NP-MRD: Showing NP-Card for (2r)-2-[(r)-{[(6r)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-2,6-dihydro-1,3-thiazine-4-carboxylic acid (NP0190627)

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Record Information

Version

2.0

Created at

2022-09-04 07:20:23 UTC

Updated at

2022-09-04 07:20:23 UTC

NP-MRD ID

NP0190627

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-2-[(r)-{[(6r)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-2,6-dihydro-1,3-thiazine-4-carboxylic acid

Description

(2R)-2-[(R)-{[(6R)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-5,6-dihydro-2H-1,3-thiazine-4-carboxylic acid belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. (2r)-2-[(r)-{[(6r)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-2,6-dihydro-1,3-thiazine-4-carboxylic acid is found in Streptomyces clavuligerus. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom (2R)-2-[(R)-{[(6R)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-5,6-dihydro-2H-1,3-thiazine-4-carboxylic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041410282D          

 29 29  0  0  1  0            999 V2000
   -6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1027    3.9055    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5690    4.1748    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  1  2  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  7  1  0  0  0  0
 12 11  1  6  0  0  0
 13  8  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
  8 16  1  6  0  0  0
 17  9  2  0  0  0  0
 11 17  1  1  0  0  0
 18 10  2  0  0  0  0
 18 12  1  0  0  0  0
  9 19  1  4  0  0  0
 20 13  2  0  0  0  0
 21 13  1  0  0  0  0
 22 14  1  0  0  0  0
 23 14  2  0  0  0  0
 24 15  2  0  0  0  0
 25 15  1  0  0  0  0
 26  6  1  0  0  0  0
 26 12  1  0  0  0  0
  8 27  1  6  0  0  0
 11 28  1  1  0  0  0
 12 29  1  1  0  0  0
M  END

     RDKit          3D

 47 47  0  0  0  0  0  0  0  0999 V2000
   -4.8216    0.6105    2.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5643    0.6545    0.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2140   -0.3837   -0.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0016   -0.9228   -1.2077 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5931    0.1891   -1.1860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3202   -0.5156   -0.7400 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0578   -1.5843   -1.6590 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0808   -2.1745   -1.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1314   -3.1939   -2.7517 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2726   -1.7963   -1.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4116   -1.3357   -1.8916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6269   -0.9513   -1.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3327    0.1713   -0.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5543    0.5525    0.6868 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5829    0.9748   -0.2428 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2512    1.6046    1.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8627    2.6901    1.6363 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2988    1.4078    2.6590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521   -0.9552    0.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5408   -0.1955    1.6446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1612   -2.3025    0.9359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7976    1.4462   -0.5749 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6795    1.6870    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7629    3.0412    0.8842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5918    3.3124    1.7706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9295    4.0378    0.4173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4861   -0.1543    2.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4221    1.2902    2.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6150   -1.2100    0.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0716    0.0769   -0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3933    0.4162   -2.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5138    0.2663   -0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0466   -4.1542   -2.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9598   -1.0353   -0.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6114   -2.7044   -0.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6359   -2.1645   -2.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1124   -0.4409   -2.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4347   -0.6768   -1.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9307   -1.8673   -0.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546    1.0118   -0.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5971   -0.2325    0.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8700   -0.3836    1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1148    0.1638   -0.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2655    1.5568    0.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6184    2.1674    2.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7895   -2.8426    1.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6853    4.8484    0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  0
  8  7  2  0
  7  6  1  0
  6 19  1  0
 19 21  1  0
 19 20  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 23  1  0
 23 22  2  0
 23 24  1  0
 24 26  1  0
 24 25  2  0
 14 16  1  0
 16 18  1  0
 16 17  2  0
 22  5  1  0
 14 42  1  1
 15 43  1  0
 15 44  1  0
 13 40  1  0
 13 41  1  0
 12 38  1  0
 12 39  1  0
 11 36  1  0
 11 37  1  0
 10 34  1  0
 10 35  1  0
  9 33  1  0
  6 32  1  1
 21 46  1  0
  5 31  1  6
  3 29  1  0
  3 30  1  0
  1 27  1  0
  1 28  1  0
 26 47  1  0
 18 45  1  0
M  END


  Mrv0541 05041410282D          

 29 29  0  0  1  0            999 V2000
   -6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1027    3.9055    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5690    4.1748    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  1  2  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  7  1  0  0  0  0
 12 11  1  6  0  0  0
 13  8  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
  8 16  1  6  0  0  0
 17  9  2  0  0  0  0
 11 17  1  1  0  0  0
 18 10  2  0  0  0  0
 18 12  1  0  0  0  0
  9 19  1  4  0  0  0
 20 13  2  0  0  0  0
 21 13  1  0  0  0  0
 22 14  1  0  0  0  0
 23 14  2  0  0  0  0
 24 15  2  0  0  0  0
 25 15  1  0  0  0  0
 26  6  1  0  0  0  0
 26 12  1  0  0  0  0
  8 27  1  6  0  0  0
 11 28  1  1  0  0  0
 12 29  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0190627

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](N)(CCCCC(O)=N[C@]([H])(C(O)=O)[C@@]1([H])SCC(=C)C(=N1)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H21N3O7S/c1-7-6-26-12(18-10(7)14(22)23)11(15(24)25)17-9(19)5-3-2-4-8(16)13(20)21/h8,11-12H,1-6,16H2,(H,17,19)(H,20,21)(H,22,23)(H,24,25)/t8-,11+,12-/m1/s1

> <INCHI_KEY>
JGKXEMYIHDYWCZ-JFUSQASVSA-N

> <FORMULA>
C15H21N3O7S

> <MOLECULAR_WEIGHT>
387.408

> <EXACT_MASS>
387.110020731

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
36.35434658896941

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(R)-{[(6R)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-5,6-dihydro-2H-1,3-thiazine-4-carboxylic acid

> <ALOGPS_LOGP>
-1.83

> <JCHEM_LOGP>
-1.1955145947961467

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.277561090525224

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.068221721293715

> <JCHEM_PKA_STRONGEST_BASIC>
9.529362477681286

> <JCHEM_POLAR_SURFACE_AREA>
182.86999999999998

> <JCHEM_REFRACTIVITY>
91.00339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(R)-{[(6R)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-2,6-dihydro-1,3-thiazine-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
HETATM   27  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    9                                                       
CONECT    6    7   26                                                       
CONECT    7    1    6   10                                                  
CONECT    8    4   13   16   27                                             
CONECT    9    5   17   19                                                  
CONECT   10    7   14   18                                                  
CONECT   11   12   15   17   28                                             
CONECT   12   11   18   26   29                                             
CONECT   13    8   20   21                                                  
CONECT   14   10   22   23                                                  
CONECT   15   11   24   25                                                  
CONECT   16    8                                                            
CONECT   17    9   11                                                       
CONECT   18   10   12                                                       
CONECT   19    9                                                            
CONECT   20   13                                                            
CONECT   21   13                                                            
CONECT   22   14                                                            
CONECT   23   14                                                            
CONECT   24   15                                                            
CONECT   25   15                                                            
CONECT   26    6   12                                                       
CONECT   27    8                                                            
CONECT   28   11                                                            
CONECT   29   12                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   58    0
END

View in JSmol

Synonyms

Value	Source
(2R)-2-[(R)-{[(6R)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-5,6-dihydro-2H-1,3-thiazine-4-carboxylate	Generator

Chemical Formula

C₁₅H₂₁N₃O₇S

Average Mass

387.4080 Da

Monoisotopic Mass

387.11002 Da

IUPAC Name

(2R)-2-[(R)-{[(6R)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-5,6-dihydro-2H-1,3-thiazine-4-carboxylic acid

Traditional Name

(2R)-2-[(R)-{[(6R)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-2,6-dihydro-1,3-thiazine-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](N)(CCCCC(O)=N[C@]([H])(C(O)=O)[C@@]1([H])SCC(=C)C(=N1)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C15H21N3O7S/c1-7-6-26-12(18-10(7)14(22)23)11(15(24)25)17-9(19)5-3-2-4-8(16)13(20)21/h8,11-12H,1-6,16H2,(H,17,19)(H,20,21)(H,22,23)(H,24,25)/t8-,11+,12-/m1/s1

InChI Key

JGKXEMYIHDYWCZ-JFUSQASVSA-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 clavuligerus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Alpha-amino acid
D-alpha-amino acid
Tricarboxylic acid or derivatives
Meta-thiazine
Fatty amide
N-acyl-amine
Fatty acyl
Amino acid
Carboxamide group
Ketimine
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Carboxylic acid
Dialkylthioether
Organic 1,3-dipolar compound
Thioether
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Imine
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Amine
Organic oxygen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-1.8	ALOGPS
logP	-1.2	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	2.07	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	182.87 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	91 m³·mol⁻¹	ChemAxon
Polarizability	36.35 Å³	ChemAxon
Number of Rings	1	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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25058126

PDB ID

REC

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-2-[(r)-{[(6r)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-2,6-dihydro-1,3-thiazine-4-carboxylic acid (NP0190627)

MOL for NP0190627 ((2r)-2-[(r)-{[(6r)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-2,6-dihydro-1,3-thiazine-4-carboxylic acid)

3D MOL for NP0190627 ((2r)-2-[(r)-{[(6r)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-2,6-dihydro-1,3-thiazine-4-carboxylic acid)

3D SDF for NP0190627 ((2r)-2-[(r)-{[(6r)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-2,6-dihydro-1,3-thiazine-4-carboxylic acid)

3D-SDF for NP0190627 ((2r)-2-[(r)-{[(6r)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-2,6-dihydro-1,3-thiazine-4-carboxylic acid)

PDB for NP0190627 ((2r)-2-[(r)-{[(6r)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-2,6-dihydro-1,3-thiazine-4-carboxylic acid)

3D PDB for NP0190627 ((2r)-2-[(r)-{[(6r)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-2,6-dihydro-1,3-thiazine-4-carboxylic acid)

SMILES for NP0190627 ((2r)-2-[(r)-{[(6r)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-2,6-dihydro-1,3-thiazine-4-carboxylic acid)

INCHI for NP0190627 ((2r)-2-[(r)-{[(6r)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-2,6-dihydro-1,3-thiazine-4-carboxylic acid)

Structure for NP0190627 ((2r)-2-[(r)-{[(6r)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-2,6-dihydro-1,3-thiazine-4-carboxylic acid)

3D Structure for NP0190627 ((2r)-2-[(r)-{[(6r)-6-amino-6-carboxy-1-hydroxyhexylidene]amino}(carboxy)methyl]-5-methylidene-2,6-dihydro-1,3-thiazine-4-carboxylic acid)