NP-MRD: Showing NP-Card for (2s,5r,6r)-6-{[(2,6-dimethoxyphenyl)(hydroxy)methylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (NP0256407)

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Record Information

Version

2.0

Created at

2022-09-07 21:13:35 UTC

Updated at

2022-09-07 21:13:36 UTC

NP-MRD ID

NP0256407

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Meticillin, also known as staphcillin or metin, 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. Meticillin is a drug which is used to treat infections caused by susceptible gram-positive bacteria, particularly beta-lactamase-producing organisms such as staphylococcus aureus that would otherwise be resistant to most penicillins. Meticillin is an extremely weak basic (essentially neutral) compound (based on its pKa). (2s,5r,6r)-6-{[(2,6-dimethoxyphenyl)(hydroxy)methylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is found in Diphasiastrum digitatum, Lycopodium deuterodensum, Streptomyces cavourensis and Tanacetum argenteum. (2s,5r,6r)-6-{[(2,6-dimethoxyphenyl)(hydroxy)methylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid was first documented in 2014 (PMID: 24433925). A penicillin that is 6-aminopenicillanic acid in which one of the amino hydrogens is replaced by a 2,6-dimethoxybenzoyl group.

Structure

MOL 3D MOL SDF PDB SMILES InChI

1603
  Mrv0541 02231215352D          

 27 29  0  0  1  0            999 V2000
    7.0379    0.3543    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8393   -1.3137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7409   -2.3783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0999   -1.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8269   -0.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474    0.0516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723    2.0684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2534   -0.7257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8393    0.6873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2534    0.0993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5229   -0.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0379   -0.9806    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4215    0.1028    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4215   -0.7291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1903   -0.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1903    0.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2929   -1.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0420    0.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4598    1.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625    0.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750    1.8564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0803    1.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929    2.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2955    2.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6875    2.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1514    0.7514    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
  2 14  2  0  0  0  0
  3 17  1  0  0  0  0
  4 17  2  0  0  0  0
  5 18  2  0  0  0  0
  6 20  1  0  0  0  0
  6 25  1  0  0  0  0
  7 21  1  0  0  0  0
  7 26  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  1  0  0  0  0
  8 14  1  0  0  0  0
 13  9  1  1  0  0  0
  9 18  1  0  0  0  0
 10 13  1  0  0  0  0
 10 27  1  6  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  6  0  0  0
 13 14  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
 20 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
M  END

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
    5.4915    2.5996   -0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    2.0982   -0.6151 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8700    1.4957    0.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8002    1.3681    1.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4914    0.7596    2.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200    0.2865    2.9820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2903    0.4233    1.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0364   -0.0815    2.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6618   -0.7013    3.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5749    1.0139    0.7696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6046    1.1553   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0114    1.7299   -1.3879 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2749    0.7558   -0.3188 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5424    0.9886   -1.4953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8458    1.6552   -1.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1085    2.8766   -1.0068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5966    0.4605   -1.3732 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6395   -0.5127   -1.3273 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1624   -0.7681   -2.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6755   -0.1561   -3.6457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1906   -1.6591   -2.9711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1388   -1.7093   -0.5751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3491   -1.4780    0.9023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7553   -3.0081   -0.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3465   -1.6682   -0.9832 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3929   -0.1242   -1.9795 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6397    3.4232   -0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5935    3.0449   -1.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2740    1.8462   -0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8091    1.7444    1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2143    0.6540    3.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9153   -0.1914    3.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685   -1.5282    3.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3370   -1.1552    3.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6581   -0.0152    4.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1796    0.2919    0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0228    1.4779   -2.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4916   -0.1098   -0.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9082   -2.4878   -3.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2054   -2.0843    1.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6259   -0.4179    1.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4681   -1.7920    1.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8299   -2.9915   -1.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1965   -3.4326   -1.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5821   -3.7731   -0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4347   -0.3036   -3.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 25  1  0
 25 22  1  0
 22 23  1  0
 22 24  1  0
 22 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 10  3  2  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
 18 19  1  0
 19 21  1  0
 19 20  2  0
 17 26  1  0
  7 10  1  0
 14 26  1  0
 26 46  1  6
 23 40  1  0
 23 41  1  0
 23 42  1  0
 24 43  1  0
 24 44  1  0
 24 45  1  0
 18 38  1  1
 14 37  1  6
 13 36  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 21 39  1  0
M  END

1603
  Mrv0541 02231215352D          

 27 29  0  0  1  0            999 V2000
    7.0379    0.3543    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8393   -1.3137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7409   -2.3783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0999   -1.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8269   -0.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474    0.0516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723    2.0684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2534   -0.7257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8393    0.6873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2534    0.0993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5229   -0.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0379   -0.9806    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4215    0.1028    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4215   -0.7291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1903   -0.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1903    0.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2929   -1.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0420    0.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4598    1.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625    0.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750    1.8564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0803    1.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929    2.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2955    2.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6875    2.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1514    0.7514    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
  2 14  2  0  0  0  0
  3 17  1  0  0  0  0
  4 17  2  0  0  0  0
  5 18  2  0  0  0  0
  6 20  1  0  0  0  0
  6 25  1  0  0  0  0
  7 21  1  0  0  0  0
  7 26  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  1  0  0  0  0
  8 14  1  0  0  0  0
 13  9  1  1  0  0  0
  9 18  1  0  0  0  0
 10 13  1  0  0  0  0
 10 27  1  6  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  6  0  0  0
 13 14  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
 20 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256407

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(OC)C=CC=C1OC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H20N2O6S/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23)/t11-,12+,15-/m1/s1

> <INCHI_KEY>
RJQXTJLFIWVMTO-TYNCELHUSA-N

> <FORMULA>
C17H20N2O6S

> <MOLECULAR_WEIGHT>
380.415

> <EXACT_MASS>
380.104207072

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
37.271308308670214

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
0.7851700403333338

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.328155958919588

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.964298910682354

> <JCHEM_PKA_STRONGEST_BASIC>
-1.839287035616584

> <JCHEM_POLAR_SURFACE_AREA>
105.17

> <JCHEM_REFRACTIVITY>
93.40280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methicillin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1603                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      13.137   0.661   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       9.033  -2.452   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.583  -4.439   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      15.120  -3.615   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.144  -0.599   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.568   0.096   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       8.348   3.861   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      11.673  -1.355   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       9.033   1.283   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      11.673   0.185   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.043  -0.585   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.137  -1.830   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.120   0.192   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.120  -1.361   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.289  -1.490   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.289   0.321   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.613  -3.295   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.545   0.887   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.458   1.979   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.970   1.583   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.860   3.465   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.883   2.674   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.773   4.557   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.285   4.161   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080  -0.299   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.750   5.348   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0      11.483   1.403   0.000  0.00  0.00           H+0
CONECT    1   10   11                                                       
CONECT    2   14                                                            
CONECT    3   17                                                            
CONECT    4   17                                                            
CONECT    5   18                                                            
CONECT    6   20   25                                                       
CONECT    7   21   26                                                       
CONECT    8   10   12   14                                                  
CONECT    9   13   18                                                       
CONECT   10    1    8   13   27                                             
CONECT   11    1   12   15   16                                             
CONECT   12    8   11   17                                                  
CONECT   13    9   10   14                                                  
CONECT   14    2    8   13                                                  
CONECT   15   11                                                            
CONECT   16   11                                                            
CONECT   17    3    4   12                                                  
CONECT   18    5    9   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20    6   19   22                                                  
CONECT   21    7   19   23                                                  
CONECT   22   20   24                                                       
CONECT   23   21   24                                                       
CONECT   24   22   23                                                       
CONECT   25    6                                                            
CONECT   26    7                                                            
CONECT   27   10                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
(2S,5R,6R)-6-[(2,6-Dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
6beta-(2,6-Dimethoxybenzamido)penicillanic acid	ChEBI
Meticilina	ChEBI
Meticilline	ChEBI
Meticillinum	ChEBI
(2S,5R,6R)-6-[(2,6-Dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
6b-(2,6-Dimethoxybenzamido)penicillanate	Generator
6b-(2,6-Dimethoxybenzamido)penicillanic acid	Generator
6beta-(2,6-Dimethoxybenzamido)penicillanate	Generator
6Β-(2,6-dimethoxybenzamido)penicillanate	Generator
6Β-(2,6-dimethoxybenzamido)penicillanic acid	Generator
(2,6-Dimethoxyphenyl)penicillin	HMDB
6-(2,6-Dimethoxybenzamido)penicillanic acid	HMDB
Methicillinum	HMDB
Methycillin	HMDB
Staphcillin	HMDB
CSL Brand OF methicillin sodium	HMDB
Dimethoxyphenyl penicillin	HMDB
Penicillin, dimethoxyphenyl	HMDB
Methicillin hydrate, monosodium salt	HMDB
Methicillin monohydrate, monosodium salt	HMDB
Methicillin sodium	HMDB
Metin	HMDB
Meticillin	ChEBI

Chemical Formula

C₁₇H₂₀N₂O₆S

Average Mass

380.4150 Da

Monoisotopic Mass

380.10421 Da

IUPAC Name

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

Traditional Name

methicillin

CAS Registry Number

Not Available

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(OC)C=CC=C1OC)C(O)=O

InChI Identifier

InChI=1S/C17H20N2O6S/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23)/t11-,12+,15-/m1/s1

InChI Key

RJQXTJLFIWVMTO-TYNCELHUSA-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
Diphasiastrum digitatum	LOTUS Database	35616633
Lycopodium deuterodensum	LOTUS Database	35616633
Streptomyces cavourensis	LOTUS Database	35616633
Tanacetum argenteum	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
Dimethoxybenzene
M-dimethoxybenzene
Benzoic acid or derivatives
Benzamide
Penam
Phenoxy compound
Phenol ether
Benzoyl
Anisole
Methoxybenzene
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Beta-lactam
Thiazolidine
Tertiary carboxylic acid amide
Carboxamide group
Azetidine
Lactam
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Dialkylthioether
Hemithioaminal
Thioether
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

penicillin (CHEBI:6827 )

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	1.79	ALOGPS
logP	0.79	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	2.96	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.17 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93.4 m³·mol⁻¹	ChemAxon
Polarizability	37.27 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

HMDB0015541

DrugBank ID

DB01603

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5862

KEGG Compound ID

C07177

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Meticillin

METLIN ID

Not Available

PubChem Compound

6087

PDB ID

MII

ChEBI ID

6827

Good Scents ID

Not Available

References

General References

Cavalcante FS, Schuenck RP, Ferreira DC, da Costa CR, Nouer SA, dos Santos KR: Meticillin-resistant Staphylococcus aureus: spread of specific lineages among patients in different wards at a Brazilian teaching hospital. J Hosp Infect. 2014 Feb;86(2):151-4. doi: 10.1016/j.jhin.2013.12.004. Epub 2013 Dec 21. [PubMed:24433925 ]
LOTUS database [Link]

Showing NP-Card for (2s,5r,6r)-6-{[(2,6-dimethoxyphenyl)(hydroxy)methylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (NP0256407)

MOL for NP0256407 ((2s,5r,6r)-6-{[(2,6-dimethoxyphenyl)(hydroxy)methylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D MOL for NP0256407 ((2s,5r,6r)-6-{[(2,6-dimethoxyphenyl)(hydroxy)methylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D SDF for NP0256407 ((2s,5r,6r)-6-{[(2,6-dimethoxyphenyl)(hydroxy)methylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D-SDF for NP0256407 ((2s,5r,6r)-6-{[(2,6-dimethoxyphenyl)(hydroxy)methylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

PDB for NP0256407 ((2s,5r,6r)-6-{[(2,6-dimethoxyphenyl)(hydroxy)methylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D PDB for NP0256407 ((2s,5r,6r)-6-{[(2,6-dimethoxyphenyl)(hydroxy)methylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

SMILES for NP0256407 ((2s,5r,6r)-6-{[(2,6-dimethoxyphenyl)(hydroxy)methylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

INCHI for NP0256407 ((2s,5r,6r)-6-{[(2,6-dimethoxyphenyl)(hydroxy)methylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

Structure for NP0256407 ((2s,5r,6r)-6-{[(2,6-dimethoxyphenyl)(hydroxy)methylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D Structure for NP0256407 ((2s,5r,6r)-6-{[(2,6-dimethoxyphenyl)(hydroxy)methylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)