Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 04:06:03 UTC

Update Date

2021-09-26 23:00:33 UTC

HMDB ID

HMDB0249584

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Canin

Description

Canin belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Based on a literature review a significant number of articles have been published on Canin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Canin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Canin 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

HMDB0249584
     RDKit          3D
Canin
 38 42  0  0  0  0  0  0  0  0999 V2000
    4.1469    0.2654   -0.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9102    0.7449   -0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5321    2.1428   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3488    3.1003    0.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1489    2.1713    0.0810 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6565    0.8606    0.3537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6394   -0.0034   -0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8227   -1.3496    0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5282   -1.9312    0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082   -1.7244   -0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5450   -2.9294    0.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1827   -1.7436   -1.4803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4327   -0.5032    0.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7317   -0.5762   -0.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4985   -0.3401    0.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6311    1.1471    1.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5787    1.6452    2.0445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5747    1.7906    0.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7086    3.1880    0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7378    0.7851   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3503   -0.7837   -0.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9947    0.9146   -0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7313    0.6711    1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4736   -0.0926   -1.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4583   -1.1818    1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3907   -2.0247   -0.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490   -1.5751    1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6993   -3.0415    0.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9681   -3.8681    0.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2459   -3.0240   -0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1558   -2.7995    0.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8389   -2.2350   -2.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9011   -1.0379    1.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6352    1.5890    1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4333    3.2112   -0.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345    3.8190    0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7513    3.6300   -0.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7872    1.0891   -1.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
  7  2  1  0
 15 13  1  0
 18 16  1  0
 20  6  1  0
 20 13  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 15 33  1  0
 16 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 20 38  1  0
M  END

  Mrv1533004251516452D          

 20 24  0  0  0  0            999 V2000
   -0.6115   -0.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786   -0.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7874   -1.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6023   -0.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0096   -0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7027    0.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9126    0.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343    0.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4220    0.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5268    0.0336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1493    1.6306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6755    1.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2793    2.3355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4366    1.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3361    1.1127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0345    0.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8003    0.9805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8327   -0.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613   -0.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287   -1.1886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  2  0  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249584

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12OC1C1OC11C2C2OC(=O)C(=C)C2CCC1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O5/c1-6-7-4-5-13(2,17)15-9(8(7)18-12(6)16)14(3)10(19-14)11(15)20-15/h7-11,17H,1,4-5H2,2-3H3

> <INCHI_KEY>
KXLUWEYBZBGJRZ-UHFFFAOYSA-N

> <FORMULA>
C15H18O5

> <MOLECULAR_WEIGHT>
278.304

> <EXACT_MASS>
278.11542368

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.952837662665747

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-2,11-dimethyl-6-methylidene-8,12,15-trioxapentacyclo[8.5.0.0¹,¹⁴.0⁵,⁹.0¹¹,¹³]pentadecan-7-one

> <ALOGPS_LOGP>
0.73

> <JCHEM_LOGP>
0.768883353

> <ALOGPS_LOGS>
-1.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.767612281302565

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3378463881582574

> <JCHEM_POLAR_SURFACE_AREA>
71.59

> <JCHEM_REFRACTIVITY>
66.24390000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.92e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-2,11-dimethyl-6-methylidene-8,12,15-trioxapentacyclo[8.5.0.0¹,¹⁴.0⁵,⁹.0¹¹,¹³]pentadecan-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249584
     RDKit          3D
Canin
 38 42  0  0  0  0  0  0  0  0999 V2000
    4.1469    0.2654   -0.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9102    0.7449   -0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5321    2.1428   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3488    3.1003    0.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1489    2.1713    0.0810 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6565    0.8606    0.3537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6394   -0.0034   -0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8227   -1.3496    0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5282   -1.9312    0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082   -1.7244   -0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5450   -2.9294    0.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1827   -1.7436   -1.4803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4327   -0.5032    0.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7317   -0.5762   -0.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4985   -0.3401    0.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6311    1.1471    1.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5787    1.6452    2.0445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5747    1.7906    0.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7086    3.1880    0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7378    0.7851   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3503   -0.7837   -0.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9947    0.9146   -0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7313    0.6711    1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4736   -0.0926   -1.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4583   -1.1818    1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3907   -2.0247   -0.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490   -1.5751    1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6993   -3.0415    0.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9681   -3.8681    0.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2459   -3.0240   -0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1558   -2.7995    0.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8389   -2.2350   -2.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9011   -1.0379    1.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6352    1.5890    1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4333    3.2112   -0.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345    3.8190    0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7513    3.6300   -0.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7872    1.0891   -1.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
  7  2  1  0
 15 13  1  0
 18 16  1  0
 20  6  1  0
 20 13  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 15 33  1  0
 16 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 20 38  1  0
M  END

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -1.141  -0.436   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.333  -0.879   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.470  -1.919   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.991  -1.678   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.751  -0.339   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.178   1.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.703   1.534   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.437   0.657   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.788   1.590   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.983   0.063   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.279   3.044   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.261   3.009   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.521   4.360   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.682   3.603   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.361   2.077   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.664   1.257   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.094   1.830   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.288  -0.236   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.274  -1.418   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.427  -2.219   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8   20                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    2    9   10                                             
CONECT    9    8   10   11                                                  
CONECT   10    9    8                                                       
CONECT   11    9   12   13                                                  
CONECT   12   11    7   13   14                                             
CONECT   13   12   11                                                       
CONECT   14   12                                                            
CONECT   15    6   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    5   19                                                  
CONECT   19   18                                                            
CONECT   20    2                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   48    0
END

COMPND    HMDB0249584
HETATM    1  C1  UNL     1       4.147   0.265  -0.160  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.910   0.745  -0.174  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.532   2.143  -0.009  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.349   3.100   0.035  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.149   2.171   0.081  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.656   0.861   0.354  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.639  -0.003  -0.356  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.823  -1.350   0.317  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.528  -1.931   0.799  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.608  -1.724  -0.149  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.545  -2.929   0.009  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.183  -1.744  -1.480  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.433  -0.503   0.149  1.00  0.00           C  
HETATM   14  O4  UNL     1      -2.732  -0.576  -0.396  1.00  0.00           O  
HETATM   15  C11 UNL     1      -2.498  -0.340   0.964  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.631   1.147   1.310  1.00  0.00           C  
HETATM   17  O5  UNL     1      -1.579   1.645   2.045  1.00  0.00           O  
HETATM   18  C13 UNL     1      -1.575   1.791   0.630  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.709   3.188   0.083  1.00  0.00           C  
HETATM   20  C15 UNL     1      -0.738   0.785  -0.155  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.350  -0.784  -0.288  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.995   0.915  -0.018  1.00  0.00           H  
HETATM   23  H3  UNL     1       0.731   0.671   1.434  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.474  -0.093  -1.442  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.458  -1.182   1.234  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.391  -2.025  -0.326  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.249  -1.575   1.814  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.699  -3.042   0.908  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.968  -3.868   0.110  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.246  -3.024  -0.818  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.156  -2.800   0.948  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.839  -2.235  -2.049  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.901  -1.038   1.709  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.635   1.589   1.365  1.00  0.00           H  
HETATM   35  H15 UNL     1      -2.433   3.211  -0.768  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.134   3.819   0.908  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.751   3.630  -0.213  1.00  0.00           H  
HETATM   38  H18 UNL     1      -0.787   1.089  -1.205  1.00  0.00           H  
CONECT    1    2    2   21   22
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   20   23
CONECT    7    8   24
CONECT    8    9   25   26
CONECT    9   10   27   28
CONECT   10   11   12   13
CONECT   11   29   30   31
CONECT   12   32
CONECT   13   14   15   20
CONECT   14   15
CONECT   15   16   33
CONECT   16   17   18   34
CONECT   17   18
CONECT   18   19   20
CONECT   19   35   36   37
CONECT   20   38
END

HMDB0249584
     RDKit          3D
Canin
 38 42  0  0  0  0  0  0  0  0999 V2000
    4.1469    0.2654   -0.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9102    0.7449   -0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5321    2.1428   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3488    3.1003    0.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1489    2.1713    0.0810 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6565    0.8606    0.3537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6394   -0.0034   -0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8227   -1.3496    0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5282   -1.9312    0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082   -1.7244   -0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5450   -2.9294    0.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1827   -1.7436   -1.4803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4327   -0.5032    0.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7317   -0.5762   -0.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4985   -0.3401    0.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6311    1.1471    1.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5787    1.6452    2.0445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5747    1.7906    0.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7086    3.1880    0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7378    0.7851   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3503   -0.7837   -0.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9947    0.9146   -0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7313    0.6711    1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4736   -0.0926   -1.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4583   -1.1818    1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3907   -2.0247   -0.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490   -1.5751    1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6993   -3.0415    0.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9681   -3.8681    0.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2459   -3.0240   -0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1558   -2.7995    0.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8389   -2.2350   -2.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9011   -1.0379    1.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6352    1.5890    1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4333    3.2112   -0.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345    3.8190    0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7513    3.6300   -0.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7872    1.0891   -1.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
  7  2  1  0
 15 13  1  0
 18 16  1  0
 20  6  1  0
 20 13  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 15 33  1  0
 16 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 20 38  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₅

Average Molecular Weight

278.304

Monoisotopic Molecular Weight

278.11542368

IUPAC Name

2-hydroxy-2,11-dimethyl-6-methylidene-8,12,15-trioxapentacyclo[8.5.0.0¹,¹⁴.0⁵,⁹.0¹¹,¹³]pentadecan-7-one

Traditional Name

2-hydroxy-2,11-dimethyl-6-methylidene-8,12,15-trioxapentacyclo[8.5.0.0¹,¹⁴.0⁵,⁹.0¹¹,¹³]pentadecan-7-one

CAS Registry Number

Not Available

SMILES

CC12OC1C1OC11C2C2OC(=O)C(=C)C2CCC1(C)O

InChI Identifier

InChI=1S/C15H18O5/c1-6-7-4-5-13(2,17)15-9(8(7)18-12(6)16)14(3)10(19-14)11(15)20-15/h7-11,17H,1,4-5H2,2-3H3

InChI Key

KXLUWEYBZBGJRZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Sesquiterpenoid
1,4-dioxepane
Dioxepane
Gamma butyrolactone
Oxane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Oxacycle
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.73	ALOGPS
logP	0.77	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	13.77	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.59 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.24 m³·mol⁻¹	ChemAxon
Polarizability	27.95 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	191.011	30932474
DeepCCS	[M+Na]+	166.534	30932474
AllCCS	[M+H]+	163.5	32859911
AllCCS	[M+H-H2O]+	160.1	32859911
AllCCS	[M+NH4]+	166.7	32859911
AllCCS	[M+Na]+	167.6	32859911
AllCCS	[M-H]-	169.5	32859911
AllCCS	[M+Na-2H]-	168.9	32859911
AllCCS	[M+HCOO]-	168.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Canin	CC12OC1C1OC11C2C2OC(=O)C(=C)C2CCC1(C)O	3236.3	Standard polar	33892256
Canin	CC12OC1C1OC11C2C2OC(=O)C(=C)C2CCC1(C)O	1994.4	Standard non polar	33892256
Canin	CC12OC1C1OC11C2C2OC(=O)C(=C)C2CCC1(C)O	2353.4	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 - Canin GC-MS (Non-derivatized) - 70eV, Positive	splash10-11vi-3940000000-a260ff2ce0893f98a2db	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Canin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Canin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Canin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - Canin 10V, Positive-QTOF	splash10-004i-0090000000-7e364fc8fcf25bda78d8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canin 20V, Positive-QTOF	splash10-004i-0290000000-d3f0d311c038dad608ba	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canin 40V, Positive-QTOF	splash10-03k9-2970000000-b1045bdf4282a3d83ce7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canin 10V, Negative-QTOF	splash10-004i-0090000000-abea1c522af17e3f81ae	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canin 20V, Negative-QTOF	splash10-004i-0090000000-e23ed3a1904a40cb0550	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canin 40V, Negative-QTOF	splash10-00b9-1290000000-3d7afae01f5b282c3b57	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	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

147150

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Canin

METLIN ID

Not Available

PubChem Compound

168225

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 Canin (HMDB0249584)

MOL for HMDB0249584 (Canin)

3D MOL for HMDB0249584 (Canin)

3D SDF for HMDB0249584 (Canin)

3D-SDF for HMDB0249584 (Canin)

PDB for HMDB0249584 (Canin)

3D PDB for HMDB0249584 (Canin)

SMILES for HMDB0249584 (Canin)

INCHI for HMDB0249584 (Canin)

Structure for HMDB0249584 (Canin)

3D Structure for HMDB0249584 (Canin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra