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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:08 UTC

Update Date

2022-03-07 02:52:30 UTC

HMDB ID

HMDB0030327

Secondary Accession Numbers

HMDB30327

Metabolite Identification

Common Name

Perlolyrine

Description

Perlolyrine, also known as substance ys, belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. Perlolyrine has been detected, but not quantified in, a few different foods, such as herbs and spices, saffrons (Crocus sativus), and soy beans (Glycine max). This could make perlolyrine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Perlolyrine.

Structure

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

HMDB0030327
     RDKit          3D
Perlolyrine
 32 35  0  0  0  0  0  0  0  0999 V2000
    5.6846    1.0255   -0.4783 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402    1.3864   -0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229    0.1727   -0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9854   -1.1122   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8659   -1.9140    0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841   -1.0588    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4067   -1.5218    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0880   -2.7964    0.4888 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1439   -3.2592    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1993   -2.3601    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9364   -1.0220    0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6267   -0.5913    0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6546    0.7342   -0.0158 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9109    1.2053   -0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4769    2.4694   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407    2.6695   -0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6401    1.5681    0.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0949    0.3130    0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7196    0.1067    0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2154    0.1478   -0.1128 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2807    1.7806   -0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1381    2.1635    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0360    1.8555   -1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0059   -1.4753   -0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590   -2.9896    0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076   -4.2905    0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2273   -2.6747    0.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920    1.3148   -0.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419    3.3265   -0.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2706    3.6606   -0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7089    1.7283    0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7046   -0.5624    0.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20  3  1  0
 12  7  1  0
 19 14  1  0
 19 11  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
M  END

  Mrv0541 05061305092D          

 20 23  0  0  0  0            999 V2000
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046   -2.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6895   -1.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475   -2.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800   -2.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1612   -3.5421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800   -1.4117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  2  0  0  0  0
 10  5  2  0  0  0  0
 10  9  1  0  0  0  0
 11  3  2  0  0  0  0
 12  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13  4  2  0  0  0  0
 13 11  1  0  0  0  0
 14  6  2  0  0  0  0
 15 12  2  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 17 16  2  0  0  0  0
 18 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19  9  1  0  0  0  0
 20 10  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030327

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1=CC=C(O1)C1=NC=CC2=C1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C16H12N2O2/c19-9-10-5-6-14(20-10)16-15-12(7-8-17-16)11-3-1-2-4-13(11)18-15/h1-8,18-19H,9H2

> <INCHI_KEY>
KFUCYPGCMLPUMT-UHFFFAOYSA-N

> <FORMULA>
C16H12N2O2

> <MOLECULAR_WEIGHT>
264.2787

> <EXACT_MASS>
264.089877638

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.588973991252445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5-{9H-pyrido[3,4-b]indol-1-yl}furan-2-yl)methanol

> <ALOGPS_LOGP>
2.66

> <JCHEM_LOGP>
2.119186950333333

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.751026894203264

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.433887143113587

> <JCHEM_PKA_STRONGEST_BASIC>
2.788122435059806

> <JCHEM_POLAR_SURFACE_AREA>
62.05

> <JCHEM_REFRACTIVITY>
75.1638

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
perlolyrine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030327
     RDKit          3D
Perlolyrine
 32 35  0  0  0  0  0  0  0  0999 V2000
    5.6846    1.0255   -0.4783 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402    1.3864   -0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229    0.1727   -0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9854   -1.1122   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8659   -1.9140    0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841   -1.0588    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4067   -1.5218    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0880   -2.7964    0.4888 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1439   -3.2592    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1993   -2.3601    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9364   -1.0220    0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6267   -0.5913    0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6546    0.7342   -0.0158 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9109    1.2053   -0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4769    2.4694   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407    2.6695   -0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6401    1.5681    0.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0949    0.3130    0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7196    0.1067    0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2154    0.1478   -0.1128 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2807    1.7806   -0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1381    2.1635    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0360    1.8555   -1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0059   -1.4753   -0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590   -2.9896    0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076   -4.2905    0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2273   -2.6747    0.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920    1.3148   -0.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419    3.3265   -0.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2706    3.6606   -0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7089    1.7283    0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7046   -0.5624    0.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20  3  1  0
 12  7  1  0
 19 14  1  0
 19 11  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.393   0.450   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.411   2.235   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.382  -4.651   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.287  -3.405   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.329  -5.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.083  -4.175   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.382  -2.159   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -0.173   0.450   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -2.168  -6.612   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.083  -2.635   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   11                                                       
CONECT    4    2   13                                                       
CONECT    5    6   10                                                       
CONECT    6    5   14                                                       
CONECT    7    8   12                                                       
CONECT    8    7   17                                                       
CONECT    9   10   19                                                       
CONECT   10    5    9   20                                                  
CONECT   11    3   12   13                                                  
CONECT   12    7   11   15                                                  
CONECT   13    4   11   18                                                  
CONECT   14    6   16   20                                                  
CONECT   15   12   16   18                                                  
CONECT   16   14   15   17                                                  
CONECT   17    8   16                                                       
CONECT   18   13   15                                                       
CONECT   19    9                                                            
CONECT   20   10   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0030327
HETATM    1  O1  UNL     1       5.685   1.025  -0.478  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.340   1.386  -0.447  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.523   0.173  -0.203  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.985  -1.112  -0.032  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.866  -1.914   0.168  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.784  -1.059   0.105  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.407  -1.522   0.268  1.00  0.00           C  
HETATM    8  N1  UNL     1       0.088  -2.796   0.489  1.00  0.00           N  
HETATM    9  C7  UNL     1      -1.144  -3.259   0.642  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.199  -2.360   0.571  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.936  -1.022   0.344  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.627  -0.591   0.190  1.00  0.00           C  
HETATM   13  N2  UNL     1      -0.655   0.734  -0.016  1.00  0.00           N  
HETATM   14  C11 UNL     1      -1.911   1.205  -0.007  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.477   2.469  -0.168  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.841   2.669  -0.109  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.640   1.568   0.116  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.095   0.313   0.277  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.720   0.107   0.218  1.00  0.00           C  
HETATM   20  O2  UNL     1       2.215   0.148  -0.113  1.00  0.00           O  
HETATM   21  H1  UNL     1       6.281   1.781  -0.233  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.138   2.163   0.331  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.036   1.856  -1.421  1.00  0.00           H  
HETATM   24  H4  UNL     1       5.006  -1.475  -0.042  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.859  -2.990   0.337  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.408  -4.291   0.821  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.227  -2.675   0.688  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.192   1.315  -0.162  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.842   3.327  -0.344  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.271   3.661  -0.237  1.00  0.00           H  
HETATM   31  H11 UNL     1      -5.709   1.728   0.161  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.705  -0.562   0.454  1.00  0.00           H  
CONECT    1    2   21
CONECT    2    3   22   23
CONECT    3    4    4   20
CONECT    4    5   24
CONECT    5    6    6   25
CONECT    6    7   20
CONECT    7    8    8   12
CONECT    8    9
CONECT    9   10   10   26
CONECT   10   11   27
CONECT   11   12   12   19
CONECT   12   13
CONECT   13   14   28
CONECT   14   15   15   19
CONECT   15   16   29
CONECT   16   17   17   30
CONECT   17   18   31
CONECT   18   19   19   32
END

HMDB0030327
     RDKit          3D
Perlolyrine
 32 35  0  0  0  0  0  0  0  0999 V2000
    5.6846    1.0255   -0.4783 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402    1.3864   -0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229    0.1727   -0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9854   -1.1122   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8659   -1.9140    0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841   -1.0588    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4067   -1.5218    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0880   -2.7964    0.4888 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1439   -3.2592    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1993   -2.3601    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9364   -1.0220    0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6267   -0.5913    0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6546    0.7342   -0.0158 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9109    1.2053   -0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4769    2.4694   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407    2.6695   -0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6401    1.5681    0.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0949    0.3130    0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7196    0.1067    0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2154    0.1478   -0.1128 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2807    1.7806   -0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1381    2.1635    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0360    1.8555   -1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0059   -1.4753   -0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590   -2.9896    0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076   -4.2905    0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2273   -2.6747    0.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920    1.3148   -0.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419    3.3265   -0.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2706    3.6606   -0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7089    1.7283    0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7046   -0.5624    0.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20  3  1  0
 12  7  1  0
 19 14  1  0
 19 11  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Substance ys	MeSH
Yellow substance ys	MeSH
2-(b-Carbolin-1-yl)-5-hydroxymethylfuran	HMDB
2-Dehydrocarbonylflazin	HMDB
5-(9H-pyrido(3,4-b)indol-1-yl)-2-Furanmethanol	HMDB
5-(9H-pyrido[3,4-b]indol-1-yl)-2-Furanmethanol, 9ci	HMDB
Alkaloid ys	HMDB
[5-(9H-beta-Carbolin-1-yl)-2-furyl]methanol	HMDB

Chemical Formula

C₁₆H₁₂N₂O₂

Average Molecular Weight

264.2787

Monoisotopic Molecular Weight

264.089877638

IUPAC Name

(5-{9H-pyrido[3,4-b]indol-1-yl}furan-2-yl)methanol

Traditional Name

perlolyrine

CAS Registry Number

29700-20-7

SMILES

OCC1=CC=C(O1)C1=NC=CC2=C1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C16H12N2O2/c19-9-10-5-6-14(20-10)16-15-12(7-8-17-16)11-3-1-2-4-13(11)18-15/h1-8,18-19H,9H2

InChI Key

KFUCYPGCMLPUMT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harman
Beta-carboline
Pyridoindole
Indole
Indole or derivatives
Benzenoid
Pyridine
Heteroaromatic compound
Pyrrole
Furan
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic molecular entity (CHEBI:69444 )
Indole alkaloids (C09231 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030327)
Cell membrane (HMDB: HMDB0030327)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030327)

Source

Endogenous

Endogenous (HMDB: HMDB0030327)

Plant

Plant (HMDB: HMDB0030327)
Glycine Max (HMDB: HMDB0030327)

Exogenous

Food

Food (HMDB: HMDB0030327)

Soy

Soy bean (FooDB: FOOD00085)

Herb and spice

Spice

Saffron (FooDB: FOOD00063)

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0030327)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	183 °C	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	0.089 g/L	ALOGPS
logP	2.66	ALOGPS
logP	2.12	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.43	ChemAxon
pKa (Strongest Basic)	2.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.05 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.16 m³·mol⁻¹	ChemAxon
Polarizability	28.59 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	160.736	31661259
DarkChem	[M-H]-	163.73	31661259
DeepCCS	[M-2H]-	190.73	30932474
DeepCCS	[M+Na]+	166.274	30932474
AllCCS	[M+H]+	162.2	32859911
AllCCS	[M+H-H2O]+	158.3	32859911
AllCCS	[M+NH4]+	166.0	32859911
AllCCS	[M+Na]+	167.0	32859911
AllCCS	[M-H]-	165.5	32859911
AllCCS	[M+Na-2H]-	164.6	32859911
AllCCS	[M+HCOO]-	163.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Perlolyrine	OCC1=CC=C(O1)C1=NC=CC2=C1NC1=CC=CC=C21	3693.8	Standard polar	33892256
Perlolyrine	OCC1=CC=C(O1)C1=NC=CC2=C1NC1=CC=CC=C21	2687.8	Standard non polar	33892256
Perlolyrine	OCC1=CC=C(O1)C1=NC=CC2=C1NC1=CC=CC=C21	2947.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Perlolyrine,1TMS,isomer #1	C[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2[NH]C2=CC=CC=C23)O1	2864.2	Semi standard non polar	33892256
Perlolyrine,1TMS,isomer #2	C[Si](C)(C)N1C2=CC=CC=C2C2=CC=NC(C3=CC=C(CO)O3)=C21	2844.0	Semi standard non polar	33892256
Perlolyrine,2TMS,isomer #1	C[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2N([Si](C)(C)C)C2=CC=CC=C32)O1	2844.7	Semi standard non polar	33892256
Perlolyrine,2TMS,isomer #1	C[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2N([Si](C)(C)C)C2=CC=CC=C32)O1	2744.8	Standard non polar	33892256
Perlolyrine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2[NH]C2=CC=CC=C23)O1	3096.4	Semi standard non polar	33892256
Perlolyrine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C2=CC=CC=C2C2=CC=NC(C3=CC=C(CO)O3)=C21	3039.4	Semi standard non polar	33892256
Perlolyrine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2N([Si](C)(C)C(C)(C)C)C2=CC=CC=C32)O1	3248.2	Semi standard non polar	33892256
Perlolyrine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2N([Si](C)(C)C(C)(C)C)C2=CC=CC=C32)O1	3146.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Perlolyrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000b-0190000000-366a1478638155f0b62d	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Perlolyrine GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-9263000000-7f547b2cb0cea39ddfb4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Perlolyrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Perlolyrine 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 - Perlolyrine 10V, Positive-QTOF	splash10-014i-0090000000-5aae234b5117054b9b0e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perlolyrine 20V, Positive-QTOF	splash10-014j-0090000000-c544b87c4bab088505c9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perlolyrine 40V, Positive-QTOF	splash10-014i-4960000000-89238e7378563fe9e333	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perlolyrine 10V, Negative-QTOF	splash10-03di-0090000000-4022863ec611eb08878d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perlolyrine 20V, Negative-QTOF	splash10-01qa-0190000000-05b5aa6ed9c4bfaf6e90	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perlolyrine 40V, Negative-QTOF	splash10-0gb9-3490000000-2bf143ea0acfda8a07a2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perlolyrine 10V, Negative-QTOF	splash10-03e9-0090000000-5db7fd9219b8a82d732a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perlolyrine 20V, Negative-QTOF	splash10-03di-0090000000-3ba2386f41e0df1e8c34	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perlolyrine 40V, Negative-QTOF	splash10-0006-2920000000-e2eeb6b2f419c48d29aa	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perlolyrine 10V, Positive-QTOF	splash10-014i-0090000000-e6e22b9224f216c1ee62	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perlolyrine 20V, Positive-QTOF	splash10-014i-0290000000-021deff5c273a5c42dc8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perlolyrine 40V, Positive-QTOF	splash10-05n0-0490000000-5349405c626001a3e473	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160179

PDB ID

Not Available

ChEBI ID

610215

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 Perlolyrine (HMDB0030327)

MOL for HMDB0030327 (Perlolyrine)

3D MOL for HMDB0030327 (Perlolyrine)

3D SDF for HMDB0030327 (Perlolyrine)

3D-SDF for HMDB0030327 (Perlolyrine)

PDB for HMDB0030327 (Perlolyrine)

3D PDB for HMDB0030327 (Perlolyrine)

SMILES for HMDB0030327 (Perlolyrine)

INCHI for HMDB0030327 (Perlolyrine)

Structure for HMDB0030327 (Perlolyrine)

3D Structure for HMDB0030327 (Perlolyrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra