(3'S,4'S,5'R,8R)-3',4',5-trihydroxy-5'-(hydroxymethyl)-2-(4-hydroxyphenyl)spiro[9H-furo[2,3-h]chromene-8,2'-oxolane]-4-one

Details

• Internal ID: 40a04dbf-2a27-47c8-b784-99885a797c28
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones
• IUPAC Name: (3'S,4'S,5'R,8R)-3',4',5-trihydroxy-5'-(hydroxymethyl)-2-(4-hydroxyphenyl)spiro[9H-furo[2,3-h]chromene-8,2'-oxolane]-4-one
• SMILES (Canonical): C1C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=C(C=C4)O)O)OC15C(C(C(O5)CO)O)O
• SMILES (Isomeric): C1C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=C(C=C4)O)O)O[C@@]15[C@H]([C@@H]([C@H](O5)CO)O)O
• InChI: InChI=1S/C21H18O9/c22-8-16-18(26)20(27)21(30-16)7-11-15(29-21)6-13(25)17-12(24)5-14(28-19(11)17)9-1-3-10(23)4-2-9/h1-6,16,18,20,22-23,25-27H,7-8H2/t16-,18-,20+,21+/m1/s1
• InChI Key: DIURSMXCAHQJJE-LMQGHGSNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₈O₉
• Molecular Weight: 414.40 g/mol
• Exact Mass: 414.09508215 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.62
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5625	56.25%
Caco-2	-	0.8893	88.93%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7358	73.58%
OATP2B1 inhibitior	-	0.5514	55.14%
OATP1B1 inhibitior	+	0.8912	89.12%
OATP1B3 inhibitior	+	0.9469	94.69%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8100	81.00%
P-glycoprotein inhibitior	-	0.6231	62.31%
P-glycoprotein substrate	-	0.6722	67.22%
CYP3A4 substrate	+	0.6234	62.34%
CYP2C9 substrate	-	0.6163	61.63%
CYP2D6 substrate	-	0.8359	83.59%
CYP3A4 inhibition	-	0.8413	84.13%
CYP2C9 inhibition	-	0.8916	89.16%
CYP2C19 inhibition	-	0.8496	84.96%
CYP2D6 inhibition	-	0.9355	93.55%
CYP1A2 inhibition	-	0.9096	90.96%
CYP2C8 inhibition	+	0.7370	73.70%
CYP inhibitory promiscuity	-	0.8467	84.67%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6538	65.38%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.8220	82.20%
Skin irritation	-	0.7904	79.04%
Skin corrosion	-	0.9585	95.85%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4569	45.69%
Micronuclear	+	0.5874	58.74%
Hepatotoxicity	-	0.7321	73.21%
skin sensitisation	-	0.8771	87.71%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.4590	45.90%
Acute Oral Toxicity (c)	III	0.3980	39.80%
Estrogen receptor binding	+	0.8810	88.10%
Androgen receptor binding	+	0.8271	82.71%
Thyroid receptor binding	-	0.4923	49.23%
Glucocorticoid receptor binding	+	0.7489	74.89%
Aromatase binding	+	0.7720	77.20%
PPAR gamma	+	0.8584	85.84%
Honey bee toxicity	-	0.7205	72.05%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9092	90.92%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.59%	91.11%
CHEMBL242	Q92731	Estrogen receptor beta	95.87%	98.35%
CHEMBL2581	P07339	Cathepsin D	95.78%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.38%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.72%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.60%	97.09%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	90.02%	89.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.19%	94.45%
CHEMBL3194	P02766	Transthyretin	88.27%	90.71%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.69%	91.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.35%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	86.20%	91.49%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.81%	95.83%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.45%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.05%	93.99%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.82%	97.28%
CHEMBL3038469	P24941	CDK2/Cyclin A	84.43%	91.38%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.53%	85.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.88%	90.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.51%	96.21%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.88%	96.77%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.49%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.10%	100.00%

Plants that contains it

• Crataegus pinnatifida

Cross-Links

• PubChem: 102019454
• LOTUS: LTS0242297
• wikiData: Q104981692