NP-MRD: Showing NP-Card for (6r,7s)-3-[(acetyloxy)methyl]-7-{[(5s)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0207351)

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Record Information

Version

2.0

Created at

2022-09-05 03:55:44 UTC

Updated at

2022-09-05 03:55:45 UTC

NP-MRD ID

NP0207351

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(6R,7S)-3-[(acetyloxy)methyl]-7-{[(5S)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]Oct-2-ene-2-carboxylic acid belongs to the class of organic compounds known as cephalosporin 3'-esters. These are cephalosporins that are esterified at the 3'-position. (6r,7s)-3-[(acetyloxy)methyl]-7-{[(5s)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is found in Streptomyces microflavus. Based on a literature review very few articles have been published on (6R,7S)-3-[(acetyloxy)methyl]-7-{[(5S)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]Oct-2-ene-2-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052205552D          

 30 31  0  0  1  0            999 V2000
    1.8414   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5559   -0.3020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1283   -1.5395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9134   -1.9239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  4  5  2  0  0  0  0
  5  6  1  4  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  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
 19 21  1  0  0  0  0
 18 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 17  1  6  0  0  0
  3 30  1  0  0  0  0
M  END

     RDKit          3D

 53 54  0  0  0  0  0  0  0  0999 V2000
   -0.7643    2.3591   -2.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8755    0.9834   -2.4316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1479    0.3535   -1.4250 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6263    0.6596   -0.1283 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7944    0.5039    0.3528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9785    0.8960    1.6676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8702   -0.0592   -0.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0675    0.7970   -0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8206    1.1800    0.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4171    0.0635    1.3936 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5044   -0.9022    1.9076 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4670   -0.6708    0.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4414   -1.9224    0.4997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5091    0.0359   -0.0160 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1416   -1.0695   -1.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233   -2.0586   -2.1434 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4894   -0.7968   -1.3873 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7424   -1.3292   -0.9371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2840   -2.4660   -1.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281   -3.0823   -1.4361 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5634   -2.9465   -2.7867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3395   -0.8111    0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6229   -1.2830    0.6429 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5963   -0.1969    0.6295 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8781   -0.4739    1.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9695    0.5213    1.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1320   -1.6423    1.4816 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6778    0.3361    0.8692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891    1.5390   -0.3947 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3282    0.6152   -1.6547 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1753    2.6254   -1.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2574    2.7095   -2.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4227    2.8613   -2.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6484    1.7403    2.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5245   -0.3233   -1.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1076   -1.0664    0.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7496    1.7291   -1.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7732    0.2647   -1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2632    1.9092    1.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7020    1.7918    0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0049    0.5557    2.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3584   -0.6929    2.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8607   -1.8963    1.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9258    0.7986    0.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6775   -2.3964   -3.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1178   -2.0830    0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5220   -1.6262    1.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5063    1.5272    0.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5732    0.4617    2.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6499    0.3500    0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3881    0.7537    1.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7775   -0.0751    1.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5716    0.9487   -2.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  1
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 14  1  0
 12 13  2  0
  3 30  1  0
 30 29  1  0
 29 28  1  0
 28 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 22 18  2  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 18 19  1  0
 19 21  1  0
 19 20  2  0
 15  3  1  0
 17 30  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  1
 11 42  1  0
 11 43  1  0
 14 44  1  0
 30 53  1  6
 28 51  1  0
 28 52  1  0
 23 46  1  0
 23 47  1  0
 26 48  1  0
 26 49  1  0
 26 50  1  0
 21 45  1  0
M  END


  Mrv1652309052205552D          

 30 31  0  0  1  0            999 V2000
    1.8414   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5559   -0.3020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1283   -1.5395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9134   -1.9239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  4  5  2  0  0  0  0
  5  6  1  4  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  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
 19 21  1  0  0  0  0
 18 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 17  1  6  0  0  0
  3 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0207351

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@]1(N=C(O)CCC[C@H](N)C(O)=O)[C@H]2SCC(COC(C)=O)=C(N2C1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H23N3O9S/c1-8(21)29-6-9-7-30-16-17(28-2,15(27)20(16)12(9)14(25)26)19-11(22)5-3-4-10(18)13(23)24/h10,16H,3-7,18H2,1-2H3,(H,19,22)(H,23,24)(H,25,26)/t10-,16+,17-/m0/s1

> <INCHI_KEY>
ORQHMODRGXTBFU-HKJPBSJPSA-N

> <FORMULA>
C17H23N3O9S

> <MOLECULAR_WEIGHT>
445.44

> <EXACT_MASS>
445.115500507

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
42.491585370183884

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R,7S)-3-[(acetyloxy)methyl]-7-{[(5S)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <JCHEM_LOGP>
-2.9324175309295963

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.6441118380873427

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.607576865966927

> <JCHEM_PKA_STRONGEST_BASIC>
9.52705133806539

> <JCHEM_POLAR_SURFACE_AREA>
189.04999999999998

> <JCHEM_REFRACTIVITY>
102.24249999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(6R,7S)-3-[(acetyloxy)methyl]-7-{[(5S)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       3.437  -4.001   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.207  -2.667   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.437  -1.334   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       4.771  -0.564   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.105  -1.334   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.105  -2.874   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.438  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.772  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.106  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.439  -1.334   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      11.439  -2.874   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      12.773  -0.564   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      14.107  -1.334   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      12.773   0.976   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.104  -2.104   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.705  -3.591   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   29  S   UNK     0       2.667   1.540   0.000  0.00  0.00           S+0
HETATM   30  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15   30                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    3   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   30                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   17    3                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
(6R,7S)-3-[(Acetyloxy)methyl]-7-{[(5S)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator

Chemical Formula

C₁₇H₂₃N₃O₉S

Average Mass

445.4400 Da

Monoisotopic Mass

445.11550 Da

IUPAC Name

(6R,7S)-3-[(acetyloxy)methyl]-7-{[(5S)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

(6R,7S)-3-[(acetyloxy)methyl]-7-{[(5S)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CO[C@]1(N=C(O)CCC[C@H](N)C(O)=O)[C@H]2SCC(COC(C)=O)=C(N2C1=O)C(O)=O

InChI Identifier

InChI=1S/C17H23N3O9S/c1-8(21)29-6-9-7-30-16-17(28-2,15(27)20(16)12(9)14(25)26)19-11(22)5-3-4-10(18)13(23)24/h10,16H,3-7,18H2,1-2H3,(H,19,22)(H,23,24)(H,25,26)/t10-,16+,17-/m0/s1

InChI Key

ORQHMODRGXTBFU-HKJPBSJPSA-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
Streptomyces microflavus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cephalosporin 3'-esters. These are cephalosporins that are esterified at the 3'-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Cephalosporin 3'-esters

Alternative Parents

Substituents

Cephalosporin 3'-ester
Cephamycin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Tricarboxylic acid or derivatives
Meta-thiazine
N-acyl-amine
Fatty amide
Fatty acyl
Tertiary carboxylic acid amide
Carboxylic acid ester
Carboxamide group
Azetidine
Secondary carboxylic acid amide
Amino acid
Amino acid or derivatives
Azacycle
Carboxylic acid derivative
Dialkylthioether
Carboxylic acid
Hemithioaminal
Thioether
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Primary aliphatic amine
Primary amine
Organooxygen compound
Organonitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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	-2.9	ChemAxon
pKa (Strongest Acidic)	1.61	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	189.05 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	102.24 m³·mol⁻¹	ChemAxon
Polarizability	42.49 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

59702359

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162908003

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6r,7s)-3-[(acetyloxy)methyl]-7-{[(5s)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (NP0207351)

MOL for NP0207351 ((6r,7s)-3-[(acetyloxy)methyl]-7-{[(5s)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D MOL for NP0207351 ((6r,7s)-3-[(acetyloxy)methyl]-7-{[(5s)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D SDF for NP0207351 ((6r,7s)-3-[(acetyloxy)methyl]-7-{[(5s)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D-SDF for NP0207351 ((6r,7s)-3-[(acetyloxy)methyl]-7-{[(5s)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

PDB for NP0207351 ((6r,7s)-3-[(acetyloxy)methyl]-7-{[(5s)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D PDB for NP0207351 ((6r,7s)-3-[(acetyloxy)methyl]-7-{[(5s)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

SMILES for NP0207351 ((6r,7s)-3-[(acetyloxy)methyl]-7-{[(5s)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

INCHI for NP0207351 ((6r,7s)-3-[(acetyloxy)methyl]-7-{[(5s)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

Structure for NP0207351 ((6r,7s)-3-[(acetyloxy)methyl]-7-{[(5s)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

3D Structure for NP0207351 ((6r,7s)-3-[(acetyloxy)methyl]-7-{[(5s)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)