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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:39:40 UTC

Update Date

2022-11-23 22:29:18 UTC

HMDB ID

HMDB0257008

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pyrrolostatin

Description

4-(3,7-dimethylocta-2,6-dien-1-yl)-1H-pyrrole-2-carboxylic acid belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Based on a literature review very few articles have been published on 4-(3,7-dimethylocta-2,6-dien-1-yl)-1H-pyrrole-2-carboxylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Pyrrolostatin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Pyrrolostatin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0257008
     RDKit          3D
pyrrolostatin
 39 39  0  0  0  0  0  0  0  0999 V2000
   -4.7830    1.5292   -1.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5776    0.6689   -1.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4942    0.7744   -2.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4038   -0.2166   -0.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2022   -1.0926   -0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5136   -0.7951    1.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128   -1.6032    1.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5294   -3.1015    1.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8843   -1.1617    1.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273    0.2629    1.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1984    0.6244    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0051    1.0473   -0.7135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2028    1.2477   -1.2974 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1754    0.9647   -0.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6276    1.0377   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1349    1.3990   -1.7021 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4958    0.7025    0.4085 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5633    0.5732    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9970    1.8658   -0.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6414    2.3564   -1.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6703    0.9538   -1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7922    1.4833   -2.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300   -0.2059   -2.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6024    1.1664   -1.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1892   -0.3019    0.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4545   -2.1495   -0.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4889   -0.7921   -0.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4463    0.2779    1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3133   -1.0859    2.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4318   -3.5157    0.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2491   -3.5477    2.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5051   -3.3255    1.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6867   -1.9299    1.7589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.5452    2.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3393    0.8812    1.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0307    1.1894   -1.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3863    1.5765   -2.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7018    1.4264    1.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0809    0.2706    1.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  3
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 13 37  1  0
 17 38  1  0
 18 39  1  0
M  END

  Mrv1533004171508082D          

 18 18  0  0  0  0            999 V2000
    5.5691    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8546    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1401    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8546    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  9 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  6 17  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257008

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCCC(C)=CCC1=CNC(=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H21NO2/c1-11(2)5-4-6-12(3)7-8-13-9-14(15(17)18)16-10-13/h5,7,9-10,16H,4,6,8H2,1-3H3,(H,17,18)

> <INCHI_KEY>
UEQIBCOZMSTCSW-UHFFFAOYSA-N

> <FORMULA>
C15H21NO2

> <MOLECULAR_WEIGHT>
247.338

> <EXACT_MASS>
247.15722892

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.24233006640189

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(3,7-dimethylocta-2,6-dien-1-yl)-1H-pyrrole-2-carboxylic acid

> <ALOGPS_LOGP>
3.86

> <JCHEM_LOGP>
4.018995234666665

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.847500000410975

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.145329613395409

> <JCHEM_POLAR_SURFACE_AREA>
53.09

> <JCHEM_REFRACTIVITY>
75.99589999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(3,7-dimethylocta-2,6-dien-1-yl)-1H-pyrrole-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0257008
     RDKit          3D
pyrrolostatin
 39 39  0  0  0  0  0  0  0  0999 V2000
   -4.7830    1.5292   -1.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5776    0.6689   -1.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4942    0.7744   -2.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4038   -0.2166   -0.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2022   -1.0926   -0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5136   -0.7951    1.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128   -1.6032    1.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5294   -3.1015    1.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8843   -1.1617    1.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273    0.2629    1.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1984    0.6244    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0051    1.0473   -0.7135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2028    1.2477   -1.2974 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1754    0.9647   -0.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6276    1.0377   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1349    1.3990   -1.7021 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4958    0.7025    0.4085 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5633    0.5732    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9970    1.8658   -0.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6414    2.3564   -1.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6703    0.9538   -1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7922    1.4833   -2.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300   -0.2059   -2.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6024    1.1664   -1.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1892   -0.3019    0.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4545   -2.1495   -0.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4889   -0.7921   -0.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4463    0.2779    1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3133   -1.0859    2.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4318   -3.5157    0.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2491   -3.5477    2.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5051   -3.3255    1.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6867   -1.9299    1.7589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.5452    2.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3393    0.8812    1.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0307    1.1894   -1.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3863    1.5765   -2.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7018    1.4264    1.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0809    0.2706    1.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  3
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 13 37  1  0
 17 38  1  0
 18 39  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      10.396   4.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.062   3.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.728   4.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.395   3.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.061   4.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.727   3.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.011  -2.943   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.147  -1.375   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.727   2.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.062   2.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    9                                                       
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    6                                                            
CONECT   18    2                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0257008
HETATM    1  C1  UNL     1      -4.783   1.529  -1.154  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.578   0.669  -1.094  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.494   0.774  -2.135  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.404  -0.217  -0.136  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.202  -1.093  -0.054  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.514  -0.795   1.277  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.313  -1.603   1.467  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.529  -3.101   1.476  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.884  -1.162   1.625  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.227   0.263   1.636  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.198   0.624   0.567  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.005   1.047  -0.714  1.00  0.00           C  
HETATM   13  N1  UNL     1       3.203   1.248  -1.297  1.00  0.00           N  
HETATM   14  C13 UNL     1       4.175   0.965  -0.425  1.00  0.00           C  
HETATM   15  C14 UNL     1       5.628   1.038  -0.620  1.00  0.00           C  
HETATM   16  O1  UNL     1       6.135   1.399  -1.702  1.00  0.00           O  
HETATM   17  O2  UNL     1       6.496   0.702   0.409  1.00  0.00           O  
HETATM   18  C15 UNL     1       3.563   0.573   0.746  1.00  0.00           C  
HETATM   19  H1  UNL     1      -4.997   1.866  -0.117  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.641   2.356  -1.864  1.00  0.00           H  
HETATM   21  H3  UNL     1      -5.670   0.954  -1.501  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.792   1.483  -2.936  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.330  -0.206  -2.614  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.602   1.166  -1.608  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.189  -0.302   0.630  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.455  -2.149  -0.148  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.489  -0.792  -0.845  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.446   0.278   1.349  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.313  -1.086   2.043  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.432  -3.516   0.446  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.249  -3.548   2.158  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.505  -3.325   1.937  1.00  0.00           H  
HETATM   33  H15 UNL     1       1.687  -1.930   1.759  1.00  0.00           H  
HETATM   34  H16 UNL     1       1.689   0.545   2.608  1.00  0.00           H  
HETATM   35  H17 UNL     1       0.339   0.881   1.472  1.00  0.00           H  
HETATM   36  H18 UNL     1       1.031   1.189  -1.160  1.00  0.00           H  
HETATM   37  H19 UNL     1       3.386   1.577  -2.287  1.00  0.00           H  
HETATM   38  H20 UNL     1       6.702   1.426   1.080  1.00  0.00           H  
HETATM   39  H21 UNL     1       4.081   0.271   1.669  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4    4
CONECT    3   22   23   24
CONECT    4    5   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8    9    9
CONECT    8   30   31   32
CONECT    9   10   33
CONECT   10   11   34   35
CONECT   11   12   12   18
CONECT   12   13   36
CONECT   13   14   37
CONECT   14   15   18   18
CONECT   15   16   16   17
CONECT   17   38
CONECT   18   39
END

HMDB0257008
     RDKit          3D
pyrrolostatin
 39 39  0  0  0  0  0  0  0  0999 V2000
   -4.7830    1.5292   -1.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5776    0.6689   -1.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4942    0.7744   -2.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4038   -0.2166   -0.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2022   -1.0926   -0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5136   -0.7951    1.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128   -1.6032    1.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5294   -3.1015    1.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8843   -1.1617    1.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273    0.2629    1.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1984    0.6244    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0051    1.0473   -0.7135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2028    1.2477   -1.2974 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1754    0.9647   -0.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6276    1.0377   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1349    1.3990   -1.7021 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4958    0.7025    0.4085 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5633    0.5732    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9970    1.8658   -0.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6414    2.3564   -1.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6703    0.9538   -1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7922    1.4833   -2.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300   -0.2059   -2.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6024    1.1664   -1.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1892   -0.3019    0.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4545   -2.1495   -0.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4889   -0.7921   -0.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4463    0.2779    1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3133   -1.0859    2.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4318   -3.5157    0.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2491   -3.5477    2.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5051   -3.3255    1.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6867   -1.9299    1.7589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.5452    2.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3393    0.8812    1.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0307    1.1894   -1.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3863    1.5765   -2.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7018    1.4264    1.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0809    0.2706    1.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  3
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 13 37  1  0
 17 38  1  0
 18 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(3,7-Dimethylocta-2,6-dien-1-yl)-1H-pyrrole-2-carboxylate	Generator
4-Geranylpyrrole-2-carboxylic acid	MeSH
Pyrrolostatin	MeSH

Chemical Formula

C₁₅H₂₁NO₂

Average Molecular Weight

247.338

Monoisotopic Molecular Weight

247.15722892

IUPAC Name

4-(3,7-dimethylocta-2,6-dien-1-yl)-1H-pyrrole-2-carboxylic acid

Traditional Name

4-(3,7-dimethylocta-2,6-dien-1-yl)-1H-pyrrole-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC(C)=CCC1=CNC(=C1)C(O)=O

InChI Identifier

InChI=1S/C15H21NO2/c1-11(2)5-4-6-12(3)7-8-13-9-14(15(17)18)16-10-13/h5,7,9-10,16H,4,6,8H2,1-3H3,(H,17,18)

InChI Key

UEQIBCOZMSTCSW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

Aromatic monoterpenoid
Monocyclic monoterpenoid
Pyrrole-2-carboxylic acid
Pyrrole-2-carboxylic acid or derivatives
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

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
logP	3.86	ALOGPS
logP	4.02	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	5.15	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	76 m³·mol⁻¹	ChemAxon
Polarizability	29.24 Å³	ChemAxon
Number of Rings	1	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
DeepCCS	[M+H]+	155.867	30932474
DeepCCS	[M-H]-	153.509	30932474
DeepCCS	[M-2H]-	187.323	30932474
DeepCCS	[M+Na]+	162.926	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
pyrrolostatin	CC(C)=CCCC(C)=CCC1=CNC(=C1)C(O)=O	2986.8	Standard polar	33892256
pyrrolostatin	CC(C)=CCCC(C)=CCC1=CNC(=C1)C(O)=O	2011.1	Standard non polar	33892256
pyrrolostatin	CC(C)=CCCC(C)=CCC1=CNC(=C1)C(O)=O	2138.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
pyrrolostatin,2TMS,isomer #1	CC(C)=CCCC(C)=CCC1=CN([Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C1	2248.7	Semi standard non polar	33892256
pyrrolostatin,2TMS,isomer #1	CC(C)=CCCC(C)=CCC1=CN([Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C1	2270.7	Standard non polar	33892256
pyrrolostatin,2TMS,isomer #1	CC(C)=CCCC(C)=CCC1=CN([Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C1	2396.8	Standard polar	33892256
pyrrolostatin,2TBDMS,isomer #1	CC(C)=CCCC(C)=CCC1=CN([Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C1	2686.5	Semi standard non polar	33892256
pyrrolostatin,2TBDMS,isomer #1	CC(C)=CCCC(C)=CCC1=CN([Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C1	2685.0	Standard non polar	33892256
pyrrolostatin,2TBDMS,isomer #1	CC(C)=CCCC(C)=CCC1=CN([Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C1	2582.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrrolostatin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0159-9750000000-0e94e9d696822098722a	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrrolostatin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrrolostatin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrrolostatin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrrolostatin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrrolostatin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4823

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4997

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Pyrrolostatin (HMDB0257008)

MOL for HMDB0257008 (Pyrrolostatin)

3D MOL for HMDB0257008 (Pyrrolostatin)

3D SDF for HMDB0257008 (Pyrrolostatin)

3D-SDF for HMDB0257008 (Pyrrolostatin)

PDB for HMDB0257008 (Pyrrolostatin)

3D PDB for HMDB0257008 (Pyrrolostatin)

SMILES for HMDB0257008 (Pyrrolostatin)

INCHI for HMDB0257008 (Pyrrolostatin)

Structure for HMDB0257008 (Pyrrolostatin)

3D Structure for HMDB0257008 (Pyrrolostatin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra