Cefluprenam

ID: ALA2074822

Cas Number: 116853-25-9

PubChem CID: 6536774

Product Number: C608452, Order Now?

Max Phase: Phase

Molecular Formula: C20H25FN8O6S2

Molecular Weight: 556.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[N+](C)(C/C=C/C1=C(C(=O)[O-])N2C(=O)[C@@H](NC(=O)/C(=N\OCF)c3nsc(N)n3)[C@H]2SC1)CC(N)=O

Standard InChI:  InChI=1S/C20H25FN8O6S2/c1-3-29(2,7-11(22)30)6-4-5-10-8-36-18-13(17(32)28(18)14(10)19(33)34)24-16(31)12(26-35-9-21)15-25-20(23)37-27-15/h4-5,13,18H,3,6-9H2,1-2H3,(H5-,22,23,24,25,27,30,31,33,34)/b5-4+,26-12-/t13-,18-,29?/m1/s1

Standard InChI Key:  XAKKNLNAJBNLPC-MAYKBZFQSA-N

Molfile:  

     RDKit          2D

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    5.2628    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5635   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9924   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 11 10  1  0
 11 12  1  0
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  8 13  1  0
 11 14  1  0
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 14 29  1  0
 10 29  1  0
 29 30  2  0
  9 31  1  0
 31 32  1  0
 31 33  2  0
  3 34  1  0
 34 35  1  0
 35 36  1  0
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 11 38  1  6
M  CHG  2   3   1  32  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2074822

   cefluprenam

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: 556.60

Molecular Weight (Monoisotopic): 556.1323

AlogP: -2.32

#Rotatable Bonds: 12

Polar Surface Area: 206.02

Molecular Species: ACID

HBA: 12

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.14

CX Basic pKa: 0.07

CX LogP: -5.19

CX LogD: -4.48

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.11

Np Likeness Score: -0.08

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]

Source

Source(3):

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