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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:53:58 UTC

Update Date

2022-09-22 18:34:24 UTC

HMDB ID

HMDB0033143

Secondary Accession Numbers

HMDB33143

Metabolite Identification

Common Name

Pyrraline

Description

Pyrraline, also known as 2-FHMPN, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Based on a literature review very few articles have been published on Pyrraline.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0033143
     RDKit          3D
Pyrraline
 36 36  0  0  0  0  0  0  0  0999 V2000
    3.7920    0.0437    1.2875 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1493    0.0163   -0.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9150   -0.8678    0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9097   -0.3839    0.9978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3504   -1.1277    1.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3135   -1.1460   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8441    0.1549   -0.3875 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4871    0.9481   -1.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6278    0.7057   -2.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0978   -0.3781   -2.8276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2220    2.1351   -1.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0045    1.9984   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7636    0.7465    0.4246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3938    0.1599    1.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7600    0.5352    1.6919 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0820   -0.4842   -1.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2402   -0.8072   -0.7072 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6565   -0.5850   -2.3389 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7197   -0.8535    1.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7390    0.4300    1.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8117    1.0533   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2808   -1.8993    0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4928   -1.0022   -0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4255   -0.4289    2.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7775    0.7137    0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9278   -0.7645    2.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466   -2.2358    1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394   -1.8343    0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7835   -1.6239   -0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4164    1.5176   -3.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1497    2.9871   -1.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6905    2.7366    0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3290   -0.9260    1.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8757    0.4877    2.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3135   -0.2060    1.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6450    0.1843   -2.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  8 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  2  0
 16 18  1  0
 13  7  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  1  0
M  END


  Mrv1652309121709232D          

 18 18  0  0  0  0            999 V2000
   -3.3159    1.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7638    2.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0101    2.1304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0964    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9034    1.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833    0.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6548   -0.0491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2957    2.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5812    2.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1333    2.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8477    2.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622    2.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2767    2.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9912    2.5429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2767    1.3054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622    3.3679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9353    3.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3223    3.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033143

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(CCCCN1C(CO)=CC=C1C=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H18N2O4/c13-11(12(17)18)3-1-2-6-14-9(7-15)4-5-10(14)8-16/h4-5,7,11,16H,1-3,6,8,13H2,(H,17,18)

> <INCHI_KEY>
VTYFITADLSVOAS-UHFFFAOYSA-N

> <FORMULA>
C12H18N2O4

> <MOLECULAR_WEIGHT>
254.2823

> <EXACT_MASS>
254.126657074

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.658317639728928

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]hexanoic acid

> <ALOGPS_LOGP>
-1.59

> <JCHEM_LOGP>
-2.2856380641666174

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.630287988067721

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.025976806842895

> <JCHEM_PKA_STRONGEST_BASIC>
9.326523050009708

> <JCHEM_POLAR_SURFACE_AREA>
105.55

> <JCHEM_REFRACTIVITY>
66.75909999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-6-[2-formyl-5-(hydroxymethyl)pyrrol-1-yl]hexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033143
     RDKit          3D
Pyrraline
 36 36  0  0  0  0  0  0  0  0999 V2000
    3.7920    0.0437    1.2875 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1493    0.0163   -0.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9150   -0.8678    0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9097   -0.3839    0.9978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3504   -1.1277    1.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3135   -1.1460   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8441    0.1549   -0.3875 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4871    0.9481   -1.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6278    0.7057   -2.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0978   -0.3781   -2.8276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2220    2.1351   -1.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0045    1.9984   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7636    0.7465    0.4246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3938    0.1599    1.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7600    0.5352    1.6919 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0820   -0.4842   -1.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2402   -0.8072   -0.7072 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6565   -0.5850   -2.3389 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7197   -0.8535    1.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7390    0.4300    1.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8117    1.0533   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2808   -1.8993    0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4928   -1.0022   -0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4255   -0.4289    2.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7775    0.7137    0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9278   -0.7645    2.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466   -2.2358    1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394   -1.8343    0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7835   -1.6239   -0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4164    1.5176   -3.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1497    2.9871   -1.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6905    2.7366    0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3290   -0.9260    1.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8757    0.4877    2.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3135   -0.2060    1.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6450    0.1843   -2.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  8 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  2  0
 16 18  1  0
 13  7  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  1  0
M  END

HEADER    PROTEIN                                 12-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-17         0                                  
HETATM    1  C   UNK     0      -6.190   3.459   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.159   4.603   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -3.752   3.977   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -3.913   2.445   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.420   2.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.769   1.415   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.089  -0.092   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.419   4.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.085   3.977   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.249   4.747   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.582   3.977   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.916   4.747   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.250   3.977   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.583   4.747   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.250   2.437   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       2.916   6.287   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -5.479   6.109   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.335   7.140   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7                                                       
CONECT    7    6                                                            
CONECT    8    3    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12                                                            
CONECT   17    2   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0033143
HETATM    1  N1  UNL     1       3.792   0.044   1.288  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.149   0.016  -0.006  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.915  -0.868   0.008  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.910  -0.384   0.998  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.350  -1.128   1.112  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.313  -1.146  -0.033  1.00  0.00           C  
HETATM    7  N2  UNL     1      -1.844   0.155  -0.387  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.487   0.948  -1.390  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.628   0.706  -2.543  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.098  -0.378  -2.828  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.222   2.135  -1.211  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.004   1.998  -0.092  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.764   0.746   0.425  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.394   0.160   1.641  1.00  0.00           C  
HETATM   15  O2  UNL     1      -4.760   0.535   1.692  1.00  0.00           O  
HETATM   16  C12 UNL     1       4.082  -0.484  -1.036  1.00  0.00           C  
HETATM   17  O3  UNL     1       5.240  -0.807  -0.707  1.00  0.00           O  
HETATM   18  O4  UNL     1       3.656  -0.585  -2.339  1.00  0.00           O  
HETATM   19  H1  UNL     1       3.720  -0.854   1.796  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.739   0.430   1.223  1.00  0.00           H  
HETATM   21  H3  UNL     1       2.812   1.053  -0.221  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.281  -1.899   0.337  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.493  -1.002  -0.966  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.426  -0.429   2.007  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.777   0.714   0.835  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.928  -0.764   2.030  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.147  -2.236   1.332  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.139  -1.834   0.218  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.783  -1.624  -0.884  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.416   1.518  -3.224  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.150   2.987  -1.870  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.691   2.737   0.319  1.00  0.00           H  
HETATM   33  H15 UNL     1      -3.329  -0.926   1.568  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.876   0.488   2.569  1.00  0.00           H  
HETATM   35  H17 UNL     1      -5.313  -0.206   1.319  1.00  0.00           H  
HETATM   36  H18 UNL     1       3.645   0.184  -2.979  1.00  0.00           H  
CONECT    1    2   19   20
CONECT    2    3   16   21
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8   13
CONECT    8    9   11   11
CONECT    9   10   10   30
CONECT   11   12   31
CONECT   12   13   13   32
CONECT   13   14
CONECT   14   15   33   34
CONECT   15   35
CONECT   16   17   17   18
CONECT   18   36
END

HMDB0033143
     RDKit          3D
Pyrraline
 36 36  0  0  0  0  0  0  0  0999 V2000
    3.7920    0.0437    1.2875 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1493    0.0163   -0.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9150   -0.8678    0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9097   -0.3839    0.9978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3504   -1.1277    1.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3135   -1.1460   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8441    0.1549   -0.3875 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4871    0.9481   -1.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6278    0.7057   -2.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0978   -0.3781   -2.8276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2220    2.1351   -1.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0045    1.9984   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7636    0.7465    0.4246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3938    0.1599    1.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7600    0.5352    1.6919 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0820   -0.4842   -1.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2402   -0.8072   -0.7072 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6565   -0.5850   -2.3389 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7197   -0.8535    1.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7390    0.4300    1.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8117    1.0533   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2808   -1.8993    0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4928   -1.0022   -0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4255   -0.4289    2.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7775    0.7137    0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9278   -0.7645    2.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466   -2.2358    1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394   -1.8343    0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7835   -1.6239   -0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4164    1.5176   -3.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1497    2.9871   -1.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6905    2.7366    0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3290   -0.9260    1.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8757    0.4877    2.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3135   -0.2060    1.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6450    0.1843   -2.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  8 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  2  0
 16 18  1  0
 13  7  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Amino-6-(2-formyl-5-hydroxymethylpyrrol-1-yl)hexanoic acid	MeSH
2-Formyl-5-(hydroxymethyl)pyrrole-1-norleucine	MeSH
2-FHMPN	MeSH
2-Amino-6-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]hexanoate	Generator
Pyrraline	MeSH

Chemical Formula

C₁₂H₁₈N₂O₄

Average Molecular Weight

254.2823

Monoisotopic Molecular Weight

254.126657074

IUPAC Name

2-amino-6-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]hexanoic acid

Traditional Name

2-amino-6-[2-formyl-5-(hydroxymethyl)pyrrol-1-yl]hexanoic acid

CAS Registry Number

74509-14-1

SMILES

NC(CCCCN1C(CO)=CC=C1C=O)C(O)=O

InChI Identifier

InChI=1S/C12H18N2O4/c13-11(12(17)18)3-1-2-6-14-9(7-15)4-5-10(14)8-16/h4-5,7,11,16H,1-3,6,8,13H2,(H,17,18)

InChI Key

VTYFITADLSVOAS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

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 acids

Alternative Parents

Substituents

Alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Aryl-aldehyde
Substituted pyrrole
Fatty acid
Fatty acyl
Pyrrole
Heteroaromatic compound
Amino acid
Azacycle
Organoheterocyclic compound
Carboxylic acid
Monocarboxylic acid or derivatives
Aldehyde
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Aromatic alcohol
Carbonyl group
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (HMDB: HMDB0033143)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0033143)
Feces (PMID: 27543620)

Cellular substructure

Extracellular (HMDB: HMDB0033143)
Cytoplasm (HMDB: HMDB0033143)

Source

Exogenous

Food

Food (HMDB: HMDB0033143)

Not Available

Nutrient (HMDB: HMDB0033143)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.16 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-2.3	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.03	ChemAxon
pKa (Strongest Basic)	9.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.55 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	66.76 m³·mol⁻¹	ChemAxon
Polarizability	26.66 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	160.542	31661259
DarkChem	[M-H]-	158.747	31661259
DeepCCS	[M+H]+	158.126	30932474
DeepCCS	[M-H]-	155.768	30932474
DeepCCS	[M-2H]-	191.148	30932474
DeepCCS	[M+Na]+	166.786	30932474
AllCCS	[M+H]+	157.0	32859911
AllCCS	[M+H-H2O]+	153.6	32859911
AllCCS	[M+NH4]+	160.0	32859911
AllCCS	[M+Na]+	160.9	32859911
AllCCS	[M-H]-	159.0	32859911
AllCCS	[M+Na-2H]-	159.3	32859911
AllCCS	[M+HCOO]-	159.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pyrraline	NC(CCCCN1C(CO)=CC=C1C=O)C(O)=O	2975.0	Standard polar	33892256
Pyrraline	NC(CCCCN1C(CO)=CC=C1C=O)C(O)=O	2209.8	Standard non polar	33892256
Pyrraline	NC(CCCCN1C(CO)=CC=C1C=O)C(O)=O	2398.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pyrraline,1TMS,isomer #1	C[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(N)C(=O)O	2441.6	Semi standard non polar	33892256
Pyrraline,1TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)CCCCN1C(C=O)=CC=C1CO	2349.6	Semi standard non polar	33892256
Pyrraline,1TMS,isomer #3	C[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO)C(=O)O	2464.0	Semi standard non polar	33892256
Pyrraline,2TMS,isomer #1	C[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(N)C(=O)O[Si](C)(C)C	2383.4	Semi standard non polar	33892256
Pyrraline,2TMS,isomer #2	C[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO[Si](C)(C)C)C(=O)O	2495.2	Semi standard non polar	33892256
Pyrraline,2TMS,isomer #3	C[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO)C(=O)O[Si](C)(C)C	2395.0	Semi standard non polar	33892256
Pyrraline,2TMS,isomer #4	C[Si](C)(C)N(C(CCCCN1C(C=O)=CC=C1CO)C(=O)O)[Si](C)(C)C	2617.8	Semi standard non polar	33892256
Pyrraline,3TMS,isomer #1	C[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO[Si](C)(C)C)C(=O)O[Si](C)(C)C	2445.5	Semi standard non polar	33892256
Pyrraline,3TMS,isomer #1	C[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO[Si](C)(C)C)C(=O)O[Si](C)(C)C	2536.1	Standard non polar	33892256
Pyrraline,3TMS,isomer #2	C[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2657.2	Semi standard non polar	33892256
Pyrraline,3TMS,isomer #2	C[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2639.7	Standard non polar	33892256
Pyrraline,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CCCCN1C(C=O)=CC=C1CO)N([Si](C)(C)C)[Si](C)(C)C	2592.1	Semi standard non polar	33892256
Pyrraline,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CCCCN1C(C=O)=CC=C1CO)N([Si](C)(C)C)[Si](C)(C)C	2624.4	Standard non polar	33892256
Pyrraline,4TMS,isomer #1	C[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2646.8	Semi standard non polar	33892256
Pyrraline,4TMS,isomer #1	C[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2652.9	Standard non polar	33892256
Pyrraline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(N)C(=O)O	2672.5	Semi standard non polar	33892256
Pyrraline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCCCN1C(C=O)=CC=C1CO	2608.5	Semi standard non polar	33892256
Pyrraline,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO)C(=O)O	2710.7	Semi standard non polar	33892256
Pyrraline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(N)C(=O)O[Si](C)(C)C(C)(C)C	2846.8	Semi standard non polar	33892256
Pyrraline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO[Si](C)(C)C(C)(C)C)C(=O)O	2933.3	Semi standard non polar	33892256
Pyrraline,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO)C(=O)O[Si](C)(C)C(C)(C)C	2881.4	Semi standard non polar	33892256
Pyrraline,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(CCCCN1C(C=O)=CC=C1CO)C(=O)O)[Si](C)(C)C(C)(C)C	3066.4	Semi standard non polar	33892256
Pyrraline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3073.8	Semi standard non polar	33892256
Pyrraline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCCCN1C(C=O)=CC=C1CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3162.1	Standard non polar	33892256
Pyrraline,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3287.7	Semi standard non polar	33892256
Pyrraline,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3213.6	Standard non polar	33892256
Pyrraline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CCCCN1C(C=O)=CC=C1CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3254.3	Semi standard non polar	33892256
Pyrraline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CCCCN1C(C=O)=CC=C1CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3226.5	Standard non polar	33892256
Pyrraline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3502.9	Semi standard non polar	33892256
Pyrraline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC=C(C=O)N1CCCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3401.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrraline GC-MS (Non-derivatized) - 70eV, Positive	splash10-01dl-9520000000-0b433cd9cded35aa23ef	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrraline GC-MS (2 TMS) - 70eV, Positive	splash10-008l-8954000000-7e420e3240531df4ca37	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrraline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrraline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrraline 10V, Positive-QTOF	splash10-0a4i-0190000000-10655c1012b66e94ba40	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrraline 20V, Positive-QTOF	splash10-0a5c-3980000000-eea702f0360e6881ff9a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrraline 40V, Positive-QTOF	splash10-0560-9800000000-cb66f0e04f4bd6b98945	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrraline 10V, Negative-QTOF	splash10-0udi-0090000000-5fe59c9e31f9d1b82c6d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrraline 20V, Negative-QTOF	splash10-0fk9-2590000000-7fd7c78887e5c6a4c28a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrraline 40V, Negative-QTOF	splash10-00di-9400000000-db3eeb1ed3f6503bf2e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrraline 10V, Positive-QTOF	splash10-0540-8590000000-d040968f2b23fff76e53	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrraline 20V, Positive-QTOF	splash10-0a59-7960000000-10b916022566e97e5699	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrraline 40V, Positive-QTOF	splash10-001i-9200000000-e40604bb69ce47768a7a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrraline 10V, Negative-QTOF	splash10-0uk9-3190000000-ccdcd07268989aa6afcc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrraline 20V, Negative-QTOF	splash10-0596-3950000000-3fc3da416f4839b6e60a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrraline 40V, Negative-QTOF	splash10-006x-9710000000-40f1c72a3cac98237ca9	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Cardiosvacular risk	Mar Garcia-A...	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011144

KNApSAcK ID

Not Available

Chemspider ID

19980286

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14274616

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Pyrraline (HMDB0033143)

MOL for HMDB0033143 (Pyrraline)

3D MOL for HMDB0033143 (Pyrraline)

3D SDF for HMDB0033143 (Pyrraline)

3D-SDF for HMDB0033143 (Pyrraline)

PDB for HMDB0033143 (Pyrraline)

3D PDB for HMDB0033143 (Pyrraline)

SMILES for HMDB0033143 (Pyrraline)

INCHI for HMDB0033143 (Pyrraline)

Structure for HMDB0033143 (Pyrraline)

3D Structure for HMDB0033143 (Pyrraline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra