(4S,5R,6R)-6-[(1S)-1-hydroxyethyl]-4-methyl-7-oxo-3-{[(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid hydrate

• ChemBase ID: 72647
• Molecular Formular: C15H26N4O7S2
• Molecular Mass: 438.51954
• Monoisotopic Mass: 438.12429119
• SMILES: C1(=O)[C@H]([C@H]2N1C(=C([C@H]2C)S[C@@H]1CN[C@@H](C1)CNS(=O)(=O)N)C(=O)O)[C@H](C)O.O
• Canonical SMILES: C[C@@H]([C@@H]1C(=O)N2[C@H]1[C@H](C)C(=C2C(=O)O)S[C@@H]1CN[C@@H](C1)CNS(=O)(=O)N)O.O
• InChI: InChI=1S/C15H24N4O6S2.H2O/c1-6-11-10(7(2)20)14(21)19(11)12(15(22)23)13(6)26-9-3-8(17-5-9)4-18-27(16,24)25;/h6-11,17-18,20H,3-5H2,1-2H3,(H,22,23)(H2,16,24,25);1H2/t6-,7-,8-,9-,10-,11-;/m0./s1
• InChIKey: NTUBEBXBDGKBTJ-LGAOZOLISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5R,6R)-6-[(1S)-1-hydroxyethyl]-4-methyl-7-oxo-3-{[(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid hydrate
• IUPAC Traditional name: (4S,5R,6R)-6-[(1S)-1-hydroxyethyl]-4-methyl-7-oxo-3-{[(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid hydrate
• Synonyms: Doribax; Doripenem monohydrate; S-4661; Finib; Doripenem Hydrate; Finibax; Doripenem

Database IDs

• CAS Number: 148016-81-3; 364622-82-2
• PubChem SID: 162037572
• PubChem CID: 46931008

CALCULATED PROPERTIES

• Acid pKa: 3.5350504
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -5.5664563
• LogD (pH = 7.4): -5.565607
• Log P: -5.5638638
• Molar Refractivity: 99.8802 cm^3
• Polarizability: 39.91681 Å^3
• Polar Surface Area: 162.06 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: H2O; Hydrate
• Application(s): Ultra-broad spectrum antibacterial agent

DETAILS

Selleck Chemicals - S1374

Research Area: Infection
Biological Activity:
Doripenem (doripenem monohydrate) is an ultra-broad spectrum injectable antibiotic. It is a beta-lactam and belongs to the subgroup of carbapenems. It is particularly active against Pseudomonas aeruginosa. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Doripenem
• Eur. Pat., 1993, Shionogi, 528 678; CA, 119, 72425r, (synth, activity)
• Iso, Y. et al., J. Antibiot., 1996, 49, 199-209; 478-484, (synth, ir, pmr, activity)
• Tsuji, M. et al., Antimicrob. Agents Chemother., 1998, 42, 94-99, (activity)