(2R,3R,4R,5R)-2-[(1R)-4-(1,7-dioxaspiro[5.5]undecan-2-yl)-1-hydroxybutyl]-5-(hydroxymethyl)pyrrolidine-3,4-diol

Details

• Internal ID: bb91cd77-4d75-4dac-8eef-836c23259873
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Ethers > Acetals > Ketals
• IUPAC Name: (2R,3R,4R,5R)-2-[(1R)-4-(1,7-dioxaspiro[5.5]undecan-2-yl)-1-hydroxybutyl]-5-(hydroxymethyl)pyrrolidine-3,4-diol
• SMILES (Canonical): C1CCOC2(C1)CCCC(O2)CCCC(C3C(C(C(N3)CO)O)O)O
• SMILES (Isomeric): C1CCOC2(C1)CCCC(O2)CCC[C@H]([C@@H]3[C@H]([C@@H]([C@H](N3)CO)O)O)O
• InChI: InChI=1S/C18H33NO6/c20-11-13-16(22)17(23)15(19-13)14(21)7-3-5-12-6-4-9-18(25-12)8-1-2-10-24-18/h12-17,19-23H,1-11H2/t12?,13-,14-,15-,16-,17-,18?/m1/s1
• InChI Key: LIWCKHSHUMELES-HUJYPYJOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₃₃NO₆
• Molecular Weight: 359.50 g/mol
• Exact Mass: 359.23078777 g/mol
• Topological Polar Surface Area (TPSA): 111.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.04
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• RefChem:917623
• (2R,3R,4R,5R)-2-((1R)-4-(1,7-dioxaspiro(5.5)undecan-2-yl)-1-hydroxybutyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol
• 211732-77-3
• SCHEMBL29431972

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8196	81.96%
Caco-2	-	0.8410	84.10%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4447	44.47%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.9268	92.68%
OATP1B3 inhibitior	+	0.9492	94.92%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9073	90.73%
P-glycoprotein inhibitior	-	0.8853	88.53%
P-glycoprotein substrate	-	0.5278	52.78%
CYP3A4 substrate	+	0.6080	60.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6582	65.82%
CYP3A4 inhibition	-	0.9899	98.99%
CYP2C9 inhibition	-	0.9527	95.27%
CYP2C19 inhibition	-	0.9459	94.59%
CYP2D6 inhibition	-	0.9209	92.09%
CYP1A2 inhibition	-	0.9325	93.25%
CYP2C8 inhibition	-	0.6431	64.31%
CYP inhibitory promiscuity	-	0.9786	97.86%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6539	65.39%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.9554	95.54%
Skin irritation	-	0.7808	78.08%
Skin corrosion	-	0.9196	91.96%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6800	68.00%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	-	0.7044	70.44%
skin sensitisation	-	0.8709	87.09%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.5795	57.95%
Acute Oral Toxicity (c)	III	0.5022	50.22%
Estrogen receptor binding	+	0.5448	54.48%
Androgen receptor binding	-	0.5664	56.64%
Thyroid receptor binding	+	0.6645	66.45%
Glucocorticoid receptor binding	+	0.5628	56.28%
Aromatase binding	+	0.6919	69.19%
PPAR gamma	-	0.5642	56.42%
Honey bee toxicity	-	0.8441	84.41%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.8155	81.55%
Fish aquatic toxicity	-	0.9386	93.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.04%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.95%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.76%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.58%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.13%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.69%	96.61%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	93.65%	92.88%
CHEMBL2581	P07339	Cathepsin D	93.20%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.69%	97.25%
CHEMBL5103	Q969S8	Histone deacetylase 10	89.50%	90.08%
CHEMBL2996	Q05655	Protein kinase C delta	87.67%	97.79%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	86.98%	89.05%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.90%	95.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.97%	100.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.82%	89.67%
CHEMBL2094135	Q96BI3	Gamma-secretase	85.38%	98.05%
CHEMBL1075317	P61964	WD repeat-containing protein 5	84.70%	96.33%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	84.61%	97.29%
CHEMBL213	P08588	Beta-1 adrenergic receptor	83.73%	95.56%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	83.52%	95.00%
CHEMBL237	P41145	Kappa opioid receptor	83.34%	98.10%
CHEMBL3310	Q96DB2	Histone deacetylase 11	83.32%	88.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.95%	95.89%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.89%	98.75%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.67%	100.00%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	82.58%	98.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.12%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.93%	93.04%
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	81.80%	95.52%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	80.96%	95.36%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.91%	92.62%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	80.86%	97.31%
CHEMBL5646	Q6L5J4	FML2_HUMAN	80.19%	100.00%

Plants that contains it

• Broussonetia kazinoki

Cross-Links

• PubChem: 102120241
• LOTUS: LTS0275574
• wikiData: Q105152388