(2R,3R,4R,5R)-2-(4-Methoxyphenyl)-1,5-dimethylpyrrolidine-3,4-diol

Details

• Internal ID: 416aa671-9dde-42b1-8d04-669dd5ad72f5
• Taxonomy: Organoheterocyclic compounds > Pyrrolidines > Phenylpyrrolidines
• IUPAC Name: (2R,3R,4R,5R)-2-(4-methoxyphenyl)-1,5-dimethylpyrrolidine-3,4-diol
• SMILES (Canonical): CC1C(C(C(N1C)C2=CC=C(C=C2)OC)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H]([C@H](N1C)C2=CC=C(C=C2)OC)O)O
• InChI: InChI=1S/C13H19NO3/c1-8-12(15)13(16)11(14(8)2)9-4-6-10(17-3)7-5-9/h4-8,11-13,15-16H,1-3H3/t8-,11-,12-,13-/m1/s1
• InChI Key: GJZNAEFHIYPPEM-HUXSOILUSA-N
• Popularity: 15 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₉NO₃
• Molecular Weight: 237.29 g/mol
• Exact Mass: 237.13649347 g/mol
• Topological Polar Surface Area (TPSA): 52.90 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.79
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• CTK1B9185
• 32490-07-6
• CHEMBL4528898
• DTXSID90447309

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8559	85.59%
Caco-2	+	0.8263	82.63%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8336	83.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9383	93.83%
OATP1B3 inhibitior	+	0.9443	94.43%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6014	60.14%
P-glycoprotein inhibitior	-	0.9416	94.16%
P-glycoprotein substrate	-	0.8681	86.81%
CYP3A4 substrate	-	0.5297	52.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.6310	63.10%
CYP3A4 inhibition	-	0.8604	86.04%
CYP2C9 inhibition	-	0.8501	85.01%
CYP2C19 inhibition	-	0.7345	73.45%
CYP2D6 inhibition	-	0.7235	72.35%
CYP1A2 inhibition	-	0.6707	67.07%
CYP2C8 inhibition	-	0.9528	95.28%
CYP inhibitory promiscuity	-	0.5996	59.96%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9018	90.18%
Carcinogenicity (trinary)	Non-required	0.4426	44.26%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.9701	97.01%
Skin irritation	-	0.7866	78.66%
Skin corrosion	-	0.9173	91.73%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6423	64.23%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8726	87.26%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8875	88.75%
Acute Oral Toxicity (c)	III	0.6594	65.94%
Estrogen receptor binding	-	0.8462	84.62%
Androgen receptor binding	-	0.4864	48.64%
Thyroid receptor binding	-	0.6388	63.88%
Glucocorticoid receptor binding	-	0.7617	76.17%
Aromatase binding	-	0.8505	85.05%
PPAR gamma	-	0.6673	66.73%
Honey bee toxicity	-	0.9420	94.20%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	-	0.6366	63.66%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.56%	96.09%
CHEMBL4208	P20618	Proteasome component C5	90.69%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.54%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.74%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.83%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	87.10%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.26%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.57%	95.89%

Plants that contains it

• Callicarpa macrophylla
• Chaiturus marrubiastrum
• Codonopsis clematidea
• Curcuma heyneana

Cross-Links

• PubChem: 10889945
• NPASS: NPC102206
• LOTUS: LTS0071743
• wikiData: Q82266167