Enterobactin

Details

• Internal ID: 43a85ad7-7158-4d6e-9f1d-3a326c082600
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxybenzoyl)amino]-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl]-2,3-dihydroxybenzamide
• InChI: InChI=1S/C30H27N3O15/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42)/t16-,17-,18-/m0/s1
• InChI Key: SERBHKJMVBATSJ-BZSNNMDCSA-N
• Popularity: 1,872 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₇N₃O₁₅
• Molecular Weight: 669.50 g/mol
• Exact Mass: 669.14421716 g/mol
• Topological Polar Surface Area (TPSA): 288.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): -0.74
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 6

Synonyms

• Enterochelin
• 28384-96-5
• Enterochellin
• CHEBI:28855
• 35C9R2N24F
• Cyclotris(N-2,3-dihydroxybenzoyl-L-seryl)
• Chymosin preparation, Escherichia coli K-12
• tri-(2,3-dihydroxy-N-benzoyl-L-serine)-ester
• tri-(N-(2,3-dihydroxybenzoyl)-L-serine)-ester
• N,N',N''-((3S,7S,11S)-2,6,10-Trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxybenzamide)
• N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris(2,3-dihydroxybenzamide)
• Benzamide, N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris[2,3-dihydroxy-, [3S-(3R*,7R*,11R*)]-
• N,N',N''-((3S,7S,11S)-2,6,10- trioxo-1,5,9-trioxacyclododecane- 3,7,11-triyl)tris(2,3-dihydroxybenzamide)
• N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxybenzoyl)amino]-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl]-2,3-dihydroxybenzamide
• UNII-35C9R2N24F
• 2xuz
• H6ent
• BENZAMIDE, N,N',N''-((3S,7S,11S)-2,6,10-TRIOXO-1,5,9-TRIOXACYCLODODECANE-3,7,11-TRIYL)TRIS(2,3-DIHYDROXY-
• Benzamide, N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxy-, (3S-(3R*,7R*,11R*))-
• benzamide, N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris[2,3-dihydroxy-
• EB4
• ENTEROBACTIN [MI]
• SCHEMBL263621
• CHEMBL432995
• DTXSID40182617
• 1,5,9-Trioxacyclododecane, benzamide deriv.
• C05821
• F77042
• Q523354
• N-(2,3-DIHYDROXYBENZOYL)-L-SERINE TRIMOLECULAR CYCLIC ESTER
• (3S-(3R*,7R*,11R*))-N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxybenzamide)
• Benzamide, N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxy-, (3S-(3R*,7R*,11R*)))-
• Benzamide, N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris[2,3-dihydroxy- (9CI)
• N-(2,3-dihydroxybenzoyl)-O-[N-(2,3-dihydroxybenzoyl)-O-[N-(2,3-dihydroxybenzoyl)-L-seryl]-L-seryl]-L-serine-(3->1(3))-lactone
• N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxybenzene)amido]-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzamide
• o-Pyrocatechuamide, N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris- (8CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6606	66.06%
Caco-2	-	0.8872	88.72%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Nucleus	0.5949	59.49%
OATP2B1 inhibitior	-	0.8537	85.37%
OATP1B1 inhibitior	+	0.9402	94.02%
OATP1B3 inhibitior	+	0.9361	93.61%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9008	90.08%
P-glycoprotein inhibitior	+	0.7413	74.13%
P-glycoprotein substrate	-	0.6703	67.03%
CYP3A4 substrate	-	0.5822	58.22%
CYP2C9 substrate	-	0.8067	80.67%
CYP2D6 substrate	-	0.8708	87.08%
CYP3A4 inhibition	-	0.7618	76.18%
CYP2C9 inhibition	-	0.8698	86.98%
CYP2C19 inhibition	-	0.8988	89.88%
CYP2D6 inhibition	-	0.9250	92.50%
CYP1A2 inhibition	-	0.8232	82.32%
CYP2C8 inhibition	-	0.8945	89.45%
CYP inhibitory promiscuity	-	0.8803	88.03%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.7405	74.05%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9209	92.09%
Skin irritation	-	0.8114	81.14%
Skin corrosion	-	0.9553	95.53%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.8770	87.70%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.5901	59.01%
Acute Oral Toxicity (c)	III	0.5915	59.15%
Estrogen receptor binding	+	0.7004	70.04%
Androgen receptor binding	+	0.7510	75.10%
Thyroid receptor binding	-	0.5073	50.73%
Glucocorticoid receptor binding	-	0.4750	47.50%
Aromatase binding	-	0.5971	59.71%
PPAR gamma	+	0.7490	74.90%
Honey bee toxicity	-	0.9608	96.08%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.8451	84.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.94%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.49%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.82%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.33%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.62%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.52%	99.23%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	85.24%	83.57%
CHEMBL4531	P17931	Galectin-3	81.93%	96.90%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.92%	91.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.82%	97.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 34231
• LOTUS: LTS0146167
• wikiData: Q523354