5-[(2R,3R,4R,5S)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol

Details

• Internal ID: 447d85d7-6219-4832-9885-1704002e29ea
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 7,8-epoxylignans
• IUPAC Name: 5-[(2R,3R,4R,5S)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol
• SMILES (Canonical): C1=CC(=CC=C1C2C(C(C(O2)C3=CC=C(C=C3)O)C4=CC(=CC(=C4)O)O)C5=CC(=CC(=C5)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@H]2[C@H]([C@@H]([C@H](O2)C3=CC=C(C=C3)O)C4=CC(=CC(=C4)O)O)C5=CC(=CC(=C5)O)O)O
• InChI: InChI=1S/C28H24O7/c29-19-5-1-15(2-6-19)27-25(17-9-21(31)13-22(32)10-17)26(18-11-23(33)14-24(34)12-18)28(35-27)16-3-7-20(30)8-4-16/h1-14,25-34H/t25-,26-,27-,28+/m0/s1
• InChI Key: IRMTUHFNJGIEEV-LAJGZZDBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₄O₇
• Molecular Weight: 472.50 g/mol
• Exact Mass: 472.15220310 g/mol
• Topological Polar Surface Area (TPSA): 131.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 5.30
• H-Bond Acceptor: 7
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9547	95.47%
Caco-2	-	0.6927	69.27%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7169	71.69%
OATP2B1 inhibitior	-	0.5711	57.11%
OATP1B1 inhibitior	+	0.7586	75.86%
OATP1B3 inhibitior	+	0.8411	84.11%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.4889	48.89%
P-glycoprotein inhibitior	-	0.6343	63.43%
P-glycoprotein substrate	-	0.9703	97.03%
CYP3A4 substrate	-	0.6493	64.93%
CYP2C9 substrate	-	0.7613	76.13%
CYP2D6 substrate	+	0.3455	34.55%
CYP3A4 inhibition	+	0.6989	69.89%
CYP2C9 inhibition	+	0.7674	76.74%
CYP2C19 inhibition	+	0.7455	74.55%
CYP2D6 inhibition	-	0.9264	92.64%
CYP1A2 inhibition	+	0.7956	79.56%
CYP2C8 inhibition	-	0.5899	58.99%
CYP inhibitory promiscuity	+	0.9502	95.02%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.3928	39.28%
Eye corrosion	-	0.9836	98.36%
Eye irritation	+	0.7077	70.77%
Skin irritation	-	0.5461	54.61%
Skin corrosion	-	0.9097	90.97%
Ames mutagenesis	-	0.5937	59.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7943	79.43%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.5007	50.07%
skin sensitisation	-	0.7683	76.83%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.6710	67.10%
Acute Oral Toxicity (c)	III	0.7099	70.99%
Estrogen receptor binding	+	0.6449	64.49%
Androgen receptor binding	+	0.7843	78.43%
Thyroid receptor binding	+	0.6770	67.70%
Glucocorticoid receptor binding	+	0.6373	63.73%
Aromatase binding	+	0.6912	69.12%
PPAR gamma	+	0.8211	82.11%
Honey bee toxicity	-	0.9463	94.63%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9379	93.79%

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	97.80%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	90.96%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	88.48%	94.73%
CHEMBL242	Q92731	Estrogen receptor beta	84.08%	98.35%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.52%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.66%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.59%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.52%	89.00%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	80.47%	90.93%
CHEMBL226	P30542	Adenosine A1 receptor	80.07%	95.93%

Plants that contains it

• Parthenocissus tricuspidata

Cross-Links

• PubChem: 132504659
• LOTUS: LTS0132413
• wikiData: Q105118961