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

ID: ALA368819

PubChem CID: 44386364

Max Phase: Preclinical

Molecular Formula: C37H52ClN9O13

Molecular Weight: 866.33

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)c1ccccc1

Standard InChI:  InChI=1S/C37H52ClN9O13/c1-20(48)44(58)17-7-12-25(39)32(51)40-26(13-8-18-45(59)21(2)49)33(52)41-27(14-9-19-46(60)22(3)50)34(53)42-29(23-10-5-4-6-11-23)35(54)43-30-28-16-15-24(38)31(37(56)57)47(28)36(30)55/h4-6,10-11,25-30,58-60H,7-9,12-19,39H2,1-3H3,(H,40,51)(H,41,52)(H,42,53)(H,43,54)(H,56,57)/t25-,26-,27-,28+,29+,30?/m0/s1

Standard InChI Key:  YXTBOLFVQWCWJQ-PKAXTMRISA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA368819

   (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-phenylacetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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: 866.33

Molecular Weight (Monoisotopic): 865.3373

AlogP: -0.78

#Rotatable Bonds: 22

Polar Surface Area: 321.65

Molecular Species: ACID

HBA: 13

HBD: 9

#RO5 Violations: 3

HBA (Lipinski): 22

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.20

CX Basic pKa: 7.58

CX LogP: -6.29

CX LogD: -6.54

Aromatic Rings: 1

Heavy Atoms: 60

QED Weighted: 0.04

Np Likeness Score: 0.15

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