(2R)-2-[(2R)-4-methoxy-2,3-dihydrofuro[2,3-b]quinolin-2-yl]propane-1,2-diol

Details

• Internal ID: f0373943-0170-44a2-8e19-03714c57d084
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Dihydrofuranoquinolines
• IUPAC Name: (2R)-2-[(2R)-4-methoxy-2,3-dihydrofuro[2,3-b]quinolin-2-yl]propane-1,2-diol
• SMILES (Canonical): CC(CO)(C1CC2=C(C3=CC=CC=C3N=C2O1)OC)O
• SMILES (Isomeric): C[C@@](CO)([C@H]1CC2=C(C3=CC=CC=C3N=C2O1)OC)O
• InChI: InChI=1S/C15H17NO4/c1-15(18,8-17)12-7-10-13(19-2)9-5-3-4-6-11(9)16-14(10)20-12/h3-6,12,17-18H,7-8H2,1-2H3/t12-,15-/m1/s1
• InChI Key: NETGEQWGGLFVRL-IUODEOHRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₇NO₄
• Molecular Weight: 275.30 g/mol
• Exact Mass: 275.11575802 g/mol
• Topological Polar Surface Area (TPSA): 71.80 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.29
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9330	93.30%
Caco-2	-	0.5690	56.90%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5026	50.26%
OATP2B1 inhibitior	-	0.8575	85.75%
OATP1B1 inhibitior	+	0.9109	91.09%
OATP1B3 inhibitior	+	0.9477	94.77%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6412	64.12%
P-glycoprotein inhibitior	-	0.9578	95.78%
P-glycoprotein substrate	-	0.7694	76.94%
CYP3A4 substrate	+	0.5593	55.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7163	71.63%
CYP3A4 inhibition	-	0.9061	90.61%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.6052	60.52%
CYP inhibitory promiscuity	-	0.8682	86.82%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5481	54.81%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9596	95.96%
Skin irritation	-	0.7943	79.43%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7902	79.02%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.5073	50.73%
skin sensitisation	-	0.8415	84.15%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.7491	74.91%
Acute Oral Toxicity (c)	III	0.6260	62.60%
Estrogen receptor binding	+	0.8365	83.65%
Androgen receptor binding	-	0.4838	48.38%
Thyroid receptor binding	+	0.5976	59.76%
Glucocorticoid receptor binding	+	0.5485	54.85%
Aromatase binding	-	0.5400	54.00%
PPAR gamma	+	0.7825	78.25%
Honey bee toxicity	-	0.9120	91.20%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	-	0.4506	45.06%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	2.8 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	56.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.11%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.62%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.64%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.60%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.21%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.34%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.33%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.59%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.69%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	83.00%	94.73%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.96%	96.39%

Plants that contains it

• Haplophyllum griffithianum

Cross-Links

• PubChem: 673466
• LOTUS: LTS0097669
• wikiData: Q105178184