MiMeDB: Showing metabocard for (2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline (MMDBc0009662)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 02:06:32 UTC

Update Date

2025-10-07 16:05:38 UTC

Metabolite ID

MMDBc0009662

Metabolite Identification

Common Name

(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline

Description

(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline is a natural product belonging to the class of alkaloids. There is limited literature available on this metabolite, indicating a need for further research to fully understand its properties and potential biological activities.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152104062D          

 39 44  0  0  1  0            999 V2000
    9.2963   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2130    0.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5362   -1.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287    0.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4520    1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5578    0.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8988    0.6634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6270   -0.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0390    0.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2866    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0549   -1.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530    1.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8054    1.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3025   -1.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4530   -0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5304   -1.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7976   -0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1222    0.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7241   -0.9410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7005   -0.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9456   -0.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4669    0.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6174    0.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0452   -0.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3837    0.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3959    0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0379    0.7509    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8746   -0.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7904    1.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8885    0.2182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6410   -0.1202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2193   -0.2643    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8111    0.9254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6240   -0.5523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5428    1.4276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5500   -0.7467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6313    1.2333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9717   -0.6026    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1211    1.5717    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  2  0  0  0  0
 10  9  2  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 18  9  1  0  0  0  0
 18 15  2  0  0  0  0
 19 11  1  0  0  0  0
 19 16  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  1  0  0  0  0
 21 20  1  0  0  0  0
 22 17  2  0  0  0  0
 23 10  1  0  0  0  0
 23 20  2  0  0  0  0
 24 17  1  0  0  0  0
 25 12  2  0  0  0  0
 25 22  1  0  0  0  0
 26 21  2  0  0  0  0
 27 24  1  0  0  0  0
 28  2  1  0  0  0  0
 28  3  1  0  0  0  0
 28  8  1  0  0  0  0
 28 18  1  0  0  0  0
 29  4  1  0  0  0  0
 29  5  1  0  0  0  0
 27 29  1  1  0  0  0
 30  6  1  1  0  0  0
 30 13  1  0  0  0  0
 31  7  1  6  0  0  0
 31 19  1  0  0  0  0
 31 26  1  0  0  0  0
 31 30  1  0  0  0  0
 32 14  1  0  0  0  0
 32 22  1  0  0  0  0
 32 30  1  0  0  0  0
 33 23  1  0  0  0  0
 33 26  1  0  0  0  0
 34 24  2  0  0  0  0
 35 29  1  0  0  0  0
 32 36  1  6  0  0  0
 37 25  1  0  0  0  0
 37 27  1  0  0  0  0
 19 38  1  1  0  0  0
 27 39  1  6  0  0  0
M  END


  Mrv1652305152104062D          

 39 44  0  0  1  0            999 V2000
    9.2963   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2130    0.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5362   -1.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287    0.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4520    1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5578    0.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8988    0.6634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6270   -0.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0390    0.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2866    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0549   -1.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530    1.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8054    1.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3025   -1.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4530   -0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5304   -1.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7976   -0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1222    0.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7241   -0.9410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7005   -0.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9456   -0.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4669    0.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6174    0.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0452   -0.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3837    0.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3959    0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0379    0.7509    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8746   -0.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7904    1.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8885    0.2182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6410   -0.1202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2193   -0.2643    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8111    0.9254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6240   -0.5523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5428    1.4276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5500   -0.7467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6313    1.2333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9717   -0.6026    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1211    1.5717    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  2  0  0  0  0
 10  9  2  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 18  9  1  0  0  0  0
 18 15  2  0  0  0  0
 19 11  1  0  0  0  0
 19 16  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  1  0  0  0  0
 21 20  1  0  0  0  0
 22 17  2  0  0  0  0
 23 10  1  0  0  0  0
 23 20  2  0  0  0  0
 24 17  1  0  0  0  0
 25 12  2  0  0  0  0
 25 22  1  0  0  0  0
 26 21  2  0  0  0  0
 27 24  1  0  0  0  0
 28  2  1  0  0  0  0
 28  3  1  0  0  0  0
 28  8  1  0  0  0  0
 28 18  1  0  0  0  0
 29  4  1  0  0  0  0
 29  5  1  0  0  0  0
 27 29  1  1  0  0  0
 30  6  1  1  0  0  0
 30 13  1  0  0  0  0
 31  7  1  6  0  0  0
 31 19  1  0  0  0  0
 31 26  1  0  0  0  0
 31 30  1  0  0  0  0
 32 14  1  0  0  0  0
 32 22  1  0  0  0  0
 32 30  1  0  0  0  0
 33 23  1  0  0  0  0
 33 26  1  0  0  0  0
 34 24  2  0  0  0  0
 35 29  1  0  0  0  0
 32 36  1  6  0  0  0
 37 25  1  0  0  0  0
 37 27  1  0  0  0  0
 19 38  1  1  0  0  0
 27 39  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0009662

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]12CC3=C(NC4=C3C=C(C=C4)C(C)(C)C=C)[C@]1(C)[C@@]1(C)CC=C3O[C@@]([H])(C(=O)C=C3[C@]1(O)CC2)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C32H39NO4/c1-8-28(2,3)18-9-10-23-20(15-18)21-16-19-11-14-32(36)22-17-24(34)27(29(4,5)35)37-25(22)12-13-30(32,6)31(19,7)26(21)33-23/h8-10,12,15,17,19,27,33,35-36H,1,11,13-14,16H2,2-7H3/t19-,27-,30+,31+,32+/m0/s1

> <INCHI_KEY>
FNTKJPWOQYZZSM-LGTSKZSNSA-N

> <FORMULA>
C32H39NO4

> <MOLECULAR_WEIGHT>
501.667

> <EXACT_MASS>
501.28790874

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
59.03315180679875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-19-(2-methylbut-3-en-2-yl)-6-oxa-23-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{16,24}.0^{17,22}]tetracosa-4,9,16(24),17(22),18,20-hexaen-8-one

> <ALOGPS_LOGP>
5.77

> <JCHEM_LOGP>
4.976463607000003

> <ALOGPS_LOGS>
-6.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.439053185106406

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.065588439895437

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1861438500195485

> <JCHEM_POLAR_SURFACE_AREA>
82.55000000000001

> <JCHEM_REFRACTIVITY>
148.02089999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.85e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-19-(2-methylbut-3-en-2-yl)-6-oxa-23-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{16,24}.0^{17,22}]tetracosa-4,9,16(24),17(22),18,20-hexaen-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      17.353  -0.224   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.331   0.911   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.068  -1.898   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.107   0.629   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.844   3.438   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.641   1.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.278   1.238   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.104  -1.125   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.140   1.671   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.735   2.302   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.702  -2.657   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.832   2.571   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.237   1.939   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.298  -2.025   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.046  -0.762   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.457  -2.082   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.489  -0.762   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.295   0.138   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.952  -1.757   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.641  -0.131   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.232  -0.752   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.738   0.138   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.486   1.402   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.084  -0.131   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.583   1.671   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.206   0.397   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.071   1.402   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.699  -0.493   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.475   2.033   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.392   0.407   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.796  -0.224   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.143  -0.493   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       8.981   1.727   0.000  0.00  0.00           N+0
HETATM   34  O   UNK     0      -1.165  -1.031   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -2.880   2.665   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       2.893  -1.394   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       1.178   2.302   0.000  0.00  0.00           O+0
HETATM   38  H   UNK     0       5.547  -1.125   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.226   2.934   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2   28                                                            
CONECT    3   28                                                            
CONECT    4   29                                                            
CONECT    5   29                                                            
CONECT    6   30                                                            
CONECT    7   31                                                            
CONECT    8    1   28                                                       
CONECT    9   10   18                                                       
CONECT   10    9   23                                                       
CONECT   11   14   19                                                       
CONECT   12   13   25                                                       
CONECT   13   12   30                                                       
CONECT   14   11   32                                                       
CONECT   15   18   20                                                       
CONECT   16   19   21                                                       
CONECT   17   22   24                                                       
CONECT   18    9   15   28                                                  
CONECT   19   11   16   31   38                                             
CONECT   20   15   21   23                                                  
CONECT   21   16   20   26                                                  
CONECT   22   17   25   32                                                  
CONECT   23   10   20   33                                                  
CONECT   24   17   27   34                                                  
CONECT   25   12   22   37                                                  
CONECT   26   21   31   33                                                  
CONECT   27   24   29   37   39                                             
CONECT   28    2    3    8   18                                             
CONECT   29    4    5   27   35                                             
CONECT   30    6   13   31   32                                             
CONECT   31    7   19   26   30                                             
CONECT   32   14   22   30   36                                             
CONECT   33   23   26                                                       
CONECT   34   24                                                            
CONECT   35   29                                                            
CONECT   36   32                                                            
CONECT   37   25   27                                                       
CONECT   38   19                                                            
CONECT   39   27                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

Synonyms

Not Available

Molecular Formula

C₃₂H₃₉NO₄

Average Mass

501.667

Monoisotopic Mass

501.28790874

IUPAC Name

(1S,2R,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-19-(2-methylbut-3-en-2-yl)-6-oxa-23-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{16,24}.0^{17,22}]tetracosa-4,9,16(24),17(22),18,20-hexaen-8-one

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@]12CC3=C(NC4=C3C=C(C=C4)C(C)(C)C=C)[C@]1(C)[C@@]1(C)CC=C3O[C@@]([H])(C(=O)C=C3[C@]1(O)CC2)C(C)(C)O

InChI Identifier

InChI=1S/C32H39NO4/c1-8-28(2,3)18-9-10-23-20(15-18)21-16-19-11-14-32(36)22-17-24(34)27(29(4,5)35)37-25(22)12-13-30(32,6)31(19,7)26(21)33-23/h8-10,12,15,17,19,27,33,35-36H,1,11,13-14,16H2,2-7H3/t19-,27-,30+,31+,32+/m0/s1

InChI Key

FNTKJPWOQYZZSM-LGTSKZSNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
3-alkylindole
Naphthalene
Indole or derivatives
Indole
Dihydropyranone
Benzenoid
Pyran
Heteroaromatic compound
Tertiary alcohol
Pyrrole
Cyclic alcohol
Cyclic ketone
Ketone
Oxacycle
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00018 g/L	ALOGPS
logP	5.77	ALOGPS
logP	4.98	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	12.07	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	148.02 m³·mol⁻¹	ChemAxon
Polarizability	59.03 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-23	20.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-23	35.1
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	682.1
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	842.0
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	957.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	252.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	3696.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	95.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	339.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	626.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	311.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	164.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	225.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	8.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	170.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	194.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	533.5
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1868.4
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1368.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_1	C=CC(C)(C)C1=CC=C2[NH]C3=C(C[C@@H]4CC[C@@]5(O[Si](C)(C)C)C6=CC(=O)[C@@H](C(C)(C)O)OC6=CC[C@]5(C)[C@@]34C)C2=C1	standard non polar	2025-10-23	1944.19
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_2	C=CC(C)(C)C1=CC=C2[NH]C3=C(C[C@@H]4CC[C@@]5(O)C6=CC(=O)[C@@H](C(C)(C)O[Si](C)(C)C)OC6=CC[C@]5(C)[C@@]34C)C2=C1	standard non polar	2025-10-23	1213.53
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_3	C=CC(C)(C)C1=CC=C2[NH]C3=C(C[C@@H]4CC[C@@]5(O)C6=CC(O[Si](C)(C)C)=C(C(C)(C)O)OC6=CC[C@]5(C)[C@@]34C)C2=C1	standard non polar	2025-10-23	3061.4
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_4	C=CC(C)(C)C1=CC=C2C(=C1)C1=C(N2[Si](C)(C)C)[C@@]2(C)[C@@H](CC[C@@]3(O)C4=CC(=O)[C@@H](C(C)(C)O)OC4=CC[C@@]32C)C1	standard non polar	2025-10-23	2172.01
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_5	C=CC(C)(C)C1=CC=C2[NH]C3=C(C[C@@H]4CC[C@@]5(O[Si](C)(C)C)C6=CC(=O)[C@@H](C(C)(C)O[Si](C)(C)C)OC6=CC[C@]5(C)[C@@]34C)C2=C1	standard non polar	2025-10-23	1226.87
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_6	C=CC(C)(C)C1=CC=C2[NH]C3=C(C[C@@H]4CC[C@@]5(O[Si](C)(C)C)C6=CC(O[Si](C)(C)C)=C(C(C)(C)O)OC6=CC[C@]5(C)[C@@]34C)C2=C1	standard non polar	2025-10-23	2994.05
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_7	C=CC(C)(C)C1=CC=C2C(=C1)C1=C(N2[Si](C)(C)C)[C@@]2(C)[C@@H](CC[C@@]3(O[Si](C)(C)C)C4=CC(=O)[C@@H](C(C)(C)O)OC4=CC[C@@]32C)C1	standard non polar	2025-10-23	2015.58
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_8	C=CC(C)(C)C1=CC=C2[NH]C3=C(C[C@@H]4CC[C@@]5(O)C6=CC(O[Si](C)(C)C)=C(C(C)(C)O[Si](C)(C)C)OC6=CC[C@]5(C)[C@@]34C)C2=C1	standard non polar	2025-10-23	2218.8
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_9	C=CC(C)(C)C1=CC=C2C(=C1)C1=C(N2[Si](C)(C)C)[C@@]2(C)[C@@H](CC[C@@]3(O)C4=CC(=O)[C@@H](C(C)(C)O[Si](C)(C)C)OC4=CC[C@@]32C)C1	standard non polar	2025-10-23	2403.21
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_10	C=CC(C)(C)C1=CC=C2C(=C1)C1=C(N2[Si](C)(C)C)[C@@]2(C)[C@@H](CC[C@@]3(O)C4=CC(O[Si](C)(C)C)=C(C(C)(C)O)OC4=CC[C@@]32C)C1	standard non polar	2025-10-23	2140.75
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_11	C=CC(C)(C)C1=CC=C2[NH]C3=C(C[C@@H]4CC[C@@]5(O[Si](C)(C)C)C6=CC(O[Si](C)(C)C)=C(C(C)(C)O[Si](C)(C)C)OC6=CC[C@]5(C)[C@@]34C)C2=C1	standard non polar	2025-10-23	1381.42
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_12	C=CC(C)(C)C1=CC=C2C(=C1)C1=C(N2[Si](C)(C)C)[C@@]2(C)[C@@H](CC[C@@]3(O[Si](C)(C)C)C4=CC(=O)[C@@H](C(C)(C)O[Si](C)(C)C)OC4=CC[C@@]32C)C1	standard non polar	2025-10-23	2946.83
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_13	C=CC(C)(C)C1=CC=C2C(=C1)C1=C(N2[Si](C)(C)C)[C@@]2(C)[C@@H](CC[C@@]3(O[Si](C)(C)C)C4=CC(O[Si](C)(C)C)=C(C(C)(C)O)OC4=CC[C@@]32C)C1	standard non polar	2025-10-23	1602.25
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_14	C=CC(C)(C)C1=CC=C2C(=C1)C1=C(N2[Si](C)(C)C)[C@@]2(C)[C@@H](CC[C@@]3(O)C4=CC(O[Si](C)(C)C)=C(C(C)(C)O[Si](C)(C)C)OC4=CC[C@@]32C)C1	standard non polar	2025-10-23	1750.26
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_15	C=CC(C)(C)C1=CC=C2C(=C1)C1=C(N2[Si](C)(C)C)[C@@]2(C)[C@@H](CC[C@@]3(O[Si](C)(C)C)C4=CC(O[Si](C)(C)C)=C(C(C)(C)O[Si](C)(C)C)OC4=CC[C@@]32C)C1	standard non polar	2025-10-23	201.539
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_1	C=CC(C)(C)C1=CC=C2[NH]C3=C(C[C@@H]4CC[C@@]5(O[Si](C)(C)C)C6=CC(=O)[C@@H](C(C)(C)O)OC6=CC[C@]5(C)[C@@]34C)C2=C1	standard polar	2025-10-23	2708.37
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_2	C=CC(C)(C)C1=CC=C2[NH]C3=C(C[C@@H]4CC[C@@]5(O)C6=CC(=O)[C@@H](C(C)(C)O[Si](C)(C)C)OC6=CC[C@]5(C)[C@@]34C)C2=C1	standard polar	2025-10-23	1659.88
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_3	C=CC(C)(C)C1=CC=C2[NH]C3=C(C[C@@H]4CC[C@@]5(O)C6=CC(O[Si](C)(C)C)=C(C(C)(C)O)OC6=CC[C@]5(C)[C@@]34C)C2=C1	standard polar	2025-10-23	2821.68
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_4	C=CC(C)(C)C1=CC=C2C(=C1)C1=C(N2[Si](C)(C)C)[C@@]2(C)[C@@H](CC[C@@]3(O)C4=CC(=O)[C@@H](C(C)(C)O)OC4=CC[C@@]32C)C1	standard polar	2025-10-23	1445.83
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_5	C=CC(C)(C)C1=CC=C2[NH]C3=C(C[C@@H]4CC[C@@]5(O[Si](C)(C)C)C6=CC(=O)[C@@H](C(C)(C)O[Si](C)(C)C)OC6=CC[C@]5(C)[C@@]34C)C2=C1	standard polar	2025-10-23	2371.19
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_6	C=CC(C)(C)C1=CC=C2[NH]C3=C(C[C@@H]4CC[C@@]5(O[Si](C)(C)C)C6=CC(O[Si](C)(C)C)=C(C(C)(C)O)OC6=CC[C@]5(C)[C@@]34C)C2=C1	standard polar	2025-10-23	1421.19
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_7	C=CC(C)(C)C1=CC=C2C(=C1)C1=C(N2[Si](C)(C)C)[C@@]2(C)[C@@H](CC[C@@]3(O[Si](C)(C)C)C4=CC(=O)[C@@H](C(C)(C)O)OC4=CC[C@@]32C)C1	standard polar	2025-10-23	2484.9
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_8	C=CC(C)(C)C1=CC=C2[NH]C3=C(C[C@@H]4CC[C@@]5(O)C6=CC(O[Si](C)(C)C)=C(C(C)(C)O[Si](C)(C)C)OC6=CC[C@]5(C)[C@@]34C)C2=C1	standard polar	2025-10-23	1801.8
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_9	C=CC(C)(C)C1=CC=C2C(=C1)C1=C(N2[Si](C)(C)C)[C@@]2(C)[C@@H](CC[C@@]3(O)C4=CC(=O)[C@@H](C(C)(C)O[Si](C)(C)C)OC4=CC[C@@]32C)C1	standard polar	2025-10-23	3109.43
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_10	C=CC(C)(C)C1=CC=C2C(=C1)C1=C(N2[Si](C)(C)C)[C@@]2(C)[C@@H](CC[C@@]3(O)C4=CC(O[Si](C)(C)C)=C(C(C)(C)O)OC4=CC[C@@]32C)C1	standard polar	2025-10-23	3589.84
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_11	C=CC(C)(C)C1=CC=C2[NH]C3=C(C[C@@H]4CC[C@@]5(O[Si](C)(C)C)C6=CC(O[Si](C)(C)C)=C(C(C)(C)O[Si](C)(C)C)OC6=CC[C@]5(C)[C@@]34C)C2=C1	standard polar	2025-10-23	2393.7
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_12	C=CC(C)(C)C1=CC=C2C(=C1)C1=C(N2[Si](C)(C)C)[C@@]2(C)[C@@H](CC[C@@]3(O[Si](C)(C)C)C4=CC(=O)[C@@H](C(C)(C)O[Si](C)(C)C)OC4=CC[C@@]32C)C1	standard polar	2025-10-23	3643.9
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_13	C=CC(C)(C)C1=CC=C2C(=C1)C1=C(N2[Si](C)(C)C)[C@@]2(C)[C@@H](CC[C@@]3(O[Si](C)(C)C)C4=CC(O[Si](C)(C)C)=C(C(C)(C)O)OC4=CC[C@@]32C)C1	standard polar	2025-10-23	1926.91
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_14	C=CC(C)(C)C1=CC=C2C(=C1)C1=C(N2[Si](C)(C)C)[C@@]2(C)[C@@H](CC[C@@]3(O)C4=CC(O[Si](C)(C)C)=C(C(C)(C)O[Si](C)(C)C)OC4=CC[C@@]32C)C1	standard polar	2025-10-23	3242.18
Gas Chromatography	(2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline_TMS_15	C=CC(C)(C)C1=CC=C2C(=C1)C1=C(N2[Si](C)(C)C)[C@@]2(C)[C@@H](CC[C@@]3(O[Si](C)(C)C)C4=CC(O[Si](C)(C)C)=C(C(C)(C)O[Si](C)(C)C)OC4=CC[C@@]32C)C1	standard polar	2025-10-23	1690.1

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	2	Human feces; Human sputum; Human	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

34981555

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585644

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for (2R,4bS,6aS,12bS,12cR)-9-isopentenylpaxilline (MMDBc0009662)

MOL for #<Metabolite:0x00007f9aa209f350>

3D MOL for #<Metabolite:0x00007f9aa209f350>

3D SDF for #<Metabolite:0x00007f9aa209f350>

3D-SDF for #<Metabolite:0x00007f9aa209f350>

PDB for #<Metabolite:0x00007f9aa209f350>

3D PDB for #<Metabolite:0x00007f9aa209f350>

SMILES for #<Metabolite:0x00007f9aa209f350>

INCHI for #<Metabolite:0x00007f9aa209f350>

Structure for #<Metabolite:0x00007f9aa209f350>

3D Structure for #<Metabolite:0x00007f9aa209f350>