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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:46:26 UTC

Update Date

2022-03-07 02:53:10 UTC

HMDB ID

HMDB0031911

Secondary Accession Numbers

HMDB31911

Metabolite Identification

Common Name

Porric acid B

Description

Muridienin 4 belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Muridienin 4 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0031911
     RDKit          3D
Porric acid B
 33 35  0  0  0  0  0  0  0  0999 V2000
    5.0735   -0.1559    0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119    0.0048    1.5845 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888   -0.0317    0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6006   -0.2195   -0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726   -0.2594   -1.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3103   -0.4613   -2.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2491   -0.1023   -0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3377    0.0883    1.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882    0.2073    1.5595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7723    0.1105    0.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555    0.1769    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8566    0.3846    1.9153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0923    0.4389    1.9240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1341    0.5171    3.0787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8408    0.0394   -0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1683   -0.1557   -1.7190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9111   -0.2909   -2.9075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7814   -0.2233   -1.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975   -0.0863   -0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5556    0.1251    1.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6238    0.3162    3.1013 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0090   -1.0532    0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9208   -0.3174    1.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2563    0.7757    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862   -0.3454   -1.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8268   -1.4157   -2.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3690   -0.5586   -2.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9071    0.4172   -3.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4168   -0.1609    3.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9396    0.0914   -0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9198   -0.2440   -2.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036   -0.3784   -2.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7788    0.4288    3.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  8 20  2  0
 20 21  1  0
 20  3  1  0
 19  7  1  0
 19 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  1  0
M  END


  Mrv0541 05061306132D          

 21 23  0  0  0  0            999 V2000
   -0.5881    0.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9669    3.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6501    1.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0860    1.2599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1479    2.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8431    1.2599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8930    1.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5340    1.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5959    2.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9050    2.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910    1.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3530    2.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7889    2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5460    2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8508    3.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4450    0.8183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6079    3.6137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2988    4.2268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6578    3.7852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7120    2.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215    3.1425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  7  5  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  3  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15  9  1  0  0  0  0
 16  7  1  0  0  0  0
 17 12  1  0  0  0  0
 18 15  2  0  0  0  0
 19 15  1  0  0  0  0
 20  2  1  0  0  0  0
 20 10  1  0  0  0  0
 21 13  1  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031911

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C2=C(C3=C(O2)C(=CC(O)=C3)C(O)=O)C(C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O6/c1-6-3-10(20-2)12(17)14-11(6)8-4-7(16)5-9(15(18)19)13(8)21-14/h3-5,16-17H,1-2H3,(H,18,19)

> <INCHI_KEY>
YRDAFVVZXCAVIU-UHFFFAOYSA-N

> <FORMULA>
C15H12O6

> <MOLECULAR_WEIGHT>
288.2522

> <EXACT_MASS>
288.063388116

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.73392475408338

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,10-dihydroxy-11-methoxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
2.5574494853333327

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.215095251262989

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.18016194579888

> <JCHEM_PKA_STRONGEST_BASIC>
-3.888438318849595

> <JCHEM_POLAR_SURFACE_AREA>
100.13000000000001

> <JCHEM_REFRACTIVITY>
73.9492

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,10-dihydroxy-11-methoxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031911
     RDKit          3D
Porric acid B
 33 35  0  0  0  0  0  0  0  0999 V2000
    5.0735   -0.1559    0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119    0.0048    1.5845 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888   -0.0317    0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6006   -0.2195   -0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726   -0.2594   -1.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3103   -0.4613   -2.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2491   -0.1023   -0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3377    0.0883    1.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882    0.2073    1.5595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7723    0.1105    0.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555    0.1769    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8566    0.3846    1.9153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0923    0.4389    1.9240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1341    0.5171    3.0787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8408    0.0394   -0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1683   -0.1557   -1.7190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9111   -0.2909   -2.9075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7814   -0.2233   -1.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975   -0.0863   -0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5556    0.1251    1.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6238    0.3162    3.1013 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0090   -1.0532    0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9208   -0.3174    1.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2563    0.7757    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862   -0.3454   -1.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8268   -1.4157   -2.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3690   -0.5586   -2.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9071    0.4172   -3.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4168   -0.1609    3.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9396    0.0914   -0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9198   -0.2440   -2.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036   -0.3784   -2.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7788    0.4288    3.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  8 20  2  0
 20 21  1  0
 20  3  1  0
 19  7  1  0
 19 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.098   0.887   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.538   5.921   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.080   2.672   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.027   2.352   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.009   4.137   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.574   2.352   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.534   2.672   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.997   3.496   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.979   5.281   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.556   4.137   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.543   3.496   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.526   5.281   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.473   4.961   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.019   4.961   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.455   6.746   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.564   1.527   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -3.001   6.746   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.424   7.890   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.961   7.066   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.062   4.457   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.227   5.866   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   20                                                            
CONECT    3    6   10                                                       
CONECT    4    7    8                                                       
CONECT    5    7    9                                                       
CONECT    6    1    3   11                                                  
CONECT    7    4    5   16                                                  
CONECT    8    4   11   13                                                  
CONECT    9    5   13   15                                                  
CONECT   10    3   12   20                                                  
CONECT   11    6    8   14                                                  
CONECT   12   10   14   17                                                  
CONECT   13    8    9   21                                                  
CONECT   14   11   12   21                                                  
CONECT   15    9   18   19                                                  
CONECT   16    7                                                            
CONECT   17   12                                                            
CONECT   18   15                                                            
CONECT   19   15                                                            
CONECT   20    2   10                                                       
CONECT   21   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0031911
HETATM    1  C1  UNL     1       5.074  -0.156   0.796  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.912   0.005   1.584  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.689  -0.032   0.951  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.601  -0.219  -0.411  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.373  -0.259  -1.070  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.310  -0.461  -2.526  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.249  -0.102  -0.296  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.338   0.088   1.088  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.888   0.207   1.560  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.772   0.111   0.601  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.156   0.177   0.651  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.857   0.385   1.915  1.00  0.00           C  
HETATM   13  O3  UNL     1      -5.092   0.439   1.924  1.00  0.00           O  
HETATM   14  O4  UNL     1      -3.134   0.517   3.079  1.00  0.00           O  
HETATM   15  C11 UNL     1      -3.841   0.039  -0.536  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.168  -0.156  -1.719  1.00  0.00           C  
HETATM   17  O5  UNL     1      -3.911  -0.291  -2.907  1.00  0.00           O  
HETATM   18  C13 UNL     1      -1.781  -0.223  -1.776  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.097  -0.086  -0.593  1.00  0.00           C  
HETATM   20  C15 UNL     1       1.556   0.125   1.721  1.00  0.00           C  
HETATM   21  O6  UNL     1       1.624   0.316   3.101  1.00  0.00           O  
HETATM   22  H1  UNL     1       5.009  -1.053   0.142  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.921  -0.317   1.521  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.256   0.776   0.188  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.486  -0.345  -1.037  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.827  -1.416  -2.829  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.369  -0.559  -2.914  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.907   0.417  -3.056  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.417  -0.161   3.319  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.940   0.091  -0.502  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.920  -0.244  -2.882  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.304  -0.378  -2.734  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.779   0.429   3.645  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   25
CONECT    5    6    7    7
CONECT    6   26   27   28
CONECT    7    8   19
CONECT    8    9   20   20
CONECT    9   10
CONECT   10   11   11   19
CONECT   11   12   15
CONECT   12   13   13   14
CONECT   14   29
CONECT   15   16   16   30
CONECT   16   17   18
CONECT   17   31
CONECT   18   19   19   32
CONECT   20   21
CONECT   21   33
END

HMDB0031911
     RDKit          3D
Porric acid B
 33 35  0  0  0  0  0  0  0  0999 V2000
    5.0735   -0.1559    0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119    0.0048    1.5845 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888   -0.0317    0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6006   -0.2195   -0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726   -0.2594   -1.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3103   -0.4613   -2.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2491   -0.1023   -0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3377    0.0883    1.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882    0.2073    1.5595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7723    0.1105    0.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555    0.1769    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8566    0.3846    1.9153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0923    0.4389    1.9240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1341    0.5171    3.0787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8408    0.0394   -0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1683   -0.1557   -1.7190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9111   -0.2909   -2.9075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7814   -0.2233   -1.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975   -0.0863   -0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5556    0.1251    1.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6238    0.3162    3.1013 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0090   -1.0532    0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9208   -0.3174    1.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2563    0.7757    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862   -0.3454   -1.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8268   -1.4157   -2.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3690   -0.5586   -2.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9071    0.4172   -3.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4168   -0.1609    3.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9396    0.0914   -0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9198   -0.2440   -2.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036   -0.3784   -2.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7788    0.4288    3.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  8 20  2  0
 20 21  1  0
 20  3  1  0
 19  7  1  0
 19 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(15,19-Dotriacontadienyl)-5-methyl-2(5H)-furanone	HMDB
2,6-Dihydroxy-7-methoxy-9-methyl-4-dibenzofurancarboxylic acid	HMDB
4,10-Dihydroxy-11-methoxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylate	Generator
Porrate b	Generator

Chemical Formula

C₁₅H₁₂O₆

Average Molecular Weight

288.2522

Monoisotopic Molecular Weight

288.063388116

IUPAC Name

4,10-dihydroxy-11-methoxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid

Traditional Name

4,10-dihydroxy-11-methoxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid

CAS Registry Number

207285-02-7

SMILES

COC1=C(O)C2=C(C3=C(O2)C(=CC(O)=C3)C(O)=O)C(C)=C1

InChI Identifier

InChI=1S/C15H12O6/c1-6-3-10(20-2)12(17)14-11(6)8-4-7(16)5-9(15(18)19)13(8)21-14/h3-5,16-17H,1-2H3,(H,18,19)

InChI Key

YRDAFVVZXCAVIU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0031911)

Cellular substructure

Membrane (HMDB: HMDB0031911)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031911)

Source

Endogenous

Endogenous (HMDB: HMDB0031911)

Plant

Plant (HMDB: HMDB0031911)

Exogenous

Food

Food (HMDB: HMDB0031911)

Herb and spice

Herb

Welsh onion (FooDB: FOOD00241)

Vegetable

Onion-family vegetable

Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	217 - 219 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.31 g/L	ALOGPS
logP	2.51	ALOGPS
logP	2.56	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.18	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.95 m³·mol⁻¹	ChemAxon
Polarizability	28.73 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
DarkChem	[M+H]+	166.777	31661259
DarkChem	[M-H]-	169.205	31661259
DeepCCS	[M+H]+	176.951	30932474
DeepCCS	[M-H]-	174.475	30932474
DeepCCS	[M-2H]-	208.885	30932474
DeepCCS	[M+Na]+	185.036	30932474
AllCCS	[M+H]+	163.6	32859911
AllCCS	[M+H-H2O]+	160.0	32859911
AllCCS	[M+NH4]+	167.0	32859911
AllCCS	[M+Na]+	167.9	32859911
AllCCS	[M-H]-	165.9	32859911
AllCCS	[M+Na-2H]-	165.2	32859911
AllCCS	[M+HCOO]-	164.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Porric acid B	COC1=C(O)C2=C(C3=C(O2)C(=CC(O)=C3)C(O)=O)C(C)=C1	4319.2	Standard polar	33892256
Porric acid B	COC1=C(O)C2=C(C3=C(O2)C(=CC(O)=C3)C(O)=O)C(C)=C1	2577.6	Standard non polar	33892256
Porric acid B	COC1=C(O)C2=C(C3=C(O2)C(=CC(O)=C3)C(O)=O)C(C)=C1	2937.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Porric acid B,1TMS,isomer #1	COC1=CC(C)=C2C(=C1O[Si](C)(C)C)OC1=C(C(=O)O)C=C(O)C=C12	2823.7	Semi standard non polar	33892256
Porric acid B,1TMS,isomer #2	COC1=CC(C)=C2C(=C1O)OC1=C(C(=O)O)C=C(O[Si](C)(C)C)C=C12	2931.5	Semi standard non polar	33892256
Porric acid B,1TMS,isomer #3	COC1=CC(C)=C2C(=C1O)OC1=C(C(=O)O[Si](C)(C)C)C=C(O)C=C12	2921.1	Semi standard non polar	33892256
Porric acid B,2TMS,isomer #1	COC1=CC(C)=C2C(=C1O[Si](C)(C)C)OC1=C(C(=O)O[Si](C)(C)C)C=C(O)C=C12	2778.2	Semi standard non polar	33892256
Porric acid B,2TMS,isomer #2	COC1=CC(C)=C2C(=C1O[Si](C)(C)C)OC1=C(C(=O)O)C=C(O[Si](C)(C)C)C=C12	2836.2	Semi standard non polar	33892256
Porric acid B,2TMS,isomer #3	COC1=CC(C)=C2C(=C1O)OC1=C(C(=O)O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C12	2983.5	Semi standard non polar	33892256
Porric acid B,3TMS,isomer #1	COC1=CC(C)=C2C(=C1O[Si](C)(C)C)OC1=C(C(=O)O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C12	2897.1	Semi standard non polar	33892256
Porric acid B,1TBDMS,isomer #1	COC1=CC(C)=C2C(=C1O[Si](C)(C)C(C)(C)C)OC1=C(C(=O)O)C=C(O)C=C12	3107.1	Semi standard non polar	33892256
Porric acid B,1TBDMS,isomer #2	COC1=CC(C)=C2C(=C1O)OC1=C(C(=O)O)C=C(O[Si](C)(C)C(C)(C)C)C=C12	3197.1	Semi standard non polar	33892256
Porric acid B,1TBDMS,isomer #3	COC1=CC(C)=C2C(=C1O)OC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C(O)C=C12	3181.7	Semi standard non polar	33892256
Porric acid B,2TBDMS,isomer #1	COC1=CC(C)=C2C(=C1O[Si](C)(C)C(C)(C)C)OC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C(O)C=C12	3289.0	Semi standard non polar	33892256
Porric acid B,2TBDMS,isomer #2	COC1=CC(C)=C2C(=C1O[Si](C)(C)C(C)(C)C)OC1=C(C(=O)O)C=C(O[Si](C)(C)C(C)(C)C)C=C12	3376.4	Semi standard non polar	33892256
Porric acid B,2TBDMS,isomer #3	COC1=CC(C)=C2C(=C1O)OC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C12	3418.6	Semi standard non polar	33892256
Porric acid B,3TBDMS,isomer #1	COC1=CC(C)=C2C(=C1O[Si](C)(C)C(C)(C)C)OC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C12	3534.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Porric acid B GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-0190000000-70242ef807b2aa58930b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porric acid B GC-MS (3 TMS) - 70eV, Positive	splash10-001c-1201900000-7e0b6d5b1491a3570cb4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porric acid B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Porric acid B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porric acid B 10V, Positive-QTOF	splash10-000i-0090000000-838852ec44bfe85d02b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porric acid B 20V, Positive-QTOF	splash10-0076-0090000000-d70ed097eaf6016a9af6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porric acid B 40V, Positive-QTOF	splash10-006x-1190000000-6ae3aa7542f2a4503db4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porric acid B 10V, Negative-QTOF	splash10-000l-0090000000-344597db8aecae27ba43	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porric acid B 20V, Negative-QTOF	splash10-002f-0090000000-76718f4ccdf074aabf7c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porric acid B 40V, Negative-QTOF	splash10-004i-0290000000-b7668b23dc045c5501a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porric acid B 10V, Positive-QTOF	splash10-0079-0090000000-6081a931933f97746b48	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porric acid B 20V, Positive-QTOF	splash10-00dr-0090000000-4a9fbcb449552fa6785c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porric acid B 40V, Positive-QTOF	splash10-02vl-0290000000-d6c09985b1d3449cae67	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porric acid B 10V, Negative-QTOF	splash10-000i-0090000000-74127368fd472a94be09	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porric acid B 20V, Negative-QTOF	splash10-03g3-0090000000-b9b949e8f1d38cd652d4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Porric acid B 40V, Negative-QTOF	splash10-01t9-0090000000-d5f9798732476e330d08	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008593

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751208

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Porric acid B (HMDB0031911)

MOL for HMDB0031911 (Porric acid B)

3D MOL for HMDB0031911 (Porric acid B)

3D SDF for HMDB0031911 (Porric acid B)

3D-SDF for HMDB0031911 (Porric acid B)

PDB for HMDB0031911 (Porric acid B)

3D PDB for HMDB0031911 (Porric acid B)

SMILES for HMDB0031911 (Porric acid B)

INCHI for HMDB0031911 (Porric acid B)

Structure for HMDB0031911 (Porric acid B)

3D Structure for HMDB0031911 (Porric acid B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra