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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:38:37 UTC

Update Date

2022-03-07 02:54:56 UTC

HMDB ID

HMDB0036487

Secondary Accession Numbers

HMDB36487

Metabolite Identification

Common Name

Achillicin

Description

Achillicin belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Achillicin has been detected, but not quantified in, herbs and spices. This could make achillicin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Achillicin.

Structure

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

HMDB0036487
     RDKit          3D
Achillicin
 44 46  0  0  0  0  0  0  0  0999 V2000
   -4.0026   -2.5361   -1.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0473   -2.0133   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4009   -2.0999    0.9474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8283   -1.4562   -0.5969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9478   -0.9721    0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3359   -1.7461    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4043   -1.2116    1.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3419   -2.2890    1.6903 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7447   -0.7088    2.3474 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350   -0.1149    0.5013 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4041    0.1813    0.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7865    1.3204   -0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5138    1.6433   -0.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2820    2.7141   -1.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5888    0.8131   -0.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1758    0.8484   -0.9504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1630    2.1949   -1.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4707    2.4520   -0.8390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1208    3.5314   -1.0161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0070    1.2240   -0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8518    1.6115    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7512    0.4975    0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7270   -2.2050   -2.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9142   -3.6439   -1.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0385   -2.1886   -1.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4079   -1.1231    1.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7322   -1.6160   -0.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1493   -2.8136    0.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188   -3.2392    1.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8660   -1.9235    2.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0846   -2.4564    0.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1487   -1.4294    2.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0524   -0.3793    1.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    2.1749    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    0.9074   -0.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2331    2.9945   -2.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8322    3.5779   -1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5943    2.3630   -2.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0275    0.2557   -1.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6340    0.6575   -0.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1888    2.6731    0.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3378    1.5667    1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8030    1.0186    1.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3619    0.9449    1.1110 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
  7  9  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22  5  1  0
 15 10  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
M  END

  Mrv0541 05061309112D          

 22 24  0  0  0  0            999 V2000
    3.8305   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8656    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    3.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8217    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    2.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    2.0796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  1  1  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 13 11  1  0  0  0  0
 14  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17  4  1  0  0  0  0
 17  7  1  0  0  0  0
 17 11  1  0  0  0  0
 18 10  2  0  0  0  0
 19 16  2  0  0  0  0
 20 17  1  0  0  0  0
 21 10  1  0  0  0  0
 21 12  1  0  0  0  0
 22 15  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036487

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2C(OC1=O)C1=C(C)CC=C1C(C)(O)CC2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O5/c1-8-5-6-11-13(8)15-14(9(2)16(19)22-15)12(21-10(3)18)7-17(11,4)20/h6,9,12,14-15,20H,5,7H2,1-4H3

> <INCHI_KEY>
ZPTLTKQKVWFFNY-UHFFFAOYSA-N

> <FORMULA>
C17H22O5

> <MOLECULAR_WEIGHT>
306.3536

> <EXACT_MASS>
306.146723814

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.58040167729385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,6H,8H,9bH-azuleno[4,5-b]furan-4-yl acetate

> <ALOGPS_LOGP>
2.80

> <JCHEM_LOGP>
0.637945187

> <ALOGPS_LOGS>
-2.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.913753725381252

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.276214215001009

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1075056032121244

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
80.25309999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-3,6,9-trimethyl-2-oxo-3H,3aH,4H,5H,8H,9bH-azuleno[4,5-b]furan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036487
     RDKit          3D
Achillicin
 44 46  0  0  0  0  0  0  0  0999 V2000
   -4.0026   -2.5361   -1.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0473   -2.0133   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4009   -2.0999    0.9474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8283   -1.4562   -0.5969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9478   -0.9721    0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3359   -1.7461    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4043   -1.2116    1.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3419   -2.2890    1.6903 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7447   -0.7088    2.3474 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350   -0.1149    0.5013 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4041    0.1813    0.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7865    1.3204   -0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5138    1.6433   -0.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2820    2.7141   -1.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5888    0.8131   -0.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1758    0.8484   -0.9504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1630    2.1949   -1.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4707    2.4520   -0.8390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1208    3.5314   -1.0161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0070    1.2240   -0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8518    1.6115    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7512    0.4975    0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7270   -2.2050   -2.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9142   -3.6439   -1.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0385   -2.1886   -1.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4079   -1.1231    1.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7322   -1.6160   -0.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1493   -2.8136    0.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188   -3.2392    1.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8660   -1.9235    2.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0846   -2.4564    0.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1487   -1.4294    2.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0524   -0.3793    1.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    2.1749    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    0.9074   -0.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2331    2.9945   -2.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8322    3.5779   -1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5943    2.3630   -2.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0275    0.2557   -1.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6340    0.6575   -0.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1888    2.6731    0.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3378    1.5667    1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8030    1.0186    1.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3619    0.9449    1.1110 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
  7  9  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22  5  1  0
 15 10  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.150  -3.052   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.616   1.186   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.507   5.824   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.001   2.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.711   4.864   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.145   5.426   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.766  -2.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.803   3.882   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.482   3.341   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   17                                                            
CONECT    5    6    8                                                       
CONECT    6    5   11                                                       
CONECT    7   12   17                                                       
CONECT    8    1    5   13                                                  
CONECT    9    2   14   16                                                  
CONECT   10    3   18   21                                                  
CONECT   11    6   13   17                                                  
CONECT   12    7   14   21                                                  
CONECT   13    8   11   15                                                  
CONECT   14    9   12   15                                                  
CONECT   15   13   14   22                                                  
CONECT   16    9   19   22                                                  
CONECT   17    4    7   11   20                                             
CONECT   18   10                                                            
CONECT   19   16                                                            
CONECT   20   17                                                            
CONECT   21   10   12                                                       
CONECT   22   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0036487
HETATM    1  C1  UNL     1      -4.003  -2.536  -1.275  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.047  -2.013  -0.261  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.401  -2.100   0.947  1.00  0.00           O  
HETATM    4  O2  UNL     1      -1.828  -1.456  -0.597  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.948  -0.972   0.371  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.336  -1.746   0.278  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.404  -1.212   1.227  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.342  -2.289   1.690  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.745  -0.709   2.347  1.00  0.00           O  
HETATM   10  C7  UNL     1       2.135  -0.115   0.501  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.404   0.181   0.641  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.786   1.320  -0.230  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.514   1.643  -0.910  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.282   2.714  -1.914  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.589   0.813  -0.477  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.176   0.848  -0.950  1.00  0.00           C  
HETATM   17  O4  UNL     1      -0.163   2.195  -1.201  1.00  0.00           O  
HETATM   18  C14 UNL     1      -1.471   2.452  -0.839  1.00  0.00           C  
HETATM   19  O5  UNL     1      -2.121   3.531  -1.016  1.00  0.00           O  
HETATM   20  C15 UNL     1      -2.007   1.224  -0.190  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.852   1.611   0.992  1.00  0.00           C  
HETATM   22  C17 UNL     1      -0.751   0.498   0.189  1.00  0.00           C  
HETATM   23  H1  UNL     1      -3.727  -2.205  -2.307  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.914  -3.644  -1.265  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.039  -2.189  -1.079  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.408  -1.123   1.377  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.732  -1.616  -0.751  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.149  -2.814   0.432  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.819  -3.239   1.839  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.866  -1.924   2.595  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.085  -2.456   0.876  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.149  -1.429   2.667  1.00  0.00           H  
HETATM   33  H11 UNL     1       4.052  -0.379   1.332  1.00  0.00           H  
HETATM   34  H12 UNL     1       4.206   2.175   0.336  1.00  0.00           H  
HETATM   35  H13 UNL     1       4.547   0.907  -0.954  1.00  0.00           H  
HETATM   36  H14 UNL     1       3.233   2.995  -2.445  1.00  0.00           H  
HETATM   37  H15 UNL     1       1.832   3.578  -1.392  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.594   2.363  -2.735  1.00  0.00           H  
HETATM   39  H17 UNL     1       0.028   0.256  -1.850  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.634   0.657  -0.908  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.189   2.673   0.840  1.00  0.00           H  
HETATM   42  H20 UNL     1      -2.338   1.567   1.952  1.00  0.00           H  
HETATM   43  H21 UNL     1      -3.803   1.019   1.006  1.00  0.00           H  
HETATM   44  H22 UNL     1      -0.362   0.945   1.111  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   22   26
CONECT    6    7   27   28
CONECT    7    8    9   10
CONECT    8   29   30   31
CONECT    9   32
CONECT   10   11   11   15
CONECT   11   12   33
CONECT   12   13   34   35
CONECT   13   14   15   15
CONECT   14   36   37   38
CONECT   15   16
CONECT   16   17   22   39
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   21   22   40
CONECT   21   41   42   43
CONECT   22   44
END

HMDB0036487
     RDKit          3D
Achillicin
 44 46  0  0  0  0  0  0  0  0999 V2000
   -4.0026   -2.5361   -1.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0473   -2.0133   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4009   -2.0999    0.9474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8283   -1.4562   -0.5969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9478   -0.9721    0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3359   -1.7461    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4043   -1.2116    1.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3419   -2.2890    1.6903 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7447   -0.7088    2.3474 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350   -0.1149    0.5013 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4041    0.1813    0.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7865    1.3204   -0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5138    1.6433   -0.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2820    2.7141   -1.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5888    0.8131   -0.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1758    0.8484   -0.9504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1630    2.1949   -1.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4707    2.4520   -0.8390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1208    3.5314   -1.0161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0070    1.2240   -0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8518    1.6115    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7512    0.4975    0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7270   -2.2050   -2.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9142   -3.6439   -1.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0385   -2.1886   -1.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4079   -1.1231    1.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7322   -1.6160   -0.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1493   -2.8136    0.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188   -3.2392    1.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8660   -1.9235    2.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0846   -2.4564    0.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1487   -1.4294    2.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0524   -0.3793    1.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    2.1749    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    0.9074   -0.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2331    2.9945   -2.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8322    3.5779   -1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5943    2.3630   -2.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0275    0.2557   -1.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6340    0.6575   -0.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1888    2.6731    0.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3378    1.5667    1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8030    1.0186    1.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3619    0.9449    1.1110 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
  7  9  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22  5  1  0
 15 10  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,2-dichloro-N-Methyl-acetamide	HMDB
2,2-dichloro-N-Methylacetamide	HMDB
8-Acetoxyartabsin	HMDB
6-Hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3ah,4H,5H,6H,8H,9BH-azuleno[4,5-b]furan-4-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₂O₅

Average Molecular Weight

306.3536

Monoisotopic Molecular Weight

306.146723814

IUPAC Name

6-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,6H,8H,9bH-azuleno[4,5-b]furan-4-yl acetate

Traditional Name

6-hydroxy-3,6,9-trimethyl-2-oxo-3H,3aH,4H,5H,8H,9bH-azuleno[4,5-b]furan-4-yl acetate

CAS Registry Number

71616-00-7

SMILES

CC1C2C(OC1=O)C1=C(C)CC=C1C(C)(O)CC2OC(C)=O

InChI Identifier

InChI=1S/C17H22O5/c1-8-5-6-11-13(8)15-14(9(2)16(19)22-15)12(21-10(3)18)7-17(11,4)20/h6,9,12,14-15,20H,5,7H2,1-4H3

InChI Key

ZPTLTKQKVWFFNY-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036487)

Source

Endogenous

Endogenous (HMDB: HMDB0036487)

Plant

Plant (HMDB: HMDB0036487)

Exogenous

Food

Food (HMDB: HMDB0036487)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0036487)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036487)

Role

Biological role

Energy source (HMDB: HMDB0036487)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036487)

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	3095 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.82 g/L	ALOGPS
logP	2.8	ALOGPS
logP	0.64	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	14.28	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.25 m³·mol⁻¹	ChemAxon
Polarizability	32.58 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	172.945	31661259
DarkChem	[M-H]-	166.085	31661259
DeepCCS	[M+H]+	175.854	30932474
DeepCCS	[M-H]-	173.496	30932474
DeepCCS	[M-2H]-	206.707	30932474
DeepCCS	[M+Na]+	181.948	30932474
AllCCS	[M+H]+	171.6	32859911
AllCCS	[M+H-H2O]+	168.4	32859911
AllCCS	[M+NH4]+	174.5	32859911
AllCCS	[M+Na]+	175.3	32859911
AllCCS	[M-H]-	176.5	32859911
AllCCS	[M+Na-2H]-	176.5	32859911
AllCCS	[M+HCOO]-	176.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Achillicin	CC1C2C(OC1=O)C1=C(C)CC=C1C(C)(O)CC2OC(C)=O	3570.5	Standard polar	33892256
Achillicin	CC1C2C(OC1=O)C1=C(C)CC=C1C(C)(O)CC2OC(C)=O	2185.6	Standard non polar	33892256
Achillicin	CC1C2C(OC1=O)C1=C(C)CC=C1C(C)(O)CC2OC(C)=O	2313.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Achillicin,1TMS,isomer #1	CC(=O)OC1CC(C)(O[Si](C)(C)C)C2=CCC(C)=C2C2OC(=O)C(C)C12	2366.5	Semi standard non polar	33892256
Achillicin,1TBDMS,isomer #1	CC(=O)OC1CC(C)(O[Si](C)(C)C(C)(C)C)C2=CCC(C)=C2C2OC(=O)C(C)C12	2566.9	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 - Achillicin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fu-5890000000-4c01d3deb7b1eed29bc3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Achillicin GC-MS (1 TMS) - 70eV, Positive	splash10-002f-7869000000-9fd0ad439d09106adf07	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Achillicin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Achillicin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achillicin 10V, Negative-QTOF	splash10-0bt9-1096000000-16a539f456aa419f52a3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achillicin 20V, Negative-QTOF	splash10-0bta-2091000000-a41577dbcc3177a23e23	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achillicin 40V, Negative-QTOF	splash10-0a4r-9660000000-0d5f1d51eaac0be0be8e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achillicin 10V, Negative-QTOF	splash10-03di-0090000000-b1574c55be79e83ef64b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achillicin 20V, Negative-QTOF	splash10-01ot-1090000000-9bfaec8e1f32279da492	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achillicin 40V, Negative-QTOF	splash10-0a6u-9360000000-71225273d00873fc6811	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achillicin 10V, Positive-QTOF	splash10-052r-0092000000-355fb2eace891efd3544	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achillicin 20V, Positive-QTOF	splash10-014s-1290000000-bb73a688a3d500ca3fce	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achillicin 40V, Positive-QTOF	splash10-0udl-9350000000-603410c2d4b48a58873e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achillicin 10V, Positive-QTOF	splash10-0002-0191000000-20154b664ebc9cb01276	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achillicin 20V, Positive-QTOF	splash10-004i-3392000000-eed430f0d7ce0656856b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achillicin 40V, Positive-QTOF	splash10-0007-9240000000-ac794cc0b5be26ee8e68	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015382

KNApSAcK ID

C00020476

Chemspider ID

35014157

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752003

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1855541

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Achillicin (HMDB0036487)

MOL for HMDB0036487 (Achillicin)

3D MOL for HMDB0036487 (Achillicin)

3D SDF for HMDB0036487 (Achillicin)

3D-SDF for HMDB0036487 (Achillicin)

PDB for HMDB0036487 (Achillicin)

3D PDB for HMDB0036487 (Achillicin)

SMILES for HMDB0036487 (Achillicin)

INCHI for HMDB0036487 (Achillicin)

Structure for HMDB0036487 (Achillicin)

3D Structure for HMDB0036487 (Achillicin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra