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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:16:32 UTC

Update Date

2022-03-07 02:57:05 UTC

HMDB ID

HMDB0041582

Secondary Accession Numbers

HMDB41582

Metabolite Identification

Common Name

Sapidolide A

Description

Sapidolide A belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Sapidolide A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, sapidolide a has been detected, but not quantified in, fruits. This could make sapidolide a a potential biomarker for the consumption of these foods.

Structure

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

HMDB0041582
     RDKit          3D
Sapidolide A
 37 40  0  0  0  0  0  0  0  0999 V2000
    3.9539    0.2618   -0.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9970   -0.3605   -1.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5827   -0.0916   -0.8851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9895   -1.2597   -0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894   -1.0481    1.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1331   -1.9544    1.9476 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7277    0.3226    1.3960 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4180    0.9819    0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0515    1.3756    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2967    2.5366    0.8214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3841    1.5033   -1.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7948    1.5952   -1.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131    0.5398   -0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5668   -0.7065   -0.9309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2862   -1.5185   -1.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4670   -1.1033    0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8024   -1.9628    1.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9093    0.2640    0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2045    0.3904    2.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8364    1.0134    0.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9908    0.0012   -0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3075   -1.1083   -1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9853    0.1068   -1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1917   -2.2205   -0.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0730    1.8528    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3205    2.5601    1.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2410    1.4130   -2.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0166    2.5925   -0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0022    0.9229    0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9518   -0.4249   -1.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867   -1.2703   -0.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929   -1.3083   -1.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951   -2.5867   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4018   -2.6809    0.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2881    0.7628    2.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5531   -0.5670    2.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9911    1.1755    2.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  8  3  1  0
 18  9  1  0
 16  4  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  4 24  1  0
  8 25  1  0
 10 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
M  END


  Mrv0541 02241214282D          

 19 22  0  0  0  0            999 V2000
   -0.8696    0.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8696   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1561   -1.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5561   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5561    0.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1561    0.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3280    1.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1488    1.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857    0.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0687    0.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0687   -0.6985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8696    0.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4269    1.1537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0828   -1.4631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2711   -1.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0687   -0.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5686   -0.3630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0406   -0.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331    0.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  2 11  1  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  1  0  0  0  0
  4 15  1  0  0  0  0
  5  6  1  0  0  0  0
  5 18  1  0  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 15 16  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041582

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12C3CCC1(O)C1C(C=C)C(OC1=O)C2(O)OC3

> <INCHI_IDENTIFIER>
InChI=1S/C14H18O5/c1-3-8-9-11(15)19-10(8)14(17)12(2)7(6-18-14)4-5-13(9,12)16/h3,7-10,16-17H,1,4-6H2,2H3

> <INCHI_KEY>
OZRZMHKATMSFPV-UHFFFAOYSA-N

> <FORMULA>
C14H18O5

> <MOLECULAR_WEIGHT>
266.2897

> <EXACT_MASS>
266.115423686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.107144017711164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-ethenyl-1,7-dihydroxy-12-methyl-2,10-dioxatetracyclo[5.4.1.1⁸,¹¹.0⁴,¹²]tridecan-9-one

> <ALOGPS_LOGP>
0.10

> <JCHEM_LOGP>
0.506315969333333

> <ALOGPS_LOGS>
-1.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.820942645149458

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.659452859644889

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3588904178061787

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
64.4501

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-ethenyl-1,7-dihydroxy-12-methyl-2,10-dioxatetracyclo[5.4.1.1⁸,¹¹.0⁴,¹²]tridecan-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041582
     RDKit          3D
Sapidolide A
 37 40  0  0  0  0  0  0  0  0999 V2000
    3.9539    0.2618   -0.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9970   -0.3605   -1.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5827   -0.0916   -0.8851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9895   -1.2597   -0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894   -1.0481    1.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1331   -1.9544    1.9476 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7277    0.3226    1.3960 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4180    0.9819    0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0515    1.3756    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2967    2.5366    0.8214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3841    1.5033   -1.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7948    1.5952   -1.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131    0.5398   -0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5668   -0.7065   -0.9309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2862   -1.5185   -1.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4670   -1.1033    0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8024   -1.9628    1.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9093    0.2640    0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2045    0.3904    2.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8364    1.0134    0.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9908    0.0012   -0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3075   -1.1083   -1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9853    0.1068   -1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1917   -2.2205   -0.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0730    1.8528    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3205    2.5601    1.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2410    1.4130   -2.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0166    2.5925   -0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0022    0.9229    0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9518   -0.4249   -1.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867   -1.2703   -0.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929   -1.3083   -1.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951   -2.5867   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4018   -2.6809    0.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2881    0.7628    2.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5531   -0.5670    2.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9911    1.1755    2.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  8  3  1  0
 18  9  1  0
 16  4  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  4 24  1  0
  8 25  1  0
 10 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.623   0.298   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.623  -1.242   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.291  -2.012   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.038  -1.242   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.038   0.298   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.291   1.065   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.612   2.569   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.144   2.731   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.773   1.324   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.862   0.236   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.862  -1.304   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.623   1.838   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.797   2.154   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.021  -2.731   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.373  -2.012   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.862  -1.614   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.061  -0.678   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.076  -0.110   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.435   0.511   0.000  0.00  0.00           O+0
CONECT    1    2    6    9   12                                             
CONECT    2    1    3   11   14                                             
CONECT    3    2    4   17                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6   18                                                  
CONECT    6    1    5    7   13                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    1    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11    2   10                                                       
CONECT   12    1                                                            
CONECT   13    6                                                            
CONECT   14    2                                                            
CONECT   15    4   16                                                       
CONECT   16   15                                                            
CONECT   17    3   18                                                       
CONECT   18    5   17   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

COMPND    HMDB0041582
HETATM    1  C1  UNL     1       3.954   0.262  -0.464  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.997  -0.360  -1.120  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.583  -0.092  -0.885  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.989  -1.260  -0.077  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.689  -1.048   1.214  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.133  -1.954   1.948  1.00  0.00           O  
HETATM    7  O2  UNL     1       1.728   0.323   1.396  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.418   0.982   0.167  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.051   1.376   0.107  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.297   2.537   0.821  1.00  0.00           O  
HETATM   11  O4  UNL     1      -0.384   1.503  -1.237  1.00  0.00           O  
HETATM   12  C8  UNL     1      -1.795   1.595  -1.200  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.213   0.540  -0.168  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.567  -0.706  -0.931  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.286  -1.519  -1.028  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.467  -1.103   0.167  1.00  0.00           C  
HETATM   17  O5  UNL     1      -0.802  -1.963   1.235  1.00  0.00           O  
HETATM   18  C13 UNL     1      -0.909   0.264   0.563  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.205   0.390   2.043  1.00  0.00           C  
HETATM   20  H1  UNL     1       3.836   1.013   0.295  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.991   0.001  -0.701  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.307  -1.108  -1.869  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.985   0.107  -1.792  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.192  -2.220  -0.540  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.073   1.853   0.005  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.321   2.560   1.609  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.241   1.413  -2.179  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.017   2.592  -0.771  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.002   0.923   0.476  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.952  -0.425  -1.944  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.387  -1.270  -0.445  1.00  0.00           H  
HETATM   32  H13 UNL     1      -0.793  -1.308  -1.984  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.595  -2.587  -0.916  1.00  0.00           H  
HETATM   34  H15 UNL     1      -1.402  -2.681   0.966  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.288   0.763   2.546  1.00  0.00           H  
HETATM   36  H17 UNL     1      -1.553  -0.567   2.490  1.00  0.00           H  
HETATM   37  H18 UNL     1      -1.991   1.176   2.201  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   22
CONECT    3    4    8   23
CONECT    4    5   16   24
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   25
CONECT    9   10   11   18
CONECT   10   26
CONECT   11   12
CONECT   12   13   27   28
CONECT   13   14   18   29
CONECT   14   15   30   31
CONECT   15   16   32   33
CONECT   16   17   18
CONECT   17   34
CONECT   18   19
CONECT   19   35   36   37
END

HMDB0041582
     RDKit          3D
Sapidolide A
 37 40  0  0  0  0  0  0  0  0999 V2000
    3.9539    0.2618   -0.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9970   -0.3605   -1.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5827   -0.0916   -0.8851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9895   -1.2597   -0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894   -1.0481    1.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1331   -1.9544    1.9476 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7277    0.3226    1.3960 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4180    0.9819    0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0515    1.3756    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2967    2.5366    0.8214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3841    1.5033   -1.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7948    1.5952   -1.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131    0.5398   -0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5668   -0.7065   -0.9309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2862   -1.5185   -1.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4670   -1.1033    0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8024   -1.9628    1.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9093    0.2640    0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2045    0.3904    2.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8364    1.0134    0.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9908    0.0012   -0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3075   -1.1083   -1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9853    0.1068   -1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1917   -2.2205   -0.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0730    1.8528    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3205    2.5601    1.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2410    1.4130   -2.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0166    2.5925   -0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0022    0.9229    0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9518   -0.4249   -1.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867   -1.2703   -0.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929   -1.3083   -1.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951   -2.5867   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4018   -2.6809    0.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2881    0.7628    2.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5531   -0.5670    2.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9911    1.1755    2.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  8  3  1  0
 18  9  1  0
 16  4  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  4 24  1  0
  8 25  1  0
 10 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₁₈O₅

Average Molecular Weight

266.2897

Monoisotopic Molecular Weight

266.115423686

IUPAC Name

13-ethenyl-1,7-dihydroxy-12-methyl-2,10-dioxatetracyclo[5.4.1.1⁸,¹¹.0⁴,¹²]tridecan-9-one

Traditional Name

13-ethenyl-1,7-dihydroxy-12-methyl-2,10-dioxatetracyclo[5.4.1.1⁸,¹¹.0⁴,¹²]tridecan-9-one

CAS Registry Number

182191-87-3

SMILES

CC12C3CCC1(O)C1C(C=C)C(OC1=O)C2(O)OC3

InChI Identifier

InChI=1S/C14H18O5/c1-3-8-9-11(15)19-10(8)14(17)12(2)7(6-18-14)4-5-13(9,12)16/h3,7-10,16-17H,1,4-6H2,2H3

InChI Key

OZRZMHKATMSFPV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041582)
Cytoplasm (HMDB: HMDB0041582)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041582)

Source

Exogenous

Food

Food (HMDB: HMDB0041582)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0041582)

Not Available

Nutrient (HMDB: HMDB0041582)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0041582)

Emulsifier (HMDB: HMDB0041582)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	147 °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	18 g/L	ALOGPS
logP	0.1	ALOGPS
logP	0.51	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	10.66	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	64.45 m³·mol⁻¹	ChemAxon
Polarizability	26.11 Å³	ChemAxon
Number of Rings	4	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]+	160.471	31661259
DarkChem	[M-H]-	158.029	31661259
DeepCCS	[M-2H]-	196.284	30932474
DeepCCS	[M+Na]+	171.741	30932474
AllCCS	[M+H]+	160.1	32859911
AllCCS	[M+H-H2O]+	156.5	32859911
AllCCS	[M+NH4]+	163.5	32859911
AllCCS	[M+Na]+	164.4	32859911
AllCCS	[M-H]-	165.0	32859911
AllCCS	[M+Na-2H]-	164.6	32859911
AllCCS	[M+HCOO]-	164.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sapidolide A	CC12C3CCC1(O)C1C(C=C)C(OC1=O)C2(O)OC3	3251.0	Standard polar	33892256
Sapidolide A	CC12C3CCC1(O)C1C(C=C)C(OC1=O)C2(O)OC3	2110.3	Standard non polar	33892256
Sapidolide A	CC12C3CCC1(O)C1C(C=C)C(OC1=O)C2(O)OC3	2287.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sapidolide A,1TMS,isomer #1	C=CC1C2OC(=O)C1C1(O[Si](C)(C)C)CCC3COC2(O)C31C	2065.2	Semi standard non polar	33892256
Sapidolide A,1TMS,isomer #2	C=CC1C2C(=O)OC1C1(O[Si](C)(C)C)OCC3CCC2(O)C31C	2057.0	Semi standard non polar	33892256
Sapidolide A,2TMS,isomer #1	C=CC1C2C(=O)OC1C1(O[Si](C)(C)C)OCC3CCC2(O[Si](C)(C)C)C31C	2161.2	Semi standard non polar	33892256
Sapidolide A,1TBDMS,isomer #1	C=CC1C2OC(=O)C1C1(O[Si](C)(C)C(C)(C)C)CCC3COC2(O)C31C	2296.6	Semi standard non polar	33892256
Sapidolide A,1TBDMS,isomer #2	C=CC1C2C(=O)OC1C1(O[Si](C)(C)C(C)(C)C)OCC3CCC2(O)C31C	2302.9	Semi standard non polar	33892256
Sapidolide A,2TBDMS,isomer #1	C=CC1C2C(=O)OC1C1(O[Si](C)(C)C(C)(C)C)OCC3CCC2(O[Si](C)(C)C(C)(C)C)C31C	2609.4	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 - Sapidolide A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pb9-2960000000-78130230edff068879d4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sapidolide A GC-MS (2 TMS) - 70eV, Positive	splash10-000i-9004000000-3210efd61cf0b2e8b697	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sapidolide A 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 - Sapidolide A 10V, Positive-QTOF	splash10-00kb-0090000000-ff1d4db8330473d160b5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sapidolide A 20V, Positive-QTOF	splash10-00kb-0090000000-34c3c8424b7f50c569f3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sapidolide A 40V, Positive-QTOF	splash10-001i-4390000000-ae036373a32a43ee7e86	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sapidolide A 10V, Negative-QTOF	splash10-014i-0090000000-8c403c84986dffbe43d1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sapidolide A 20V, Negative-QTOF	splash10-01ba-0090000000-59e7bd50b8f5ab99d9cb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sapidolide A 40V, Negative-QTOF	splash10-014l-4970000000-9208d06fbf2390a23109	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sapidolide A 10V, Positive-QTOF	splash10-014i-0090000000-217dac9cdc002dbfa8f2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sapidolide A 20V, Positive-QTOF	splash10-066r-0390000000-e12cf184973fbefdda19	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sapidolide A 40V, Positive-QTOF	splash10-014i-3190000000-9c9cfcde25c25350f2f4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sapidolide A 10V, Negative-QTOF	splash10-014i-0090000000-569df53f621f3bfc4e5e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sapidolide A 20V, Negative-QTOF	splash10-014i-0090000000-4f658ff6c2210f38e400	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sapidolide A 40V, Negative-QTOF	splash10-014j-0290000000-50c923d1d12e357e0827	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB021574

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

85214158

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 Sapidolide A (HMDB0041582)

MOL for HMDB0041582 (Sapidolide A)

3D MOL for HMDB0041582 (Sapidolide A)

3D SDF for HMDB0041582 (Sapidolide A)

3D-SDF for HMDB0041582 (Sapidolide A)

PDB for HMDB0041582 (Sapidolide A)

3D PDB for HMDB0041582 (Sapidolide A)

SMILES for HMDB0041582 (Sapidolide A)

INCHI for HMDB0041582 (Sapidolide A)

Structure for HMDB0041582 (Sapidolide A)

3D Structure for HMDB0041582 (Sapidolide A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra