1-(1-(2-aminothiazol-4-yl)-2-oxo-2-((3S,4R)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)-1-sulfoazetidin-3-ylamino)ethylideneaminooxy)cyclopropanecarboxylic acid

ID: ALA4206129

Cas Number: 1810051-96-7

PubChem CID: 118379834

Max Phase: Phase

Molecular Formula: C16H18N6O10S2

Molecular Weight: 518.49

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BOS-228 | LYS-228 | Ancremonam|Ancremonam [USAN]|BOS-228|LYS-228|29H7N9XI1B|UNII-29H7N9XI1B|1810051-96-7|CHEMBL4206129|WHO 11371|Cyclopropanecarboxylic acid, 1-(((Z)-(1-(2-amino-4-thiazolyl)-2-oxo-2-(((3S,4R)-2-oxo-4-((2-oxo-3-oxazolidinyl)methyl)-1-sulfo-3-azetidinyl)amino)ethylidene)amino)oxy)-|LYS228|ANCREMONAM [INN]|SCHEMBL17094086|BDBM50454542|AKOS040748861|HY-120129|CS-0076960|1-((((Z)-1-(2-aminothiazol-4-yl)-2-oxo-2-(((3S,4R)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)-1-sulfoazetidin-3-yl)amiShow More⌵

Canonical SMILES:  Nc1nc(/C(=N/OC2(C(=O)O)CC2)C(=O)N[C@@H]2C(=O)N(S(=O)(=O)O)[C@@H]2CN2CCOC2=O)cs1

Standard InChI:  InChI=1S/C16H18N6O10S2/c17-14-18-7(6-33-14)9(20-32-16(1-2-16)13(25)26)11(23)19-10-8(5-21-3-4-31-15(21)27)22(12(10)24)34(28,29)30/h6,8,10H,1-5H2,(H2,17,18)(H,19,23)(H,25,26)(H,28,29,30)/b20-9-/t8-,10+/m1/s1

Standard InChI Key:  FWTGYTRQUBRVDW-NRABZWKMSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   -2.0447    1.2743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121    0.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4572    0.0048    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6322    0.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3773    0.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4968    1.0443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927    1.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4211    1.8513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8051    0.7472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1511   -0.3147    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4620   -0.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2799   -0.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3876   -1.5770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5697   -1.6847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0674   -2.3392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0421   -2.0792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5399   -2.7338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5444   -1.4247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966   -2.5815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7822   -0.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6001   -0.2122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1680    0.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9937   -0.9372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8049   -0.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126    0.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0176    1.1974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3635    2.1062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4712    2.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2837    3.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3530    2.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7534    3.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7340    3.6919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7963    2.2643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  1  5  1  0
  2  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 12 11  1  1
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 12  1  0
 15 16  2  0
 14 17  1  0
 17 18  1  0
 17 19  2  0
 17 20  2  0
 13 21  1  1
 21 22  1  0
 24 25  1  0
 25 26  1  0
 23 26  1  0
 23 22  1  0
 22 24  1  0
 23 27  2  0
  8 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
 32 30  1  0
 31 33  1  0
 31 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4206129

   ANCREMONAM

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 518.49

Molecular Weight (Monoisotopic): 518.0526

AlogP: -1.99

#Rotatable Bonds: 9

Polar Surface Area: 231.12

Molecular Species: ACID

HBA: 12

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -1.48

CX Basic pKa: 3.87

CX LogP: -4.05

CX LogD: -7.12

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.12

Np Likeness Score: -0.28

References

1. Reck F, Bermingham A, Blais J, Capka V, Cariaga T, Casarez A, Colvin R, Dean CR, Fekete A, Gong W, Growcott E, Guo H, Jones AK, Li C, Li F, Lin X, Lindvall M, Lopez S, McKenney D, Metzger L, Moser HE, Prathapam R, Rasper D, Rudewicz P, Sethuraman V, Shen X, Shaul J, Simmons RL, Tashiro K, Tang D, Tjandra M, Turner N, Uehara T, Vitt C, Whitebread S, Yifru A, Zang X, Zhu Q..  (2018)  Optimization of novel monobactams with activity against carbapenem-resistant Enterobacteriaceae - Identification of LYS228.,  28  (4): [PMID:29336873] [10.1016/j.bmcl.2018.01.006]

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names