Aerobactin

Details

• Internal ID: 74642873-bbc7-47f7-ab27-db915a5e5393
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > N-acyl-alpha amino acids
• IUPAC Name: 4-[[(1S)-5-[acetyl(hydroxy)amino]-1-carboxypentyl]amino]-2-[2-[[(1S)-5-[acetyl(hydroxy)amino]-1-carboxypentyl]amino]-2-oxoethyl]-2-hydroxy-4-oxobutanoic acid
• SMILES (Canonical): CC(=O)N(CCCCC(C(=O)O)NC(=O)CC(CC(=O)NC(CCCCN(C(=O)C)O)C(=O)O)(C(=O)O)O)O
• SMILES (Isomeric): CC(=O)N(CCCC[C@@H](C(=O)O)NC(=O)CC(CC(=O)N[C@@H](CCCCN(C(=O)C)O)C(=O)O)(C(=O)O)O)O
• InChI: InChI=1S/C22H36N4O13/c1-13(27)25(38)9-5-3-7-15(19(31)32)23-17(29)11-22(37,21(35)36)12-18(30)24-16(20(33)34)8-4-6-10-26(39)14(2)28/h15-16,37-39H,3-12H2,1-2H3,(H,23,29)(H,24,30)(H,31,32)(H,33,34)(H,35,36)/t15-,16-/m0/s1
• InChI Key: KDHHWXGBNUCREU-HOTGVXAUSA-N
• Popularity: 434 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₆N₄O₁₃
• Molecular Weight: 564.50 g/mol
• Exact Mass: 564.22788722 g/mol
• Topological Polar Surface Area (TPSA): 271.00 Ų
• XlogP: -3.10
• Atomic LogP (AlogP): -1.46
• H-Bond Acceptor: 10
• H-Bond Donor: 8
• Rotatable Bonds: 19

Synonyms

• 26198-65-2
• Ferric-aerobactin
• 3,9,15,21-Tetraazatricosane-8,12,16-tricarboxylic acid, 3,12,21-trihydroxy-2,10,14,22-tetraoxo-, (S-(R*,R*))-
• (8S,16S)-3,12,21-trihydroxy-2,10,14,22-tetraoxo-3,9,15,21-tetraazatricosane-8,12,16-tricarboxylic acid
• 3,9,15,21-Tetraazatricosane-8,12,16-tricarboxylic acid, 3,12,21-trihydroxy-2,10,14,22-tetraoxo-, (8S,16S)-
• 3,9,15,21-Tetraazatricosane-8,12,16-tricarboxylic acid, 3,12,21-trihydroxy-2,10,14,22-tetraoxo-, [S-(R*,R*)]-
• SCHEMBL404110
• CHEBI:18157
• DTXSID90904341
• AKOS040750155
• C05554
• Q2875340
• N(2),N(2)'-(3-carboxy-3-hydroxypentanedioyl)bis(N(6)-acetyl-N(6)-hydroxy-L-lysine)
• (2S)-2-[3-carboxy-3-({[(1S)-1-carboxy-5-(N-hydroxyacetamido)pentyl]carbamoyl}methyl)-3-hydroxypropanamido]-6-(N-hydroxyacetamido)hexanoic acid
• (8S,16S)-3,12,21-trihydroxy-2,10,14,22-tetraoxo-3,9,15,21-tetraazatricosane-8,12,16-tricarboxylicacid
• 4-[[(1S)-5-[acetyl(hydroxy)amino]-1-carboxypentyl]amino]-2-[2-[[(1S)-5-[acetyl(hydroxy)amino]-1-carboxypentyl]amino]-2-oxoethyl]-2-hydroxy-4-oxobutanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8662	86.62%
Caco-2	-	0.8566	85.66%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7673	76.73%
OATP2B1 inhibitior	-	0.7168	71.68%
OATP1B1 inhibitior	+	0.9051	90.51%
OATP1B3 inhibitior	+	0.9366	93.66%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7009	70.09%
P-glycoprotein inhibitior	+	0.6454	64.54%
P-glycoprotein substrate	-	0.7162	71.62%
CYP3A4 substrate	+	0.5600	56.00%
CYP2C9 substrate	-	0.5872	58.72%
CYP2D6 substrate	-	0.8686	86.86%
CYP3A4 inhibition	-	0.8984	89.84%
CYP2C9 inhibition	-	0.8311	83.11%
CYP2C19 inhibition	-	0.7837	78.37%
CYP2D6 inhibition	-	0.9014	90.14%
CYP1A2 inhibition	-	0.8503	85.03%
CYP2C8 inhibition	-	0.9516	95.16%
CYP inhibitory promiscuity	-	0.9570	95.70%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.6200	62.00%
Carcinogenicity (trinary)	Non-required	0.4755	47.55%
Eye corrosion	-	0.9802	98.02%
Eye irritation	-	0.8663	86.63%
Skin irritation	-	0.7835	78.35%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5243	52.43%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	-	0.5948	59.48%
skin sensitisation	-	0.8449	84.49%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.5517	55.17%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.5114	51.14%
Acute Oral Toxicity (c)	III	0.6007	60.07%
Estrogen receptor binding	+	0.6850	68.50%
Androgen receptor binding	+	0.6894	68.94%
Thyroid receptor binding	+	0.5311	53.11%
Glucocorticoid receptor binding	-	0.5233	52.33%
Aromatase binding	+	0.6231	62.31%
PPAR gamma	+	0.5717	57.17%
Honey bee toxicity	-	0.8998	89.98%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.8010	80.10%
Fish aquatic toxicity	-	0.4599	45.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.82%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.82%	99.17%
CHEMBL4040	P28482	MAP kinase ERK2	92.96%	83.82%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	88.97%	92.29%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.36%	96.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.23%	93.56%
CHEMBL3784	Q09472	Histone acetyltransferase p300	86.03%	93.33%
CHEMBL340	P08684	Cytochrome P450 3A4	84.69%	91.19%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	84.26%	100.00%
CHEMBL1255126	O15151	Protein Mdm4	83.40%	90.20%
CHEMBL3401	O75469	Pregnane X receptor	83.09%	94.73%
CHEMBL2514	O95665	Neurotensin receptor 2	81.80%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.22%	91.11%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.89%	93.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.61%	96.00%
CHEMBL1795117	Q8TEK3	Histone-lysine N-methyltransferase, H3 lysine-79 specific	80.35%	93.56%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.02%	96.90%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 123762
• LOTUS: LTS0180467
• wikiData: Q2875340