(4S)-2-((S)-4-((Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetamido)-3-oxoisoxazolidin-2-yl)-4-(1,5-dihydroxy-4-oxo-1,4-dihydropyridine-2-carboxamido)-5-oxotetrahydrofuran-2-carboxylic acid

ID: ALA3265225

PubChem CID: 90656112

Max Phase: Preclinical

Molecular Formula: C23H23N7O14S

Molecular Weight: 653.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(O/N=C(\C(=O)N[C@H]1CON(C2(C(=O)O)C[C@H](NC(=O)c3cc(=O)c(O)cn3O)C(=O)O2)C1=O)c1csc(N)n1)C(=O)O

Standard InChI:  InChI=1S/C23H23N7O14S/c1-22(2,19(37)38)44-28-14(10-7-45-21(24)27-10)16(34)26-9-6-42-30(17(9)35)23(20(39)40)4-8(18(36)43-23)25-15(33)11-3-12(31)13(32)5-29(11)41/h3,5,7-9,32,41H,4,6H2,1-2H3,(H2,24,27)(H,25,33)(H,26,34)(H,37,38)(H,39,40)/b28-14-/t8-,9-,23?/m0/s1

Standard InChI Key:  REGJNQQIMGOTAR-BWYJCOHISA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3265225

   (4S)-2-[(4S)-4-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-3-oxo-1,2-oxazolidin-2-yl]-4-[(1,5-dihydroxy-4-oxopyridine-2-carbonyl)amino]-5-oxooxolane-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: 653.54

Molecular Weight (Monoisotopic): 653.1024

AlogP: -2.80

#Rotatable Bonds: 10

Polar Surface Area: 311.60

Molecular Species: ACID

HBA: 17

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 21

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.28

CX Basic pKa: 3.92

CX LogP: -2.56

CX LogD: -8.11

Aromatic Rings: 2

Heavy Atoms: 45

QED Weighted: 0.06

Np Likeness Score: 0.12

References

1. Starr J, Brown MF, Aschenbrenner L, Caspers N, Che Y, Gerstenberger BS, Huband M, Knafels JD, Lemmon MM, Li C, McCurdy SP, McElroy E, Rauckhorst MR, Tomaras AP, Young JA, Zaniewski RP, Shanmugasundaram V, Han S..  (2014)  Siderophore receptor-mediated uptake of lactivicin analogues in gram-negative bacteria.,  57  (9): [PMID:24694215] [10.1021/jm500219c]

Source

Source(1):

• Scientific Literature