Cefoselis

ID: ALA2105940

Cas Number: 122841-10-5

PubChem CID: 5748845

Product Number: C608456, Order Now?

Max Phase: Phase

Molecular Formula: C19H22N8O6S2

Molecular Weight: 522.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[n+]3ccc(N)n3CCO)CS[C@H]12)c1csc(N)n1

Standard InChI:  InChI=1S/C19H22N8O6S2/c1-33-24-12(10-8-35-19(21)22-10)15(29)23-13-16(30)27-14(18(31)32)9(7-34-17(13)27)6-25-3-2-11(20)26(25)4-5-28/h2-3,8,13,17,20,28H,4-7H2,1H3,(H4,21,22,23,29,31,32)/b24-12-/t13-,17-/m1/s1

Standard InChI Key:  BHXLLRXDAYEMPP-SBGRAJFYSA-N

Molfile:  

     RDKit          2D

 36 39  0  0  1  0  0  0  0  0999 V2000
    0.8542    0.3458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.3125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542    0.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4583   -0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -0.3125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208   -0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0833   -0.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4208   -0.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -0.6792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417    0.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167    0.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5875   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292    0.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542    1.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2250   -1.2625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208    0.3458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833    0.8083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708   -1.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    1.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8167    1.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -1.1000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2708   -0.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208    0.9333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -1.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208    1.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6085   -1.3236    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4  1  1  0
  5 17  1  0
  6  7  2  0
  7  1  1  0
  8 10  1  0
  9  5  1  0
 10 13  1  0
 11  8  1  0
  3 12  1  6
 13 12  1  0
  4 14  1  0
 15  9  1  0
 16 19  1  0
 17  6  1  0
 18 11  2  0
 19  5  2  0
 20  7  1  0
 21  8  2  0
 22 21  1  0
 23  6  1  0
 24 10  2  0
 25  2  2  0
 26 13  2  0
 27 20  1  0
 28 20  2  0
 29  9  1  0
 30 15  1  0
 31 18  1  0
 32 24  1  0
 33 34  1  0
 34 29  1  0
 35 32  1  0
  2  3  1  0
 14 23  1  0
 15 16  2  0
 18 22  1  0
  4 36  1  1
M  CHG  2   5   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2105940

   cefoselis

2. Alternative Forms:

   

   ALA2105940

   Niosh/XI0367350

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: 522.57

Molecular Weight (Monoisotopic): 522.1104

AlogP: -3.16

#Rotatable Bonds: 9

Polar Surface Area: 205.10

Molecular Species: ACID

HBA: 13

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.78

CX Basic pKa: 3.44

CX LogP: -5.40

CX LogD: -4.71

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.11

Np Likeness Score: -0.17

References

1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V..  (2000)  beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter.,  275  (1): [PMID:10636865] [10.1074/jbc.275.3.1699]

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

3. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

4. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(3):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names
• TP-search Transporter Database