinale

Cross-Links

• PubChem: 5318569
• NPASS: NPC150908
• ChEMBL: CHEMBL1208903
• LOTUS: LTS0061203
• wikiData: Q27148149