NP-MRD: Showing NP-Card for (2s,5r,6r)-6-{[(2r)-2-carboxy-1-hydroxy-2-(thiophen-3-yl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (NP0217440)

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Record Information

Version

2.0

Created at

2022-09-05 17:47:19 UTC

Updated at

2022-09-05 17:47:20 UTC

NP-MRD ID

NP0217440

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,5r,6r)-6-{[(2r)-2-carboxy-1-hydroxy-2-(thiophen-3-yl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Description

Ticarcillin, also known as TIPC or ticillin, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Ticarcillin is a drug which is used for the treatment of bacterial infections. Ticarcillin is an extremely weak basic (essentially neutral) compound (based on its pKa). (2s,5r,6r)-6-{[(2r)-2-carboxy-1-hydroxy-2-(thiophen-3-yl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is found in Apis cerana. (2s,5r,6r)-6-{[(2r)-2-carboxy-1-hydroxy-2-(thiophen-3-yl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid was first documented in 2014 (PMID: 23775821). A penicillin compound having a 6beta-amino side-group (PMID: 24369293).

Structure

MOL 3D MOL SDF PDB SMILES InChI

1607
  Mrv0541 02231215352D          

 26 28  0  0  1  0            999 V2000
    7.3584    0.3193    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8619    0.0884    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1597   -1.3486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0613   -2.4133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4203   -1.9718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1472   -0.3560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4132    2.4060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7928    2.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5737   -0.7607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1597    0.6523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5737    0.0644    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8433   -0.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3584   -1.0156    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7419    0.0677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7419   -0.7641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5107   -0.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5107    0.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6133   -1.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3624    0.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7803    1.0250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9829    0.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9954    1.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6857    0.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4718    0.7164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  2 24  1  0  0  0  0
  2 25  1  0  0  0  0
  3 15  2  0  0  0  0
  4 18  1  0  0  0  0
  5 18  2  0  0  0  0
  6 19  2  0  0  0  0
  7 22  1  0  0  0  0
  8 22  2  0  0  0  0
  9 11  1  0  0  0  0
  9 13  1  0  0  0  0
  9 15  1  0  0  0  0
 14 10  1  1  0  0  0
 10 19  1  0  0  0  0
 11 14  1  0  0  0  0
 11 26  1  6  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  6  0  0  0
 14 15  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  2  0  0  0  0
 23 25  2  0  0  0  0
M  END

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -4.2452   -0.7889   -1.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2626   -0.9135   -0.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7539   -1.8395    0.8672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7005   -1.5643   -0.9488 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3173    0.0545   -1.6576 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0031    0.6727   -1.3851 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7078    0.2506   -0.2302 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1094    0.0512   -0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7164    0.2572   -1.3683 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8845   -0.3918    0.9200 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7861    0.5780    2.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3450    0.2290    3.1477 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1774    1.8943    1.8546 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3338   -0.4945    0.4928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0100   -1.6481    0.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3185   -1.6097    0.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5560    0.0437   -0.2778 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0029    0.6334    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8777    1.8502   -1.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8483    3.0779   -1.3025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7879    0.9352   -0.5661 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7500    0.3892    0.2845 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8401    1.3872    0.4930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8032    1.0930    1.2266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7891    2.6191   -0.1141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086    0.0072   -2.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2419   -1.7600   -1.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2737   -0.6077   -1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9546   -2.5279    1.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0910   -1.2604    1.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6137   -2.4069    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7278    0.2797   -2.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6529    0.8190   -2.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2095    0.0827    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4703   -1.3800    1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5127    2.5379    1.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5810   -2.6336    0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0259   -2.4552   -0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6307    1.6661    0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3594    0.1624    1.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8811    2.7107   -1.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  2 22  1  0
 22 21  1  0
 21 19  1  0
 19 20  2  0
 19  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
 10 14  1  0
 14 18  2  0
 18 17  1  0
 17 16  1  0
 16 15  2  0
 22 23  1  0
 23 25  1  0
 23 24  2  0
 21  5  1  0
 15 14  1  0
  6  5  1  0
  5 32  1  6
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
 22 40  1  1
  6 33  1  6
  7 34  1  0
 10 35  1  1
 13 36  1  0
 18 39  1  0
 16 38  1  0
 15 37  1  0
 25 41  1  0
M  END

1607
  Mrv0541 02231215352D          

 26 28  0  0  1  0            999 V2000
    7.3584    0.3193    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8619    0.0884    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1597   -1.3486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0613   -2.4133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4203   -1.9718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1472   -0.3560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4132    2.4060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7928    2.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5737   -0.7607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1597    0.6523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5737    0.0644    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8433   -0.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3584   -1.0156    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7419    0.0677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7419   -0.7641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5107   -0.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5107    0.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6133   -1.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3624    0.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7803    1.0250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9829    0.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9954    1.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6857    0.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4718    0.7164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  2 24  1  0  0  0  0
  2 25  1  0  0  0  0
  3 15  2  0  0  0  0
  4 18  1  0  0  0  0
  5 18  2  0  0  0  0
  6 19  2  0  0  0  0
  7 22  1  0  0  0  0
  8 22  2  0  0  0  0
  9 11  1  0  0  0  0
  9 13  1  0  0  0  0
  9 15  1  0  0  0  0
 14 10  1  1  0  0  0
 10 19  1  0  0  0  0
 11 14  1  0  0  0  0
 11 26  1  6  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  6  0  0  0
 14 15  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  2  0  0  0  0
 23 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0217440

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](C(O)=O)C1=CSC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H16N2O6S2/c1-15(2)9(14(22)23)17-11(19)8(12(17)25-15)16-10(18)7(13(20)21)6-3-4-24-5-6/h3-5,7-9,12H,1-2H3,(H,16,18)(H,20,21)(H,22,23)/t7-,8-,9+,12-/m1/s1

> <INCHI_KEY>
OHKOGUYZJXTSFX-KZFFXBSXSA-N

> <FORMULA>
C15H16N2O6S2

> <MOLECULAR_WEIGHT>
384.427

> <EXACT_MASS>
384.044977634

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
36.14269831493392

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,5R,6R)-6-[(2R)-2-carboxy-2-(thiophen-3-yl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
0.5957987833333339

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.122551213409252

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0920584971992358

> <JCHEM_PKA_STRONGEST_BASIC>
-6.31815645554628

> <JCHEM_POLAR_SURFACE_AREA>
124.01

> <JCHEM_REFRACTIVITY>
87.92530000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ticarcillin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1607                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      13.736   0.596   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0       3.476   0.165   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       9.631  -2.517   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.181  -4.505   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      15.718  -3.681   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       7.741  -0.665   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       6.371   4.491   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       8.947   3.795   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      12.271  -1.420   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       9.631   1.218   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      12.271   0.120   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.641  -0.650   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.736  -1.896   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.718   0.126   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.718  -1.426   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.887  -1.555   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.887   0.255   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.211  -3.360   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.143   0.822   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.057   1.913   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.568   1.518   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.458   3.400   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.373   2.489   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.013   0.081   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080   1.653   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0      12.081   1.337   0.000  0.00  0.00           H+0
CONECT    1   11   12                                                       
CONECT    2   24   25                                                       
CONECT    3   15                                                            
CONECT    4   18                                                            
CONECT    5   18                                                            
CONECT    6   19                                                            
CONECT    7   22                                                            
CONECT    8   22                                                            
CONECT    9   11   13   15                                                  
CONECT   10   14   19                                                       
CONECT   11    1    9   14   26                                             
CONECT   12    1   13   16   17                                             
CONECT   13    9   12   18                                                  
CONECT   14   10   11   15                                                  
CONECT   15    3    9   14                                                  
CONECT   16   12                                                            
CONECT   17   12                                                            
CONECT   18    4    5   13                                                  
CONECT   19    6   10   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   23   24                                                  
CONECT   22    7    8   20                                                  
CONECT   23   21   25                                                       
CONECT   24    2   21                                                       
CONECT   25    2   23                                                       
CONECT   26   11                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

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Synonyms

Value	Source
(2S,5R,6R)-6-{[(2R)-2-carboxy-2-thiophen-3-ylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
alpha-Carboxy-3-thienylmethylpenicillin	ChEBI
Ticarcilina	ChEBI
Ticarcilline	ChEBI
Ticarcillinum	ChEBI
TIPC	Kegg
Ticillin	Kegg
(2S,5R,6R)-6-{[(2R)-2-carboxy-2-thiophen-3-ylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
a-Carboxy-3-thienylmethylpenicillin	Generator
Α-carboxy-3-thienylmethylpenicillin	Generator
Ticarcillin supplement	HMDB
Ticar	HMDB
Ticarcillin disodium	HMDB
Ticarpen	HMDB
SmithKline beecham brand OF ticarcillin disodium salt	HMDB
Tarcil	HMDB
GlaxoSmithKline brand OF ticarcillin disodium	HMDB
CSL Brand OF ticarcillin disodium	HMDB
Disodium, ticarcillin	HMDB
GlaxoSmithKline brand OF ticarcillin disodium salt	HMDB
SmithKline beecham brand OF ticarcillin disodium	HMDB

Chemical Formula

C₁₅H₁₆N₂O₆S₂

Average Mass

384.4270 Da

Monoisotopic Mass

384.04498 Da

IUPAC Name

(2S,5R,6R)-6-[(2R)-2-carboxy-2-(thiophen-3-yl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

ticarcillin

CAS Registry Number

Not Available

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](C(O)=O)C1=CSC=C1)C(O)=O

InChI Identifier

InChI=1S/C15H16N2O6S2/c1-15(2)9(14(22)23)17-11(19)8(12(17)25-15)16-10(18)7(13(20)21)6-3-4-24-5-6/h3-5,7-9,12H,1-2H3,(H,16,18)(H,20,21)(H,22,23)/t7-,8-,9+,12-/m1/s1

InChI Key

OHKOGUYZJXTSFX-KZFFXBSXSA-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 dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Penicillin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Penam
Dicarboxylic acid or derivatives
1,3-dicarbonyl compound
Beta-lactam
Tertiary carboxylic acid amide
Thiazolidine
Thiophene
Heteroaromatic compound
Azetidine
Secondary carboxylic acid amide
Carboxamide group
Lactam
Hemithioaminal
Thioether
Azacycle
Organoheterocyclic compound
Dialkylthioether
Carboxylic acid
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

penicillin (CHEBI:9587 )

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	0.99	ALOGPS
logP	0.6	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	3.09	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	124.01 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.93 m³·mol⁻¹	ChemAxon
Polarizability	36.14 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015545

DrugBank ID

DB01607

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

33876

KEGG Compound ID

C07139

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ticarcillin

METLIN ID

Not Available

PubChem Compound

36921

PDB ID

Not Available

ChEBI ID

9587

Good Scents ID

Not Available

References

General References

Zobell JT, Ferdinand C, Young DC: Continuous infusion meropenem and ticarcillin-clavulanate in pediatric cystic fibrosis patients. Pediatr Pulmonol. 2014 Mar;49(3):302-6. doi: 10.1002/ppul.22820. Epub 2013 Jun 17. [PubMed:23775821 ]
Pitondo-Silva A, Martins VV, Fernandes AF, Stehling EG: High level of resistance to aztreonam and ticarcillin in Pseudomonas aeruginosa isolated from soil of different crops in Brazil. Sci Total Environ. 2014 Mar 1;473-474:155-8. doi: 10.1016/j.scitotenv.2013.12.021. Epub 2013 Dec 22. [PubMed:24369293 ]
LOTUS database [Link]

Showing NP-Card for (2s,5r,6r)-6-{[(2r)-2-carboxy-1-hydroxy-2-(thiophen-3-yl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (NP0217440)

MOL for NP0217440 ((2s,5r,6r)-6-{[(2r)-2-carboxy-1-hydroxy-2-(thiophen-3-yl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D MOL for NP0217440 ((2s,5r,6r)-6-{[(2r)-2-carboxy-1-hydroxy-2-(thiophen-3-yl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D SDF for NP0217440 ((2s,5r,6r)-6-{[(2r)-2-carboxy-1-hydroxy-2-(thiophen-3-yl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D-SDF for NP0217440 ((2s,5r,6r)-6-{[(2r)-2-carboxy-1-hydroxy-2-(thiophen-3-yl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

PDB for NP0217440 ((2s,5r,6r)-6-{[(2r)-2-carboxy-1-hydroxy-2-(thiophen-3-yl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D PDB for NP0217440 ((2s,5r,6r)-6-{[(2r)-2-carboxy-1-hydroxy-2-(thiophen-3-yl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

SMILES for NP0217440 ((2s,5r,6r)-6-{[(2r)-2-carboxy-1-hydroxy-2-(thiophen-3-yl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

INCHI for NP0217440 ((2s,5r,6r)-6-{[(2r)-2-carboxy-1-hydroxy-2-(thiophen-3-yl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

Structure for NP0217440 ((2s,5r,6r)-6-{[(2r)-2-carboxy-1-hydroxy-2-(thiophen-3-yl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D Structure for NP0217440 ((2s,5r,6r)-6-{[(2r)-2-carboxy-1-hydroxy-2-(thiophen-3-yl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)