NP-MRD: Showing NP-Card for (3s,4s,5r)-3-[2-({[(3s,4s,5r)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)pyrrol-1-yl]-4,5-dimethyloxolan-2-one (NP0311062)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 06:48:09 UTC

Updated at

2022-09-11 06:48:09 UTC

NP-MRD ID

NP0311062

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4s,5r)-3-[2-({[(3s,4s,5r)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)pyrrol-1-yl]-4,5-dimethyloxolan-2-one

Description

Funebrine belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. (3s,4s,5r)-3-[2-({[(3s,4s,5r)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)pyrrol-1-yl]-4,5-dimethyloxolan-2-one was first documented in 2004 (PMID: 15007405). Based on a literature review very few articles have been published on Funebrine (PMID: 14986999).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112208482D          

 25 27  0  0  1  0            999 V2000
    4.4805    1.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4805    0.4541    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1479   -0.0308    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9326    0.2241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5456   -0.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3303   -0.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5852    0.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4102    0.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6651   -0.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4498   -0.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0629    0.2241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9977   -0.5579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9977   -1.3829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6651   -1.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4498   -1.6129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4102   -2.6525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5852   -2.6525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1003   -3.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3303   -1.8678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5456   -1.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8930   -0.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3779   -1.4829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0680   -0.8155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8131   -0.0308    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0284    0.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  2  0  0  0  0
  5  6  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
  6 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  1  0  0  0
  3 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  6  0  0  0
M  END

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
    2.4220    1.8956   -0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1523    0.5955    0.1591 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2393   -0.2628   -1.0862 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0600   -0.9805   -1.4083 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9757   -0.7778   -0.7755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2621   -1.5099   -1.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3713   -2.4698   -2.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6654   -2.9215   -2.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3094   -2.2056   -1.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7423   -2.3488   -0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9807   -3.5800   -0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4491   -1.3689   -0.4864 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6967   -0.4463    0.5953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5625   -0.9188    1.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5371   -2.0535    2.1902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4331    0.1341    1.9828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8516    1.3471    1.4642 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8363    2.4487    1.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3920    0.8117    0.1251 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3908    1.7224   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859   -1.1487   -0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5505   -2.2990   -1.1864 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1706   -0.4530    0.1771 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6493    0.8482    0.3848 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9148    1.3739    1.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1750    2.7176   -0.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7562    2.0643    0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8482    1.9056   -1.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7238    0.0050    0.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5436    0.3693   -1.9753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9405   -0.0530    0.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4183   -2.8231   -2.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1391   -3.6561   -2.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1493   -1.5249   -0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3165   -2.4023   -1.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2036   -4.1985   -0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7391   -0.1253    1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9493    1.5891    2.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8255    2.0603    1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9235    2.9590    2.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4445    3.2036    0.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2433    0.6329   -0.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0549    1.2062   -1.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5522    1.9500    0.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9294    2.6414   -0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0043    1.4989   -0.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667    2.4567    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3460    0.7996    2.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0072    1.2912    1.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 23  1  0
 23 21  1  0
 21 22  2  0
 21  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 19  1  0
 19 20  1  0
 19 17  1  0
 17 18  1  0
 17 16  1  0
 16 14  1  0
 14 15  2  0
  3  2  1  0
  2  1  1  0
  2 24  1  0
 12  6  1  0
 14 13  1  0
 25 47  1  0
 25 48  1  0
 25 49  1  0
 24 46  1  6
  3 30  1  6
  5 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 13 37  1  1
 19 42  1  6
 20 43  1  0
 20 44  1  0
 20 45  1  0
 17 38  1  1
 18 39  1  0
 18 40  1  0
 18 41  1  0
  2 29  1  1
  1 26  1  0
  1 27  1  0
  1 28  1  0
M  END


  Mrv1652309112208482D          

 25 27  0  0  1  0            999 V2000
    4.4805    1.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4805    0.4541    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1479   -0.0308    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9326    0.2241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5456   -0.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3303   -0.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5852    0.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4102    0.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6651   -0.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4498   -0.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0629    0.2241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9977   -0.5579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9977   -1.3829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6651   -1.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4498   -1.6129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4102   -2.6525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5852   -2.6525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1003   -3.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3303   -1.8678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5456   -1.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8930   -0.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3779   -1.4829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0680   -0.8155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8131   -0.0308    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0284    0.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  2  0  0  0  0
  5  6  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
  6 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  1  0  0  0
  3 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0311062

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1OC(=O)[C@@H](N=CC2=CC=C(CO)N2[C@H]2[C@H](C)[C@@H](C)OC2=O)[C@@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C18H24N2O5/c1-9-11(3)24-17(22)15(9)19-7-13-5-6-14(8-21)20(13)16-10(2)12(4)25-18(16)23/h5-7,9-12,15-16,21H,8H2,1-4H3/t9-,10-,11-,12-,15+,16+/m1/s1

> <INCHI_KEY>
RYQKWJPWKLPCHJ-GRUDOPTHSA-N

> <FORMULA>
C18H24N2O5

> <MOLECULAR_WEIGHT>
348.399

> <EXACT_MASS>
348.168521881

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
36.428817004097745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4S,5R)-3-[2-({[(3S,4S,5R)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)-1H-pyrrol-1-yl]-4,5-dimethyloxolan-2-one

> <JCHEM_LOGP>
1.5386324613333329

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.680653692003627

> <JCHEM_PKA_STRONGEST_BASIC>
2.9260990544820324

> <JCHEM_POLAR_SURFACE_AREA>
90.12000000000002

> <JCHEM_REFRACTIVITY>
90.48340000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,5R)-3-[2-({[(3S,4S,5R)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)pyrrol-1-yl]-4,5-dimethyloxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       8.364   2.388   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.364   0.848   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.609  -0.058   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      11.074   0.418   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      12.219  -0.612   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.683  -0.136   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.159   1.328   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.699   1.328   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.175  -0.136   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.640  -0.612   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      18.784   0.418   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      14.929  -1.041   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      14.929  -2.581   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.175  -3.487   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      17.640  -3.011   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      15.699  -4.951   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      14.159  -4.951   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.254  -6.197   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.683  -3.487   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.219  -3.011   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.134  -1.522   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.039  -2.768   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.594  -1.522   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.118  -0.058   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.653   0.418   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9    6   13                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   13   20                                                  
CONECT   20   19                                                            
CONECT   21    3   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23    2   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₄N₂O₅

Average Mass

348.3990 Da

Monoisotopic Mass

348.16852 Da

IUPAC Name

(3S,4S,5R)-3-[2-({[(3S,4S,5R)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)-1H-pyrrol-1-yl]-4,5-dimethyloxolan-2-one

Traditional Name

(3S,4S,5R)-3-[2-({[(3S,4S,5R)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)pyrrol-1-yl]-4,5-dimethyloxolan-2-one

CAS Registry Number

Not Available

SMILES

C[C@H]1OC(=O)[C@@H](N=CC2=CC=C(CO)N2[C@H]2[C@H](C)[C@@H](C)OC2=O)[C@@H]1C

InChI Identifier

InChI=1S/C18H24N2O5/c1-9-11(3)24-17(22)15(9)19-7-13-5-6-14(8-21)20(13)16-10(2)12(4)25-18(16)23/h5-7,9-12,15-16,21H,8H2,1-4H3/t9-,10-,11-,12-,15+,16+/m1/s1

InChI Key

RYQKWJPWKLPCHJ-GRUDOPTHSA-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 alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Substituted pyrrole
Oxolane
Pyrrole
Heteroaromatic compound
Carboxylic acid ester
Lactone
Shiff base
Organoheterocyclic compound
Organic 1,3-dipolar compound
Azacycle
Aldimine
Propargyl-type 1,3-dipolar organic compound
Oxacycle
Aromatic alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Imine
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Primary alcohol
Hydrocarbon derivative
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	1.54	ChemAxon
pKa (Strongest Acidic)	14.68	ChemAxon
pKa (Strongest Basic)	2.93	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	90.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.48 m³·mol⁻¹	ChemAxon
Polarizability	36.43 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

C00002039

Chemspider ID

107562562

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442636

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jamieson AG, Sutherland A, Willis CL: The first enantioselective synthesis of the amino acid, (2S,3S,4R)-gamma-hydroxyisoleucine using a palladium(II) catalysed 3,3-sigmatropic rearrangement. Org Biomol Chem. 2004 Mar 21;2(6):808-9. doi: 10.1039/b401076k. Epub 2004 Feb 19. [PubMed:15007405 ]
Tamura O, Iyama N, Ishibashi H: Syntheses of (-)-funebrine and (-)-funebral, using sequential transesterification and intramolecular cycloaddition of a chiral nitrone. J Org Chem. 2004 Mar 5;69(5):1475-80. doi: 10.1021/jo030257q. [PubMed:14986999 ]
LOTUS database [Link]

Showing NP-Card for (3s,4s,5r)-3-[2-({[(3s,4s,5r)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)pyrrol-1-yl]-4,5-dimethyloxolan-2-one (NP0311062)

MOL for NP0311062 ((3s,4s,5r)-3-[2-({[(3s,4s,5r)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)pyrrol-1-yl]-4,5-dimethyloxolan-2-one)

3D MOL for NP0311062 ((3s,4s,5r)-3-[2-({[(3s,4s,5r)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)pyrrol-1-yl]-4,5-dimethyloxolan-2-one)

3D SDF for NP0311062 ((3s,4s,5r)-3-[2-({[(3s,4s,5r)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)pyrrol-1-yl]-4,5-dimethyloxolan-2-one)

3D-SDF for NP0311062 ((3s,4s,5r)-3-[2-({[(3s,4s,5r)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)pyrrol-1-yl]-4,5-dimethyloxolan-2-one)

PDB for NP0311062 ((3s,4s,5r)-3-[2-({[(3s,4s,5r)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)pyrrol-1-yl]-4,5-dimethyloxolan-2-one)

3D PDB for NP0311062 ((3s,4s,5r)-3-[2-({[(3s,4s,5r)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)pyrrol-1-yl]-4,5-dimethyloxolan-2-one)

SMILES for NP0311062 ((3s,4s,5r)-3-[2-({[(3s,4s,5r)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)pyrrol-1-yl]-4,5-dimethyloxolan-2-one)

INCHI for NP0311062 ((3s,4s,5r)-3-[2-({[(3s,4s,5r)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)pyrrol-1-yl]-4,5-dimethyloxolan-2-one)

Structure for NP0311062 ((3s,4s,5r)-3-[2-({[(3s,4s,5r)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)pyrrol-1-yl]-4,5-dimethyloxolan-2-one)

3D Structure for NP0311062 ((3s,4s,5r)-3-[2-({[(3s,4s,5r)-4,5-dimethyl-2-oxooxolan-3-yl]imino}methyl)-5-(hydroxymethyl)pyrrol-1-yl]-4,5-dimethyloxolan-2-one)