Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:54 UTC

Update Date

2022-03-07 02:53:31 UTC

HMDB ID

HMDB0032954

Secondary Accession Numbers

HMDB32954

Metabolite Identification

Common Name

5-Geranyloxy-7-methoxycoumarin

Description

5-Geranyloxy-7-methoxycoumarin belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a small amount of articles have been published on 5-Geranyloxy-7-methoxycoumarin.

Structure

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

HMDB0032954
     RDKit          3D
5-Geranyloxy-7-methoxycoumarin
 48 49  0  0  0  0  0  0  0  0999 V2000
   -5.3568   -3.0664   -1.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0658   -2.5704   -1.7542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9054   -1.3866   -1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6541   -0.8582   -0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4851    0.3065   -0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726    0.8788    0.1923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0321    0.2851   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164    1.1187    0.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695    0.6361    1.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8869   -0.7700    1.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1976    1.4980    1.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5304    0.9630    1.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7208    0.8081   -0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0271   -0.3639   -0.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2168   -0.5012   -2.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1967   -1.5519   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6269    0.9654    0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5389    2.1536    1.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6646    2.8104    1.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8926    2.2530    1.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9732    2.7845    1.5902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9470    1.1304    0.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8959    0.4802    0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9944   -0.6996   -0.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0131   -2.3058   -2.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3499   -3.9796   -2.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8265   -3.2227   -0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792   -1.3855   -1.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0079    0.1977   -1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0497   -0.7421    0.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1965    2.1304   -0.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9427   -1.4024    0.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9308   -0.8990    2.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6832   -1.1045    2.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0367    2.5327    1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2080    1.5488    2.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990    0.0312    1.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2927    1.7226    1.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6083    1.6609   -0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2536   -0.5983   -2.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8197   -1.3899   -2.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7928    0.4064   -2.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9211   -1.3462    0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7027   -2.3763   -0.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2707   -1.9581    0.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5324    2.5305    1.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5817    3.7361    2.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9744   -1.0907   -0.7809 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24  3  1  0
 23 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 18 46  1  0
 19 47  1  0
 24 48  1  0
M  END


  Mrv0541 05061306492D          

 24 25  0  0  0  0            999 V2000
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  2  0  0  0  0
 11 10  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  6  2  0  0  0  0
 15  3  1  0  0  0  0
 15  7  1  0  0  0  0
 15 10  2  0  0  0  0
 16 12  2  0  0  0  0
 16 13  1  0  0  0  0
 17  8  1  0  0  0  0
 18 12  1  0  0  0  0
 18 17  2  0  0  0  0
 19 13  2  0  0  0  0
 19 17  1  0  0  0  0
 20  9  1  0  0  0  0
 21 20  2  0  0  0  0
 22  4  1  0  0  0  0
 22 16  1  0  0  0  0
 23 11  1  0  0  0  0
 23 18  1  0  0  0  0
 24 19  1  0  0  0  0
 24 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032954

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(OC\C=C(/C)CCC=C(C)C)=C2C=CC(=O)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O4/c1-14(2)6-5-7-15(3)10-11-23-18-12-16(22-4)13-19-17(18)8-9-20(21)24-19/h6,8-10,12-13H,5,7,11H2,1-4H3/b15-10+

> <INCHI_KEY>
WXUOSNJWDJOHGW-XNTDXEJSSA-N

> <FORMULA>
C20H24O4

> <MOLECULAR_WEIGHT>
328.4022

> <EXACT_MASS>
328.167459256

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.094620972429894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7-methoxy-2H-chromen-2-one

> <ALOGPS_LOGP>
5.50

> <JCHEM_LOGP>
4.488977448666667

> <ALOGPS_LOGS>
-5.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5676060457645296

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
97.39579999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7-methoxychromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032954
     RDKit          3D
5-Geranyloxy-7-methoxycoumarin
 48 49  0  0  0  0  0  0  0  0999 V2000
   -5.3568   -3.0664   -1.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0658   -2.5704   -1.7542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9054   -1.3866   -1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6541   -0.8582   -0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4851    0.3065   -0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726    0.8788    0.1923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0321    0.2851   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164    1.1187    0.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695    0.6361    1.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8869   -0.7700    1.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1976    1.4980    1.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5304    0.9630    1.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7208    0.8081   -0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0271   -0.3639   -0.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2168   -0.5012   -2.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1967   -1.5519   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6269    0.9654    0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5389    2.1536    1.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6646    2.8104    1.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8926    2.2530    1.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9732    2.7845    1.5902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9470    1.1304    0.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8959    0.4802    0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9944   -0.6996   -0.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0131   -2.3058   -2.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3499   -3.9796   -2.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8265   -3.2227   -0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792   -1.3855   -1.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0079    0.1977   -1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0497   -0.7421    0.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1965    2.1304   -0.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9427   -1.4024    0.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9308   -0.8990    2.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6832   -1.1045    2.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0367    2.5327    1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2080    1.5488    2.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990    0.0312    1.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2927    1.7226    1.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6083    1.6609   -0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2536   -0.5983   -2.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8197   -1.3899   -2.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7928    0.4064   -2.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9211   -1.3462    0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7027   -2.3763   -0.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2707   -1.9581    0.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5324    2.5305    1.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5817    3.7361    2.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9744   -1.0907   -0.7809 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24  3  1  0
 23 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 18 46  1  0
 19 47  1  0
 24 48  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       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   22                                                            
CONECT    5    6    7                                                       
CONECT    6    5   14                                                       
CONECT    7    5   15                                                       
CONECT    8    9   17                                                       
CONECT    9    8   20                                                       
CONECT   10   11   15                                                       
CONECT   11   10   23                                                       
CONECT   12   16   18                                                       
CONECT   13   16   19                                                       
CONECT   14    1    2    6                                                  
CONECT   15    3    7   10                                                  
CONECT   16   12   13   22                                                  
CONECT   17    8   18   19                                                  
CONECT   18   12   17   23                                                  
CONECT   19   13   17   24                                                  
CONECT   20    9   21   24                                                  
CONECT   21   20                                                            
CONECT   22    4   16                                                       
CONECT   23   11   18                                                       
CONECT   24   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0032954
HETATM    1  C1  UNL     1      -5.357  -3.066  -1.994  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.066  -2.570  -1.754  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.905  -1.387  -1.051  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.654  -0.858  -0.789  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.485   0.307  -0.097  1.00  0.00           C  
HETATM    6  O2  UNL     1      -1.273   0.879   0.192  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.032   0.285  -0.219  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.116   1.119   0.230  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.070   0.636   1.056  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.887  -0.770   1.477  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.198   1.498   1.490  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.530   0.963   1.083  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.721   0.808  -0.361  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.027  -0.364  -0.885  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.217  -0.501  -2.368  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.197  -1.552  -0.023  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.627   0.965   0.349  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.539   2.154   1.059  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.665   2.810   1.503  1.00  0.00           C  
HETATM   20  C18 UNL     1      -5.893   2.253   1.223  1.00  0.00           C  
HETATM   21  O3  UNL     1      -6.973   2.785   1.590  1.00  0.00           O  
HETATM   22  O4  UNL     1      -5.947   1.130   0.551  1.00  0.00           O  
HETATM   23  C19 UNL     1      -4.896   0.480   0.114  1.00  0.00           C  
HETATM   24  C20 UNL     1      -4.994  -0.700  -0.590  1.00  0.00           C  
HETATM   25  H1  UNL     1      -6.013  -2.306  -2.494  1.00  0.00           H  
HETATM   26  H2  UNL     1      -5.350  -3.980  -2.593  1.00  0.00           H  
HETATM   27  H3  UNL     1      -5.826  -3.223  -0.980  1.00  0.00           H  
HETATM   28  H4  UNL     1      -1.779  -1.385  -1.145  1.00  0.00           H  
HETATM   29  H5  UNL     1      -0.008   0.198  -1.336  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.050  -0.742   0.189  1.00  0.00           H  
HETATM   31  H7  UNL     1       1.196   2.130  -0.107  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.943  -1.402   0.564  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.931  -0.899   2.022  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.683  -1.104   2.181  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.037   2.533   1.131  1.00  0.00           H  
HETATM   36  H12 UNL     1       3.208   1.549   2.617  1.00  0.00           H  
HETATM   37  H13 UNL     1       4.699   0.031   1.669  1.00  0.00           H  
HETATM   38  H14 UNL     1       5.293   1.723   1.429  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.608   1.661  -0.993  1.00  0.00           H  
HETATM   40  H16 UNL     1       4.254  -0.598  -2.897  1.00  0.00           H  
HETATM   41  H17 UNL     1       5.820  -1.390  -2.558  1.00  0.00           H  
HETATM   42  H18 UNL     1       5.793   0.406  -2.674  1.00  0.00           H  
HETATM   43  H19 UNL     1       5.921  -1.346   0.816  1.00  0.00           H  
HETATM   44  H20 UNL     1       5.703  -2.376  -0.610  1.00  0.00           H  
HETATM   45  H21 UNL     1       4.271  -1.958   0.387  1.00  0.00           H  
HETATM   46  H22 UNL     1      -2.532   2.530   1.240  1.00  0.00           H  
HETATM   47  H23 UNL     1      -4.582   3.736   2.055  1.00  0.00           H  
HETATM   48  H24 UNL     1      -5.974  -1.091  -0.781  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   24
CONECT    4    5   28
CONECT    5    6   17   17
CONECT    6    7
CONECT    7    8   29   30
CONECT    8    9    9   31
CONECT    9   10   11
CONECT   10   32   33   34
CONECT   11   12   35   36
CONECT   12   13   37   38
CONECT   13   14   14   39
CONECT   14   15   16
CONECT   15   40   41   42
CONECT   16   43   44   45
CONECT   17   18   23
CONECT   18   19   19   46
CONECT   19   20   47
CONECT   20   21   21   22
CONECT   22   23
CONECT   23   24   24
CONECT   24   48
END

HMDB0032954
     RDKit          3D
5-Geranyloxy-7-methoxycoumarin
 48 49  0  0  0  0  0  0  0  0999 V2000
   -5.3568   -3.0664   -1.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0658   -2.5704   -1.7542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9054   -1.3866   -1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6541   -0.8582   -0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4851    0.3065   -0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726    0.8788    0.1923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0321    0.2851   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164    1.1187    0.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695    0.6361    1.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8869   -0.7700    1.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1976    1.4980    1.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5304    0.9630    1.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7208    0.8081   -0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0271   -0.3639   -0.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2168   -0.5012   -2.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1967   -1.5519   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6269    0.9654    0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5389    2.1536    1.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6646    2.8104    1.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8926    2.2530    1.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9732    2.7845    1.5902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9470    1.1304    0.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8959    0.4802    0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9944   -0.6996   -0.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0131   -2.3058   -2.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3499   -3.9796   -2.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8265   -3.2227   -0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792   -1.3855   -1.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0079    0.1977   -1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0497   -0.7421    0.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1965    2.1304   -0.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9427   -1.4024    0.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9308   -0.8990    2.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6832   -1.1045    2.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0367    2.5327    1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2080    1.5488    2.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990    0.0312    1.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2927    1.7226    1.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6083    1.6609   -0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2536   -0.5983   -2.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8197   -1.3899   -2.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7928    0.4064   -2.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9211   -1.3462    0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7027   -2.3763   -0.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2707   -1.9581    0.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5324    2.5305    1.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5817    3.7361    2.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9744   -1.0907   -0.7809 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24  3  1  0
 23 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 18 46  1  0
 19 47  1  0
 24 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-((3,7-Dimethyl-2,6-octadienyl)oxy)-7-methoxycoumarin	HMDB
5-(Geranyloxy)-7-methoxycoumarin	HMDB
5-(Geranyloxy)-herniarin	HMDB
5-Geranoxy-7-methoxycoumarin	HMDB
7-Methoxy-5-geranoxycoumarin	HMDB
SAME	HMDB
5-Geranyloxy-7-methoxycoumarin	MeSH

Chemical Formula

C₂₀H₂₄O₄

Average Molecular Weight

328.4022

Monoisotopic Molecular Weight

328.167459256

IUPAC Name

5-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7-methoxy-2H-chromen-2-one

Traditional Name

5-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7-methoxychromen-2-one

CAS Registry Number

7380-39-4

SMILES

COC1=CC(OC\C=C(/C)CCC=C(C)C)=C2C=CC(=O)OC2=C1

InChI Identifier

InChI=1S/C20H24O4/c1-14(2)6-5-7-15(3)10-11-23-18-12-16(22-4)13-19-17(18)8-9-20(21)24-19/h6,8-10,12-13H,5,7,11H2,1-4H3/b15-10+

InChI Key

WXUOSNJWDJOHGW-XNTDXEJSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Coumarin
Aromatic monoterpenoid
Benzopyran
Bicyclic monoterpenoid
Monoterpenoid
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0032954)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032954)

Source

Endogenous

Endogenous (HMDB: HMDB0032954)

Plant

Plant (HMDB: HMDB0032954)

Animal

Animal (HMDB: HMDB0032954)

Exogenous

Food

Food (HMDB: HMDB0032954)

Fruit

Citrus

Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Citrus (FooDB: FOOD00859)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0032954)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0032954)

Cellular process

Cell signaling (HMDB: HMDB0032954)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0032954)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0032954)

Nutrient

Nutrient (HMDB: HMDB0032954)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	86 - 87 °C	Not Available
Boiling Point	487.10 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.097 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.970 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0015 g/L	ALOGPS
logP	5.5	ALOGPS
logP	4.49	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	97.4 m³·mol⁻¹	ChemAxon
Polarizability	37.09 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]+	179.651	31661259
DarkChem	[M-H]-	177.516	31661259
DeepCCS	[M+H]+	181.925	30932474
DeepCCS	[M-H]-	179.545	30932474
DeepCCS	[M-2H]-	213.547	30932474
DeepCCS	[M+Na]+	189.623	30932474
AllCCS	[M+H]+	180.2	32859911
AllCCS	[M+H-H2O]+	177.2	32859911
AllCCS	[M+NH4]+	183.0	32859911
AllCCS	[M+Na]+	183.8	32859911
AllCCS	[M-H]-	184.9	32859911
AllCCS	[M+Na-2H]-	184.6	32859911
AllCCS	[M+HCOO]-	184.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Geranyloxy-7-methoxycoumarin	COC1=CC(OC\C=C(/C)CCC=C(C)C)=C2C=CC(=O)OC2=C1	3607.6	Standard polar	33892256
5-Geranyloxy-7-methoxycoumarin	COC1=CC(OC\C=C(/C)CCC=C(C)C)=C2C=CC(=O)OC2=C1	2687.8	Standard non polar	33892256
5-Geranyloxy-7-methoxycoumarin	COC1=CC(OC\C=C(/C)CCC=C(C)C)=C2C=CC(=O)OC2=C1	2833.7	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 - 5-Geranyloxy-7-methoxycoumarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ec-5394000000-4df6b182eab5e78e3f7b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Geranyloxy-7-methoxycoumarin 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 - 5-Geranyloxy-7-methoxycoumarin 10V, Negative-QTOF	splash10-004i-0329000000-c0a4b6032cdbc8c831f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Geranyloxy-7-methoxycoumarin 20V, Negative-QTOF	splash10-0006-0912000000-c6dabef31809f1935f77	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Geranyloxy-7-methoxycoumarin 40V, Negative-QTOF	splash10-0002-0900000000-50568fb5f1b239e2baaf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Geranyloxy-7-methoxycoumarin 10V, Negative-QTOF	splash10-004i-0109000000-e38a893ff4e0d24916f1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Geranyloxy-7-methoxycoumarin 20V, Negative-QTOF	splash10-0096-0911000000-0cf0241b578c276b525d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Geranyloxy-7-methoxycoumarin 40V, Negative-QTOF	splash10-03dj-0900000000-a8e9a830fdd16c70d1a2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Geranyloxy-7-methoxycoumarin 10V, Positive-QTOF	splash10-004i-0539000000-65d13c1da33aa0df0a85	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Geranyloxy-7-methoxycoumarin 20V, Positive-QTOF	splash10-05n3-5942000000-bfbda5842c74fddf367b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Geranyloxy-7-methoxycoumarin 40V, Positive-QTOF	splash10-0gbc-9500000000-aba7df5f0d91fe9f2fef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Geranyloxy-7-methoxycoumarin 10V, Positive-QTOF	splash10-0006-0903000000-4df63cf8b19e29dc767a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Geranyloxy-7-methoxycoumarin 20V, Positive-QTOF	splash10-000y-9400000000-b67280a0438715e283a4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Geranyloxy-7-methoxycoumarin 40V, Positive-QTOF	splash10-0006-8910000000-ac36a849c72510dbf538	2021-09-22	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

FDB010940

KNApSAcK ID

Not Available

Chemspider ID

4945553

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

5-Geranyloxy-7-methoxycoumarin

METLIN ID

Not Available

PubChem Compound

6441377

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1427481

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 5-Geranyloxy-7-methoxycoumarin (HMDB0032954)

MOL for HMDB0032954 (5-Geranyloxy-7-methoxycoumarin)

3D MOL for HMDB0032954 (5-Geranyloxy-7-methoxycoumarin)

3D SDF for HMDB0032954 (5-Geranyloxy-7-methoxycoumarin)

3D-SDF for HMDB0032954 (5-Geranyloxy-7-methoxycoumarin)

PDB for HMDB0032954 (5-Geranyloxy-7-methoxycoumarin)

3D PDB for HMDB0032954 (5-Geranyloxy-7-methoxycoumarin)

SMILES for HMDB0032954 (5-Geranyloxy-7-methoxycoumarin)

INCHI for HMDB0032954 (5-Geranyloxy-7-methoxycoumarin)

Structure for HMDB0032954 (5-Geranyloxy-7-methoxycoumarin)

3D Structure for HMDB0032954 (5-Geranyloxy-7-methoxycoumarin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra