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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:11:03 UTC

Update Date

2022-03-07 02:54:25 UTC

HMDB ID

HMDB0035232

Secondary Accession Numbers

HMDB35232

Metabolite Identification

Common Name

Rotundine B

Description

Rotundine B belongs to the class of organic compounds known as methylpyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a methyl group. Rotundine B has been detected, but not quantified in, root vegetables. This could make rotundine b a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Rotundine B.

Structure

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

HMDB0035232
     RDKit          3D
Rotundine B
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.3738    1.9564    1.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2496    0.7782    1.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3646    0.0671    0.7591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3058   -1.0063   -0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0856   -1.3947   -0.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9581   -0.6860   -0.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0160    0.4186    0.6193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6562    0.9822    0.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1649   -0.2649    0.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6067   -0.0840    0.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2143    0.8680   -0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7422    0.9271   -0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3647   -0.4230   -0.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0006    1.4338    1.0138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5317   -0.8743   -0.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2134   -2.3410   -0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3670   -0.2039   -1.9223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5272    2.8647    1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2307    1.8161    2.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4219    2.0575    2.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2134   -1.5370   -0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0548   -2.2749   -1.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4123    1.7621    0.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4801    1.3476    1.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0738   -0.9295    1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0952   -1.0874    0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8949    0.2879    1.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8668    1.8937   -0.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0791    0.4495   -1.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0854    1.6834   -0.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6451   -1.1894   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1298   -0.3137   -1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8922   -0.7129    0.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577    1.9579    1.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0514   -2.8550   -1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6473   -2.3729   -1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1260   -2.8262    0.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3485   -0.3403   -2.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3549   -0.7276   -2.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2318    0.8931   -1.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  9 15  1  0
 15 16  1  0
 15 17  1  0
  7  2  1  0
 15  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
M  END

  Mrv0541 02241209552D          

 17 18  0  0  0  0            999 V2000
   -2.0595   -1.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0595   -2.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3460   -2.4177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338   -2.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338   -1.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3460   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0811   -2.4177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0234   -0.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588    0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1783    0.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3913    0.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931    0.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0522    0.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8496    1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2621    1.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0595    1.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7603    2.4177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  6 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035232

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(O)CCC1CC2=C(C=CN=C2C)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H23NO/c1-10(17)5-6-12-9-13-11(2)16-8-7-14(13)15(12,3)4/h7-8,10,12,17H,5-6,9H2,1-4H3

> <INCHI_KEY>
IMDXDPUTIISQIM-UHFFFAOYSA-N

> <FORMULA>
C15H23NO

> <MOLECULAR_WEIGHT>
233.3492

> <EXACT_MASS>
233.177964363

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.32017060027515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{1,5,5-trimethyl-5H,6H,7H-cyclopenta[c]pyridin-6-yl}butan-2-ol

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
2.6377481496666664

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.609001034772195

> <JCHEM_PKA_STRONGEST_BASIC>
6.59588460598392

> <JCHEM_POLAR_SURFACE_AREA>
33.120000000000005

> <JCHEM_REFRACTIVITY>
70.49560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{1,5,5-trimethyl-6H,7H-cyclopenta[c]pyridin-6-yl}butan-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0035232
     RDKit          3D
Rotundine B
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.3738    1.9564    1.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2496    0.7782    1.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3646    0.0671    0.7591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3058   -1.0063   -0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0856   -1.3947   -0.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9581   -0.6860   -0.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0160    0.4186    0.6193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6562    0.9822    0.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1649   -0.2649    0.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6067   -0.0840    0.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2143    0.8680   -0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7422    0.9271   -0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3647   -0.4230   -0.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0006    1.4338    1.0138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5317   -0.8743   -0.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2134   -2.3410   -0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3670   -0.2039   -1.9223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5272    2.8647    1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2307    1.8161    2.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4219    2.0575    2.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2134   -1.5370   -0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0548   -2.2749   -1.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4123    1.7621    0.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4801    1.3476    1.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0738   -0.9295    1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0952   -1.0874    0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8949    0.2879    1.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8668    1.8937   -0.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0791    0.4495   -1.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0854    1.6834   -0.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6451   -1.1894   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1298   -0.3137   -1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8922   -0.7129    0.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577    1.9579    1.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0514   -2.8550   -1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6473   -2.3729   -1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1260   -2.8262    0.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3485   -0.3403   -2.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3549   -0.7276   -2.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2318    0.8931   -1.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  9 15  1  0
 15 16  1  0
 15 17  1  0
  7  2  1  0
 15  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.844  -2.203   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.844  -3.743   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -2.513  -4.513   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.183  -3.743   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.183  -2.203   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.513  -1.436   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.151  -4.513   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.044  -1.177   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.670   0.224   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.199   0.060   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.597   1.549   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.534   0.830   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.097   1.559   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.586   1.957   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.356   3.291   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.844   3.689   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.419   4.513   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    5   10                                                  
CONECT    7    4                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    6    9   11   12                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0035232
HETATM    1  C1  UNL     1      -3.374   1.956   1.983  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.250   0.778   1.094  1.00  0.00           C  
HETATM    3  N1  UNL     1      -4.365   0.067   0.759  1.00  0.00           N  
HETATM    4  C3  UNL     1      -4.306  -1.006  -0.042  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.086  -1.395  -0.536  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.958  -0.686  -0.205  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.016   0.419   0.619  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.656   0.982   0.811  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.165  -0.265   0.544  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.607  -0.084   0.553  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.214   0.868  -0.421  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.742   0.927  -0.254  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.365  -0.423  -0.480  1.00  0.00           C  
HETATM   14  O1  UNL     1       4.001   1.434   1.014  1.00  0.00           O  
HETATM   15  C13 UNL     1      -0.532  -0.874  -0.594  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.213  -2.341  -0.805  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.367  -0.204  -1.922  1.00  0.00           C  
HETATM   18  H1  UNL     1      -3.527   2.865   1.372  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.231   1.816   2.697  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.422   2.057   2.541  1.00  0.00           H  
HETATM   21  H4  UNL     1      -5.213  -1.537  -0.279  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.055  -2.275  -1.190  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.412   1.762   0.071  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.480   1.348   1.826  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.074  -0.929   1.435  1.00  0.00           H  
HETATM   26  H9  UNL     1       2.095  -1.087   0.494  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.895   0.288   1.582  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.867   1.894  -0.312  1.00  0.00           H  
HETATM   29  H12 UNL     1       2.079   0.449  -1.439  1.00  0.00           H  
HETATM   30  H13 UNL     1       4.085   1.683  -0.994  1.00  0.00           H  
HETATM   31  H14 UNL     1       3.645  -1.189  -0.828  1.00  0.00           H  
HETATM   32  H15 UNL     1       5.130  -0.314  -1.271  1.00  0.00           H  
HETATM   33  H16 UNL     1       4.892  -0.713   0.454  1.00  0.00           H  
HETATM   34  H17 UNL     1       3.258   1.958   1.384  1.00  0.00           H  
HETATM   35  H18 UNL     1      -1.051  -2.855  -1.320  1.00  0.00           H  
HETATM   36  H19 UNL     1       0.647  -2.373  -1.526  1.00  0.00           H  
HETATM   37  H20 UNL     1       0.126  -2.826   0.108  1.00  0.00           H  
HETATM   38  H21 UNL     1      -1.348  -0.340  -2.470  1.00  0.00           H  
HETATM   39  H22 UNL     1       0.355  -0.728  -2.582  1.00  0.00           H  
HETATM   40  H23 UNL     1      -0.232   0.893  -1.873  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3    7
CONECT    3    4
CONECT    4    5    5   21
CONECT    5    6   22
CONECT    6    7    7   15
CONECT    7    8
CONECT    8    9   23   24
CONECT    9   10   15   25
CONECT   10   11   26   27
CONECT   11   12   28   29
CONECT   12   13   14   30
CONECT   13   31   32   33
CONECT   14   34
CONECT   15   16   17
CONECT   16   35   36   37
CONECT   17   38   39   40
END

HMDB0035232
     RDKit          3D
Rotundine B
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.3738    1.9564    1.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2496    0.7782    1.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3646    0.0671    0.7591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3058   -1.0063   -0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0856   -1.3947   -0.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9581   -0.6860   -0.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0160    0.4186    0.6193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6562    0.9822    0.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1649   -0.2649    0.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6067   -0.0840    0.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2143    0.8680   -0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7422    0.9271   -0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3647   -0.4230   -0.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0006    1.4338    1.0138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5317   -0.8743   -0.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2134   -2.3410   -0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3670   -0.2039   -1.9223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5272    2.8647    1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2307    1.8161    2.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4219    2.0575    2.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2134   -1.5370   -0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0548   -2.2749   -1.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4123    1.7621    0.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4801    1.3476    1.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0738   -0.9295    1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0952   -1.0874    0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8949    0.2879    1.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8668    1.8937   -0.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0791    0.4495   -1.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0854    1.6834   -0.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6451   -1.1894   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1298   -0.3137   -1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8922   -0.7129    0.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577    1.9579    1.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0514   -2.8550   -1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6473   -2.3729   -1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1260   -2.8262    0.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3485   -0.3403   -2.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3549   -0.7276   -2.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2318    0.8931   -1.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  9 15  1  0
 15 16  1  0
 15 17  1  0
  7  2  1  0
 15  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Rotundine b	MeSH

Chemical Formula

C₁₅H₂₃NO

Average Molecular Weight

233.3492

Monoisotopic Molecular Weight

233.177964363

IUPAC Name

4-{1,5,5-trimethyl-5H,6H,7H-cyclopenta[c]pyridin-6-yl}butan-2-ol

Traditional Name

4-{1,5,5-trimethyl-6H,7H-cyclopenta[c]pyridin-6-yl}butan-2-ol

CAS Registry Number

Not Available

SMILES

CC(O)CCC1CC2=C(C=CN=C2C)C1(C)C

InChI Identifier

InChI=1S/C15H23NO/c1-10(17)5-6-12-9-13-11(2)16-8-7-14(13)15(12,3)4/h7-8,10,12,17H,5-6,9H2,1-4H3

InChI Key

IMDXDPUTIISQIM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methylpyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a methyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Methylpyridines

Direct Parent

Methylpyridines

Alternative Parents

Substituents

Methylpyridine
Heteroaromatic compound
Secondary alcohol
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB35232)
Cell membrane (HMDB: HMDB35232)

Route of exposure

Enteral

Ingestion (HMDB: HMDB35232)

Source

Exogenous

Exogenous (HMDB: HMDB35232)

Food

Food (HMDB: HMDB35232)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Endogenous

Plant

Plant (HMDB: HMDB35232)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB35232)

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	0.22 g/L	ALOGPS
logP	3.99	ALOGPS
logP	2.64	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	17.61	ChemAxon
pKa (Strongest Basic)	6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	33.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	70.5 m³·mol⁻¹	ChemAxon
Polarizability	28.32 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	157.386	31661259
DarkChem	[M-H]-	156.201	31661259
DeepCCS	[M+H]+	157.206	30932474
DeepCCS	[M-H]-	154.848	30932474
DeepCCS	[M-2H]-	187.839	30932474
DeepCCS	[M+Na]+	163.299	30932474
AllCCS	[M+H]+	155.8	32859911
AllCCS	[M+H-H2O]+	152.1	32859911
AllCCS	[M+NH4]+	159.3	32859911
AllCCS	[M+Na]+	160.3	32859911
AllCCS	[M-H]-	163.7	32859911
AllCCS	[M+Na-2H]-	164.2	32859911
AllCCS	[M+HCOO]-	164.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rotundine B	CC(O)CCC1CC2=C(C=CN=C2C)C1(C)C	2698.7	Standard polar	33892256
Rotundine B	CC(O)CCC1CC2=C(C=CN=C2C)C1(C)C	1813.7	Standard non polar	33892256
Rotundine B	CC(O)CCC1CC2=C(C=CN=C2C)C1(C)C	1869.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rotundine B,1TMS,isomer #1	CC1=NC=CC2=C1CC(CCC(C)O[Si](C)(C)C)C2(C)C	1953.4	Semi standard non polar	33892256
Rotundine B,1TBDMS,isomer #1	CC1=NC=CC2=C1CC(CCC(C)O[Si](C)(C)C(C)(C)C)C2(C)C	2185.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Rotundine B GC-MS (Non-derivatized) - 70eV, Positive	splash10-02tj-6940000000-af8e6842ef02e5718d78	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rotundine B GC-MS (1 TMS) - 70eV, Positive	splash10-00r6-8960000000-8fe5e8a69c6f93c66cd5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rotundine B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rotundine B 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 - Rotundine B 10V, Positive-QTOF	splash10-014i-0190000000-cf0d00a83bb524c10989	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundine B 20V, Positive-QTOF	splash10-014i-4790000000-bd9bd31de5f331a15b0d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundine B 40V, Positive-QTOF	splash10-0fdo-7920000000-5da10fa89008e8b01ade	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundine B 10V, Negative-QTOF	splash10-001i-0190000000-fcd73f18e1dfd9ac0903	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundine B 20V, Negative-QTOF	splash10-01q9-0190000000-68f9ede89bbc0d5c16ed	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundine B 40V, Negative-QTOF	splash10-06dj-5970000000-18d104e26838e551a8f8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundine B 10V, Negative-QTOF	splash10-001i-0090000000-c4da52d55add11319fe1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundine B 20V, Negative-QTOF	splash10-053r-0690000000-1c5a21293cfeede30593	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundine B 40V, Negative-QTOF	splash10-05ar-0920000000-704b4cac867596fa26bd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundine B 10V, Positive-QTOF	splash10-02t9-0980000000-24d0f3592ece0c95ff5e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundine B 20V, Positive-QTOF	splash10-08mi-1910000000-2e7cec00beb48ff1cab5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundine B 40V, Positive-QTOF	splash10-0a4i-6900000000-bcc75fc82727a7ce4a1a	2021-09-24	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

FDB013932

KNApSAcK ID

C00047087

Chemspider ID

35013879

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21603505

PDB ID

Not Available

ChEBI ID

173678

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 Rotundine B (HMDB0035232)

MOL for HMDB0035232 (Rotundine B)

3D MOL for HMDB0035232 (Rotundine B)

3D SDF for HMDB0035232 (Rotundine B)

3D-SDF for HMDB0035232 (Rotundine B)

PDB for HMDB0035232 (Rotundine B)

3D PDB for HMDB0035232 (Rotundine B)

SMILES for HMDB0035232 (Rotundine B)

INCHI for HMDB0035232 (Rotundine B)

Structure for HMDB0035232 (Rotundine B)

3D Structure for HMDB0035232 (Rotundine B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra