4-[(2R,3R,4R,5R)-5-(4-hydroxyphenyl)-3,4-dimethyloxolan-2-yl]benzene-1,2-diol

Details

• Internal ID: 582f1a2c-118f-4431-804e-0cc860423e0c
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 7,7-epoxylignans
• IUPAC Name: 4-[(2R,3R,4R,5R)-5-(4-hydroxyphenyl)-3,4-dimethyloxolan-2-yl]benzene-1,2-diol
• SMILES (Canonical): CC1C(C(OC1C2=CC=C(C=C2)O)C3=CC(=C(C=C3)O)O)C
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H](O[C@H]1C2=CC=C(C=C2)O)C3=CC(=C(C=C3)O)O)C
• InChI: InChI=1S/C18H20O4/c1-10-11(2)18(13-5-8-15(20)16(21)9-13)22-17(10)12-3-6-14(19)7-4-12/h3-11,17-21H,1-2H3/t10-,11-,17-,18-/m1/s1
• InChI Key: HKSHEXWQPGOEAT-LWCUXCJMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₀O₄
• Molecular Weight: 300.30 g/mol
• Exact Mass: 300.13615911 g/mol
• Topological Polar Surface Area (TPSA): 69.90 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.89
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9659	96.59%
Caco-2	+	0.6475	64.75%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8672	86.72%
OATP2B1 inhibitior	-	0.8479	84.79%
OATP1B1 inhibitior	+	0.8531	85.31%
OATP1B3 inhibitior	+	0.9299	92.99%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9486	94.86%
P-glycoprotein inhibitior	-	0.7931	79.31%
P-glycoprotein substrate	-	0.9650	96.50%
CYP3A4 substrate	-	0.5909	59.09%
CYP2C9 substrate	-	0.7433	74.33%
CYP2D6 substrate	-	0.7159	71.59%
CYP3A4 inhibition	-	0.6722	67.22%
CYP2C9 inhibition	+	0.7584	75.84%
CYP2C19 inhibition	+	0.6829	68.29%
CYP2D6 inhibition	-	0.8703	87.03%
CYP1A2 inhibition	+	0.8735	87.35%
CYP2C8 inhibition	-	0.5966	59.66%
CYP inhibitory promiscuity	+	0.9023	90.23%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8415	84.15%
Carcinogenicity (trinary)	Non-required	0.3927	39.27%
Eye corrosion	-	0.9811	98.11%
Eye irritation	-	0.6128	61.28%
Skin irritation	-	0.7203	72.03%
Skin corrosion	-	0.8977	89.77%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6624	66.24%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.7248	72.48%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.5579	55.79%
Acute Oral Toxicity (c)	III	0.7356	73.56%
Estrogen receptor binding	+	0.7847	78.47%
Androgen receptor binding	+	0.6785	67.85%
Thyroid receptor binding	+	0.6290	62.90%
Glucocorticoid receptor binding	+	0.6263	62.63%
Aromatase binding	+	0.8005	80.05%
PPAR gamma	+	0.6205	62.05%
Honey bee toxicity	-	0.9514	95.14%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9730	97.30%

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	99.11%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.56%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	90.19%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.55%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.76%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.57%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.16%	99.15%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	83.73%	93.10%
CHEMBL4208	P20618	Proteasome component C5	83.23%	90.00%
CHEMBL2581	P07339	Cathepsin D	82.53%	98.95%
CHEMBL242	Q92731	Estrogen receptor beta	81.42%	98.35%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.06%	97.09%

Plants that contains it

• Larrea tridentata

Cross-Links

• PubChem: 14681580
• LOTUS: LTS0249122
• wikiData: Q105029938