NP-MRD: Showing NP-Card for (6r,7r)-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-3-{[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0221453)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-05 23:02:06 UTC

Updated at

2022-09-05 23:02:06 UTC

NP-MRD ID

NP0221453

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6r,7r)-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-3-{[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Description

Ceftriaxone, also known as rocephin or CTRX, belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. Ceftriaxone is a drug which is used for the treatment of the infections (respiratory, skin, soft tissue, uti, ent) caused by s. Pneumoniae, h. Influenzae, staphylococci, s. Pyogenes (group a beta-hemolytic streptococci), e. Coli, p. Mirabilis, klebsiella sp, coagulase-negative staph. Ceftriaxone is a strong basic compound (based on its pKa). Ceftriaxone is a potentially toxic compound. (6r,7r)-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-3-{[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is found in Apis cerana. It was first documented in 2000 (PMID: 11067716). A third-generation cephalosporin compound having 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetylamino and methyl side-groups (PMID: 11431418) (PMID: 11285492) (PMID: 11432680) (PMID: 11529382).

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv0541 02231215192D          
 
 37 40  0  0  1  0            999 V2000
   14.6027  -10.7254    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.6027  -11.5092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3451  -11.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0463  -11.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0463  -10.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3451  -10.3129    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.7777  -10.7254    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7777  -11.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0765  -10.3129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3752  -10.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3752  -11.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0765  -11.9216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6740  -10.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7476  -11.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9315  -10.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6027   -9.9004    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2715  -10.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6115  -10.7254    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.8590  -11.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6840  -11.5504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6740   -9.4467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3451  -12.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0463  -13.2004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6027  -13.1591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4488  -11.5504    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.1501  -11.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3641  -12.2103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1501  -12.7879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8513  -13.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5938  -12.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5938  -11.9629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8513  -11.5504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8513  -14.0254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2950  -13.2004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8513  -10.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3854   -9.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3854   -8.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  2  0  0  0  0
 10 13  1  0  0  0  0
  4 14  1  0  0  0  0
 13 15  1  0  0  0  0
  1 16  1  6  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 13 21  2  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 26 32  1  0  0  0  0
 29 33  2  0  0  0  0
 30 34  2  0  0  0  0
 32 35  1  0  0  0  0
 21 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    1.2852    2.5200   -1.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6714    1.7411   -0.3192 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9534    1.8624    0.0874 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872    0.9408    0.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4196   -0.4312    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2520   -1.3728    0.5870 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1654   -0.9413   -0.0876 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9888   -2.3951   -0.1085 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4006   -2.9338   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051   -3.2324   -2.4720 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1097   -2.9620   -0.7909 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3018   -3.0081   -0.9396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8358   -4.0120   -1.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0507   -4.8639   -2.4017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1538   -4.1672   -2.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0756   -2.1023   -0.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5378   -2.1637   -0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3191   -0.7491   -1.1959 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1147    0.7370   -0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0624    1.5304   -0.4786 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8711    2.6766    0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8629    3.3890   -0.0261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8000    3.0109    1.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6326    4.0694    1.8268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8506    2.1972    1.3785 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0041    1.0855    0.6771 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1485    0.2540    0.9406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4480   -1.0136    0.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2056   -1.8122    1.5655 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7311   -2.9199    0.5140 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1757    1.3396    0.8063 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1475    0.4376    1.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4729    1.4740    1.5278 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.7072    2.9767    1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2450    4.3064    1.3315 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5010    2.5992    0.8547 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6306    3.5812   -1.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8583    2.1492   -2.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046    2.5042   -1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3961   -0.3202   -0.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8693   -2.9846    0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4351   -4.4524   -3.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9989   -3.0793   -0.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9036   -2.1151    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5424    2.4701    2.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0246    0.5692    0.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4475    0.3014    2.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9282   -0.8290    0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2568   -0.5831    1.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9855   -0.2481   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8497   -3.9124    1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1845   -0.6400    1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6384    5.0871    1.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2472    4.4345    1.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  1  0
 29 28  1  0
 28 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 16 12  2  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  4 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
 11 30  1  0
 36 31  1  0
  8 30  1  0
 26 19  1  0
 30 51  1  1
 28 49  1  0
 28 50  1  0
 17 43  1  0
 17 44  1  0
 25 45  1  0
 27 46  1  0
 27 47  1  0
 27 48  1  0
  8 41  1  1
  7 40  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
 32 52  1  0
 35 53  1  0
 35 54  1  0
 15 42  1  0
M  END

 
  Mrv0541 02231215192D          
 
 37 40  0  0  1  0            999 V2000
   14.6027  -10.7254    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.6027  -11.5092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3451  -11.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0463  -11.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0463  -10.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3451  -10.3129    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.7777  -10.7254    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7777  -11.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0765  -10.3129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3752  -10.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3752  -11.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0765  -11.9216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6740  -10.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7476  -11.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9315  -10.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6027   -9.9004    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2715  -10.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6115  -10.7254    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.8590  -11.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6840  -11.5504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6740   -9.4467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3451  -12.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0463  -13.2004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6027  -13.1591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4488  -11.5504    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.1501  -11.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3641  -12.2103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1501  -12.7879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8513  -13.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5938  -12.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5938  -11.9629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8513  -11.5504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8513  -14.0254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2950  -13.2004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8513  -10.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3854   -9.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3854   -8.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  2  0  0  0  0
 10 13  1  0  0  0  0
  4 14  1  0  0  0  0
 13 15  1  0  0  0  0
  1 16  1  6  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 13 21  2  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 26 32  1  0  0  0  0
 29 33  2  0  0  0  0
 30 34  2  0  0  0  0
 32 35  1  0  0  0  0
 21 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221453

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12SCC(CSC3=NC(=O)C(=O)NN3C)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C1=CSC(N)=N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H18N8O7S3/c1-25-18(22-12(28)13(29)23-25)36-4-6-3-34-15-9(14(30)26(15)10(6)16(31)32)21-11(27)8(24-33-2)7-5-35-17(19)20-7/h5,9,15H,3-4H2,1-2H3,(H2,19,20)(H,21,27)(H,23,29)(H,31,32)/b24-8-/t9-,15-/m1/s1

> <INCHI_KEY>
VAAUVRVFOQPIGI-SPQHTLEESA-N

> <FORMULA>
C18H18N8O7S3

> <MOLECULAR_WEIGHT>
554.58

> <EXACT_MASS>
554.04605704

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
51.46712614184927

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <ALOGPS_LOGP>
-0.01

> <JCHEM_LOGP>
-1.7888243581242869

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.963583946696243

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1880236213884396

> <JCHEM_PKA_STRONGEST_BASIC>
4.166923225318286

> <JCHEM_POLAR_SURFACE_AREA>
208.98000000000002

> <JCHEM_REFRACTIVITY>
128.46669999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ceftriaxone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      27.258 -20.021   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      27.258 -21.484   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      28.644 -22.254   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.953 -21.484   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.953 -20.021   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0      28.644 -19.251   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0      25.718 -20.021   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.718 -21.484   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      24.409 -19.251   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      23.100 -20.021   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      23.100 -21.484   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      24.409 -22.254   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      21.791 -19.251   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.262 -22.331   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.405 -20.021   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      27.258 -18.481   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0      19.173 -19.097   0.000  0.00  0.00           C+0
HETATM   18  S   UNK     0      17.941 -20.021   0.000  0.00  0.00           S+0
HETATM   19  C   UNK     0      18.403 -21.561   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      19.943 -21.561   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0      21.791 -17.634   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      28.644 -23.794   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      29.953 -24.641   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      27.258 -24.564   0.000  0.00  0.00           O+0
HETATM   25  S   UNK     0      32.571 -21.561   0.000  0.00  0.00           S+0
HETATM   26  C   UNK     0      33.880 -22.331   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      17.480 -22.793   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0      33.880 -23.871   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      35.189 -24.641   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      36.575 -23.871   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      36.575 -22.331   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0      35.189 -21.561   0.000  0.00  0.00           N+0
HETATM   33  O   UNK     0      35.189 -26.181   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      37.884 -24.641   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      35.189 -20.021   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      23.119 -16.852   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      23.119 -15.312   0.000  0.00  0.00           C+0
CONECT    1    2    6    7   16                                             
CONECT    2    1    3    8                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8    9                                                  
CONECT    8    7    2   12                                                  
CONECT    9    7   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10                                                            
CONECT   12    8                                                            
CONECT   13   10   15   21                                                  
CONECT   14    4   25                                                       
CONECT   15   13   17   20                                                  
CONECT   16    1                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   15                                                       
CONECT   21   13   36                                                       
CONECT   22    3   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   14   26                                                       
CONECT   26   25   28   32                                                  
CONECT   27   19                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   33                                                  
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   26   35                                                  
CONECT   33   29                                                            
CONECT   34   30                                                            
CONECT   35   32                                                            
CONECT   36   21   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	ChEBI
Ceftriaxona	ChEBI
Ceftriaxonum	ChEBI
Rocephin	ChEBI
CTRX	Kegg
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulphanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulphanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	Generator
Cefatriaxone	HMDB
Ceftriazone	HMDB
Benaxona	HMDB
Irex brand OF ceftriaxone	HMDB
Longacef	HMDB
Longaceph	HMDB
Pisa brand OF ceftriaxone sodium	HMDB
Terbac	HMDB
Ceftrex	HMDB
Ceftriaxon hexal	HMDB
Ceftriaxone sodium, anhydrous	HMDB
Ceftriaxone, disodium salt, hemiheptahydrate	HMDB
Columbia brand OF ceftriaxone	HMDB
Hexal brand OF ceftriaxone sodium	HMDB
Hoffman-la roche brand OF ceftriaxone sodium	HMDB
Rocefalin	HMDB
Syntex brand OF ceftriaxone sodium	HMDB
Ceftriaxon	HMDB
Ceftriaxon curamed	HMDB
Ceftriaxona LDP torlan	HMDB
Ceftriaxone sodium	HMDB
Ceftriaxone, disodium salt	HMDB
Anhydrous ceftriaxone sodium	HMDB
Boehringer mannheim brand OF ceftriaxone sodium	HMDB
Cefaxona	HMDB
Ceftriaxona andreu	HMDB
Ceftriaxone irex	HMDB
Curamed brand OF ceftriaxone sodium	HMDB
Fustery brand OF ceftriaxone sodium	HMDB
Galen brand OF ceftriaxone sodium	HMDB
Inibsa brand OF ceftriaxone sodium	HMDB
Lendacin	HMDB
Roche brand OF ceftriaxone sodium	HMDB
Hoffman la roche brand OF ceftriaxone sodium	HMDB
Rocefin	HMDB
Rocephine	HMDB
Sodium, ceftriaxone	HMDB
Tacex	HMDB

Chemical Formula

C₁₈H₁₈N₈O₇S₃

Average Mass

554.5800 Da

Monoisotopic Mass

554.04606 Da

IUPAC Name

(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

ceftriaxone

CAS Registry Number

Not Available

SMILES

[H][C@]12SCC(CSC3=NC(=O)C(=O)NN3C)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C1=CSC(N)=N1)C(O)=O

InChI Identifier

InChI=1S/C18H18N8O7S3/c1-25-18(22-12(28)13(29)23-25)36-4-6-3-34-15-9(14(30)26(15)10(6)16(31)32)21-11(27)8(24-33-2)7-5-35-17(19)20-7/h5,9,15H,3-4H2,1-2H3,(H2,19,20)(H,21,27)(H,23,29)(H,31,32)/b24-8-/t9-,15-/m1/s1

InChI Key

VAAUVRVFOQPIGI-SPQHTLEESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminoglycosides

Alternative Parents

Substituents

Aminoglycoside core
Macrolide
Glycosyl compound
O-glycosyl compound
Oxane
Monosaccharide
Tertiary alcohol
1,2-aminoalcohol
Amino acid or derivatives
Carboxylic acid ester
Ketone
Cyclic ketone
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Lactone
Acetal
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Amine
Organopnictogen compound
Organonitrogen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

macrolide antibiotic (CHEBI:3732 )
Macrolides and lactone polyketides (C06912 )
Macrolides and lactone polyketides (LMPK04000014 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.01	ALOGPS
logP	-1.8	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	3.19	ChemAxon
pKa (Strongest Basic)	4.17	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	208.98 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	128.47 m³·mol⁻¹	ChemAxon
Polarizability	51.47 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0015343

DrugBank ID

DB01212

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4586394

KEGG Compound ID

C06683

BioCyc ID

CPD-12294

BiGG ID

Not Available

Wikipedia Link

Ceftriaxone

METLIN ID

Not Available

PubChem Compound

5479530

PDB ID

Not Available

ChEBI ID

29007

Good Scents ID

Not Available

References

General References

von Greyerz S, Bultemann G, Schnyder K, Burkhart C, Lotti B, Hari Y, Pichler WJ: Degeneracy and additional alloreactivity of drug-specific human alpha beta(+) T cell clones. Int Immunol. 2001 Jul;13(7):877-85. doi: 10.1093/intimm/13.7.877. [PubMed:11431418 ]
Authors unspecified: Ceftriaxone and otitis in children: new indication. Only in special circumstances. Prescrire Int. 2000 Aug;9(48):99-102. [PubMed:11067716 ]
Ghenghesh KS, El-Ghodban A, Dkakni R, Abeid S, Altomi A, Abdussalam T, Marialigeti K: Prevalence, species differentiation, haemolytic activity, and antibiotic susceptibility of aeromonads in untreated well water. Mem Inst Oswaldo Cruz. 2001 Feb;96(2):169-73. doi: 10.1590/s0074-02762001000200006. [PubMed:11285492 ]
Mazza A: Ceftriaxone as short-term antibiotic prophylaxis in orthopedic surgery: a cost-benefit analysis involving 808 patients. J Chemother. 2000 Sep;12 Suppl 3:29-33. doi: 10.1080/1120009x.2000.11782305. [PubMed:11432680 ]
Vilaichone A, Watana D, Chaiwatanarat T: Oral ceftibuten switch therapy for acute pyelonephritis in children. J Med Assoc Thai. 2001 Jun;84 Suppl 1:S61-7. [PubMed:11529382 ]
LOTUS database [Link]

Showing NP-Card for (6r,7r)-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-3-{[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0221453)

MOL for NP0221453 ((6r,7r)-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-3-{[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D MOL for NP0221453 ((6r,7r)-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-3-{[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D SDF for NP0221453 ((6r,7r)-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-3-{[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D-SDF for NP0221453 ((6r,7r)-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-3-{[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

PDB for NP0221453 ((6r,7r)-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-3-{[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D PDB for NP0221453 ((6r,7r)-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-3-{[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

SMILES for NP0221453 ((6r,7r)-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-3-{[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

INCHI for NP0221453 ((6r,7r)-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-3-{[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

Structure for NP0221453 ((6r,7r)-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-3-{[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D Structure for NP0221453 ((6r,7r)-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-3-{[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)