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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:43:01 UTC

Update Date

2021-09-26 23:11:58 UTC

HMDB ID

HMDB0256357

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Petrosaspongiolide m

Description

4-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-1,11,15,15-tetramethyl-5-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadecan-6-yl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 4-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-1,11,15,15-tetramethyl-5-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadecan-6-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Petrosaspongiolide m is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Petrosaspongiolide m 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


  Mrv1533004171519012D          

 33 37  0  0  0  0            999 V2000
    4.7651    3.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4951    2.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    2.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.5684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6282   -1.9592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

HMDB0256357
     RDKit          3D
Petrosaspongiolide m
 73 77  0  0  0  0  0  0  0  0999 V2000
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 33 73  1  0
M  END


  Mrv1533004171519012D          

 33 37  0  0  0  0            999 V2000
    4.7651    3.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 31 32  1  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256357

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1OC(CC2C1CCC1C2(C)CCC2C(C)(C)CCCC12C)C1=CC(=O)OC1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O6/c1-15(28)31-24-16-7-8-21-26(4,12-9-20-25(2,3)10-6-11-27(20,21)5)18(16)14-19(32-24)17-13-22(29)33-23(17)30/h13,16,18-21,23-24,30H,6-12,14H2,1-5H3

> <INCHI_KEY>
RVWQZLJUVIFAOY-UHFFFAOYSA-N

> <FORMULA>
C27H40O6

> <MOLECULAR_WEIGHT>
460.611

> <EXACT_MASS>
460.282489008

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.144413184453654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-1,11,15,15-tetramethyl-5-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadecan-6-yl acetate

> <ALOGPS_LOGP>
3.88

> <JCHEM_LOGP>
4.9142552493333325

> <ALOGPS_LOGS>
-5.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.73233573171943

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.496234493169931

> <JCHEM_PKA_STRONGEST_BASIC>
-4.30305598580737

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
122.52189999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(2-hydroxy-5-oxo-2H-furan-3-yl)-1,11,15,15-tetramethyl-5-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadecan-6-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256357
     RDKit          3D
Petrosaspongiolide m
 73 77  0  0  0  0  0  0  0  0999 V2000
   -4.0289    4.9079   -0.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3689    3.7248    0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6506    3.8343    1.0540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4897    2.4443   -0.5052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8709    1.3174    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7163    0.3249    0.4466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4411   -0.9278   -0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3230   -1.8906    0.7585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1560   -1.5713    1.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8206   -2.7578    2.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6921   -2.8617    3.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3320   -3.8033    1.4876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4003   -3.3498    0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9339   -3.6387   -0.7122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0235   -1.3867    0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0531   -0.2527   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7992    0.7431   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9370    1.8195   -1.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4504    1.6575   -0.8123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0383    0.3410   -1.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2151   -0.7578   -0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2505   -1.6503   -1.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9170   -1.6230    0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8818   -0.9269    1.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6092    0.2530    0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0008    0.2100    1.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9028    0.0592    2.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7491    1.5435    1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7720   -0.8772    0.5177 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2335   -1.5315   -0.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2840   -0.7969   -1.5390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5174    0.3069   -0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0505    1.6054   -1.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1773    4.7982   -1.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0159    5.0395   -0.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4590    5.8394   -0.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3001    1.6701    0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7571   -1.0519   -1.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3277   -0.5566    2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4008   -3.8367    0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9131   -3.7811   -0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9927   -1.6886    1.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8139   -2.2960   -0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8133    0.1880    0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3326    0.2547   -1.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7884    1.6881   -2.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3038    2.8310   -1.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0103    2.5463   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2994    1.7452    0.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0143    0.3494   -2.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1212   -2.7183   -1.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2884   -1.3896   -2.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3273   -1.4726   -2.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3702   -2.5443   -0.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1275   -2.0968    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3145   -0.5689    2.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834   -1.7417    1.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1532    1.2154    0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8103    1.0661    3.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9213   -0.2985    2.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0942   -0.5365    3.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5782    1.5356    1.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1172    2.3981    1.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2777    1.6455    0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8259   -0.5075    0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9268   -1.6764    1.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1190   -1.8738   -1.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7561   -2.5274   -0.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8506   -0.4374   -2.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5376   -1.5033   -2.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0199    2.4509   -0.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4490    1.9111   -2.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0652    1.4425   -1.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
  7 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 17  5  1  0
 32 20  1  0
 13  8  1  0
 21 16  1  0
 32 25  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  7 38  1  0
  9 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 27 59  1  0
 27 60  1  0
 27 61  1  0
 28 62  1  0
 28 63  1  0
 28 64  1  0
 29 65  1  0
 29 66  1  0
 30 67  1  0
 30 68  1  0
 31 69  1  0
 31 70  1  0
 33 71  1  0
 33 72  1  0
 33 73  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       8.895   6.300   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.391   4.844   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.879   4.553   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.399   3.680   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.903   1.061   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.375   3.098   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.366   0.188   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.375  -0.976   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.350  -1.558   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.379  -2.124   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.492  -1.476   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.179   0.479   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.350   2.516   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.407  -1.558   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.942  -1.427   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.541  -2.846   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.041  -3.195   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      11.377  -3.854   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.058  -3.058   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.639  -3.657   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   25                                                  
CONECT   14   13    9   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   13   18   26                                             
CONECT   26   25                                                            
CONECT   27    7   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   27   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

COMPND    HMDB0256357
HETATM    1  C1  UNL     1      -4.029   4.908  -0.577  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.369   3.725   0.019  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.651   3.834   1.054  1.00  0.00           O  
HETATM    4  O2  UNL     1      -3.490   2.444  -0.505  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.871   1.317   0.048  1.00  0.00           C  
HETATM    6  O3  UNL     1      -3.716   0.325   0.447  1.00  0.00           O  
HETATM    7  C4  UNL     1      -3.441  -0.928  -0.015  1.00  0.00           C  
HETATM    8  C5  UNL     1      -4.323  -1.891   0.759  1.00  0.00           C  
HETATM    9  C6  UNL     1      -5.156  -1.571   1.725  1.00  0.00           C  
HETATM   10  C7  UNL     1      -5.821  -2.758   2.220  1.00  0.00           C  
HETATM   11  O4  UNL     1      -6.692  -2.862   3.147  1.00  0.00           O  
HETATM   12  O5  UNL     1      -5.332  -3.803   1.488  1.00  0.00           O  
HETATM   13  C8  UNL     1      -4.400  -3.350   0.563  1.00  0.00           C  
HETATM   14  O6  UNL     1      -4.934  -3.639  -0.712  1.00  0.00           O  
HETATM   15  C9  UNL     1      -2.023  -1.387   0.235  1.00  0.00           C  
HETATM   16  C10 UNL     1      -1.053  -0.253  -0.057  1.00  0.00           C  
HETATM   17  C11 UNL     1      -1.799   0.743  -0.888  1.00  0.00           C  
HETATM   18  C12 UNL     1      -0.937   1.819  -1.450  1.00  0.00           C  
HETATM   19  C13 UNL     1       0.450   1.658  -0.812  1.00  0.00           C  
HETATM   20  C14 UNL     1       1.038   0.341  -1.242  1.00  0.00           C  
HETATM   21  C15 UNL     1       0.215  -0.758  -0.720  1.00  0.00           C  
HETATM   22  C16 UNL     1      -0.250  -1.650  -1.879  1.00  0.00           C  
HETATM   23  C17 UNL     1       0.917  -1.623   0.266  1.00  0.00           C  
HETATM   24  C18 UNL     1       1.882  -0.927   1.154  1.00  0.00           C  
HETATM   25  C19 UNL     1       2.609   0.253   0.603  1.00  0.00           C  
HETATM   26  C20 UNL     1       4.001   0.210   1.157  1.00  0.00           C  
HETATM   27  C21 UNL     1       3.903   0.059   2.672  1.00  0.00           C  
HETATM   28  C22 UNL     1       4.749   1.544   1.015  1.00  0.00           C  
HETATM   29  C23 UNL     1       4.772  -0.877   0.518  1.00  0.00           C  
HETATM   30  C24 UNL     1       4.233  -1.532  -0.678  1.00  0.00           C  
HETATM   31  C25 UNL     1       3.284  -0.797  -1.539  1.00  0.00           C  
HETATM   32  C26 UNL     1       2.517   0.307  -0.884  1.00  0.00           C  
HETATM   33  C27 UNL     1       3.051   1.605  -1.482  1.00  0.00           C  
HETATM   34  H1  UNL     1      -4.177   4.798  -1.677  1.00  0.00           H  
HETATM   35  H2  UNL     1      -5.016   5.039  -0.087  1.00  0.00           H  
HETATM   36  H3  UNL     1      -3.459   5.839  -0.430  1.00  0.00           H  
HETATM   37  H4  UNL     1      -2.300   1.670   0.945  1.00  0.00           H  
HETATM   38  H5  UNL     1      -3.757  -1.052  -1.070  1.00  0.00           H  
HETATM   39  H6  UNL     1      -5.328  -0.557   2.107  1.00  0.00           H  
HETATM   40  H7  UNL     1      -3.401  -3.837   0.675  1.00  0.00           H  
HETATM   41  H8  UNL     1      -5.913  -3.781  -0.675  1.00  0.00           H  
HETATM   42  H9  UNL     1      -1.993  -1.689   1.323  1.00  0.00           H  
HETATM   43  H10 UNL     1      -1.814  -2.296  -0.327  1.00  0.00           H  
HETATM   44  H11 UNL     1      -0.813   0.188   0.954  1.00  0.00           H  
HETATM   45  H12 UNL     1      -2.333   0.255  -1.720  1.00  0.00           H  
HETATM   46  H13 UNL     1      -0.788   1.688  -2.559  1.00  0.00           H  
HETATM   47  H14 UNL     1      -1.304   2.831  -1.248  1.00  0.00           H  
HETATM   48  H15 UNL     1       1.010   2.546  -1.119  1.00  0.00           H  
HETATM   49  H16 UNL     1       0.299   1.745   0.277  1.00  0.00           H  
HETATM   50  H17 UNL     1       1.014   0.349  -2.371  1.00  0.00           H  
HETATM   51  H18 UNL     1      -0.121  -2.718  -1.650  1.00  0.00           H  
HETATM   52  H19 UNL     1       0.288  -1.390  -2.823  1.00  0.00           H  
HETATM   53  H20 UNL     1      -1.327  -1.473  -2.123  1.00  0.00           H  
HETATM   54  H21 UNL     1       1.370  -2.544  -0.212  1.00  0.00           H  
HETATM   55  H22 UNL     1       0.128  -2.097   0.929  1.00  0.00           H  
HETATM   56  H23 UNL     1       1.315  -0.569   2.064  1.00  0.00           H  
HETATM   57  H24 UNL     1       2.583  -1.742   1.509  1.00  0.00           H  
HETATM   58  H25 UNL     1       2.153   1.215   0.984  1.00  0.00           H  
HETATM   59  H26 UNL     1       3.810   1.066   3.180  1.00  0.00           H  
HETATM   60  H27 UNL     1       4.921  -0.298   2.990  1.00  0.00           H  
HETATM   61  H28 UNL     1       3.094  -0.537   3.044  1.00  0.00           H  
HETATM   62  H29 UNL     1       5.578   1.536   1.791  1.00  0.00           H  
HETATM   63  H30 UNL     1       4.117   2.398   1.316  1.00  0.00           H  
HETATM   64  H31 UNL     1       5.278   1.646   0.074  1.00  0.00           H  
HETATM   65  H32 UNL     1       5.826  -0.507   0.338  1.00  0.00           H  
HETATM   66  H33 UNL     1       4.927  -1.676   1.306  1.00  0.00           H  
HETATM   67  H34 UNL     1       5.119  -1.874  -1.303  1.00  0.00           H  
HETATM   68  H35 UNL     1       3.756  -2.527  -0.422  1.00  0.00           H  
HETATM   69  H36 UNL     1       3.851  -0.437  -2.455  1.00  0.00           H  
HETATM   70  H37 UNL     1       2.538  -1.503  -2.014  1.00  0.00           H  
HETATM   71  H38 UNL     1       3.020   2.451  -0.809  1.00  0.00           H  
HETATM   72  H39 UNL     1       2.449   1.911  -2.395  1.00  0.00           H  
HETATM   73  H40 UNL     1       4.065   1.442  -1.961  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   17   37
CONECT    6    7
CONECT    7    8   15   38
CONECT    8    9    9   13
CONECT    9   10   39
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   40
CONECT   14   41
CONECT   15   16   42   43
CONECT   16   17   21   44
CONECT   17   18   45
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   21   32   50
CONECT   21   22   23
CONECT   22   51   52   53
CONECT   23   24   54   55
CONECT   24   25   56   57
CONECT   25   26   32   58
CONECT   26   27   28   29
CONECT   27   59   60   61
CONECT   28   62   63   64
CONECT   29   30   65   66
CONECT   30   31   67   68
CONECT   31   32   69   70
CONECT   32   33
CONECT   33   71   72   73
END

HMDB0256357
     RDKit          3D
Petrosaspongiolide m
 73 77  0  0  0  0  0  0  0  0999 V2000
   -4.0289    4.9079   -0.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3689    3.7248    0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6506    3.8343    1.0540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4897    2.4443   -0.5052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8709    1.3174    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7163    0.3249    0.4466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4411   -0.9278   -0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3230   -1.8906    0.7585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1560   -1.5713    1.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8206   -2.7578    2.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6921   -2.8617    3.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3320   -3.8033    1.4876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4003   -3.3498    0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9339   -3.6387   -0.7122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0235   -1.3867    0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0531   -0.2527   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7992    0.7431   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9370    1.8195   -1.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4504    1.6575   -0.8123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0383    0.3410   -1.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2151   -0.7578   -0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2505   -1.6503   -1.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9170   -1.6230    0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8818   -0.9269    1.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6092    0.2530    0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0008    0.2100    1.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9028    0.0592    2.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7491    1.5435    1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7720   -0.8772    0.5177 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2335   -1.5315   -0.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2840   -0.7969   -1.5390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5174    0.3069   -0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0505    1.6054   -1.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1773    4.7982   -1.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0159    5.0395   -0.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4590    5.8394   -0.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3001    1.6701    0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7571   -1.0519   -1.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3277   -0.5566    2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4008   -3.8367    0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9131   -3.7811   -0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9927   -1.6886    1.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8139   -2.2960   -0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8133    0.1880    0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3326    0.2547   -1.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7884    1.6881   -2.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3038    2.8310   -1.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0103    2.5463   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2994    1.7452    0.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0143    0.3494   -2.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1212   -2.7183   -1.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2884   -1.3896   -2.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3273   -1.4726   -2.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3702   -2.5443   -0.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1275   -2.0968    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3145   -0.5689    2.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834   -1.7417    1.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1532    1.2154    0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8103    1.0661    3.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9213   -0.2985    2.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0942   -0.5365    3.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5782    1.5356    1.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1172    2.3981    1.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2777    1.6455    0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8259   -0.5075    0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9268   -1.6764    1.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1190   -1.8738   -1.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7561   -2.5274   -0.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8506   -0.4374   -2.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5376   -1.5033   -2.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0199    2.4509   -0.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4490    1.9111   -2.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0652    1.4425   -1.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
  7 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 17  5  1  0
 32 20  1  0
 13  8  1  0
 21 16  1  0
 32 25  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  7 38  1  0
  9 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 27 59  1  0
 27 60  1  0
 27 61  1  0
 28 62  1  0
 28 63  1  0
 28 64  1  0
 29 65  1  0
 29 66  1  0
 30 67  1  0
 30 68  1  0
 31 69  1  0
 31 70  1  0
 33 71  1  0
 33 72  1  0
 33 73  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(2-Hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-1,11,15,15-tetramethyl-5-oxatetracyclo[8.8.0.0,.0,]octadecan-6-yl acetic acid	Generator
4-(2-Hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-1,11,15,15-tetramethyl-5-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadecan-6-yl acetic acid	Generator

Chemical Formula

C₂₇H₄₀O₆

Average Molecular Weight

460.611

Monoisotopic Molecular Weight

460.282489008

IUPAC Name

4-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-1,11,15,15-tetramethyl-5-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadecan-6-yl acetate

Traditional Name

4-(2-hydroxy-5-oxo-2H-furan-3-yl)-1,11,15,15-tetramethyl-5-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadecan-6-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1OC(CC2C1CCC1C2(C)CCC2C(C)(C)CCCC12C)C1=CC(=O)OC1O

InChI Identifier

InChI=1S/C27H40O6/c1-15(28)31-24-16-7-8-21-26(4,12-9-20-25(2,3)10-6-11-27(20,21)5)18(16)14-19(32-24)17-13-22(29)33-23(17)30/h13,16,18-21,23-24,30H,6-12,14H2,1-5H3

InChI Key

RVWQZLJUVIFAOY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Naphthopyran
Naphthalene
2-furanone
Dicarboxylic acid or derivatives
Oxane
Pyran
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Hemiacetal
Carboxylic acid ester
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.88	ALOGPS
logP	4.91	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	5.5	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	122.52 m³·mol⁻¹	ChemAxon
Polarizability	52.14 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]-	233.874	30932474
DeepCCS	[M+Na]+	209.102	30932474
AllCCS	[M+H]+	210.3	32859911
AllCCS	[M+H-H2O]+	208.3	32859911
AllCCS	[M+NH4]+	212.0	32859911
AllCCS	[M+Na]+	212.5	32859911
AllCCS	[M-H]-	211.7	32859911
AllCCS	[M+Na-2H]-	213.2	32859911
AllCCS	[M+HCOO]-	215.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Petrosaspongiolide m	CC(=O)OC1OC(CC2C1CCC1C2(C)CCC2C(C)(C)CCCC12C)C1=CC(=O)OC1O	3571.7	Standard polar	33892256
Petrosaspongiolide m	CC(=O)OC1OC(CC2C1CCC1C2(C)CCC2C(C)(C)CCCC12C)C1=CC(=O)OC1O	3435.2	Standard non polar	33892256
Petrosaspongiolide m	CC(=O)OC1OC(CC2C1CCC1C2(C)CCC2C(C)(C)CCCC12C)C1=CC(=O)OC1O	3831.9	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 - Petrosaspongiolide m GC-MS (Non-derivatized) - 70eV, Positive	splash10-052b-2297800000-5c275983875674b40873	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Petrosaspongiolide m GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Petrosaspongiolide m GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Petrosaspongiolide m GC-MS (TBDMS_1_1) - 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

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

73407439

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 Petrosaspongiolide m (HMDB0256357)

MOL for HMDB0256357 (Petrosaspongiolide m)

3D MOL for HMDB0256357 (Petrosaspongiolide m)

3D SDF for HMDB0256357 (Petrosaspongiolide m)

3D-SDF for HMDB0256357 (Petrosaspongiolide m)

PDB for HMDB0256357 (Petrosaspongiolide m)

3D PDB for HMDB0256357 (Petrosaspongiolide m)

SMILES for HMDB0256357 (Petrosaspongiolide m)

INCHI for HMDB0256357 (Petrosaspongiolide m)

Structure for HMDB0256357 (Petrosaspongiolide m)

3D Structure for HMDB0256357 (Petrosaspongiolide m)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra