Bacitracin A (8CI)

Details

• Internal ID: 2e966eee-c533-4f39-a18e-684f37b63d6b
• Taxonomy: Organic Polymers > Polypeptides
• IUPAC Name: (4R)-4-[[(2S)-2-[[2-[(1S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-5-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[(2S)-1-[[(3S,6R,9S,12R,15S,18R,21S)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-butan-2-yl-6-(carboxymethyl)-9-(1H-imidazol-5-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclopentacos-21-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-5-oxopentanoic acid
• SMILES (Canonical): CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCCCCC(C(=O)NC(C(=O)N1)CCCN)NC(=O)C(C(C)CC)NC(=O)C(CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C2CN=C(S2)C(C(C)CC)N)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC4=CC=CC=C4
• SMILES (Isomeric): CCC(C)[C@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCCCC[C@@H](C(=O)N[C@@H](C(=O)N1)CCCN)NC(=O)[C@H](C(C)CC)NC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)C2CN=C(S2)[C@H](C(C)CC)N)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC4=CC=CC=C4
• InChI: InChI=1S/C66H103N17O16S/c1-9-35(6)52(69)66-72-32-48(100-66)63(97)80-43(26-34(4)5)59(93)75-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)76-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-73-39)77-60(94)44(27-38-18-13-12-14-19-38)81-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)74-56(40)90/h12-14,18-19,31,33-37,40-48,52-54H,9-11,15-17,20-30,32,67,69H2,1-8H3,(H2,68,84)(H,70,73)(H,71,89)(H,74,90)(H,75,93)(H,76,98)(H,77,94)(H,78,96)(H,79,95)(H,80,97)(H,81,99)(H,82,91)(H,83,92)(H,85,86)(H,87,88)/t35?,36?,37?,40-,41+,42+,43-,44+,45-,46-,47+,48?,52-,53-,54-/m0/s1
• InChI Key: MNJKVJAYSVAQLU-YOJCIBLDSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₆H₁₀₃N₁₇O₁₆S
• Molecular Weight: 1422.70 g/mol
• Exact Mass: 1421.74894144 g/mol
• Topological Polar Surface Area (TPSA): 556.00 Ų
• XlogP: -4.30
• Atomic LogP (AlogP): -1.68
• H-Bond Acceptor: 19
• H-Bond Donor: 17
• Rotatable Bonds: 31

Synonyms

• Bacitracin A1 (9CI)
• SCHEMBL1059374
• CHEMBL1237057
• 1,4,7,10,13,16,19-Heptaazacyclopentacosane, cyclic peptide deriv.
• 1-[N-[[2-(1-Amino-2-methylbutyl)-4,5-dihydro-4-thiazolyl]carbonyl]-L-leucine]-Bacitracin F

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5473	54.73%
Caco-2	-	0.8662	86.62%
Blood Brain Barrier	-	0.9500	95.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4232	42.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9028	90.28%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9209	92.09%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9661	96.61%
P-glycoprotein inhibitior	+	0.7422	74.22%
P-glycoprotein substrate	+	0.8731	87.31%
CYP3A4 substrate	+	0.7479	74.79%
CYP2C9 substrate	-	0.8067	80.67%
CYP2D6 substrate	-	0.8493	84.93%
CYP3A4 inhibition	-	0.9011	90.11%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	+	0.8303	83.03%
CYP inhibitory promiscuity	-	0.9122	91.22%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6027	60.27%
Eye corrosion	-	0.9851	98.51%
Eye irritation	-	0.8957	89.57%
Skin irritation	-	0.7691	76.91%
Skin corrosion	-	0.9241	92.41%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7048	70.48%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.6477	64.77%
skin sensitisation	-	0.8334	83.34%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9484	94.84%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.7235	72.35%
Acute Oral Toxicity (c)	III	0.5690	56.90%
Estrogen receptor binding	+	0.5286	52.86%
Androgen receptor binding	+	0.7188	71.88%
Thyroid receptor binding	+	0.7281	72.81%
Glucocorticoid receptor binding	+	0.7938	79.38%
Aromatase binding	+	0.8064	80.64%
PPAR gamma	+	0.7153	71.53%
Honey bee toxicity	-	0.6647	66.47%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9177	91.77%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.93%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.65%	96.09%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	99.63%	88.42%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	99.20%	97.64%
CHEMBL221	P23219	Cyclooxygenase-1	98.81%	90.17%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	97.38%	97.23%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	96.83%	98.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.50%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	96.30%	93.00%
CHEMBL3837	P07711	Cathepsin L	96.26%	96.61%
CHEMBL4071	P08311	Cathepsin G	96.15%	94.64%
CHEMBL5103	Q969S8	Histone deacetylase 10	96.08%	90.08%
CHEMBL220	P22303	Acetylcholinesterase	96.05%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	95.95%	93.56%
CHEMBL2094135	Q96BI3	Gamma-secretase	95.65%	98.05%
CHEMBL1293287	P14735	Insulin-degrading enzyme	95.00%	88.10%
CHEMBL1255126	O15151	Protein Mdm4	94.69%	90.20%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	94.42%	93.03%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	93.84%	96.90%
CHEMBL3024	P53350	Serine/threonine-protein kinase PLK1	93.72%	97.43%
CHEMBL4462	Q8IXJ6	NAD-dependent deacetylase sirtuin 2	93.42%	90.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.97%	99.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	92.48%	100.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	91.94%	93.10%
CHEMBL4662	P28074	Proteasome Macropain subunit MB1	91.88%	93.85%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	91.76%	98.24%
CHEMBL255	P29275	Adenosine A2b receptor	90.65%	98.59%
CHEMBL226	P30542	Adenosine A1 receptor	90.29%	95.93%
CHEMBL2514	O95665	Neurotensin receptor 2	89.99%	100.00%
CHEMBL4801	P29466	Caspase-1	89.70%	96.85%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.48%	95.89%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	89.23%	82.86%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	89.22%	95.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.10%	90.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.75%	95.50%
CHEMBL4018	P49146	Neuropeptide Y receptor type 2	88.03%	98.94%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	86.94%	92.88%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.67%	95.56%
CHEMBL3310	Q96DB2	Histone deacetylase 11	86.56%	88.56%
CHEMBL4777	P25929	Neuropeptide Y receptor type 1	86.40%	96.67%
CHEMBL202	P00374	Dihydrofolate reductase	85.50%	89.92%
CHEMBL2535	P11166	Glucose transporter	85.25%	98.75%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	84.97%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.94%	97.14%
CHEMBL4296	Q15858	Sodium channel protein type IX alpha subunit	84.27%	96.11%
CHEMBL1075317	P61964	WD repeat-containing protein 5	84.01%	96.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.29%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.17%	94.45%
CHEMBL1781	P11387	DNA topoisomerase I	83.07%	97.00%
CHEMBL5028	O14672	ADAM10	81.66%	97.50%
CHEMBL2208	P49137	MAP kinase-activated protein kinase 2	81.12%	95.20%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 439542
• LOTUS: LTS0066152
• wikiData: Q105168407