[(1R,2S,5S)-5-[2,6-dihydroxy-4-(6-hydroxy-1-benzofuran-2-yl)phenyl]-2-(2,4-dihydroxyphenyl)-3-methylcyclohex-3-en-1-yl]-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]methanone

Details

• Internal ID: db161a97-f969-480b-9127-9a6dc3ce2012
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: [(1R,2S,5S)-5-[2,6-dihydroxy-4-(6-hydroxy-1-benzofuran-2-yl)phenyl]-2-(2,4-dihydroxyphenyl)-3-methylcyclohex-3-en-1-yl]-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]methanone
• SMILES (Canonical): CC1=CC(CC(C1C2=C(C=C(C=C2)O)O)C(=O)C3=C(C(=C(C=C3)O)CC=C(C)C)O)C4=C(C=C(C=C4O)C5=CC6=C(O5)C=C(C=C6)O)O
• SMILES (Isomeric): CC1=C[C@H](C[C@H]([C@@H]1C2=C(C=C(C=C2)O)O)C(=O)C3=C(C(=C(C=C3)O)CC=C(C)C)O)C4=C(C=C(C=C4O)C5=CC6=C(O5)C=C(C=C6)O)O
• InChI: InChI=1S/C39H36O9/c1-19(2)4-8-27-30(42)11-10-28(38(27)46)39(47)29-13-23(12-20(3)36(29)26-9-7-24(40)17-31(26)43)37-32(44)14-22(15-33(37)45)34-16-21-5-6-25(41)18-35(21)48-34/h4-7,9-12,14-18,23,29,36,40-46H,8,13H2,1-3H3/t23-,29-,36+/m1/s1
• InChI Key: HATOUTDTQNFTCP-FWAIKWLASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₃₆O₉
• Molecular Weight: 648.70 g/mol
• Exact Mass: 648.23593272 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 8.00
• Atomic LogP (AlogP): 8.26
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• DTXSID80420025

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9932	99.32%
Caco-2	-	0.8668	86.68%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7242	72.42%
OATP2B1 inhibitior	+	0.5760	57.60%
OATP1B1 inhibitior	+	0.8449	84.49%
OATP1B3 inhibitior	+	0.9232	92.32%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9827	98.27%
P-glycoprotein inhibitior	+	0.7680	76.80%
P-glycoprotein substrate	+	0.7261	72.61%
CYP3A4 substrate	+	0.6918	69.18%
CYP2C9 substrate	+	0.7956	79.56%
CYP2D6 substrate	-	0.8313	83.13%
CYP3A4 inhibition	-	0.5170	51.70%
CYP2C9 inhibition	+	0.9290	92.90%
CYP2C19 inhibition	+	0.8866	88.66%
CYP2D6 inhibition	-	0.6938	69.38%
CYP1A2 inhibition	+	0.9411	94.11%
CYP2C8 inhibition	+	0.8420	84.20%
CYP inhibitory promiscuity	+	0.9791	97.91%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5091	50.91%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9099	90.99%
Skin irritation	-	0.7351	73.51%
Skin corrosion	-	0.9311	93.11%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9008	90.08%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.5222	52.22%
skin sensitisation	-	0.7372	73.72%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.9240	92.40%
Acute Oral Toxicity (c)	III	0.4661	46.61%
Estrogen receptor binding	+	0.8592	85.92%
Androgen receptor binding	+	0.8371	83.71%
Thyroid receptor binding	+	0.6207	62.07%
Glucocorticoid receptor binding	+	0.7901	79.01%
Aromatase binding	-	0.4862	48.62%
PPAR gamma	+	0.7839	78.39%
Honey bee toxicity	-	0.7784	77.84%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	98.72%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.03%	98.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	93.71%	95.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.61%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.61%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	92.36%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.97%	90.71%
CHEMBL3038469	P24941	CDK2/Cyclin A	90.09%	91.38%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.56%	96.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.72%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.01%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.84%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.68%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.60%	94.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	85.53%	85.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.38%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.42%	99.17%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	83.83%	83.57%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.05%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.94%	93.56%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	80.25%	96.42%

Plants that contains it

• Morus alba
• Morus indica
• Morus notabilis
• Sorocea bonplandii
• Sorocea guilleminiana

Cross-Links

• PubChem: 5458824
• NPASS: NPC309419
• LOTUS: LTS0176888
• wikiData: Q82231276