(2S,3S,4S)-2-[(1R)-2-Amino-1-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-oxoethoxy]-3,4-dihydroxy-N-[(3S,7R)-7-methyl-2-oxoazepan-3-yl]-3,4-dihydro-2H-pyran-6-carboxamide

Details

• Internal ID: fceb8fd2-a960-44db-8bdd-b22a30774f1e
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > N-acyl-alpha amino acids and derivatives
• IUPAC Name: (2S,3S,4S)-2-[(1R)-2-amino-1-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-oxoethoxy]-3,4-dihydroxy-N-[(3S,7R)-7-methyl-2-oxoazepan-3-yl]-3,4-dihydro-2H-pyran-6-carboxamide
• SMILES (Canonical): CC1CCCC(C(=O)N1)NC(=O)C2=CC(C(C(O2)OC(C3C(C(C(O3)N4C=CC(=O)NC4=O)O)O)C(=O)N)O)O
• SMILES (Isomeric): C[C@@H]1CCC[C@@H](C(=O)N1)NC(=O)C2=C[C@@H]([C@@H]([C@H](O2)O[C@H]([C@@H]3[C@H]([C@H]([C@@H](O3)N4C=CC(=O)NC4=O)O)O)C(=O)N)O)O
• InChI: InChI=1S/C23H31N5O12/c1-8-3-2-4-9(19(35)25-8)26-20(36)11-7-10(29)13(31)22(38-11)40-17(18(24)34)16-14(32)15(33)21(39-16)28-6-5-12(30)27-23(28)37/h5-10,13-17,21-22,29,31-33H,2-4H2,1H3,(H2,24,34)(H,25,35)(H,26,36)(H,27,30,37)/t8-,9+,10+,13+,14+,15-,16+,17-,21-,22-/m1/s1
• InChI Key: BFXPEJKKPCBJOT-PQXOLBNDSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₁N₅O₁₂
• Molecular Weight: 569.50 g/mol
• Exact Mass: 569.19692144 g/mol
• Topological Polar Surface Area (TPSA): 259.00 Ų
• XlogP: -4.20
• Atomic LogP (AlogP): -4.84
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• (2S,3S,4S)-2-[(1R)-2-Amino-1-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-oxoethoxy]-3,4-dihydroxy-N-[(3S,7R)-7-methyl-2-oxoazepan-3-yl]-3,4-dihydro-2H-pyran-6-carboxamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8386	83.86%
Caco-2	-	0.8923	89.23%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.3799	37.99%
OATP2B1 inhibitior	-	0.7171	71.71%
OATP1B1 inhibitior	+	0.8983	89.83%
OATP1B3 inhibitior	+	0.9372	93.72%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8822	88.22%
BSEP inhibitior	-	0.9299	92.99%
P-glycoprotein inhibitior	-	0.4664	46.64%
P-glycoprotein substrate	+	0.6927	69.27%
CYP3A4 substrate	+	0.6686	66.86%
CYP2C9 substrate	-	0.6049	60.49%
CYP2D6 substrate	-	0.8672	86.72%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.6815	68.15%
CYP2C19 inhibition	-	0.6655	66.55%
CYP2D6 inhibition	-	0.8462	84.62%
CYP1A2 inhibition	-	0.7900	79.00%
CYP2C8 inhibition	-	0.5623	56.23%
CYP inhibitory promiscuity	-	0.7649	76.49%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.5661	56.61%
Eye corrosion	-	0.9841	98.41%
Eye irritation	-	0.9428	94.28%
Skin irritation	-	0.7775	77.75%
Skin corrosion	-	0.9282	92.82%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5365	53.65%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	+	0.6406	64.06%
skin sensitisation	-	0.8616	86.16%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.6704	67.04%
Acute Oral Toxicity (c)	III	0.6312	63.12%
Estrogen receptor binding	+	0.7616	76.16%
Androgen receptor binding	+	0.6567	65.67%
Thyroid receptor binding	-	0.5470	54.70%
Glucocorticoid receptor binding	+	0.5961	59.61%
Aromatase binding	+	0.6099	60.99%
PPAR gamma	+	0.6432	64.32%
Honey bee toxicity	-	0.7729	77.29%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9208	92.08%

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	99.01%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.11%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	90.91%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.83%	95.89%
CHEMBL2581	P07339	Cathepsin D	90.67%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.20%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.99%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.29%	97.25%
CHEMBL4040	P28482	MAP kinase ERK2	87.83%	83.82%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	87.02%	88.42%
CHEMBL3437	Q16853	Amine oxidase, copper containing	86.12%	94.00%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	85.99%	100.00%
CHEMBL3384	Q16512	Protein kinase N1	85.10%	80.71%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.13%	91.11%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.84%	93.04%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.58%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.32%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.30%	89.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.16%	93.03%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.15%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.81%	94.00%
CHEMBL220	P22303	Acetylcholinesterase	80.24%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.08%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10257415
• LOTUS: LTS0201095
• wikiData: Q104935026