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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:51:35 UTC

Update Date

2022-03-07 02:55:01 UTC

HMDB ID

HMDB0036693

Secondary Accession Numbers

HMDB36693

Metabolite Identification

Common Name

Acetylbalchanolide

Description

Acetylbalchanolide belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Based on a literature review a small amount of articles have been published on Acetylbalchanolide.

Structure

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

HMDB0036693
     RDKit          3D
Acetylbalchanolide
 45 46  0  0  0  0  0  0  0  0999 V2000
    4.7651    1.0054   -0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4449    1.0747   -0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3161    1.8182    0.9844 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3717    0.3416   -0.4302 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822    0.3534    0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104    0.8793   -0.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8080    1.8712   -0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528    2.8289    0.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1127    1.9317   -0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7865    0.9831   -1.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0339   -0.3182   -0.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6980   -0.4458    0.6627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7697    0.1494    1.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399   -0.9872    1.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047   -1.6138    0.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2682   -2.9431    0.9339 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0686   -3.2787    0.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6751   -4.3337    1.1287 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7584   -2.0805    0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -2.2937   -1.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8229   -0.9952    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5787    0.8120   -1.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301    2.0195   -0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4196    0.2282   -0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823    1.0694    1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4490    0.1103   -1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    1.4631   -1.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7325    3.7775    0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8863    3.0069    0.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2255    2.3481    1.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6725    2.7066    0.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2511    0.9652   -2.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7629    1.4648   -1.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1068   -0.5743   -0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011   -1.1276   -1.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1293    1.1282    1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5016    0.2015    2.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6853   -0.5139    1.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5294   -1.0083    2.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7240   -1.7731   -0.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7882   -1.9742    0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7754   -2.8204   -1.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5305   -3.0360   -1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9273   -1.4180   -1.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9460   -1.0026    1.8264 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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21  5  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
M  END

  Mrv0541 02241210162D          

 21 22  0  0  0  0            999 V2000
   -2.4758    0.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4758   -0.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7616   -0.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0486   -0.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0486    0.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7616    1.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3344   -0.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3785   -0.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3785    0.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3344    1.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637   -1.3315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6537   -1.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868   -0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4651    0.1287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7616   -1.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0941    1.1237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0665   -2.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946   -0.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8923    1.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1070    2.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4758    0.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 15  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 16  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  2  0  0  0  0
 13 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036693

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O4/c1-10-6-5-7-11(2)9-15-16(12(3)17(19)21-15)14(8-10)20-13(4)18/h6,9,12,14-16H,5,7-8H2,1-4H3/b10-6+,11-9+

> <INCHI_KEY>
MNQOAYZWZSDAKZ-BBYAVRKXSA-N

> <FORMULA>
C17H24O4

> <MOLECULAR_WEIGHT>
292.3701

> <EXACT_MASS>
292.167459256

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
31.645626831820003

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6,10-trimethyl-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl acetate

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
2.7704755526666665

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.745827074078162

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
80.8652

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6,10-trimethyl-2-oxo-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036693
     RDKit          3D
Acetylbalchanolide
 45 46  0  0  0  0  0  0  0  0999 V2000
    4.7651    1.0054   -0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4449    1.0747   -0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3161    1.8182    0.9844 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3717    0.3416   -0.4302 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822    0.3534    0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104    0.8793   -0.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8080    1.8712   -0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528    2.8289    0.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1127    1.9317   -0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7865    0.9831   -1.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0339   -0.3182   -0.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6980   -0.4458    0.6627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7697    0.1494    1.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399   -0.9872    1.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047   -1.6138    0.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2682   -2.9431    0.9339 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0686   -3.2787    0.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6751   -4.3337    1.1287 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7584   -2.0805    0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -2.2937   -1.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8229   -0.9952    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5787    0.8120   -1.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301    2.0195   -0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4196    0.2282   -0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823    1.0694    1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4490    0.1103   -1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    1.4631   -1.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7325    3.7775    0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8863    3.0069    0.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2255    2.3481    1.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6725    2.7066    0.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2511    0.9652   -2.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7629    1.4648   -1.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1068   -0.5743   -0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011   -1.1276   -1.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1293    1.1282    1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5016    0.2015    2.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6853   -0.5139    1.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5294   -1.0083    2.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7240   -1.7731   -0.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7882   -1.9742    0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7754   -2.8204   -1.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5305   -3.0360   -1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9273   -1.4180   -1.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9460   -1.0026    1.8264 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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21  5  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.622   1.329   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.622  -0.212   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.288  -0.983   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.957  -0.212   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.957   1.329   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.288   2.098   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.624  -0.983   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.706  -0.212   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.706   1.329   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.624   2.098   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.306  -2.485   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.220  -2.647   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.842  -1.247   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.868   0.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.288  -2.524   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.042   2.098   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.991  -3.983   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.350  -0.931   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.532   2.496   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.933   3.983   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.622   1.404   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    7                                                       
CONECT    5    6   10   14                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8   11                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   16                                                  
CONECT   10    5    9                                                       
CONECT   11    7   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13    8   12   18                                                  
CONECT   14    5                                                            
CONECT   15    3                                                            
CONECT   16    9   19                                                       
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0036693
HETATM    1  C1  UNL     1       4.765   1.005  -0.742  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.445   1.075  -0.019  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.316   1.818   0.984  1.00  0.00           O  
HETATM    4  O2  UNL     1       2.372   0.342  -0.430  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.082   0.353   0.204  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.110   0.879  -0.816  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.808   1.871  -0.186  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.153   2.829   0.780  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.113   1.932  -0.440  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.787   0.983  -1.408  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.034  -0.318  -0.782  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.698  -0.446   0.663  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.770   0.149   1.517  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.640  -0.987   1.187  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.505  -1.614   0.429  1.00  0.00           C  
HETATM   16  O3  UNL     1      -0.268  -2.943   0.934  1.00  0.00           O  
HETATM   17  C14 UNL     1       1.069  -3.279   0.820  1.00  0.00           C  
HETATM   18  O4  UNL     1       1.675  -4.334   1.129  1.00  0.00           O  
HETATM   19  C15 UNL     1       1.758  -2.081   0.214  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.711  -2.294  -1.261  1.00  0.00           C  
HETATM   21  C17 UNL     1       0.823  -0.995   0.705  1.00  0.00           C  
HETATM   22  H1  UNL     1       4.579   0.812  -1.817  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.230   2.019  -0.601  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.420   0.228  -0.277  1.00  0.00           H  
HETATM   25  H4  UNL     1       1.182   1.069   1.054  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.449   0.110  -1.351  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.654   1.463  -1.617  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.733   3.777   0.838  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.886   3.007   0.517  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.226   2.348   1.776  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.673   2.707   0.087  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.251   0.965  -2.374  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.763   1.465  -1.633  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.107  -0.574  -0.947  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.501  -1.128  -1.381  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.129   1.128   1.140  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.502   0.201   2.581  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.685  -0.514   1.479  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.529  -1.008   2.272  1.00  0.00           H  
HETATM   40  H19 UNL     1      -0.724  -1.773  -0.621  1.00  0.00           H  
HETATM   41  H20 UNL     1       2.788  -1.974   0.540  1.00  0.00           H  
HETATM   42  H21 UNL     1       0.775  -2.820  -1.593  1.00  0.00           H  
HETATM   43  H22 UNL     1       2.531  -3.036  -1.493  1.00  0.00           H  
HETATM   44  H23 UNL     1       1.927  -1.418  -1.885  1.00  0.00           H  
HETATM   45  H24 UNL     1       0.946  -1.003   1.826  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   21   25
CONECT    6    7   26   27
CONECT    7    8    9    9
CONECT    8   28   29   30
CONECT    9   10   31
CONECT   10   11   32   33
CONECT   11   12   34   35
CONECT   12   13   14   14
CONECT   13   36   37   38
CONECT   14   15   39
CONECT   15   16   21   40
CONECT   16   17
CONECT   17   18   18   19
CONECT   19   20   21   41
CONECT   20   42   43   44
CONECT   21   45
END

HMDB0036693
     RDKit          3D
Acetylbalchanolide
 45 46  0  0  0  0  0  0  0  0999 V2000
    4.7651    1.0054   -0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4449    1.0747   -0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3161    1.8182    0.9844 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3717    0.3416   -0.4302 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822    0.3534    0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104    0.8793   -0.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8080    1.8712   -0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528    2.8289    0.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1127    1.9317   -0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7865    0.9831   -1.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0339   -0.3182   -0.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6980   -0.4458    0.6627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7697    0.1494    1.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399   -0.9872    1.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047   -1.6138    0.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2682   -2.9431    0.9339 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0686   -3.2787    0.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6751   -4.3337    1.1287 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7584   -2.0805    0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -2.2937   -1.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8229   -0.9952    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5787    0.8120   -1.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301    2.0195   -0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4196    0.2282   -0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823    1.0694    1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4490    0.1103   -1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    1.4631   -1.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7325    3.7775    0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8863    3.0069    0.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2255    2.3481    1.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6725    2.7066    0.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2511    0.9652   -2.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7629    1.4648   -1.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1068   -0.5743   -0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011   -1.1276   -1.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1293    1.1282    1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5016    0.2015    2.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6853   -0.5139    1.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5294   -1.0083    2.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7240   -1.7731   -0.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7882   -1.9742    0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7754   -2.8204   -1.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5305   -3.0360   -1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9273   -1.4180   -1.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9460   -1.0026    1.8264 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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21  5  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,6,10-Trimethyl-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-4-yl acetic acid	HMDB

Chemical Formula

C₁₇H₂₄O₄

Average Molecular Weight

292.3701

Monoisotopic Molecular Weight

292.167459256

IUPAC Name

3,6,10-trimethyl-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl acetate

Traditional Name

3,6,10-trimethyl-2-oxo-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl acetate

CAS Registry Number

Not Available

SMILES

CC1C2C(OC1=O)\C=C(C)\CC\C=C(C)\CC2OC(C)=O

InChI Identifier

InChI=1S/C17H24O4/c1-10-6-5-7-11(2)9-15-16(12(3)17(19)21-15)14(8-10)20-13(4)18/h6,9,12,14-16H,5,7-8H2,1-4H3/b10-6+,11-9+

InChI Key

MNQOAYZWZSDAKZ-BBYAVRKXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
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: HMDB0036693)

Source

Endogenous

Endogenous (HMDB: HMDB0036693)

Plant

Plant (HMDB: HMDB0036693)

Animal

Animal (HMDB: HMDB0036693)

Exogenous

Food

Food (HMDB: HMDB0036693)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0036693)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036693)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036693)

Lipid metabolism pathway (HMDB: HMDB0036693)

Cellular process

Cell signaling (HMDB: HMDB0036693)

Biochemical process

Lipid transport (HMDB: HMDB0036693)

Role

Biological role

Energy source (HMDB: HMDB0036693)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036693)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	125 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	3.38	ALOGPS
logP	2.77	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.87 m³·mol⁻¹	ChemAxon
Polarizability	31.65 Å³	ChemAxon
Number of Rings	2	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]+	168.955	31661259
DarkChem	[M-H]-	167.49	31661259
DeepCCS	[M+H]+	168.546	30932474
DeepCCS	[M-H]-	166.188	30932474
DeepCCS	[M-2H]-	199.079	30932474
DeepCCS	[M+Na]+	174.64	30932474
AllCCS	[M+H]+	170.7	32859911
AllCCS	[M+H-H2O]+	167.3	32859911
AllCCS	[M+NH4]+	173.9	32859911
AllCCS	[M+Na]+	174.8	32859911
AllCCS	[M-H]-	175.3	32859911
AllCCS	[M+Na-2H]-	175.5	32859911
AllCCS	[M+HCOO]-	175.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acetylbalchanolide	CC1C2C(OC1=O)\C=C(C)\CC\C=C(C)\CC2OC(C)=O	2943.2	Standard polar	33892256
Acetylbalchanolide	CC1C2C(OC1=O)\C=C(C)\CC\C=C(C)\CC2OC(C)=O	2158.6	Standard non polar	33892256
Acetylbalchanolide	CC1C2C(OC1=O)\C=C(C)\CC\C=C(C)\CC2OC(C)=O	2157.7	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 - Acetylbalchanolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9340000000-a7ae7e8685f6d819a7cc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylbalchanolide 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 - Acetylbalchanolide 10V, Positive-QTOF	splash10-0006-0090000000-c07651421c4a0b6943b1	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylbalchanolide 20V, Positive-QTOF	splash10-0fw9-2690000000-936928530165ad3e5feb	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylbalchanolide 40V, Positive-QTOF	splash10-06e9-7930000000-d9ca28dbef1bf5754e84	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylbalchanolide 10V, Negative-QTOF	splash10-0007-0090000000-2514363e0a79098043b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylbalchanolide 20V, Negative-QTOF	splash10-052e-2090000000-54db8806e7ee38da0cfd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylbalchanolide 40V, Negative-QTOF	splash10-0abc-8930000000-06fb77fb66338573eb2d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylbalchanolide 10V, Negative-QTOF	splash10-0007-0090000000-ea182baa33a3636860be	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylbalchanolide 20V, Negative-QTOF	splash10-052f-9040000000-ee31966d867d34eda349	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylbalchanolide 40V, Negative-QTOF	splash10-0a4l-9000000000-e2b20b3aea41a3430fd0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylbalchanolide 10V, Positive-QTOF	splash10-001i-0190000000-1c32939fb08f805884ca	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylbalchanolide 20V, Positive-QTOF	splash10-001i-0290000000-7e093f6f31025d96436b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylbalchanolide 40V, Positive-QTOF	splash10-000l-8940000000-e80fb0a18eb7d9032a3b	2021-09-25	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

FDB015626

KNApSAcK ID

Not Available

Chemspider ID

35014205

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752039

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Acetylbalchanolide (HMDB0036693)

MOL for HMDB0036693 (Acetylbalchanolide)

3D MOL for HMDB0036693 (Acetylbalchanolide)

3D SDF for HMDB0036693 (Acetylbalchanolide)

3D-SDF for HMDB0036693 (Acetylbalchanolide)

PDB for HMDB0036693 (Acetylbalchanolide)

3D PDB for HMDB0036693 (Acetylbalchanolide)

SMILES for HMDB0036693 (Acetylbalchanolide)

INCHI for HMDB0036693 (Acetylbalchanolide)

Structure for HMDB0036693 (Acetylbalchanolide)

3D Structure for HMDB0036693 (Acetylbalchanolide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra