Asterobactin B

Details

• Internal ID: cbba6f93-b97a-485b-ae38-500622d1513d
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides
• IUPAC Name: [3-[[1-[1-[[5-[carbamimidoyl(hydroxy)amino]-1-(hydroxyamino)-1-oxopentan-2-yl]amino]-2-methyl-1-oxododecan-3-yl]oxy-5-[formyl(hydroxy)amino]-1-oxopentan-2-yl]amino]-2-hydroxy-3-oxopropyl] 2-hydroxybenzoate
• SMILES (Canonical): CCCCCCCCCC(C(C)C(=O)NC(CCCN(C(=N)N)O)C(=O)NO)OC(=O)C(CCCN(C=O)O)NC(=O)C(COC(=O)C1=CC=CC=C1O)O
• SMILES (Isomeric): CCCCCCCCCC(C(C)C(=O)NC(CCCN(C(=N)N)O)C(=O)NO)OC(=O)C(CCCN(C=O)O)NC(=O)C(COC(=O)C1=CC=CC=C1O)O
• InChI: InChI=1S/C35H57N7O13/c1-3-4-5-6-7-8-9-18-29(23(2)30(46)38-25(31(47)40-51)15-13-20-42(53)35(36)37)55-34(50)26(16-12-19-41(52)22-43)39-32(48)28(45)21-54-33(49)24-14-10-11-17-27(24)44/h10-11,14,17,22-23,25-26,28-29,44-45,51-53H,3-9,12-13,15-16,18-21H2,1-2H3,(H3,36,37)(H,38,46)(H,39,48)(H,40,47)
• InChI Key: HQVYJMIMXNUBLA-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₇N₇O₁₃
• Molecular Weight: 783.90 g/mol
• Exact Mass: 783.40143490 g/mol
• Topological Polar Surface Area (TPSA): 314.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 1.07
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 28

Synonyms

• (3-((1-(1-((5-(carbamimidoyl(hydroxy)amino)-1-(hydroxyamino)-1-oxopentan-2-yl)amino)-2-methyl-1-oxododecan-3-yl)oxy-5-(formyl(hydroxy)amino)-1-oxopentan-2-yl)amino)-2-hydroxy-3-oxopropyl) 2-hydroxybenzoate
• [3-[[1-[1-[[5-[carbamimidoyl(hydroxy)amino]-1-(hydroxyamino)-1-oxopentan-2-yl]amino]-2-methyl-1-oxododecan-3-yl]oxy-5-[formyl(hydroxy)amino]-1-oxopentan-2-yl]amino]-2-hydroxy-3-oxopropyl] 2-hydroxybenzoate
• 3-((2-((1,2-dihydroxy-3-(2-hydroxybenzoyloxy)propylidene)amino)-5-(N-hydroxyformamido)pentanoyl)oxy)-N-(1-(dihydroxycarbonimidoyl)-4-(N-hydroxycarbamimidamido)butyl)-2-methyldodecanimidate
• 3-[(2-{[1,2-dihydroxy-3-(2-hydroxybenzoyloxy)propylidene]amino}-5-(N-hydroxyformamido)pentanoyl)oxy]-N-[1-(dihydroxycarbonimidoyl)-4-(N-hydroxycarbamimidamido)butyl]-2-methyldodecanimidate
• RefChem:115282
• CHEBI:204138
• [3-[[1-[1-[[5-[carbamimidoyl(hydroxy)amino]-1-(hydroxyamino)-1-oxopentan-2-yl]amino]-2-methyl-1-oxododecan-3-yl]oxy-5-[ormyl(hydroxy)amino]-1-oxopentan-2-yl]amino]-2-hydroxy-3-oxopropyl] 2-hydroxybenzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8393	83.93%
Caco-2	-	0.8697	86.97%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7488	74.88%
OATP2B1 inhibitior	-	0.5730	57.30%
OATP1B1 inhibitior	+	0.8564	85.64%
OATP1B3 inhibitior	+	0.9338	93.38%
MATE1 inhibitior	-	0.6400	64.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8749	87.49%
P-glycoprotein inhibitior	+	0.7358	73.58%
P-glycoprotein substrate	+	0.7914	79.14%
CYP3A4 substrate	+	0.6904	69.04%
CYP2C9 substrate	-	0.8085	80.85%
CYP2D6 substrate	-	0.8433	84.33%
CYP3A4 inhibition	-	0.8104	81.04%
CYP2C9 inhibition	-	0.7674	76.74%
CYP2C19 inhibition	-	0.7060	70.60%
CYP2D6 inhibition	-	0.8675	86.75%
CYP1A2 inhibition	-	0.7275	72.75%
CYP2C8 inhibition	+	0.6872	68.72%
CYP inhibitory promiscuity	-	0.9554	95.54%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.6800	68.00%
Carcinogenicity (trinary)	Non-required	0.5739	57.39%
Eye corrosion	-	0.9800	98.00%
Eye irritation	-	0.9101	91.01%
Skin irritation	-	0.7609	76.09%
Skin corrosion	-	0.9199	91.99%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6498	64.98%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.6323	63.23%
skin sensitisation	-	0.8203	82.03%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6187	61.87%
Acute Oral Toxicity (c)	III	0.6033	60.33%
Estrogen receptor binding	+	0.8415	84.15%
Androgen receptor binding	+	0.7605	76.05%
Thyroid receptor binding	+	0.5142	51.42%
Glucocorticoid receptor binding	+	0.6253	62.53%
Aromatase binding	+	0.6127	61.27%
PPAR gamma	+	0.7337	73.37%
Honey bee toxicity	-	0.7890	78.90%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5537	55.37%
Fish aquatic toxicity	+	0.9553	95.53%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	99.63%	89.76%
CHEMBL2581	P07339	Cathepsin D	99.62%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	99.50%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.35%	96.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	98.25%	93.56%
CHEMBL299	P17252	Protein kinase C alpha	97.65%	98.03%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.77%	99.17%
CHEMBL2996	Q05655	Protein kinase C delta	95.43%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.30%	95.56%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	94.08%	91.81%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.38%	91.11%
CHEMBL3891	P07384	Calpain 1	91.89%	93.04%
CHEMBL3401	O75469	Pregnane X receptor	91.09%	94.73%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	91.07%	97.29%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.04%	96.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	91.01%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.74%	95.50%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	90.71%	100.00%
CHEMBL5028	O14672	ADAM10	89.87%	97.50%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.73%	90.08%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	86.95%	92.08%
CHEMBL2514	O95665	Neurotensin receptor 2	85.78%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.05%	94.45%
CHEMBL3959	P16083	Quinone reductase 2	84.58%	89.49%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.72%	89.67%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	81.65%	95.00%
CHEMBL3776	Q14790	Caspase-8	80.45%	97.06%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139585116
• LOTUS: LTS0050265
• wikiData: Q77384070