7-[2-(5-(Acetyl-hydroxy-amino)-2-{5-(acetyl-hydroxy-amino)-2-[5-(acetyl-hydroxy-amino)-2-amino-pentanoylamonium]-pentanoylamino}-pentanoylamino)-2-(4-hydroxy-phenyl)-acetylamino]-3-chloro-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

ID: ALA174626

PubChem CID: 44386240

Max Phase: Preclinical

Molecular Formula: C37H52ClN9O14

Molecular Weight: 882.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N(O)CCC[C@H](NC(=O)[C@H](CCCN(O)C(C)=O)NC(=O)[C@@H](N)CCCN(O)C(C)=O)C(=O)N[C@@H](C(=O)NC1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)c1ccc(O)cc1

Standard InChI:  InChI=1S/C37H52ClN9O14/c1-19(48)44(59)16-4-7-25(39)32(52)40-26(8-5-17-45(60)20(2)49)33(53)41-27(9-6-18-46(61)21(3)50)34(54)42-29(22-10-12-23(51)13-11-22)35(55)43-30-28-15-14-24(38)31(37(57)58)47(28)36(30)56/h10-13,25-30,51,59-61H,4-9,14-18,39H2,1-3H3,(H,40,52)(H,41,53)(H,42,54)(H,43,55)(H,57,58)/t25-,26-,27-,28+,29+,30?/m0/s1

Standard InChI Key:  ODLIZIGZSPLLOX-PKAXTMRISA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA174626

   (6R)-7-[[(2R)-2-[[(2S)-5-[acetyl(hydroxy)amino]-2-[[(2S)-5-[acetyl(hydroxy)amino]-2-[[(2S)-5-[acetyl(hydroxy)amino]-2-aminopentanoyl]amino]pentanoyl]amino]pentanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carb

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 882.32

Molecular Weight (Monoisotopic): 881.3322

AlogP: -1.08

#Rotatable Bonds: 22

Polar Surface Area: 341.88

Molecular Species: ACID

HBA: 14

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 23

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.19

CX Basic pKa: 8.22

CX LogP: -6.60

CX LogD: -6.84

Aromatic Rings: 1

Heavy Atoms: 61

QED Weighted: 0.04

Np Likeness Score: 0.24

References

1. Dolence EK, Minnick AA, Lin CE, Miller MJ, Payne SM..  (1991)  Synthesis and siderophore and antibacterial activity of N5-acetyl-N5-hydroxy-L-ornithine-derived siderophore-beta-lactam conjugates: iron-transport-mediated drug delivery.,  34  (3): [PMID:1825850] [10.1021/jm00107a014]

Source

Source(1):

• Scientific Literature