MiMeDB: Showing metabocard for Pyripyropene O (MMDBc0012131)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 03:45:45 UTC

Update Date

2025-10-07 16:05:57 UTC

Metabolite ID

MMDBc0012131

Metabolite Identification

Common Name

Pyripyropene O

Description

Pyripyropene O is a natural compound belonging to the class of metabolites isolated from the marine fungus Aspergillus fumigatus SCSIO 41220. It has garnered attention for its potential therapeutic applications, particularly in the context of prostate cancer. Research indicates that pyripyropene O induces apoptosis in prostate cancer cells, as evidenced by various assays including MTT, plate clone formation, and flow cytometry (PMID:40422804 ). Additionally, transmission electron microscopy has revealed structural changes in these cancer cells post-treatment (PMID:40422804 ). The compound's mechanism of action involves binding to the transcription factor YY1, promoting its nuclear translocation, and subsequently regulating the transcription of the DR5 gene, which is implicated in apoptosis (PMID:40422804 ). In vivo studies utilizing a zebrafish xenograft tumor model further demonstrated the efficacy of pyripyropene O in inhibiting prostate cancer development, highlighting its ability to block the cell cycle at the G2/M phase and suppress cell survival and migration (PMID:40422804 ). Collectively, these findings suggest that pyripyropene O represents a promising candidate for novel therapeutic strategies against prostate cancer, acting through well-defined molecular pathways.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152105452D          

 40 44  0  0  1  0            999 V2000
   -2.7577    1.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705    3.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502    4.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5530    2.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604    2.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7511    4.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9410    4.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401    2.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700    4.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401    4.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502    2.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0212    3.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604    4.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507    3.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6709    3.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547    3.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4635    2.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1604    3.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4009    3.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9705    4.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5908    3.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405    3.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700    3.3454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6203    3.8132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8101    4.2809    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5106    4.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101    3.9691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5401    3.5014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8903    3.0336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4811    2.8777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9839    3.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903    3.0336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405    5.6841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489    2.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203    4.4368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207    4.7486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7004    2.8777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304    3.6573    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502    3.6573    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 17  1  1  0  0  0  0
 18  2  1  0  0  0  0
 19  7  1  0  0  0  0
 19 15  2  0  0  0  0
 20 13  1  0  0  0  0
 21 14  2  0  0  0  0
 21 19  1  0  0  0  0
 22 14  1  0  0  0  0
 22 20  2  0  0  0  0
 23  8  1  0  0  0  0
 24 13  1  0  0  0  0
 25  9  1  0  0  0  0
 26 20  1  0  0  0  0
 27  3  1  1  0  0  0
 27 10  1  0  0  0  0
 27 23  1  0  0  0  0
 27 24  1  0  0  0  0
 28  4  1  1  0  0  0
 28 16  1  6  0  0  0
 28 23  1  0  0  0  0
 28 25  1  0  0  0  0
 29  5  1  1  0  0  0
 29 11  1  0  0  0  0
 29 24  1  0  0  0  0
 30 12  2  0  0  0  0
 30 15  1  0  0  0  0
 31 17  2  0  0  0  0
 32 18  2  0  0  0  0
 33 26  2  0  0  0  0
 34 16  1  0  0  0  0
 34 17  1  0  0  0  0
 35 18  1  0  0  0  0
 25 35  1  1  0  0  0
 36 21  1  0  0  0  0
 36 26  1  0  0  0  0
 37 22  1  0  0  0  0
 37 29  1  0  0  0  0
 23 38  1  6  0  0  0
 24 39  1  6  0  0  0
 25 40  1  6  0  0  0
M  END


  Mrv1652305152105452D          

 40 44  0  0  1  0            999 V2000
   -2.7577    1.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705    3.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502    4.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5530    2.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604    2.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7511    4.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9410    4.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401    2.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700    4.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401    4.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502    2.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0212    3.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604    4.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507    3.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6709    3.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547    3.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4635    2.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1604    3.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4009    3.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9705    4.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5908    3.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405    3.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700    3.3454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6203    3.8132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8101    4.2809    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5106    4.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101    3.9691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5401    3.5014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8903    3.0336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4811    2.8777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9839    3.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903    3.0336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405    5.6841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489    2.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203    4.4368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207    4.7486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7004    2.8777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304    3.6573    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502    3.6573    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 17  1  1  0  0  0  0
 18  2  1  0  0  0  0
 19  7  1  0  0  0  0
 19 15  2  0  0  0  0
 20 13  1  0  0  0  0
 21 14  2  0  0  0  0
 21 19  1  0  0  0  0
 22 14  1  0  0  0  0
 22 20  2  0  0  0  0
 23  8  1  0  0  0  0
 24 13  1  0  0  0  0
 25  9  1  0  0  0  0
 26 20  1  0  0  0  0
 27  3  1  1  0  0  0
 27 10  1  0  0  0  0
 27 23  1  0  0  0  0
 27 24  1  0  0  0  0
 28  4  1  1  0  0  0
 28 16  1  6  0  0  0
 28 23  1  0  0  0  0
 28 25  1  0  0  0  0
 29  5  1  1  0  0  0
 29 11  1  0  0  0  0
 29 24  1  0  0  0  0
 30 12  2  0  0  0  0
 30 15  1  0  0  0  0
 31 17  2  0  0  0  0
 32 18  2  0  0  0  0
 33 26  2  0  0  0  0
 34 16  1  0  0  0  0
 34 17  1  0  0  0  0
 35 18  1  0  0  0  0
 25 35  1  1  0  0  0
 36 21  1  0  0  0  0
 36 26  1  0  0  0  0
 37 22  1  0  0  0  0
 37 29  1  0  0  0  0
 23 38  1  6  0  0  0
 24 39  1  6  0  0  0
 25 40  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0012131

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CC[C@@]2(C)[C@@]([H])(CC[C@@]3(C)OC4=C(C[C@]23[H])C(=O)OC(=C4)C2=CN=CC=C2)[C@]1(C)COC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H35NO7/c1-17(31)34-16-28(4)23-8-11-29(5)24(27(23,3)10-9-25(28)35-18(2)32)13-20-22(37-29)14-21(36-26(20)33)19-7-6-12-30-15-19/h6-7,12,14-15,23-25H,8-11,13,16H2,1-5H3/t23-,24-,25+,27+,28+,29-/m1/s1

> <INCHI_KEY>
LNZRIIIDRGIMHV-QXHZFDHFSA-N

> <FORMULA>
C29H35NO7

> <MOLECULAR_WEIGHT>
509.599

> <EXACT_MASS>
509.241352471

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
55.63483634813305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(5aR,7aR,8R,9S,11aS,11bR)-9-(acetyloxy)-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphen-8-yl]methyl acetate

> <ALOGPS_LOGP>
4.58

> <JCHEM_LOGP>
2.729375942666665

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.206464980867306

> <JCHEM_POLAR_SURFACE_AREA>
101.02

> <JCHEM_REFRACTIVITY>
135.9321

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.94e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(5aR,7aR,8R,9S,11aS,11bR)-9-(acetyloxy)-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-8-yl]methyl acetate

> <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      -5.148   3.171   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.545   7.409   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.520   8.573   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.032   4.996   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.033   4.208   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.602   7.991   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.090   8.282   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.008   4.790   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.504   9.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.008   8.864   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.520   4.499   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.106   6.536   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.033   8.282   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.561   6.245   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.586   5.663   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.529   6.292   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.599   4.610   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.033   7.118   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.082   7.118   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.545   7.991   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.569   7.409   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.049   6.536   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.504   6.245   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.024   7.118   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.512   7.991   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.553   9.155   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.512   7.409   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.008   6.536   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.529   5.663   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      12.098   5.372   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0      -5.570   5.805   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -3.529   5.663   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       6.049  10.610   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -3.078   4.853   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -3.024   8.282   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       8.065   8.864   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       5.041   5.372   0.000  0.00  0.00           O+0
HETATM   38  H   UNK     0      -0.000   7.700   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.537   6.827   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.520   6.827   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2   18                                                            
CONECT    3   27                                                            
CONECT    4   28                                                            
CONECT    5   29                                                            
CONECT    6    7   12                                                       
CONECT    7    6   19                                                       
CONECT    8   11   23                                                       
CONECT    9   10   25                                                       
CONECT   10    9   27                                                       
CONECT   11    8   29                                                       
CONECT   12    6   30                                                       
CONECT   13   20   24                                                       
CONECT   14   21   22                                                       
CONECT   15   19   30                                                       
CONECT   16   28   34                                                       
CONECT   17    1   31   34                                                  
CONECT   18    2   32   35                                                  
CONECT   19    7   15   21                                                  
CONECT   20   13   22   26                                                  
CONECT   21   14   19   36                                                  
CONECT   22   14   20   37                                                  
CONECT   23    8   27   28   38                                             
CONECT   24   13   27   29   39                                             
CONECT   25    9   28   35   40                                             
CONECT   26   20   33   36                                                  
CONECT   27    3   10   23   24                                             
CONECT   28    4   16   23   25                                             
CONECT   29    5   11   24   37                                             
CONECT   30   12   15                                                       
CONECT   31   17                                                            
CONECT   32   18                                                            
CONECT   33   26                                                            
CONECT   34   16   17                                                       
CONECT   35   18   25                                                       
CONECT   36   21   26                                                       
CONECT   37   22   29                                                       
CONECT   38   23                                                            
CONECT   39   24                                                            
CONECT   40   25                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

Synonyms

Not Available

Molecular Formula

C₂₉H₃₅NO₇

Average Mass

509.599

Monoisotopic Mass

509.241352471

IUPAC Name

[(5aR,7aR,8R,9S,11aS,11bR)-9-(acetyloxy)-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphen-8-yl]methyl acetate

Traditional Name

[(5aR,7aR,8R,9S,11aS,11bR)-9-(acetyloxy)-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-8-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2(C)[C@@]([H])(CC[C@@]3(C)OC4=C(C[C@]23[H])C(=O)OC(=C4)C2=CN=CC=C2)[C@]1(C)COC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C29H35NO7/c1-17(31)34-16-28(4)23-8-11-29(5)24(27(23,3)10-9-25(28)35-18(2)32)13-20-22(37-29)14-21(36-26(20)33)19-7-6-12-30-15-19/h6-7,12,14-15,23-25H,8-11,13,16H2,1-5H3/t23-,24-,25+,27+,28+,29-/m1/s1

InChI Key

LNZRIIIDRGIMHV-QXHZFDHFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Not Available

Direct Parent

Steroids and steroid derivatives

Alternative Parents

Substituents

Steroid
Naphthopyran
Naphthalene
Alkyl aryl ether
Pyranone
Dicarboxylic acid or derivatives
Pyran
Pyridine
Heteroaromatic compound
Vinylogous ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
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	0.0039 g/L	ALOGPS
logP	4.58	ALOGPS
logP	2.73	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	4.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	101.02 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	135.93 m³·mol⁻¹	ChemAxon
Polarizability	55.63 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	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 (eluted)	2025-10-23	151.9
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-23	43.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	391.2
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	521.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	575.1
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	160.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	2413.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	166.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	314.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	496.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	317.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	146.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	210.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	16.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	216.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	124.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	346.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1674.8
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1009.5

Retention Indices

Not Available

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 sputum; Human feces; 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

C00016205

Chemspider ID

8729104

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10553713

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

LNZRIIIDRGIMHV-QXHZFDHFSA-N

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 Pyripyropene O (MMDBc0012131)

MOL for #<Metabolite:0x00007f9aa88437b8>

3D MOL for #<Metabolite:0x00007f9aa88437b8>

3D SDF for #<Metabolite:0x00007f9aa88437b8>

3D-SDF for #<Metabolite:0x00007f9aa88437b8>

PDB for #<Metabolite:0x00007f9aa88437b8>

3D PDB for #<Metabolite:0x00007f9aa88437b8>

SMILES for #<Metabolite:0x00007f9aa88437b8>

INCHI for #<Metabolite:0x00007f9aa88437b8>

Structure for #<Metabolite:0x00007f9aa88437b8>

3D Structure for #<Metabolite:0x00007f9aa88437b8>