SID93576931

ID: ALA1700858

Chembl Id: CHEMBL1700858

Cas Number: 859-07-4

PubChem CID: 68940

Max Phase: Phase

Molecular Formula: C18H18N2O6S

Molecular Weight: 390.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Cephaloram | Cefaloram|859-07-4|Cephaloram|Cefaloramum|Cefaloramo|(6R,7R)-3-(acetoxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid|K3086GQJ9Z|(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid|DTXSID9046106|Cefaloram [INN]|3-(Acetoxymethyl)-8-oxo-7-(phenylacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid|Cefaloram [INN:BAN]|Cefaloramum [INN-Latin]|Cefaloramo [INN-Spanish]|UNIIShow More⌵

Canonical SMILES:  CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)Cc3ccccc3)[C@H]2SC1

Standard InChI:  InChI=1S/C18H18N2O6S/c1-10(21)26-8-12-9-27-17-14(16(23)20(17)15(12)18(24)25)19-13(22)7-11-5-3-2-4-6-11/h2-6,14,17H,7-9H2,1H3,(H,19,22)(H,24,25)/t14-,17-/m1/s1

Standard InChI Key:  GOFCPYKUMJBHBH-RHSMWYFYSA-N

Alternative Forms

1. Parent:

   

   ALA1700858

   CEFALORAM

Molecule Features

Natural Product: Yes

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: 390.42

Molecular Weight (Monoisotopic): 390.0886

AlogP: 0.53

#Rotatable Bonds: 6

Polar Surface Area: 113.01

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.43

CX Basic pKa: ┄

CX LogP: 0.10

CX LogD: -3.29

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.54

Np Likeness Score: 0.16

References

1. PubChem BioAssay data set, 

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

3. Yan S, Miller MJ, Wencewicz TA, Möollmann U..  (2010)  Syntheses and biological evaluation of new cephalosporin-oxazolidinone conjugates.,  1  (2): [PMID:27087912] [10.1039/c0md00015a]

4. Evans LE, Krishna A, Ma Y, Webb TE, Marshall DC, Tooke CL, Spencer J, Clarke TB, Armstrong A, Edwards AM..  (2019)  Exploitation of Antibiotic Resistance as a Novel Drug Target: Development of a β-Lactamase-Activated Antibacterial Prodrug.,  62  (9): [PMID:31009558] [10.1021/acs.jmedchem.8b01923]

5. Tehrani KHME, Wade N, Mashayekhi V, Brüchle NC, Jespers W, Voskuil K, Pesce D, van Haren MJ, van Westen GJP, Martin NI..  (2021)  Novel Cephalosporin Conjugates Display Potent and Selective Inhibition of Imipenemase-Type Metallo-β-Lactamases.,  64  (13.0): [PMID:34182755] [10.1021/acs.jmedchem.1c00362]

Source

Source(3):

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