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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:46:27 UTC

Update Date

2022-03-07 02:55:22 UTC

HMDB ID

HMDB0037523

Secondary Accession Numbers

HMDB37523

Metabolite Identification

Common Name

Galanolactone

Description

Galanolactone 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. Galanolactone has been detected, but not quantified in, gingers (Zingiber officinale) and herbs and spices. This could make galanolactone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Galanolactone.

Structure

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

HMDB0037523
     RDKit          3D
Galanolactone
 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.8712   -0.0212    0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697    0.9334   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073    1.5796   -1.6268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6002    2.0631    0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3789    2.0742    1.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2091    1.2463    1.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5687   -0.0744    0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986   -0.7995    1.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4951    0.2760   -0.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983   -0.8214   -1.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3211   -2.1884   -1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0607   -2.2619   -0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6434   -3.4956   -0.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2014   -3.1491    0.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5062   -0.8797   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8180   -1.0397    0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697    0.1116    0.7279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8595    0.2964    0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7952    1.4660    0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4268    1.5480   -1.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3994    0.2360   -1.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5081   -0.5579   -0.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3149   -1.7952   -0.9554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7046   -1.0641   -0.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8573    0.2518   -0.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0116    0.1406    1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8586    1.0798   -2.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4054    1.5631   -1.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0053    2.6521   -1.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7418    3.0694    0.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4952    2.0069    1.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9640    3.1354    1.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6134    1.8838    2.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4829    1.7883    0.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3298    1.0744    2.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8463   -0.0929    2.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4746   -1.2076    2.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833   -1.6586    1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9007    1.0770   -1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -0.6055   -2.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7946   -0.8732   -1.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1696   -2.7825   -0.8183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0844   -2.7829   -2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2301   -4.3508   -0.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6566   -3.7281   -0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6348   -0.4510   -1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4126   -1.8567    0.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5494   -1.5335    1.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4208    0.8943    1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637    2.3672    0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5879    1.1392    1.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4923    1.8599   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8073    2.2577   -1.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
  9  2  1  0
 14 12  1  0
 22 18  1  0
 15  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
M  END


  Mrv0541 05061309502D          

 23 26  0  0  0  0            999 V2000
    5.3522    1.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244    1.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4812   -1.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0695   -0.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8929   -1.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6870   -1.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2976    0.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9229   -2.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2730   -0.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2753   -1.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5035    0.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9764   -3.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7239   -0.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894   -2.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8882    0.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906   -0.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2165   -3.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6824    0.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6847   -0.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2999   -0.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0398   -3.0887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7759   -3.8397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5004    0.0944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  4  1  0  0  0  0
 10  4  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 14  5  2  0  0  0  0
 14  8  1  0  0  0  0
 15  7  1  0  0  0  0
 16  6  1  0  0  0  0
 17 14  1  0  0  0  0
 18  1  1  0  0  0  0
 18  2  1  0  0  0  0
 18  9  1  0  0  0  0
 18 15  1  0  0  0  0
 19  3  1  0  0  0  0
 19 10  1  0  0  0  0
 19 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 11  1  0  0  0  0
 20 13  1  0  0  0  0
 20 16  1  0  0  0  0
 21 17  2  0  0  0  0
 22 12  1  0  0  0  0
 22 17  1  0  0  0  0
 23 13  1  0  0  0  0
 23 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037523

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)CCCC2(C)C(C\C=C3\CCOC3=O)C3(CO3)CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-18(2)9-4-10-19(3)15(18)7-11-20(13-23-20)16(19)6-5-14-8-12-22-17(14)21/h5,15-16H,4,6-13H2,1-3H3/b14-5-

> <INCHI_KEY>
MBPTXJNHCBXMBP-RZNTYIFUSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.4504

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.60155335786483

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z)-3-(2-{5,5,8a-trimethyl-octahydro-1H-spiro[naphthalene-2,2'-oxirane]-1-yl}ethylidene)oxolan-2-one

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
4.240132235

> <ALOGPS_LOGS>
-5.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.203803826241783

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
90.371

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.96e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3Z)-3-(2-{5,5,8a-trimethyl-hexahydro-1H-spiro[naphthalene-2,2'-oxirane]-1-yl}ethylidene)oxolan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0037523
     RDKit          3D
Galanolactone
 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.8712   -0.0212    0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697    0.9334   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073    1.5796   -1.6268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6002    2.0631    0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3789    2.0742    1.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2091    1.2463    1.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5687   -0.0744    0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986   -0.7995    1.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4951    0.2760   -0.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983   -0.8214   -1.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3211   -2.1884   -1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0607   -2.2619   -0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6434   -3.4956   -0.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2014   -3.1491    0.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5062   -0.8797   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8180   -1.0397    0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697    0.1116    0.7279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8595    0.2964    0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7952    1.4660    0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4268    1.5480   -1.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3994    0.2360   -1.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5081   -0.5579   -0.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3149   -1.7952   -0.9554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7046   -1.0641   -0.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8573    0.2518   -0.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0116    0.1406    1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8586    1.0798   -2.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4054    1.5631   -1.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0053    2.6521   -1.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7418    3.0694    0.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4952    2.0069    1.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9640    3.1354    1.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6134    1.8838    2.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4829    1.7883    0.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3298    1.0744    2.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8463   -0.0929    2.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4746   -1.2076    2.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833   -1.6586    1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9007    1.0770   -1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -0.6055   -2.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7946   -0.8732   -1.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1696   -2.7825   -0.8183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0844   -2.7829   -2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2301   -4.3508   -0.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6566   -3.7281   -0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6348   -0.4510   -1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4126   -1.8567    0.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5494   -1.5335    1.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4208    0.8943    1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637    2.3672    0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5879    1.1392    1.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4923    1.8599   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8073    2.2577   -1.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
  9  2  1  0
 14 12  1  0
 22 18  1  0
 15  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  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       9.991   1.947   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.072   2.435   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.498  -2.354   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.463  -1.520   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.533  -3.188   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.016  -2.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.156   1.706   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.723  -5.251   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.843  -0.027   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.981  -1.937   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.673   1.289   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.823  -6.788   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.218  -1.306   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.154  -4.681   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.258   0.631   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.396  -1.279   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.137  -5.865   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.740   1.048   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.878  -0.862   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.293  -0.204   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.674  -5.766   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.315  -7.167   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.801   0.176   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4    9   10                                                       
CONECT    5    6   14                                                       
CONECT    6    5   16                                                       
CONECT    7   11   15                                                       
CONECT    8   12   14                                                       
CONECT    9    4   18                                                       
CONECT   10    4   19                                                       
CONECT   11    7   20                                                       
CONECT   12    8   22                                                       
CONECT   13   20   23                                                       
CONECT   14    5    8   17                                                  
CONECT   15    7   18   19                                                  
CONECT   16    6   19   20                                                  
CONECT   17   14   21   22                                                  
CONECT   18    1    2    9   15                                             
CONECT   19    3   10   15   16                                             
CONECT   20   11   13   16   23                                             
CONECT   21   17                                                            
CONECT   22   12   17                                                       
CONECT   23   13   20                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0037523
HETATM    1  C1  UNL     1      -3.871  -0.021   0.092  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.770   0.933  -0.330  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.307   1.580  -1.627  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.600   2.063   0.649  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.379   2.074   1.443  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.209   1.246   1.065  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.569  -0.074   0.455  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.299  -0.800   1.569  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.495   0.276  -0.700  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.698  -0.821  -1.683  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.321  -2.188  -1.254  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.061  -2.262  -0.432  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.643  -3.496  -0.368  1.00  0.00           C  
HETATM   14  O1  UNL     1      -0.201  -3.149   0.684  1.00  0.00           O  
HETATM   15  C14 UNL     1       0.506  -0.880  -0.149  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.818  -1.040   0.499  1.00  0.00           C  
HETATM   17  C16 UNL     1       2.670   0.112   0.728  1.00  0.00           C  
HETATM   18  C17 UNL     1       3.860   0.296   0.132  1.00  0.00           C  
HETATM   19  C18 UNL     1       4.795   1.466   0.323  1.00  0.00           C  
HETATM   20  C19 UNL     1       5.427   1.548  -1.042  1.00  0.00           C  
HETATM   21  O2  UNL     1       5.399   0.236  -1.572  1.00  0.00           O  
HETATM   22  C20 UNL     1       4.508  -0.558  -0.819  1.00  0.00           C  
HETATM   23  O3  UNL     1       4.315  -1.795  -0.955  1.00  0.00           O  
HETATM   24  H1  UNL     1      -3.705  -1.064  -0.159  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.857   0.252  -0.344  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.012   0.141   1.199  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.859   1.080  -2.507  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.405   1.563  -1.655  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.005   2.652  -1.653  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.742   3.069   0.156  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.495   2.007   1.338  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.964   3.135   1.506  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.613   1.884   2.537  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.483   1.788   0.376  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.330   1.074   2.062  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.846  -0.093   2.184  1.00  0.00           H  
HETATM   37  H14 UNL     1      -0.475  -1.208   2.231  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.883  -1.659   1.264  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.901   1.077  -1.250  1.00  0.00           H  
HETATM   40  H17 UNL     1      -1.218  -0.605  -2.687  1.00  0.00           H  
HETATM   41  H18 UNL     1      -2.795  -0.873  -1.962  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.170  -2.783  -0.818  1.00  0.00           H  
HETATM   43  H20 UNL     1      -1.084  -2.783  -2.191  1.00  0.00           H  
HETATM   44  H21 UNL     1       0.230  -4.351  -0.983  1.00  0.00           H  
HETATM   45  H22 UNL     1       1.657  -3.728  -0.039  1.00  0.00           H  
HETATM   46  H23 UNL     1       0.635  -0.451  -1.215  1.00  0.00           H  
HETATM   47  H24 UNL     1       2.413  -1.857   0.048  1.00  0.00           H  
HETATM   48  H25 UNL     1       1.549  -1.534   1.521  1.00  0.00           H  
HETATM   49  H26 UNL     1       2.421   0.894   1.404  1.00  0.00           H  
HETATM   50  H27 UNL     1       4.264   2.367   0.627  1.00  0.00           H  
HETATM   51  H28 UNL     1       5.588   1.139   1.037  1.00  0.00           H  
HETATM   52  H29 UNL     1       6.492   1.860  -1.007  1.00  0.00           H  
HETATM   53  H30 UNL     1       4.807   2.258  -1.653  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4    9
CONECT    3   27   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7   34   35
CONECT    7    8    9   15
CONECT    8   36   37   38
CONECT    9   10   39
CONECT   10   11   40   41
CONECT   11   12   42   43
CONECT   12   13   14   15
CONECT   13   14   44   45
CONECT   15   16   46
CONECT   16   17   47   48
CONECT   17   18   18   49
CONECT   18   19   22
CONECT   19   20   50   51
CONECT   20   21   52   53
CONECT   21   22
CONECT   22   23   23
END

HMDB0037523
     RDKit          3D
Galanolactone
 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.8712   -0.0212    0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697    0.9334   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073    1.5796   -1.6268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6002    2.0631    0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3789    2.0742    1.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2091    1.2463    1.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5687   -0.0744    0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986   -0.7995    1.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4951    0.2760   -0.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983   -0.8214   -1.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3211   -2.1884   -1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0607   -2.2619   -0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6434   -3.4956   -0.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2014   -3.1491    0.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5062   -0.8797   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8180   -1.0397    0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697    0.1116    0.7279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8595    0.2964    0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7952    1.4660    0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4268    1.5480   -1.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3994    0.2360   -1.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5081   -0.5579   -0.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3149   -1.7952   -0.9554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7046   -1.0641   -0.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8573    0.2518   -0.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0116    0.1406    1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8586    1.0798   -2.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4054    1.5631   -1.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0053    2.6521   -1.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7418    3.0694    0.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4952    2.0069    1.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9640    3.1354    1.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6134    1.8838    2.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4829    1.7883    0.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3298    1.0744    2.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8463   -0.0929    2.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4746   -1.2076    2.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833   -1.6586    1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9007    1.0770   -1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -0.6055   -2.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7946   -0.8732   -1.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1696   -2.7825   -0.8183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0844   -2.7829   -2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2301   -4.3508   -0.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6566   -3.7281   -0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6348   -0.4510   -1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4126   -1.8567    0.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5494   -1.5335    1.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4208    0.8943    1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637    2.3672    0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5879    1.1392    1.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4923    1.8599   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8073    2.2577   -1.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
  9  2  1  0
 14 12  1  0
 22 18  1  0
 15  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₃

Average Molecular Weight

318.4504

Monoisotopic Molecular Weight

318.219494826

IUPAC Name

(3Z)-3-(2-{5,5,8a-trimethyl-octahydro-1H-spiro[naphthalene-2,2'-oxirane]-1-yl}ethylidene)oxolan-2-one

Traditional Name

(3Z)-3-(2-{5,5,8a-trimethyl-hexahydro-1H-spiro[naphthalene-2,2'-oxirane]-1-yl}ethylidene)oxolan-2-one

CAS Registry Number

115753-79-2

SMILES

CC1(C)CCCC2(C)C(C\C=C3\CCOC3=O)C3(CO3)CCC12

InChI Identifier

InChI=1S/C20H30O3/c1-18(2)9-4-10-19(3)15(18)7-11-20(13-23-20)16(19)6-5-14-8-12-22-17(14)21/h5,15-16H,4,6-13H2,1-3H3/b14-5-

InChI Key

MBPTXJNHCBXMBP-RZNTYIFUSA-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
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037523)

Cellular substructure

Extracellular (HMDB: HMDB0037523)
Membrane (HMDB: HMDB0037523)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037523)

Source

Endogenous

Endogenous (HMDB: HMDB0037523)

Plant

Plant (HMDB: HMDB0037523)

Exogenous

Food

Food (HMDB: HMDB0037523)

Herb and spice

Spice

Ginger (FooDB: FOOD00206)

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0037523)

Role

Biological role

anti 5-hydroxytryptamine (HMDB: HMDB0037523)
anti emetic (HMDB: HMDB0037523)
anti thromboxane (HMDB: HMDB0037523)
gastrostimulant (HMDB: HMDB0037523)
Membrane stabilizer (HMDB: HMDB0037523)

Nutrient

Nutrient (HMDB: HMDB0037523)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037523)

Emulsifier (HMDB: HMDB0037523)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	125.5 - 126 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.05 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	0.0005 g/L	ALOGPS
logP	3.81	ALOGPS
logP	4.24	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	90.37 m³·mol⁻¹	ChemAxon
Polarizability	36.6 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	175.038	31661259
DarkChem	[M-H]-	167.822	31661259
DeepCCS	[M-2H]-	213.562	30932474
DeepCCS	[M+Na]+	189.128	30932474
AllCCS	[M+H]+	177.7	32859911
AllCCS	[M+H-H2O]+	174.6	32859911
AllCCS	[M+NH4]+	180.5	32859911
AllCCS	[M+Na]+	181.4	32859911
AllCCS	[M-H]-	186.6	32859911
AllCCS	[M+Na-2H]-	186.8	32859911
AllCCS	[M+HCOO]-	187.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Galanolactone	CC1(C)CCCC2(C)C(C\C=C3\CCOC3=O)C3(CO3)CCC12	3090.3	Standard polar	33892256
Galanolactone	CC1(C)CCCC2(C)C(C\C=C3\CCOC3=O)C3(CO3)CCC12	2507.3	Standard non polar	33892256
Galanolactone	CC1(C)CCCC2(C)C(C\C=C3\CCOC3=O)C3(CO3)CCC12	2815.8	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 - Galanolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-0691000000-76ff2be2a471bb872fd2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Galanolactone 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 - Galanolactone 10V, Positive-QTOF	splash10-014i-1079000000-1752926143446e156771	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galanolactone 20V, Positive-QTOF	splash10-0fsj-2192000000-34665ab35024bcaec03b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galanolactone 40V, Positive-QTOF	splash10-0udi-8920000000-9070c224eeba82a073c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galanolactone 10V, Negative-QTOF	splash10-014i-1019000000-c8e6f08fa9a4c772c41e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galanolactone 20V, Negative-QTOF	splash10-01b9-3095000000-9f4bfe9957ad918fccc7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galanolactone 40V, Negative-QTOF	splash10-0pb9-4090000000-bec7fcb4c3d0c3bfeb83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galanolactone 10V, Positive-QTOF	splash10-014i-0009000000-f44b8f78f028f8f8f3b6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galanolactone 20V, Positive-QTOF	splash10-0g29-0913000000-29e7ab868d79d3e36a1a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galanolactone 40V, Positive-QTOF	splash10-0fi0-6923000000-8d5099da71cc9b483052	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galanolactone 10V, Negative-QTOF	splash10-014i-0009000000-062ad2a35e11d303cf23	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galanolactone 20V, Negative-QTOF	splash10-014i-0029000000-eefd64fbf57a97fa197a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Galanolactone 40V, Negative-QTOF	splash10-0a4i-2091000000-300e0967ce3af0cdcdf5	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Galanolactone

METLIN ID

Not Available

PubChem Compound

57457805

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1861711

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 Galanolactone (HMDB0037523)

MOL for HMDB0037523 (Galanolactone)

3D MOL for HMDB0037523 (Galanolactone)

3D SDF for HMDB0037523 (Galanolactone)

3D-SDF for HMDB0037523 (Galanolactone)

PDB for HMDB0037523 (Galanolactone)

3D PDB for HMDB0037523 (Galanolactone)

SMILES for HMDB0037523 (Galanolactone)

INCHI for HMDB0037523 (Galanolactone)

Structure for HMDB0037523 (Galanolactone)

3D Structure for HMDB0037523 (Galanolactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra