(E)-13-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1-hydroxytridec-10-en-5-one

Details

• Internal ID: 5246db36-821e-46fc-b580-17c41fe96695
• Taxonomy: Organoheterocyclic compounds > Pyrrolidines
• IUPAC Name: (E)-13-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1-hydroxytridec-10-en-5-one
• SMILES (Canonical): C(CCC(=O)CCCCO)CC=CCCC1C(C(C(N1)CO)O)O
• SMILES (Isomeric): C(CCC(=O)CCCCO)C/C=C/CC[C@@H]1[C@H]([C@H]([C@H](N1)CO)O)O
• InChI: InChI=1S/C18H33NO5/c20-12-8-7-10-14(22)9-5-3-1-2-4-6-11-15-17(23)18(24)16(13-21)19-15/h2,4,15-21,23-24H,1,3,5-13H2/b4-2+/t15-,16-,17-,18+/m1/s1
• InChI Key: YBRVYOIXKVKQGF-DLMSYOMMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₃₃NO₅
• Molecular Weight: 343.50 g/mol
• Exact Mass: 343.23587315 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.67
• H-Bond Acceptor: 6
• H-Bond Donor: 5
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8529	85.29%
Caco-2	-	0.8581	85.81%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6808	68.08%
OATP2B1 inhibitior	-	0.8525	85.25%
OATP1B1 inhibitior	+	0.8662	86.62%
OATP1B3 inhibitior	+	0.9396	93.96%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6066	60.66%
P-glycoprotein inhibitior	-	0.8275	82.75%
P-glycoprotein substrate	-	0.8220	82.20%
CYP3A4 substrate	-	0.5177	51.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6908	69.08%
CYP3A4 inhibition	-	0.9788	97.88%
CYP2C9 inhibition	-	0.9440	94.40%
CYP2C19 inhibition	-	0.9509	95.09%
CYP2D6 inhibition	-	0.9194	91.94%
CYP1A2 inhibition	-	0.8268	82.68%
CYP2C8 inhibition	-	0.8177	81.77%
CYP inhibitory promiscuity	-	0.9804	98.04%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7109	71.09%
Eye corrosion	-	0.9733	97.33%
Eye irritation	-	0.9327	93.27%
Skin irritation	-	0.7545	75.45%
Skin corrosion	-	0.8897	88.97%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6699	66.99%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.7578	75.78%
skin sensitisation	-	0.8780	87.80%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.6781	67.81%
Acute Oral Toxicity (c)	III	0.6013	60.13%
Estrogen receptor binding	-	0.5136	51.36%
Androgen receptor binding	-	0.6290	62.90%
Thyroid receptor binding	-	0.5408	54.08%
Glucocorticoid receptor binding	-	0.5454	54.54%
Aromatase binding	-	0.6716	67.16%
PPAR gamma	+	0.6362	63.62%
Honey bee toxicity	-	0.8837	88.37%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6544	65.44%
Fish aquatic toxicity	-	0.9360	93.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	94.63%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.44%	96.09%
CHEMBL1829	O15379	Histone deacetylase 3	88.25%	95.00%
CHEMBL325	Q13547	Histone deacetylase 1	87.28%	95.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.86%	97.09%
CHEMBL1781	P11387	DNA topoisomerase I	85.87%	97.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.16%	91.11%
CHEMBL1907589	P17787	Neuronal acetylcholine receptor; alpha4/beta2	85.08%	94.55%
CHEMBL2581	P07339	Cathepsin D	84.82%	98.95%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	84.10%	95.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.05%	96.95%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.86%	98.75%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.05%	96.47%

Plants that contains it

• Broussonetia papyrifera

Cross-Links

• PubChem: 15894674
• LOTUS: LTS0225816
• wikiData: Q105346021