NP-MRD: Showing NP-Card for (6r,7r)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0249538)

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Record Information

Version

2.0

Created at

2022-09-07 12:07:08 UTC

Updated at

2022-09-07 12:07:08 UTC

NP-MRD ID

NP0249538

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6r,7r)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Description

(6r,7r)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is found in Sarocladium strictum and Lysobacter lactamgenus.

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv1533006041520192D          
 
 26 27  0  0  1  0            999 V2000
   16.8640  -10.7806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8640   -9.9556    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.5755  -11.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0390  -10.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0390   -9.9556    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.5755   -9.5468    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.2985  -10.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5680  -11.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4562  -11.3635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0090   -9.8259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2985   -9.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0100  -11.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8527  -12.3117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2795  -12.3231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0444   -9.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7253  -10.7882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3330   -9.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0444   -8.4617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6176   -9.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9061   -9.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1946   -9.2024    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4794   -9.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1946   -8.5039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7678   -9.1987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4831  -10.4363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8640   -9.1764    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  1  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  2  0  0  0  0
 10 15  1  0  0  0  0
 12 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  6  0  0  0
 22 24  1  0  0  0  0
 22 25  2  0  0  0  0
  4  5  1  0  0  0  0
  7 11  1  0  0  0  0
  2 26  1  6  0  0  0
M  END

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -5.2766   -1.6728    0.3948 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6502   -0.3600    0.3801 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4287    0.1415   -1.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5800   -0.6947   -1.8880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1725   -0.9342   -1.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979    0.3180   -1.4392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571    1.3864   -1.8031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0549    0.2851   -0.9862 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7050    1.4937   -0.9337 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0461    1.4848   -1.5619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4763    1.6131   -2.7312 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5801    1.2718   -0.2633 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7339    0.8559    0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9982    1.5179    0.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0782    2.4872   -0.6185 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1968    1.1718    0.7818 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6496   -0.1389    1.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7361   -0.5699    2.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1430   -1.8904    2.0709 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2936   -0.8181    1.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0155    0.4407    1.6652 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3388    1.6902    0.4196 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4878   -0.3061    1.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8320    0.7563    1.3802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304   -1.4066    2.0035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8058   -1.7500    1.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9798   -1.6868   -0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4182    0.3397    0.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0295    1.1922   -0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4204    0.2713   -1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1134   -1.6680   -2.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5549   -0.2300   -2.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0839   -1.5077   -0.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6734   -1.6283   -2.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3620   -0.6101   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1232    2.3835   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0931    1.2289    0.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4967    0.1553    2.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2142   -0.6145    3.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6195   -1.9049    1.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3244   -1.4407    2.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1337   -1.4766    0.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3248    2.7370    0.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7352   -1.9128    2.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 17  1  0
 17 18  1  0
 18 19  1  0
 17 13  2  0
 13 12  1  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  2 23  1  0
 23 25  1  0
 23 24  2  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
 12 22  1  0
  9 22  1  0
 22 43  1  1
 20 41  1  0
 20 42  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
  9 36  1  6
  8 35  1  0
  5 33  1  0
  5 34  1  0
  4 31  1  0
  4 32  1  0
  3 29  1  0
  3 30  1  0
  2 28  1  1
  1 26  1  0
  1 27  1  0
 25 44  1  0
 16 37  1  0
M  END

 
  Mrv1533006041520192D          
 
 26 27  0  0  1  0            999 V2000
   16.8640  -10.7806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8640   -9.9556    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.5755  -11.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0390  -10.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0390   -9.9556    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.5755   -9.5468    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.2985  -10.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5680  -11.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4562  -11.3635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0090   -9.8259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2985   -9.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0100  -11.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8527  -12.3117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2795  -12.3231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0444   -9.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7253  -10.7882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3330   -9.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0444   -8.4617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6176   -9.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9061   -9.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1946   -9.2024    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4794   -9.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1946   -8.5039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7678   -9.1987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4831  -10.4363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8640   -9.1764    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  1  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  2  0  0  0  0
 10 15  1  0  0  0  0
 12 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  6  0  0  0
 22 24  1  0  0  0  0
 22 25  2  0  0  0  0
  4  5  1  0  0  0  0
  7 11  1  0  0  0  0
  2 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0249538

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12SCC(CO)=C(N1C(=O)[C@H]2NC(=O)CCC[C@@H](N)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H19N3O7S/c15-7(13(21)22)2-1-3-8(19)16-9-11(20)17-10(14(23)24)6(4-18)5-25-12(9)17/h7,9,12,18H,1-5,15H2,(H,16,19)(H,21,22)(H,23,24)/t7-,9-,12-/m1/s1

> <INCHI_KEY>
XWCFYHBHOFBVIV-JWKOBGCHSA-N

> <FORMULA>
C14H19N3O7S

> <MOLECULAR_WEIGHT>
373.38

> <EXACT_MASS>
373.094371138

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.84761321295444

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R,7R)-7-[(5R)-5-amino-5-carboxypentanamido]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <ALOGPS_LOGP>
-2.74

> <JCHEM_LOGP>
-4.794395895902001

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.713488373083261

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8378710714191882

> <JCHEM_PKA_STRONGEST_BASIC>
9.224842367684785

> <JCHEM_POLAR_SURFACE_AREA>
170.26000000000002

> <JCHEM_REFRACTIVITY>
86.27569999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
deacetylcephalosporin C

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-15         0                                  
HETATM    1  N   UNK     0      31.480 -20.124   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      31.480 -18.584   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.808 -20.922   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.940 -20.124   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.940 -18.584   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0      32.808 -17.821   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0      34.157 -20.138   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.794 -22.226   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      28.852 -21.212   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      28.017 -18.342   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      34.157 -18.584   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.485 -20.908   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      31.458 -22.982   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      34.122 -23.003   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      26.216 -17.178   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      36.821 -20.138   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      24.888 -17.948   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      26.216 -15.795   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      23.553 -17.178   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.225 -17.948   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.897 -17.178   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.562 -17.948   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      20.897 -15.874   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0      18.233 -17.171   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      19.568 -19.481   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0      31.480 -17.129   0.000  0.00  0.00           H+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6   26                                             
CONECT    3    1    7    8                                                  
CONECT    4    1    9    5                                                  
CONECT    5    2   10    4                                                  
CONECT    6    2   11                                                       
CONECT    7    3   12   11                                                  
CONECT    8    3   13   14                                                  
CONECT    9    4                                                            
CONECT   10    5   15                                                       
CONECT   11    6    7                                                       
CONECT   12    7   16                                                       
CONECT   13    8                                                            
CONECT   14    8                                                            
CONECT   15   10   17   18                                                  
CONECT   16   12                                                            
CONECT   17   15   19                                                       
CONECT   18   15                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21   24   25                                                  
CONECT   23   21                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26    2                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
Deacetylcephalosporin C, sodium salt	MeSH
Deacetylcephalosporin C, (6R-(6alpha,7beta))-isomer	MeSH
Deacetylcephalosporin C, potassium salt	MeSH
Deacetylcephalosporin C, monopotassium salt	MeSH
Deacetylcephalosporin C, monosodium salt	MeSH

Chemical Formula

C₁₄H₁₉N₃O₇S

Average Mass

373.3800 Da

Monoisotopic Mass

373.09437 Da

IUPAC Name

(6R,7R)-7-[(5R)-5-amino-5-carboxypentanamido]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

deacetylcephalosporin C

CAS Registry Number

Not Available

SMILES

[H][C@]12SCC(CO)=C(N1C(=O)[C@H]2NC(=O)CCC[C@@H](N)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C14H19N3O7S/c15-7(13(21)22)2-1-3-8(19)16-9-11(20)17-10(14(23)24)6(4-18)5-25-12(9)17/h7,9,12,18H,1-5,15H2,(H,16,19)(H,21,22)(H,23,24)/t7-,9-,12-/m1/s1

InChI Key

XWCFYHBHOFBVIV-JWKOBGCHSA-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
Acremonium strictum	LOTUS Database	35616633
Lysobacter lactamgenus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cephalosporins. Cephalosporins are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]Oct-2-ene-2-carboxylic acid moiety or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Cephalosporins

Alternative Parents

Substituents

Cephalosporin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
D-alpha-amino acid
Medium-chain fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Dicarboxylic acid or derivatives
Fatty amide
Fatty acyl
Meta-thiazine
N-acyl-amine
Tertiary carboxylic acid amide
Amino acid or derivatives
Azetidine
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Azacycle
Dialkylthioether
Hemithioaminal
Thioether
Organic nitrogen compound
Organopnictogen compound
Primary amine
Organic oxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

3-hydroxymethylcephalosporin (CHEBI:18065 )

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	-2.7	ALOGPS
logP	-4.8	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.84	ChemAxon
pKa (Strongest Basic)	9.22	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.26 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	86.28 m³·mol⁻¹	ChemAxon
Polarizability	35.85 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C03112

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

18065

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6r,7r)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0249538)

MOL for NP0249538 ((6r,7r)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D MOL for NP0249538 ((6r,7r)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D SDF for NP0249538 ((6r,7r)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D-SDF for NP0249538 ((6r,7r)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

PDB for NP0249538 ((6r,7r)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D PDB for NP0249538 ((6r,7r)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

SMILES for NP0249538 ((6r,7r)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

INCHI for NP0249538 ((6r,7r)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

Structure for NP0249538 ((6r,7r)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D Structure for NP0249538 ((6r,7r)-7-{[(5r)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)