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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:22:41 UTC

Update Date

2021-09-26 23:12:44 UTC

HMDB ID

HMDB0256794

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Prodolic acid

Description

Prodolic acid, also known as prodolate, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. Based on a literature review very few articles have been published on Prodolic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Prodolic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Prodolic acid 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

HMDB0256794
     RDKit          3D
Prodolic acid
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.2277   -2.5599    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1298   -1.8210    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3839   -0.3614    0.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935    0.4624   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6570    1.8937   -0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7457    2.8827   -0.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4903    2.8987   -0.5846 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2640    3.8556   -1.6464 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3583    0.0303   -1.7112 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3878    0.4359   -2.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0291    0.1707   -2.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1121    0.0254   -0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0215    0.1707    0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3965   -0.0132    1.4416 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7230   -0.2820    1.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5631   -0.5438    2.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8867   -0.7855    2.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3667   -0.7707    0.9628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5088   -0.5066   -0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1704   -0.2581    0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8941   -3.0969    0.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7513   -3.3123    1.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7926   -1.8896    1.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1255   -2.1339    0.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1393   -2.1286   -0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3290   -0.1112   -0.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4279   -0.0071    1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7231    2.1038   -0.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5848    2.0723    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9152    4.8131   -1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5591   -0.1515   -3.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5652    1.4990   -2.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4716   -0.6812   -2.6962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6153    1.0857   -2.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1815    0.0265    2.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2513   -0.5702    3.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6100   -0.9991    3.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4050   -0.9636    0.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8149   -0.4793   -1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 13  4  1  0
 20 15  1  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END


  Mrv1652309112119232D          

 20 22  0  0  0  0            999 V2000
    4.8652    0.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8364    1.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1080    1.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.5840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    1.5105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0993    1.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6072    2.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2982    3.3771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4242    2.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256794

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC1(CC(O)=O)OCCC2=C1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO3/c1-2-8-16(10-14(18)19)15-12(7-9-20-16)11-5-3-4-6-13(11)17-15/h3-6,17H,2,7-10H2,1H3,(H,18,19)

> <INCHI_KEY>
IZGMROSLQHXRDZ-UHFFFAOYSA-N

> <FORMULA>
C16H19NO3

> <MOLECULAR_WEIGHT>
273.332

> <EXACT_MASS>
273.136493476

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.9751105061014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{1-propyl-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetic acid

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
2.9301050183333333

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.90980082513396

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.665314667260211

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2129512423208455

> <JCHEM_POLAR_SURFACE_AREA>
62.32000000000001

> <JCHEM_REFRACTIVITY>
76.1161

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
prodolic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256794
     RDKit          3D
Prodolic acid
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.2277   -2.5599    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1298   -1.8210    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3839   -0.3614    0.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935    0.4624   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6570    1.8937   -0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7457    2.8827   -0.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4903    2.8987   -0.5846 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2640    3.8556   -1.6464 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3583    0.0303   -1.7112 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3878    0.4359   -2.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0291    0.1707   -2.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1121    0.0254   -0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0215    0.1707    0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3965   -0.0132    1.4416 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7230   -0.2820    1.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5631   -0.5438    2.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8867   -0.7855    2.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3667   -0.7707    0.9628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5088   -0.5066   -0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1704   -0.2581    0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8941   -3.0969    0.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7513   -3.3123    1.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7926   -1.8896    1.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1255   -2.1339    0.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1393   -2.1286   -0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3290   -0.1112   -0.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4279   -0.0071    1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7231    2.1038   -0.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5848    2.0723    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9152    4.8131   -1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5591   -0.1515   -3.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5652    1.4990   -2.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4716   -0.6812   -2.6962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6153    1.0857   -2.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1815    0.0265    2.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2513   -0.5702    3.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6100   -0.9991    3.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4050   -0.9636    0.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8149   -0.4793   -1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 13  4  1  0
 20 15  1  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       9.082   0.789   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.028   2.328   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.668   3.051   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.362   2.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.856   1.914   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.380   0.450   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.410  -0.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.917  -0.374   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.393   1.090   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.810  -0.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.303  -0.374   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.173   1.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.858   2.235   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.364   1.914   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       3.610   2.820   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       5.785   3.662   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.733   4.876   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.157   6.304   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.258   4.662   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9   17                                             
CONECT    5    4    6   16                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    6   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15    5                                                       
CONECT   17    4   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0256794
HETATM    1  C1  UNL     1       3.228  -2.560   0.927  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.130  -1.821   0.178  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.384  -0.361   0.323  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.294   0.462  -0.413  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.657   1.894  -0.192  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.746   2.883  -0.795  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.490   2.899  -0.585  1.00  0.00           O  
HETATM    8  O2  UNL     1       1.264   3.856  -1.646  1.00  0.00           O  
HETATM    9  O3  UNL     1       1.358   0.030  -1.711  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.388   0.436  -2.573  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.029   0.171  -2.143  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.112   0.025  -0.665  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.021   0.171   0.159  1.00  0.00           C  
HETATM   14  N1  UNL     1      -0.397  -0.013   1.442  1.00  0.00           N  
HETATM   15  C11 UNL     1      -1.723  -0.282   1.499  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.563  -0.544   2.559  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.887  -0.785   2.256  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.367  -0.771   0.963  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.509  -0.507  -0.081  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.170  -0.258   0.184  1.00  0.00           C  
HETATM   21  H1  UNL     1       3.894  -3.097   0.244  1.00  0.00           H  
HETATM   22  H2  UNL     1       2.751  -3.312   1.620  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.793  -1.890   1.583  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.125  -2.134   0.582  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.139  -2.129  -0.890  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.329  -0.111  -0.191  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.428  -0.007   1.350  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.723   2.104  -0.419  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.585   2.072   0.925  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.915   4.813  -1.472  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.559  -0.152  -3.532  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.565   1.499  -2.909  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.472  -0.681  -2.696  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.615   1.086  -2.450  1.00  0.00           H  
HETATM   35  H15 UNL     1       0.182   0.026   2.318  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.251  -0.570   3.592  1.00  0.00           H  
HETATM   37  H17 UNL     1      -4.610  -0.999   3.037  1.00  0.00           H  
HETATM   38  H18 UNL     1      -5.405  -0.964   0.734  1.00  0.00           H  
HETATM   39  H19 UNL     1      -3.815  -0.479  -1.107  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5    9   13
CONECT    5    6   28   29
CONECT    6    7    7    8
CONECT    8   30
CONECT    9   10
CONECT   10   11   31   32
CONECT   11   12   33   34
CONECT   12   13   13   20
CONECT   13   14
CONECT   14   15   35
CONECT   15   16   16   20
CONECT   16   17   36
CONECT   17   18   18   37
CONECT   18   19   38
CONECT   19   20   20   39
END

HMDB0256794
     RDKit          3D
Prodolic acid
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.2277   -2.5599    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1298   -1.8210    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3839   -0.3614    0.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935    0.4624   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6570    1.8937   -0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7457    2.8827   -0.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4903    2.8987   -0.5846 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2640    3.8556   -1.6464 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3583    0.0303   -1.7112 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3878    0.4359   -2.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0291    0.1707   -2.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1121    0.0254   -0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0215    0.1707    0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3965   -0.0132    1.4416 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7230   -0.2820    1.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5631   -0.5438    2.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8867   -0.7855    2.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3667   -0.7707    0.9628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5088   -0.5066   -0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1704   -0.2581    0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8941   -3.0969    0.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7513   -3.3123    1.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7926   -1.8896    1.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1255   -2.1339    0.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1393   -2.1286   -0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3290   -0.1112   -0.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4279   -0.0071    1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7231    2.1038   -0.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5848    2.0723    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9152    4.8131   -1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5591   -0.1515   -3.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5652    1.4990   -2.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4716   -0.6812   -2.6962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6153    1.0857   -2.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1815    0.0265    2.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2513   -0.5702    3.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6100   -0.9991    3.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4050   -0.9636    0.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8149   -0.4793   -1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 13  4  1  0
 20 15  1  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Prodolate	Generator
2-{1-propyl-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetate	HMDB
1,3,4,9-Tetrahydro-1-propylpyrano(3,4-b)indole-1-acetic acid	HMDB

Chemical Formula

C₁₆H₁₉NO₃

Average Molecular Weight

273.332

Monoisotopic Molecular Weight

273.136493476

IUPAC Name

2-{1-propyl-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetic acid

Traditional Name

prodolic acid

CAS Registry Number

Not Available

SMILES

CCCC1(CC(O)=O)OCCC2=C1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C16H19NO3/c1-2-8-16(10-14(18)19)15-12(7-9-20-16)11-5-3-4-6-13(11)17-15/h3-6,17H,2,7-10H2,1H3,(H,18,19)

InChI Key

IZGMROSLQHXRDZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
3-alkylindole
Indole
Medium-chain fatty acid
Amino fatty acid
Heterocyclic fatty acid
Fatty acyl
Fatty acid
Benzenoid
Pyrrole
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Organopnictogen compound
Organic oxygen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.77	ALOGPS
logP	2.93	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.67	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.12 m³·mol⁻¹	ChemAxon
Polarizability	29.98 Å³	ChemAxon
Number of Rings	3	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-2H]-	192.163	30932474
DeepCCS	[M+Na]+	167.728	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prodolic acid	CCCC1(CC(O)=O)OCCC2=C1NC1=CC=CC=C21	3577.0	Standard polar	33892256
Prodolic acid	CCCC1(CC(O)=O)OCCC2=C1NC1=CC=CC=C21	2236.7	Standard non polar	33892256
Prodolic acid	CCCC1(CC(O)=O)OCCC2=C1NC1=CC=CC=C21	2388.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prodolic acid,2TMS,isomer #1	CCCC1(CC(=O)O[Si](C)(C)C)OCCC2=C1N([Si](C)(C)C)C1=CC=CC=C21	2485.7	Semi standard non polar	33892256
Prodolic acid,2TMS,isomer #1	CCCC1(CC(=O)O[Si](C)(C)C)OCCC2=C1N([Si](C)(C)C)C1=CC=CC=C21	2388.8	Standard non polar	33892256
Prodolic acid,2TMS,isomer #1	CCCC1(CC(=O)O[Si](C)(C)C)OCCC2=C1N([Si](C)(C)C)C1=CC=CC=C21	2703.7	Standard polar	33892256
Prodolic acid,2TBDMS,isomer #1	CCCC1(CC(=O)O[Si](C)(C)C(C)(C)C)OCCC2=C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2887.9	Semi standard non polar	33892256
Prodolic acid,2TBDMS,isomer #1	CCCC1(CC(=O)O[Si](C)(C)C(C)(C)C)OCCC2=C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2837.1	Standard non polar	33892256
Prodolic acid,2TBDMS,isomer #1	CCCC1(CC(=O)O[Si](C)(C)C(C)(C)C)OCCC2=C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2904.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Prodolic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-01r6-8790000000-957779970ae05d343e8d	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prodolic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prodolic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prodolic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prodolic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prodolic acid 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

34367

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

37462

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 Prodolic acid (HMDB0256794)

MOL for HMDB0256794 (Prodolic acid)

3D MOL for HMDB0256794 (Prodolic acid)

3D SDF for HMDB0256794 (Prodolic acid)

3D-SDF for HMDB0256794 (Prodolic acid)

PDB for HMDB0256794 (Prodolic acid)

3D PDB for HMDB0256794 (Prodolic acid)

SMILES for HMDB0256794 (Prodolic acid)

INCHI for HMDB0256794 (Prodolic acid)

Structure for HMDB0256794 (Prodolic acid)

3D Structure for HMDB0256794 (Prodolic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra