(2S,3S,4R,5S)-2-(3,4-dimethoxyphenyl)-5-(hydroxymethyl)-1-methylpyrrolidine-3,4-diol

Details

• Internal ID: ae0e2a59-8022-458b-8789-1caec0b37e08
• Taxonomy: Organoheterocyclic compounds > Pyrrolidines > Phenylpyrrolidines
• IUPAC Name: (2S,3S,4R,5S)-2-(3,4-dimethoxyphenyl)-5-(hydroxymethyl)-1-methylpyrrolidine-3,4-diol
• SMILES (Canonical): CN1C(C(C(C1C2=CC(=C(C=C2)OC)OC)O)O)CO
• SMILES (Isomeric): CN1[C@H]([C@H]([C@H]([C@@H]1C2=CC(=C(C=C2)OC)OC)O)O)CO
• InChI: InChI=1S/C14H21NO5/c1-15-9(7-16)13(17)14(18)12(15)8-4-5-10(19-2)11(6-8)20-3/h4-6,9,12-14,16-18H,7H2,1-3H3/t9-,12-,13+,14-/m0/s1
• InChI Key: VGEPCNNJGKDQTM-WTDIUWLJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₁NO₅
• Molecular Weight: 283.32 g/mol
• Exact Mass: 283.14197277 g/mol
• Topological Polar Surface Area (TPSA): 82.40 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): -0.23
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6519	65.19%
Caco-2	+	0.6777	67.77%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5327	53.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9385	93.85%
OATP1B3 inhibitior	+	0.9419	94.19%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6135	61.35%
P-glycoprotein inhibitior	-	0.9322	93.22%
P-glycoprotein substrate	-	0.6548	65.48%
CYP3A4 substrate	-	0.5483	54.83%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	+	0.5797	57.97%
CYP3A4 inhibition	-	0.8881	88.81%
CYP2C9 inhibition	-	0.8531	85.31%
CYP2C19 inhibition	-	0.8544	85.44%
CYP2D6 inhibition	-	0.7480	74.80%
CYP1A2 inhibition	-	0.7414	74.14%
CYP2C8 inhibition	-	0.8511	85.11%
CYP inhibitory promiscuity	-	0.7906	79.06%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9755	97.55%
Skin irritation	-	0.7837	78.37%
Skin corrosion	-	0.9255	92.55%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8214	82.14%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	-	0.6019	60.19%
skin sensitisation	-	0.8465	84.65%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.8164	81.64%
Acute Oral Toxicity (c)	III	0.6532	65.32%
Estrogen receptor binding	-	0.7284	72.84%
Androgen receptor binding	-	0.5643	56.43%
Thyroid receptor binding	-	0.5539	55.39%
Glucocorticoid receptor binding	-	0.6258	62.58%
Aromatase binding	-	0.6596	65.96%
PPAR gamma	-	0.6091	60.91%
Honey bee toxicity	-	0.9523	95.23%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	-	0.6017	60.17%

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	99.16%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.78%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.44%	89.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.43%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.62%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.46%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.35%	86.33%
CHEMBL4208	P20618	Proteasome component C5	85.60%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.84%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.02%	99.17%
CHEMBL2535	P11166	Glucose transporter	83.38%	98.75%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.28%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.80%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.39%	95.56%

Plants that contains it

• Codonopsis clematidea

Cross-Links

• PubChem: 163106287
• LOTUS: LTS0275479
• wikiData: Q105285751