NP-MRD: Showing NP-Card for n-[(3s,7r,8r,9s)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid (NP0221764)

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Record Information

Version

2.0

Created at

2022-09-05 23:25:26 UTC

Updated at

2022-09-05 23:25:26 UTC

NP-MRD ID

NP0221764

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(3s,7r,8r,9s)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid

Description

UK-3A, also known as uk 3A, belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. UK-3A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. n-[(3s,7r,8r,9s)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid was first documented in 1997 (PMID: 9711246). Based on a literature review a small amount of articles have been published on UK-3A (PMID: 20621723) (PMID: 9510913).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062201252D          

 35 37  0  0  1  0            999 V2000
    1.6851   12.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8726   11.9773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3423   12.6093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5905   11.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2220   11.0588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1208   10.5701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8386    9.7948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4706    9.2645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1850    9.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6138    8.4521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013    7.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7316    7.1056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4261    7.4554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4261    6.6304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406    6.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8550    6.6304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406    5.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4261    4.9804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4261    4.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406    3.7429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8550    4.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8550    4.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5695    5.3929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492    7.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7617    8.4521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184    9.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3329    9.6770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0136    9.7948    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2686   10.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0810   10.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6113   10.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4238   10.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7060   10.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1757   11.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3632   11.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  4  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
M  END


  Mrv1652309062201252D          

 35 37  0  0  1  0            999 V2000
    1.6851   12.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8726   11.9773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3423   12.6093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5905   11.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2220   11.0588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1208   10.5701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8386    9.7948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4706    9.2645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1850    9.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6138    8.4521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013    7.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7316    7.1056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4261    7.4554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4261    6.6304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406    6.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8550    6.6304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406    5.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4261    4.9804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4261    4.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406    3.7429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8550    4.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8550    4.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5695    5.3929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492    7.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7617    8.4521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184    9.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3329    9.6770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0136    9.7948    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2686   10.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0810   10.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6113   10.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4238   10.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7060   10.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1757   11.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3632   11.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  4  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221764

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)O[C@H]1[C@H](C)OC(=O)[C@H](COC(=O)[C@@H]1CC1=CC=CC=C1)N=C(O)C1=NC=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H28N2O8/c1-14(2)23(30)35-21-15(3)34-25(32)18(27-22(29)20-19(28)10-7-11-26-20)13-33-24(31)17(21)12-16-8-5-4-6-9-16/h4-11,14-15,17-18,21,28H,12-13H2,1-3H3,(H,27,29)/t15-,17+,18-,21-/m0/s1

> <INCHI_KEY>
LATFDMCUVSRKNK-DKXUYOFUSA-N

> <FORMULA>
C25H28N2O8

> <MOLECULAR_WEIGHT>
484.505

> <EXACT_MASS>
484.18456587

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
48.603668304662996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(3S,7R,8R,9S)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid

> <JCHEM_LOGP>
4.499224223666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.027244698186461

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.942177090414735

> <JCHEM_PKA_STRONGEST_BASIC>
2.2615063457619424

> <JCHEM_POLAR_SURFACE_AREA>
144.61

> <JCHEM_REFRACTIVITY>
122.19460000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-[(3S,7R,8R,9S)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       3.145  22.625   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.629  22.358   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.639  23.537   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.102  20.911   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.414  20.643   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.092  19.731   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.565  18.284   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.745  17.294   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.079  18.064   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.012  15.777   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.242  14.444   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.232  13.264   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.795  13.917   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.795  12.377   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.129  11.607   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.463  12.377   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.129  10.067   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       0.795   9.297   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       0.795   7.757   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.129   6.987   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.463   7.757   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.463   9.297   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.796  10.067   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.652  14.444   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.422  15.777   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.154  17.294   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.488  18.064   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.025  18.284   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.501  19.731   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.018  19.998   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.008  18.819   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.524  19.086   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.051  20.533   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.061  21.713   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.545  21.445   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   28                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17   23                                                  
CONECT   23   22                                                            
CONECT   24   13   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    7   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
(3S,6S,7R,8R)-8-Benzyl-3-{[(3-hydroxypyridin-2-yl)carbonyl]amino}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate	ChEBI
(3S,6S,7R,8R)-8-Benzyl-3-{[(3-hydroxypyridin-2-yl)carbonyl]amino}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoic acid	Generator
UK 3a	MeSH

Chemical Formula

C₂₅H₂₈N₂O₈

Average Mass

484.5050 Da

Monoisotopic Mass

484.18457 Da

IUPAC Name

N-[(3S,7R,8R,9S)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid

Traditional Name

N-[(3S,7R,8R,9S)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)O[C@H]1[C@H](C)OC(=O)[C@H](COC(=O)[C@@H]1CC1=CC=CC=C1)N=C(O)C1=NC=CC=C1O

InChI Identifier

InChI=1S/C25H28N2O8/c1-14(2)23(30)35-21-15(3)34-25(32)18(27-22(29)20-19(28)10-7-11-26-20)13-33-24(31)17(21)12-16-8-5-4-6-9-16/h4-11,14-15,17-18,21,28H,12-13H2,1-3H3,(H,27,29)/t15-,17+,18-,21-/m0/s1

InChI Key

LATFDMCUVSRKNK-DKXUYOFUSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen 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-alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid ester
N-acyl-alpha amino acid or derivatives
Pyridine carboxylic acid or derivatives
Tricarboxylic acid or derivatives
2-heteroaryl carboxamide
Hydroxypyridine
Monocyclic benzene moiety
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary carboxylic acid amide
Lactone
Carboxylic acid ester
Carboxamide group
Oxacycle
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:66341 )
monohydroxypyridine (CHEBI:66341 )
aromatic amide (CHEBI:66341 )
lactone (CHEBI:66341 )

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	4.5	ChemAxon
pKa (Strongest Acidic)	5.94	ChemAxon
pKa (Strongest Basic)	2.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	144.61 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	122.19 m³·mol⁻¹	ChemAxon
Polarizability	48.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

416802

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

474760

PDB ID

Not Available

ChEBI ID

66341

Good Scents ID

Not Available

References

General References

Ueki M, Kusumoto A, Hanafi M, Shibata K, Tanaka T, Taniguchi M: UK-3A, a novel antifungal antibiotic from Streptomyces sp. 517-02: fermentation, isolation, structural elucidation and biological properties. J Antibiot (Tokyo). 1997 Jul;50(7):551-5. doi: 10.7164/antibiotics.50.551. [PubMed:9711246 ]
Arsianti A, Hanafi M, Saepudin E, Morimoto T, Kakiuchi K: Synthesis and biological activity of 2-hydroxynicotinoyl-serine-butyl esters related to antibiotic UK-3A. Bioorg Med Chem Lett. 2010 Jul 15;20(14):4018-20. doi: 10.1016/j.bmcl.2010.05.104. Epub 2010 Jun 2. [PubMed:20621723 ]
Ueki M, Taniguchi M: The mode of action of UK-2A and UK-3A, novel antifungal antibiotics from Streptomyces sp. 517-02. J Antibiot (Tokyo). 1997 Dec;50(12):1052-7. doi: 10.7164/antibiotics.50.1052. [PubMed:9510913 ]
LOTUS database [Link]

Showing NP-Card for n-[(3s,7r,8r,9s)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid (NP0221764)

MOL for NP0221764 (n-[(3s,7r,8r,9s)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid)

3D MOL for NP0221764 (n-[(3s,7r,8r,9s)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid)

3D SDF for NP0221764 (n-[(3s,7r,8r,9s)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid)

3D-SDF for NP0221764 (n-[(3s,7r,8r,9s)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid)

PDB for NP0221764 (n-[(3s,7r,8r,9s)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid)

3D PDB for NP0221764 (n-[(3s,7r,8r,9s)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid)

SMILES for NP0221764 (n-[(3s,7r,8r,9s)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid)

INCHI for NP0221764 (n-[(3s,7r,8r,9s)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid)

Structure for NP0221764 (n-[(3s,7r,8r,9s)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid)

3D Structure for NP0221764 (n-[(3s,7r,8r,9s)-7-benzyl-9-methyl-8-[(2-methylpropanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxypyridine-2-carboximidic acid)