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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:55 UTC

Update Date

2022-03-07 02:53:01 UTC

HMDB ID

HMDB0031534

Secondary Accession Numbers

HMDB31534

Metabolite Identification

Common Name

(+)-Galeon

Description

(+)-Galeon, also known as galeon, belongs to the class of organic compounds known as meta,para-diphenylether diarylheptanoids. These are cyclic diarylheptanoids where the two benzene rings are linked to each other by an ether group conjugated to the 3-position of one benzene ring and the 4-position of the other ring. Based on a literature review a significant number of articles have been published on (+)-Galeon.

Structure

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

HMDB0031534
     RDKit          3D
(+)-Galeon
 46 48  0  0  0  0  0  0  0  0999 V2000
    2.4377    0.7292    3.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423    1.4435    1.9650 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9159    0.9700    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4757   -0.3550    0.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -1.0001   -0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1487   -0.3964   -1.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5939    0.9190   -1.7124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4841    1.5390   -0.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7725    2.8773   -0.5348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6589    2.5863   -0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3415    1.5627   -0.8808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6421    1.3889   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1870    2.2556    0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4944    3.2963    1.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639    3.4356    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4721    4.4942    1.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5200    0.1792   -0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8645   -0.9495    0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9910   -1.8682   -0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4944   -2.8829   -1.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5369   -1.7216   -0.7663 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315   -2.7755   -0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4386   -3.2249   -0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.5071   -0.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9089   -0.2230    3.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5276    0.4905    3.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3191    1.3793    3.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948   -0.6472    1.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1639   -0.6531   -2.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3396    1.2834   -2.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9422    0.9762   -1.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2333    2.1254    0.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9117    3.9505    1.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4842    4.7124    1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8417   -0.0808   -1.6527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5125    0.3112   -0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2776   -0.4669    0.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6601   -1.5157    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2449   -0.7567   -0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3260   -1.6135   -1.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692   -2.4562    0.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3450   -3.6738    0.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1869   -2.9731   -2.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6099   -4.3124   -0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3075   -2.9734    0.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4366   -2.8787   -1.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 15 10  2  0
 24  5  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  1  0
M  END

  Mrv0541 02241209062D          

 24 26  0  0  0  0            999 V2000
    2.0553   -0.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4808   -1.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6573   -1.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0828   -1.8091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229   -1.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629   -1.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2209   -1.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2209   -0.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629   -0.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629    0.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7749    1.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4932    1.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3276    1.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9048    1.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7270    1.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2209    0.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8911   -0.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0689    0.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4931   -0.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9871   -0.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629   -2.7147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229    2.7147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4808   -2.3016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7694   -2.7120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  2 23  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 20  2  0  0  0  0
  6  7  2  0  0  0  0
  6 21  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 20  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 22  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031534

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=CC=C1OC1=CC(CCC(=O)CCCC2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O4/c1-23-20-13-14-4-2-3-5-16(21)9-6-15-7-10-17(22)19(12-15)24-18(20)11-8-14/h7-8,10-13,22H,2-6,9H2,1H3

> <INCHI_KEY>
QUSSPXNPULRXKG-UHFFFAOYSA-N

> <FORMULA>
C20H22O4

> <MOLECULAR_WEIGHT>
326.3863

> <EXACT_MASS>
326.151809192

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.37332610001858

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-18-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one

> <ALOGPS_LOGP>
4.49

> <JCHEM_LOGP>
4.619038887333334

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.402683647052765

> <JCHEM_PKA_STRONGEST_BASIC>
-4.897785561993321

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
92.6695

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.26e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-18-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031534
     RDKit          3D
(+)-Galeon
 46 48  0  0  0  0  0  0  0  0999 V2000
    2.4377    0.7292    3.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423    1.4435    1.9650 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9159    0.9700    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4757   -0.3550    0.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -1.0001   -0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1487   -0.3964   -1.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5939    0.9190   -1.7124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4841    1.5390   -0.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7725    2.8773   -0.5348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6589    2.5863   -0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3415    1.5627   -0.8808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6421    1.3889   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1870    2.2556    0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4944    3.2963    1.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639    3.4356    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4721    4.4942    1.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5200    0.1792   -0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8645   -0.9495    0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9910   -1.8682   -0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4944   -2.8829   -1.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5369   -1.7216   -0.7663 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315   -2.7755   -0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4386   -3.2249   -0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.5071   -0.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9089   -0.2230    3.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5276    0.4905    3.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3191    1.3793    3.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948   -0.6472    1.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1639   -0.6531   -2.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3396    1.2834   -2.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9422    0.9762   -1.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2333    2.1254    0.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9117    3.9505    1.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4842    4.7124    1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8417   -0.0808   -1.6527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5125    0.3112   -0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2776   -0.4669    0.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6601   -1.5157    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2449   -0.7567   -0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3260   -1.6135   -1.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692   -2.4562    0.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3450   -3.6738    0.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1869   -2.9731   -2.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6099   -4.3124   -0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3075   -2.9734    0.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4366   -2.8787   -1.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 15 10  2  0
 24  5  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  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       3.837  -1.689   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.764  -2.764   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.227  -2.608   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.155  -3.377   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.536  -2.764   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.917  -3.530   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.146  -2.608   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.146  -1.074   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.917  -0.154   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.917   1.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.446   1.927   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.921   3.530   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.612   3.686   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.689   2.608   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.224   2.608   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.146   1.383   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.530  -0.154   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.995   0.152   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.920  -1.074   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.843  -1.227   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.917  -5.067   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.536   5.067   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.764  -4.296   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.436  -5.062   0.000  0.00  0.00           C+0
CONECT    1    2   17                                                       
CONECT    2    1    3   23                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17    1   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19    3   18                                                       
CONECT   20    5    9                                                       
CONECT   21    6                                                            
CONECT   22   12                                                            
CONECT   23    2   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0031534
HETATM    1  C1  UNL     1       2.438   0.729   3.032  1.00  0.00           C  
HETATM    2  O1  UNL     1       1.942   1.444   1.965  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.916   0.970   0.605  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.476  -0.355   0.495  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.565  -1.000  -0.713  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.149  -0.396  -1.862  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.594   0.919  -1.712  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.484   1.539  -0.509  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.773   2.877  -0.535  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.659   2.586  -0.281  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.341   1.563  -0.881  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.642   1.389  -0.450  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.187   2.256   0.519  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.494   3.296   1.099  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.164   3.436   0.653  1.00  0.00           C  
HETATM   16  O3  UNL     1      -0.472   4.494   1.255  1.00  0.00           O  
HETATM   17  C14 UNL     1      -3.520   0.179  -0.679  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.864  -0.949   0.148  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.991  -1.868  -0.572  1.00  0.00           C  
HETATM   20  O4  UNL     1      -2.494  -2.883  -1.081  1.00  0.00           O  
HETATM   21  C17 UNL     1      -0.537  -1.722  -0.766  1.00  0.00           C  
HETATM   22  C18 UNL     1       0.332  -2.775  -0.138  1.00  0.00           C  
HETATM   23  C19 UNL     1       1.439  -3.225  -0.994  1.00  0.00           C  
HETATM   24  C20 UNL     1       2.807  -2.507  -0.795  1.00  0.00           C  
HETATM   25  H1  UNL     1       1.909  -0.223   3.272  1.00  0.00           H  
HETATM   26  H2  UNL     1       3.528   0.490   3.002  1.00  0.00           H  
HETATM   27  H3  UNL     1       2.319   1.379   3.939  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.795  -0.647   1.526  1.00  0.00           H  
HETATM   29  H5  UNL     1       2.164  -0.653  -2.966  1.00  0.00           H  
HETATM   30  H6  UNL     1       1.340   1.283  -2.740  1.00  0.00           H  
HETATM   31  H7  UNL     1      -0.942   0.976  -1.781  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.233   2.125   0.854  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.912   3.950   1.823  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.484   4.712   1.032  1.00  0.00           H  
HETATM   35  H11 UNL     1      -3.842  -0.081  -1.653  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.512   0.311  -0.119  1.00  0.00           H  
HETATM   37  H13 UNL     1      -2.278  -0.467   0.989  1.00  0.00           H  
HETATM   38  H14 UNL     1      -3.660  -1.516   0.730  1.00  0.00           H  
HETATM   39  H15 UNL     1      -0.245  -0.757  -0.278  1.00  0.00           H  
HETATM   40  H16 UNL     1      -0.326  -1.614  -1.859  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.669  -2.456   0.876  1.00  0.00           H  
HETATM   42  H18 UNL     1      -0.345  -3.674   0.014  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.187  -2.973  -2.065  1.00  0.00           H  
HETATM   44  H20 UNL     1       1.610  -4.312  -0.885  1.00  0.00           H  
HETATM   45  H21 UNL     1       3.307  -2.973   0.079  1.00  0.00           H  
HETATM   46  H22 UNL     1       3.437  -2.879  -1.595  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   28
CONECT    5    6    6   24
CONECT    6    7   29
CONECT    7    8    8   30
CONECT    8    9
CONECT    9   10
CONECT   10   11   15   15
CONECT   11   12   12   31
CONECT   12   13   17
CONECT   13   14   14   32
CONECT   14   15   33
CONECT   15   16
CONECT   16   34
CONECT   17   18   35   36
CONECT   18   19   37   38
CONECT   19   20   20   21
CONECT   21   22   39   40
CONECT   22   23   41   42
CONECT   23   24   43   44
CONECT   24   45   46
END

HMDB0031534
     RDKit          3D
(+)-Galeon
 46 48  0  0  0  0  0  0  0  0999 V2000
    2.4377    0.7292    3.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423    1.4435    1.9650 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9159    0.9700    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4757   -0.3550    0.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -1.0001   -0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1487   -0.3964   -1.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5939    0.9190   -1.7124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4841    1.5390   -0.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7725    2.8773   -0.5348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6589    2.5863   -0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3415    1.5627   -0.8808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6421    1.3889   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1870    2.2556    0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4944    3.2963    1.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639    3.4356    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4721    4.4942    1.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5200    0.1792   -0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8645   -0.9495    0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9910   -1.8682   -0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4944   -2.8829   -1.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5369   -1.7216   -0.7663 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315   -2.7755   -0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4386   -3.2249   -0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.5071   -0.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9089   -0.2230    3.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5276    0.4905    3.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3191    1.3793    3.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948   -0.6472    1.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1639   -0.6531   -2.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3396    1.2834   -2.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9422    0.9762   -1.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2333    2.1254    0.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9117    3.9505    1.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4842    4.7124    1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8417   -0.0808   -1.6527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5125    0.3112   -0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2776   -0.4669    0.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6601   -1.5157    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2449   -0.7567   -0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3260   -1.6135   -1.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692   -2.4562    0.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3450   -3.6738    0.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1869   -2.9731   -2.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6099   -4.3124   -0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3075   -2.9734    0.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4366   -2.8787   -1.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 15 10  2  0
 24  5  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Galeon	HMDB

Chemical Formula

C₂₀H₂₂O₄

Average Molecular Weight

326.3863

Monoisotopic Molecular Weight

326.151809192

IUPAC Name

4-hydroxy-18-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one

Traditional Name

4-hydroxy-18-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one

CAS Registry Number

191999-64-1

SMILES

COC1=CC2=CC=C1OC1=CC(CCC(=O)CCCC2)=CC=C1O

InChI Identifier

InChI=1S/C20H22O4/c1-23-20-13-14-4-2-3-5-16(21)9-6-15-7-10-17(22)19(12-15)24-18(20)11-8-14/h7-8,10-13,22H,2-6,9H2,1H3

InChI Key

QUSSPXNPULRXKG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as meta,para-diphenylether diarylheptanoids. These are cyclic diarylheptanoids where the two benzene rings are linked to each other by an ether group conjugated to the 3-position of one benzene ring and the 4-position of the other ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Cyclic diarylheptanoids

Direct Parent

Meta,para-diphenylether diarylheptanoids

Alternative Parents

Substituents

Meta,para-diphenylether diarylheptanoid
Oxyneolignan skeleton
Diaryl ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Ketone
Cyclic ketone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB31534)

Food

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	178 - 180 °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	0.0083 g/L	ALOGPS
logP	4.49	ALOGPS
logP	4.62	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.4	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.67 m³·mol⁻¹	ChemAxon
Polarizability	34.37 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]+	177.091	31661259
DarkChem	[M-H]-	178.532	31661259
DeepCCS	[M+H]+	173.298	30932474
DeepCCS	[M-H]-	170.94	30932474
DeepCCS	[M-2H]-	204.634	30932474
DeepCCS	[M+Na]+	179.861	30932474
AllCCS	[M+H]+	180.9	32859911
AllCCS	[M+H-H2O]+	177.4	32859911
AllCCS	[M+NH4]+	184.1	32859911
AllCCS	[M+Na]+	185.1	32859911
AllCCS	[M-H]-	186.5	32859911
AllCCS	[M+Na-2H]-	186.5	32859911
AllCCS	[M+HCOO]-	186.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+)-Galeon	COC1=CC2=CC=C1OC1=CC(CCC(=O)CCCC2)=CC=C1O	3572.1	Standard polar	33892256
(+)-Galeon	COC1=CC2=CC=C1OC1=CC(CCC(=O)CCCC2)=CC=C1O	2705.0	Standard non polar	33892256
(+)-Galeon	COC1=CC2=CC=C1OC1=CC(CCC(=O)CCCC2)=CC=C1O	2760.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(+)-Galeon,1TMS,isomer #1	COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C)C=CC(=C1)CCC(=O)CCCC2	2937.4	Semi standard non polar	33892256
(+)-Galeon,1TMS,isomer #2	COC1=CC2=CC=C1OC1=C(O)C=CC(=C1)CCC(O[Si](C)(C)C)=CCCC2	2887.9	Semi standard non polar	33892256
(+)-Galeon,1TMS,isomer #3	COC1=CC2=CC=C1OC1=C(O)C=CC(=C1)CC=C(O[Si](C)(C)C)CCCC2	2883.4	Semi standard non polar	33892256
(+)-Galeon,2TMS,isomer #1	COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C)C=CC(=C1)CCC(O[Si](C)(C)C)=CCCC2	2910.7	Semi standard non polar	33892256
(+)-Galeon,2TMS,isomer #1	COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C)C=CC(=C1)CCC(O[Si](C)(C)C)=CCCC2	2718.3	Standard non polar	33892256
(+)-Galeon,2TMS,isomer #2	COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C)C=CC(=C1)CC=C(O[Si](C)(C)C)CCCC2	2931.8	Semi standard non polar	33892256
(+)-Galeon,2TMS,isomer #2	COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C)C=CC(=C1)CC=C(O[Si](C)(C)C)CCCC2	2715.2	Standard non polar	33892256
(+)-Galeon,1TBDMS,isomer #1	COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C(C)(C)C)C=CC(=C1)CCC(=O)CCCC2	3154.0	Semi standard non polar	33892256
(+)-Galeon,1TBDMS,isomer #2	COC1=CC2=CC=C1OC1=C(O)C=CC(=C1)CCC(O[Si](C)(C)C(C)(C)C)=CCCC2	3107.0	Semi standard non polar	33892256
(+)-Galeon,1TBDMS,isomer #3	COC1=CC2=CC=C1OC1=C(O)C=CC(=C1)CC=C(O[Si](C)(C)C(C)(C)C)CCCC2	3121.2	Semi standard non polar	33892256
(+)-Galeon,2TBDMS,isomer #1	COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C(C)(C)C)C=CC(=C1)CCC(O[Si](C)(C)C(C)(C)C)=CCCC2	3350.9	Semi standard non polar	33892256
(+)-Galeon,2TBDMS,isomer #1	COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C(C)(C)C)C=CC(=C1)CCC(O[Si](C)(C)C(C)(C)C)=CCCC2	3098.2	Standard non polar	33892256
(+)-Galeon,2TBDMS,isomer #2	COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C(C)(C)C)C=CC(=C1)CC=C(O[Si](C)(C)C(C)(C)C)CCCC2	3381.2	Semi standard non polar	33892256
(+)-Galeon,2TBDMS,isomer #2	COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C(C)(C)C)C=CC(=C1)CC=C(O[Si](C)(C)C(C)(C)C)CCCC2	3080.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Galeon GC-MS (Non-derivatized) - 70eV, Positive	splash10-002b-0096000000-adec5086c229b4118c10	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Galeon GC-MS (1 TMS) - 70eV, Positive	splash10-008a-3039000000-56238ad213bbdc49b2f5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Galeon 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 - (+)-Galeon 10V, Positive-QTOF	splash10-004i-0009000000-22562d9b33c1b5ee013b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Galeon 20V, Positive-QTOF	splash10-004i-0019000000-9961b7891c3e00985773	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Galeon 40V, Positive-QTOF	splash10-0a6u-0094000000-9b3e7c919a6f02b440be	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Galeon 10V, Negative-QTOF	splash10-004i-0009000000-659f2d6bb10c91dbc25a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Galeon 20V, Negative-QTOF	splash10-004i-0009000000-4936bc3da2815eff2fbe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Galeon 40V, Negative-QTOF	splash10-0a4l-2096000000-d6b77a3595f3bf03e1b1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Galeon 10V, Positive-QTOF	splash10-004i-0009000000-d133ab50982257e6dd6b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Galeon 20V, Positive-QTOF	splash10-0a6r-0009000000-88b108bce63b66e6aba5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Galeon 40V, Positive-QTOF	splash10-0059-0090000000-545cc8edd9030b74befd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Galeon 10V, Negative-QTOF	splash10-004i-0009000000-976dd6ecdf84064dc4ff	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Galeon 20V, Negative-QTOF	splash10-056r-0029000000-e641917637d2faaf1eb8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Galeon 40V, Negative-QTOF	splash10-0a4i-0090000000-1eb05daf300d5f36d472	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB008142

KNApSAcK ID

Not Available

Chemspider ID

17273581

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16116346

PDB ID

Not Available

ChEBI ID

175168

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1827051

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

(+)-Galeon → 3,4,5-trihydroxy-6-({17-methoxy-10-oxo-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3,5,7(20),15,18-hexaen-4-yl}oxy)oxane-2-carboxylic acid	details

Showing metabocard for (+)-Galeon (HMDB0031534)

MOL for HMDB0031534 ((+)-Galeon)

3D MOL for HMDB0031534 ((+)-Galeon)

3D SDF for HMDB0031534 ((+)-Galeon)

3D-SDF for HMDB0031534 ((+)-Galeon)

PDB for HMDB0031534 ((+)-Galeon)

3D PDB for HMDB0031534 ((+)-Galeon)

SMILES for HMDB0031534 ((+)-Galeon)

INCHI for HMDB0031534 ((+)-Galeon)

Structure for HMDB0031534 ((+)-Galeon)

3D Structure for HMDB0031534 ((+)-Galeon)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions