2'-((4'-((S)-3-((R)-4-amino-4-oxo-2-tetradecanamidobutanamido)butyl)-3',6'-dioxo-2',3'-dihydrospiro[cyclopropane-1,1'-pyrrolo[3,4-c]pyridin]-5'(6'H)-yl)methyl)-[2,4'-bithiazole]-4-carboxylic acid

Details

• Internal ID: 4b7b07af-40f3-46b3-8858-c698758732d2
• Taxonomy: Organoheterocyclic compounds > Pyrrolopyridines
• IUPAC Name: 2-[2-[[4-[(3S)-3-[[(2R)-4-amino-4-oxo-2-(tetradecanoylamino)butanoyl]amino]butyl]-3,6-dioxospiro[2H-pyrrolo[3,4-c]pyridine-1,1'-cyclopropane]-5-yl]methyl]-1,3-thiazol-4-yl]-1,3-thiazole-4-carboxylic acid
• SMILES (Canonical): CCCCCCCCCCCCCC(=O)NC(CC(=O)N)C(=O)NC(C)CCC1=C2C(=CC(=O)N1CC3=NC(=CS3)C4=NC(=CS4)C(=O)O)C5(CC5)NC2=O
• SMILES (Isomeric): CCCCCCCCCCCCCC(=O)N[C@H](CC(=O)N)C(=O)N[C@@H](C)CCC1=C2C(=CC(=O)N1CC3=NC(=CS3)C4=NC(=CS4)C(=O)O)C5(CC5)NC2=O
• InChI: InChI=1S/C39H53N7O7S2/c1-3-4-5-6-7-8-9-10-11-12-13-14-31(48)42-26(20-30(40)47)35(50)41-24(2)15-16-29-34-25(39(17-18-39)45-36(34)51)19-33(49)46(29)21-32-43-27(22-54-32)37-44-28(23-55-37)38(52)53/h19,22-24,26H,3-18,20-21H2,1-2H3,(H2,40,47)(H,41,50)(H,42,48)(H,45,51)(H,52,53)/t24-,26+/m0/s1
• InChI Key: KPISWKUSQUAIIS-AZGAKELHSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₅₃N₇O₇S₂
• Molecular Weight: 796.00 g/mol
• Exact Mass: 795.34478940 g/mol
• Topological Polar Surface Area (TPSA): 270.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 5.41
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 24

Synonyms

• precolibactin C
• Precolibactin-795

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7168	71.68%
Caco-2	-	0.8612	86.12%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5201	52.01%
OATP2B1 inhibitior	+	0.5583	55.83%
OATP1B1 inhibitior	+	0.8283	82.83%
OATP1B3 inhibitior	+	0.9314	93.14%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9099	90.99%
BSEP inhibitior	+	0.9404	94.04%
P-glycoprotein inhibitior	+	0.7468	74.68%
P-glycoprotein substrate	+	0.8399	83.99%
CYP3A4 substrate	+	0.6920	69.20%
CYP2C9 substrate	-	0.7795	77.95%
CYP2D6 substrate	-	0.8909	89.09%
CYP3A4 inhibition	-	0.7706	77.06%
CYP2C9 inhibition	-	0.7096	70.96%
CYP2C19 inhibition	-	0.6983	69.83%
CYP2D6 inhibition	-	0.8986	89.86%
CYP1A2 inhibition	-	0.7472	74.72%
CYP2C8 inhibition	+	0.7040	70.40%
CYP inhibitory promiscuity	-	0.8422	84.22%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6425	64.25%
Eye corrosion	-	0.9852	98.52%
Eye irritation	-	0.9094	90.94%
Skin irritation	-	0.7699	76.99%
Skin corrosion	-	0.9189	91.89%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5344	53.44%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.6324	63.24%
skin sensitisation	-	0.8342	83.42%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.7015	70.15%
Acute Oral Toxicity (c)	III	0.5722	57.22%
Estrogen receptor binding	+	0.7337	73.37%
Androgen receptor binding	+	0.7454	74.54%
Thyroid receptor binding	+	0.5342	53.42%
Glucocorticoid receptor binding	+	0.5725	57.25%
Aromatase binding	+	0.6310	63.10%
PPAR gamma	+	0.6865	68.65%
Honey bee toxicity	-	0.8216	82.16%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6189	61.89%
Fish aquatic toxicity	+	0.9839	98.39%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL230	P35354	Cyclooxygenase-2	99.91%	89.63%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	99.71%	95.17%
CHEMBL2581	P07339	Cathepsin D	99.70%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.44%	96.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	98.34%	93.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	98.10%	93.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.54%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.42%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.36%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.98%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	94.42%	90.71%
CHEMBL221	P23219	Cyclooxygenase-1	93.99%	90.17%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	93.46%	92.29%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	92.72%	95.34%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	92.31%	92.08%
CHEMBL3891	P07384	Calpain 1	91.46%	93.04%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.43%	96.38%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	91.06%	98.33%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	90.11%	91.81%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.31%	86.33%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	88.99%	95.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	88.88%	96.90%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.79%	93.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.22%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.43%	82.69%
CHEMBL4105838	Q96GG9	DCN1-like protein 1	86.36%	95.00%
CHEMBL1781	P11387	DNA topoisomerase I	85.62%	97.00%
CHEMBL299	P17252	Protein kinase C alpha	84.53%	98.03%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	83.67%	96.00%
CHEMBL4816	Q9Y243	Serine/threonine-protein kinase AKT3	83.52%	96.28%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.30%	89.34%
CHEMBL2094135	Q96BI3	Gamma-secretase	82.12%	98.05%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.43%	95.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.39%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.39%	96.21%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 121232610
• LOTUS: LTS0156962
• wikiData: Q77376283