NP-MRD: Showing NP-Card for (+)-Obafluorin (NP0062205)

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Record Information

Version

2.0

Created at

2022-04-28 06:51:46 UTC

Updated at

2022-04-28 06:51:46 UTC

NP-MRD ID

NP0062205

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Obafluorin

Description

Obafluorin 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. (+)-Obafluorin is found in Pseudomonas fluorescens and Pseudomonas fluorescens SC 12936 (ATCC 39502). (+)-Obafluorin was first documented in 2017 (PMID: 28649989). Based on a literature review a small amount of articles have been published on Obafluorin (PMID: 33337128) (PMID: 31675206) (PMID: 31366889) (PMID: 28504677).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208512D          

 26 28  0  0  1  0            999 V2000
    1.9341   -1.3583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5175   -1.9417    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9341   -2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9341   -3.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3508   -1.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3425   -1.9417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7550   -2.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3425   -3.3706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5800   -2.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8175   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300   -2.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8175   -3.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925   -3.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5800   -4.0851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300   -4.0851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9341   -0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486   -0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486    0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3631    1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0776    0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0776   -0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3631   -0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7920    1.1167    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.7920    1.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5065    0.7042    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
  1 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  CHG  2  24   1  26  -1
M  END

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    2.7315   -1.9325   -0.1942 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4429   -0.7072   -0.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1350   -0.4353   -0.9303 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406   -1.5657   -1.1316 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3989   -1.4528   -2.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934   -1.9553   -3.6048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3065   -0.5534   -1.8860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1840   -1.3109   -0.6973 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3187   -0.5190    0.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7517   -0.3482    0.8804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3984    0.7601    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7369    0.9925    0.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4498    0.0937    1.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8489    0.3148    1.6268 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.4060    1.3195    1.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5558   -0.5824    2.3873 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.8036   -1.0142    1.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4677   -1.2454    1.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4462    0.2975   -0.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1483    1.6301   -0.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0764    2.6531   -0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3263    2.3508    0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6278    1.0463    0.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8766    0.7106    1.0171 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6950    0.0089    0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0874   -1.2599    0.5832 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8318    0.5123   -1.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6597   -2.5426   -0.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7713   -2.2315   -0.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7566   -0.9833    1.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8680    0.4828    0.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8795    1.5088   -0.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2214    1.8684    0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4094   -1.7088    2.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9997   -2.1240    2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1677    1.8817   -0.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8189    3.6889   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0565    3.1515    0.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6081    1.3504    1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7497   -2.1503    0.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 25  2  0
 25 26  1  0
 25 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 19  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 17  1  0
 17 18  2  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
 22 23  1  0
  5  4  1  0
 18 10  1  0
 24 39  1  0
 26 40  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
  3 27  1  0
  4 28  1  1
  8 29  1  6
  9 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 17 34  1  0
 18 35  1  0
M  CHG  2  14   1  16  -1
M  END


  Mrv1652304282208512D          

 26 28  0  0  1  0            999 V2000
    1.9341   -1.3583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5175   -1.9417    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9341   -2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9341   -3.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3508   -1.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3425   -1.9417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7550   -2.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3425   -3.3706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5800   -2.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8175   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300   -2.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8175   -3.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925   -3.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5800   -4.0851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300   -4.0851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9341   -0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486   -0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486    0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3631    1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0776    0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0776   -0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3631   -0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7920    1.1167    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.7920    1.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5065    0.7042    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
  1 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  CHG  2  24   1  26  -1
M  END
> <DATABASE_ID>
NP0062205

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(O)C(=CC=C1)C(=O)N[C@H]1[C@@H](CC2=CC=C(C=C2)[N+]([O-])=O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H14N2O7/c20-12-3-1-2-11(15(12)21)16(22)18-14-13(26-17(14)23)8-9-4-6-10(7-5-9)19(24)25/h1-7,13-14,20-21H,8H2,(H,18,22)/t13-,14+/m1/s1

> <INCHI_KEY>
AINNQKIVZOTQBB-KGLIPLIRSA-N

> <FORMULA>
C17H14N2O7

> <MOLECULAR_WEIGHT>
358.306

> <EXACT_MASS>
358.080100799

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
34.1237362235773

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-dihydroxy-N-[(2R,3S)-2-[(4-nitrophenyl)methyl]-4-oxooxetan-3-yl]benzamide

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
2.7676258229999995

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.915797796037538

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.299508319624065

> <JCHEM_PKA_STRONGEST_BASIC>
-1.899712804106997

> <JCHEM_POLAR_SURFACE_AREA>
139.0

> <JCHEM_REFRACTIVITY>
87.98320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dihydroxy-N-[(2R,3S)-2-[(4-nitrophenyl)methyl]-4-oxooxetan-3-yl]benzamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       3.610  -2.536   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.699  -3.624   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.610  -4.713   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.610  -6.253   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.521  -3.624   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       6.239  -3.624   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.009  -4.958   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.239  -6.292   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.549  -4.958   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.319  -3.624   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.859  -3.624   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.629  -4.958   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.859  -6.292   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.319  -6.292   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.549  -7.626   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      11.629  -7.626   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.610  -0.996   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.944  -0.226   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.944   1.314   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.278   2.084   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.611   1.314   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.611  -0.226   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.278  -0.996   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       8.945   2.084   0.000  0.00  0.00           N+1
HETATM   25  O   UNK     0       8.945   3.624   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      10.279   1.314   0.000  0.00  0.00           O-1
CONECT    1    2    5   17                                                  
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    1                                                       
CONECT    6    2    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16   13                                                            
CONECT   17    1   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₄N₂O₇

Average Mass

358.3060 Da

Monoisotopic Mass

358.08010 Da

IUPAC Name

2,3-dihydroxy-N-[(2R,3S)-2-[(4-nitrophenyl)methyl]-4-oxooxetan-3-yl]benzamide

Traditional Name

2,3-dihydroxy-N-[(2R,3S)-2-[(4-nitrophenyl)methyl]-4-oxooxetan-3-yl]benzamide

CAS Registry Number

Not Available

SMILES

OC1=C(O)C(=CC=C1)C(=O)N[C@H]1[C@@H](CC2=CC=C(C=C2)[N+]([O-])=O)OC1=O

InChI Identifier

InChI=1S/C17H14N2O7/c20-12-3-1-2-11(15(12)21)16(22)18-14-13(26-17(14)23)8-9-4-6-10(7-5-9)19(24)25/h1-7,13-14,20-21H,8H2,(H,18,22)/t13-,14+/m1/s1

InChI Key

AINNQKIVZOTQBB-KGLIPLIRSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Pseudomonas fluorescens	LOTUS Database	35616633
Pseudomonas fluorescens SC 12936 (ATCC 39502)	Bacteria	KNApSAcK

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
Salicylamide
Salicylic acid or derivatives
Benzamide
Benzoic acid or derivatives
Nitrobenzene
Nitroaromatic compound
Benzoyl
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Beta_propiolactone
Secondary carboxylic acid amide
Organic nitro compound
Carboxamide group
Carboxylic acid ester
Oxetane
Lactone
C-nitro compound
Organoheterocyclic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Allyl-type 1,3-dipolar organic compound
Oxacycle
Monocarboxylic acid or derivatives
Organic oxoazanium
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organic oxygen compound
Organic oxide
Organonitrogen compound
Hydrocarbon derivative
Organic zwitterion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	2.58	ALOGPS
logP	2.77	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.3	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.98 m³·mol⁻¹	ChemAxon
Polarizability	34.12 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018594

Chemspider ID

129096

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Obafluorin

METLIN ID

Not Available

PubChem Compound

146354

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kumar P, Meza A, Ellis JM, Carlson GA, Bingman CA, Buller AR: l-Threonine Transaldolase Activity Is Enabled by a Persistent Catalytic Intermediate. ACS Chem Biol. 2021 Jan 15;16(1):86-95. doi: 10.1021/acschembio.0c00753. Epub 2020 Dec 18. [PubMed:33337128 ]
Scott TA, Batey SFD, Wiencek P, Chandra G, Alt S, Francklyn CS, Wilkinson B: Immunity-Guided Identification of Threonyl-tRNA Synthetase as the Molecular Target of Obafluorin, a beta-Lactone Antibiotic. ACS Chem Biol. 2019 Dec 20;14(12):2663-2671. doi: 10.1021/acschembio.9b00590. Epub 2019 Nov 14. [PubMed:31675206 ]
Kreitler DF, Gemmell EM, Schaffer JE, Wencewicz TA, Gulick AM: The structural basis of N-acyl-alpha-amino-beta-lactone formation catalyzed by a nonribosomal peptide synthetase. Nat Commun. 2019 Jul 31;10(1):3432. doi: 10.1038/s41467-019-11383-7. [PubMed:31366889 ]
Scott TA, Heine D, Qin Z, Wilkinson B: An L-threonine transaldolase is required for L-threo-beta-hydroxy-alpha-amino acid assembly during obafluorin biosynthesis. Nat Commun. 2017 Jun 26;8:15935. doi: 10.1038/ncomms15935. [PubMed:28649989 ]
Schaffer JE, Reck MR, Prasad NK, Wencewicz TA: beta-Lactone formation during product release from a nonribosomal peptide synthetase. Nat Chem Biol. 2017 Jul;13(7):737-744. doi: 10.1038/nchembio.2374. Epub 2017 May 15. [PubMed:28504677 ]

Showing NP-Card for (+)-Obafluorin (NP0062205)

MOL for NP0062205 ((+)-Obafluorin)

3D MOL for NP0062205 ((+)-Obafluorin)

3D SDF for NP0062205 ((+)-Obafluorin)

3D-SDF for NP0062205 ((+)-Obafluorin)

PDB for NP0062205 ((+)-Obafluorin)

3D PDB for NP0062205 ((+)-Obafluorin)

SMILES for NP0062205 ((+)-Obafluorin)

INCHI for NP0062205 ((+)-Obafluorin)

Structure for NP0062205 ((+)-Obafluorin)

3D Structure for NP0062205 ((+)-Obafluorin)