(1S,5R)-2-((S)-azepan-4-ylcarbamoyl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic acid

ID: ALA598776

Chembl Id: CHEMBL598776

PubChem CID: 24763066

Max Phase: Preclinical

Molecular Formula: C12H20N4O5S

Molecular Weight: 332.38

Molecule Type: Small molecule

Names and Identifiers

Synonyms: MK-8712 | CHEMBL598776|(1S,5R)-2-((S)-azepan-4-ylcarbamoyl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic acid|SCHEMBL3605329|AWYIBQKIKNJPFA-AEJSXWLSSA-N|BDBM50309899|MK-8712|PD194087|(1S,5R)-2-[[(4S)-azepan-4-yl]carbamoyl]-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic acid|(1S,5R)-2-{[(4S)-azepan-4-ylamino]carbonyl}-7-oxo-2,6-diazabicyclo-[3.2.0]-heptane-6-sulfonic acid|(1S,5R)-2-{[(4S)-azepan-4-ylamino]carbonyl}-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic acid

Canonical SMILES:  O=C(N[C@H]1CCCNCC1)N1CC[C@@H]2[C@H]1C(=O)N2S(=O)(=O)O

Standard InChI:  InChI=1S/C12H20N4O5S/c17-11-10-9(16(11)22(19,20)21)4-7-15(10)12(18)14-8-2-1-5-13-6-3-8/h8-10,13H,1-7H2,(H,14,18)(H,19,20,21)/t8-,9+,10-/m0/s1

Standard InChI Key:  AWYIBQKIKNJPFA-AEJSXWLSSA-N

Alternative Forms

1. Parent:

   

   ALA598776

   (1S,5R)-2-((S)-azepan-4-ylcarbamoyl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic 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: 332.38

Molecular Weight (Monoisotopic): 332.1154

AlogP: -1.07

#Rotatable Bonds: 2

Polar Surface Area: 119.05

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -1.63

CX Basic pKa: 10.37

CX LogP: -3.26

CX LogD: -3.26

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.44

Np Likeness Score: -0.51

References

1. Blizzard TA, Chen H, Kim S, Wu J, Young K, Park YW, Ogawa A, Raghoobar S, Painter RE, Hairston N, Lee SH, Misura A, Felcetto T, Fitzgerald P, Sharma N, Lu J, Ha S, Hickey E, Hermes J, Hammond ML..  (2010)  Side chain SAR of bicyclic beta-lactamase inhibitors (BLIs). 1. Discovery of a class C BLI for combination with imipinem.,  20  (3): [PMID:20044254] [10.1016/j.bmcl.2009.12.069]

2. Chen H, Blizzard TA, Kim S, Wu J, Young K, Park YW, Ogawa AM, Raghoobar S, Painter RE, Wisniewski D, Hairston N, Fitzgerald P, Sharma N, Scapin G, Lu J, Hermes J, Hammond ML..  (2011)  Side chain SAR of bicyclic β-lactamase inhibitors (BLIs). 2. N-Alkylated and open chain analogs of MK-8712.,  21  (14): [PMID:21676616] [10.1016/j.bmcl.2011.05.065]

Source

Source(1):

• Scientific Literature