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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 19:53:06 UTC

Update Date

2021-09-23 19:53:06 UTC

HMDB ID

HMDB0302700

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Artecanin

Description

Artecanin belongs to guaianolides and derivatives class of compounds. Those 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. Artecanin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Artecanin can be found in sweet bay, which makes artecanin a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302700
     RDKit          3D
Artecanin
 38 42  0  0  0  0  0  0  0  0999 V2000
    3.9375   -0.1850    0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912    0.4283    0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4620    1.7706   -0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2570    2.5736   -0.7173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1142    1.9953    0.2090 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5238    0.6838    0.0802 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5128   -0.0613    0.9410 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3854   -1.5250    0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0188   -2.0780    0.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7782   -1.7975   -0.2947 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0145   -1.8978   -1.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7030   -2.8838   -0.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5690   -0.5502   -0.1342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9170   -0.8009    0.4870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7237   -0.1126   -0.7221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8316    1.3915   -0.5480 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9679    1.9013    0.7631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6664    1.8135    0.1038 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0459    3.1865    0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8730    0.6177    0.5054 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1370   -1.1787    0.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7757    0.3240   -0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6045    0.4762   -0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4570    0.4309    1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8028   -1.8512    1.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0893   -2.0417    0.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878   -3.1839    1.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5560   -1.6690    1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0831   -1.8080   -1.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236   -1.1888   -2.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347   -2.9044   -2.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6259   -2.5552   -0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1630   -0.5597   -1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3253    1.9730   -1.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8556    3.9680   -0.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5139    3.4817    0.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4339    3.3340   -0.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9176    0.4828    1.6084 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  6
 10 13  1  0
 13 14  1  1
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 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  6
  7 24  1  1
  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  6
 16 34  1  6
 19 35  1  0
 19 36  1  0
 19 37  1  0
 20 38  1  1
M  END


  Mrv0541 02241221262D          

 20 24  0  0  1  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  1  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  2  0  0  0  0  0  0  0  0  0
    1.7027    0.5842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9126    0.8216    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2343    0.3520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4220    0.8519    0.0000 C   0  0  1  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  2  0  0  0  0  0  0  0  0  0
    0.6755    1.6118    0.0000 C   0  0  1  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
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  2  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  8 10  1  1  0  0  0
  9 11  1  0  0  0  0
 12 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 13  1  1  0  0  0
 12 14  1  6  0  0  0
  6 15  1  1  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  6  0  0  0
 18 19  2  0  0  0  0
  2 20  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0302700

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@]12O[C@@H]1[C@@H]1O[C@]11[C@H]2[C@H]2OC(=O)C(=C)[C@@H]2CC[C@@]1(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/t7-,8-,9-,10+,11-,13+,14-,15+/m0/s1

> <INCHI_KEY>
KXLUWEYBZBGJRZ-POEOZHCLSA-N

> <FORMULA>
C15H18O5

> <MOLECULAR_WEIGHT>
278.3004

> <EXACT_MASS>
278.115423686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.95490160894991

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5S,9S,10S,11S,13R,14S)-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>
0.7688833529999998

> <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>
canin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302700
     RDKit          3D
Artecanin
 38 42  0  0  0  0  0  0  0  0999 V2000
    3.9375   -0.1850    0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912    0.4283    0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4620    1.7706   -0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2570    2.5736   -0.7173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1142    1.9953    0.2090 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5238    0.6838    0.0802 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5128   -0.0613    0.9410 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3854   -1.5250    0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0188   -2.0780    0.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7782   -1.7975   -0.2947 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0145   -1.8978   -1.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7030   -2.8838   -0.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5690   -0.5502   -0.1342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9170   -0.8009    0.4870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7237   -0.1126   -0.7221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8316    1.3915   -0.5480 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9679    1.9013    0.7631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6664    1.8135    0.1038 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0459    3.1865    0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8730    0.6177    0.5054 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1370   -1.1787    0.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7757    0.3240   -0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6045    0.4762   -0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4570    0.4309    1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8028   -1.8512    1.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0893   -2.0417    0.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878   -3.1839    1.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5560   -1.6690    1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0831   -1.8080   -1.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236   -1.1888   -2.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347   -2.9044   -2.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6259   -2.5552   -0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1630   -0.5597   -1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3253    1.9730   -1.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8556    3.9680   -0.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5139    3.4817    0.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4339    3.3340   -0.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9176    0.4828    1.6084 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  6
 10 13  1  0
 13 14  1  1
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 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  6
  7 24  1  1
  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  6
 16 34  1  6
 19 35  1  0
 19 36  1  0
 19 37  1  0
 20 38  1  1
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      -1.141  -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   1.091   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.704   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    HMDB0302700
HETATM    1  C1  UNL     1       3.938  -0.185   0.271  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.791   0.428   0.352  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.462   1.771  -0.121  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.257   2.574  -0.717  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.114   1.995   0.209  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.524   0.684   0.080  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.513  -0.061   0.941  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.385  -1.525   0.987  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.019  -2.078   0.924  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.778  -1.797  -0.295  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.014  -1.898  -1.590  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.703  -2.884  -0.365  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.569  -0.550  -0.134  1.00  0.00           C  
HETATM   14  O4  UNL     1      -2.917  -0.801   0.487  1.00  0.00           O  
HETATM   15  C11 UNL     1      -2.724  -0.113  -0.722  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.832   1.392  -0.548  1.00  0.00           C  
HETATM   17  O5  UNL     1      -2.968   1.901   0.763  1.00  0.00           O  
HETATM   18  C13 UNL     1      -1.666   1.814   0.104  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.046   3.186   0.037  1.00  0.00           C  
HETATM   20  C15 UNL     1      -0.873   0.618   0.505  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.137  -1.179   0.634  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.776   0.324  -0.195  1.00  0.00           H  
HETATM   23  H3  UNL     1       0.604   0.476  -0.995  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.457   0.431   1.958  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.803  -1.851   1.993  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.089  -2.042   0.269  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.088  -3.184   1.149  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.556  -1.669   1.802  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.083  -1.808  -1.480  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.424  -1.189  -2.370  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.135  -2.904  -2.097  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.626  -2.555  -0.417  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.163  -0.560  -1.644  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.325   1.973  -1.363  1.00  0.00           H  
HETATM   35  H15 UNL     1      -1.856   3.968  -0.077  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.514   3.482   0.955  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.434   3.334  -0.898  1.00  0.00           H  
HETATM   38  H18 UNL     1      -0.918   0.483   1.608  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

HMDB0302700
     RDKit          3D
Artecanin
 38 42  0  0  0  0  0  0  0  0999 V2000
    3.9375   -0.1850    0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912    0.4283    0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4620    1.7706   -0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2570    2.5736   -0.7173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1142    1.9953    0.2090 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5238    0.6838    0.0802 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5128   -0.0613    0.9410 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3854   -1.5250    0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0188   -2.0780    0.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7782   -1.7975   -0.2947 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0145   -1.8978   -1.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7030   -2.8838   -0.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5690   -0.5502   -0.1342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9170   -0.8009    0.4870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7237   -0.1126   -0.7221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8316    1.3915   -0.5480 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9679    1.9013    0.7631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6664    1.8135    0.1038 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0459    3.1865    0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8730    0.6177    0.5054 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1370   -1.1787    0.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7757    0.3240   -0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6045    0.4762   -0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4570    0.4309    1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8028   -1.8512    1.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0893   -2.0417    0.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878   -3.1839    1.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5560   -1.6690    1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0831   -1.8080   -1.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236   -1.1888   -2.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347   -2.9044   -2.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6259   -2.5552   -0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1630   -0.5597   -1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3253    1.9730   -1.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8556    3.9680   -0.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5139    3.4817    0.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4339    3.3340   -0.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9176    0.4828    1.6084 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  6
 10 13  1  0
 13 14  1  1
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 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  6
  7 24  1  1
  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  6
 16 34  1  6
 19 35  1  0
 19 36  1  0
 19 37  1  0
 20 38  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₅

Average Molecular Weight

278.3004

Monoisotopic Molecular Weight

278.115423686

IUPAC Name

(1R,2R,5S,9S,10S,11S,13R,14S)-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

canin

CAS Registry Number

Not Available

SMILES

C[C@@]12O[C@@H]1[C@@H]1O[C@]11[C@H]2[C@H]2OC(=O)C(=C)[C@@H]2CC[C@@]1(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/t7-,8-,9-,10+,11-,13+,14-,15+/m0/s1

InChI Key

KXLUWEYBZBGJRZ-POEOZHCLSA-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

sesquiterpene lactone (CHEBI:3356 )
Guaianolide (C09354 )

Ontology

Not Available

Exogenous (HMDB: HMDB0302700)

Food

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)

Process

Not Available

Role

Biological role

Industrial application

Pharmaceutical industry

Antisecretory (HMDB: HMDB0302700)

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
AllCCS	[M+H]+	163.529	32859911
AllCCS	[M+H-H2O]+	160.136	32859911
AllCCS	[M+Na]+	167.579	32859911
AllCCS	[M+NH4]+	166.675	32859911
AllCCS	[M-H]-	169.48	32859911
AllCCS	[M+Na-2H]-	168.868	32859911
AllCCS	[M+HCOO]-	168.318	32859911
DeepCCS	[M-2H]-	193.413	30932474
DeepCCS	[M+Na]+	168.265	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.8788 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.63 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1449.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	200.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	112.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	154.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	53.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	371.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	399.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	461.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	665.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	100.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	795.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	280.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	231.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	336.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	178.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	116.8 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artecanin 10V, Positive-QTOF	splash10-004i-0090000000-1d79f6cd69c7a2f47516	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artecanin 20V, Positive-QTOF	splash10-0bvi-0390000000-eb302757a3b9f1476998	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artecanin 40V, Positive-QTOF	splash10-052f-9650000000-cec2da2a89a380eba96a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artecanin 10V, Negative-QTOF	splash10-004i-0090000000-d7defeb3436e8b8d075b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artecanin 20V, Negative-QTOF	splash10-057i-0090000000-bbe4ad4c1b03567c1ecc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artecanin 40V, Negative-QTOF	splash10-08i0-2920000000-aef09b7ae96016e51fb4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artecanin 10V, Positive-QTOF	splash10-004i-0090000000-7e364fc8fcf25bda78d8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artecanin 20V, Positive-QTOF	splash10-004i-0290000000-d3f0d311c038dad608ba	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artecanin 40V, Positive-QTOF	splash10-03k9-2970000000-b1045bdf4282a3d83ce7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artecanin 10V, Negative-QTOF	splash10-004i-0090000000-abea1c522af17e3f81ae	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artecanin 20V, Negative-QTOF	splash10-004i-0090000000-e23ed3a1904a40cb0550	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artecanin 40V, Negative-QTOF	splash10-00b9-1290000000-3d7afae01f5b282c3b57	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442175

PDB ID

Not Available

ChEBI ID

3356

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

Not Available

Showing metabocard for Artecanin (HMDB0302700)

MOL for HMDB0302700 (Artecanin)

3D MOL for HMDB0302700 (Artecanin)

3D SDF for HMDB0302700 (Artecanin)

3D-SDF for HMDB0302700 (Artecanin)

PDB for HMDB0302700 (Artecanin)

3D PDB for HMDB0302700 (Artecanin)

SMILES for HMDB0302700 (Artecanin)

INCHI for HMDB0302700 (Artecanin)

Structure for HMDB0302700 (Artecanin)

3D Structure for HMDB0302700 (Artecanin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra