(2S,3S)-3-(3,5-dihydroxyphenyl)-4,6-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydroinden-1-one

Details

• Internal ID: 47018b0f-6ea1-4f87-9c7e-edb7f7b9305a
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: (2S,3S)-3-(3,5-dihydroxyphenyl)-4,6-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydroinden-1-one
• SMILES (Canonical): C1=CC(=CC=C1C2C(C3=C(C2=O)C=C(C=C3O)O)C4=CC(=CC(=C4)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@@H]2[C@H](C3=C(C2=O)C=C(C=C3O)O)C4=CC(=CC(=C4)O)O)O
• InChI: InChI=1S/C21H16O6/c22-12-3-1-10(2-4-12)19-18(11-5-13(23)7-14(24)6-11)20-16(21(19)27)8-15(25)9-17(20)26/h1-9,18-19,22-26H/t18-,19-/m1/s1
• InChI Key: BADTYSQKXNDGFG-RTBURBONSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₆O₆
• Molecular Weight: 364.30 g/mol
• Exact Mass: 364.09468823 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.33
• H-Bond Acceptor: 6
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

• SCHEMBL13169711
• NSC819305
• NSC-819305
• (2S,3S)-3-(3,5-dihydroxyphenyl)-4,6-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydroinden-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9926	99.26%
Caco-2	-	0.7478	74.78%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7912	79.12%
OATP2B1 inhibitior	-	0.5594	55.94%
OATP1B1 inhibitior	+	0.8873	88.73%
OATP1B3 inhibitior	-	0.3604	36.04%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6806	68.06%
P-glycoprotein inhibitior	-	0.8788	87.88%
P-glycoprotein substrate	-	0.9384	93.84%
CYP3A4 substrate	-	0.5264	52.64%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.7838	78.38%
CYP3A4 inhibition	+	0.6085	60.85%
CYP2C9 inhibition	+	0.8863	88.63%
CYP2C19 inhibition	+	0.8194	81.94%
CYP2D6 inhibition	-	0.8652	86.52%
CYP1A2 inhibition	+	0.9406	94.06%
CYP2C8 inhibition	+	0.4639	46.39%
CYP inhibitory promiscuity	+	0.7782	77.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5432	54.32%
Eye corrosion	-	0.9954	99.54%
Eye irritation	+	0.8887	88.87%
Skin irritation	+	0.7430	74.30%
Skin corrosion	-	0.9692	96.92%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8255	82.55%
Micronuclear	+	0.7959	79.59%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.6509	65.09%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.6163	61.63%
Acute Oral Toxicity (c)	III	0.6001	60.01%
Estrogen receptor binding	-	0.4821	48.21%
Androgen receptor binding	+	0.7827	78.27%
Thyroid receptor binding	+	0.5900	59.00%
Glucocorticoid receptor binding	+	0.8310	83.10%
Aromatase binding	+	0.5926	59.26%
PPAR gamma	+	0.8739	87.39%
Honey bee toxicity	-	0.8327	83.27%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9847	98.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	97.84%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.00%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.07%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.94%	95.56%
CHEMBL3194	P02766	Transthyretin	87.73%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.58%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.43%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.67%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.58%	96.09%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.49%	85.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.24%	97.09%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.49%	89.67%

Plants that contains it

• Vatica pauciflora

Cross-Links

• PubChem: 11417183
• LOTUS: LTS0068868
• wikiData: Q104922118