CAS 28384-96-5|N-[(3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzamide|enterobactin|Enterobactin|Tri-(N-(2,3-dihydroxybenzoyl)-L-serine)-e...

General Information

Structure

Molecular Formula

C₃₀H₂₇N₃O₁₅

Molecular Mass

669.54648

Exact Mass

669.14421718

Charge

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

InChIKey

SERBHKJMVBATSJ-BZSNNMDCSA-N

Canonic Smiles

O=C(c1cccc(c1O)O)N[C@H]1COC(=O)[C@H](COC(=O)[C@H](COC1=O)NC(=O)c1cccc(c1O)O)NC(=O)c1cccc(c1O)O

Isomeric Smiles

c1cc(c(c(c1)O)O)C(=O)N[C@@H]1COC(=O)[C@@H](COC(=O)[C@@H](COC1=O)NC(=O)c1cccc(c1O)O)NC(=O)c1cccc(c1O)O

Calculated Properties

JChem

LogD (pH = 7.4)

2.11

LogD (pH = 5.5)

2.26

Log P

2.26

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

7.82

Polar Surface Area

287.58

Polarizability

60.39

Molar Refractivity

157.87

LOG S

-4.12

Data Source

Academic Data

Data Source

Names and Identifiers

IUPAC name

N-[(3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzamide

IUPAC Traditional name

enterobactin

Synonyms

EnterobactinTri-(N-(2,3-dihydroxybenzoyl)-L-serine)-esterTri-(2,3-dihydroxy-N-benzoyl-L-serine)-esterEnterobactinEnterochelin(3S-(3R*,7R*,11R*))-N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxybenzamide)enterobactinH6ent

Names and Identifiers

Registration numbers

Wikipedia Title

Chemspider ID

PubChem CID

CAS Number

CHEBI ID

28855CHEBI:23923CHEBI:4799CHEBI:28855