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Showing NP-Card for 5-Geranyloxy-7-methoxycoumarin (NP0047504)

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Record Information
Version2.0
Created at2022-03-17 20:41:17 UTC
Updated at2022-03-17 20:41:17 UTC
NP-MRD IDNP0047504
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Geranyloxy-7-methoxycoumarin
Description5-Geranyloxy-7-methoxycoumarin, also known as 5-(geranyloxy)-herniarin or 7-methoxy-5-geranoxycoumarin, belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 5-Geranyloxy-7-methoxycoumarin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5-Geranyloxy-7-methoxycoumarin has been detected, but not quantified in, a few different foods, such as citrus, lemons, and limes. This could make 5-geranyloxy-7-methoxycoumarin a potential biomarker for the consumption of these foods. 5-Geranyloxy-7-methoxycoumarin is a natural coumarin with the molecular formula C20H24O4.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0047504 (5-Geranyloxy-7-methoxycoumarin)


  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
Download

3D MOL for NP0047504 (5-Geranyloxy-7-methoxycoumarin)

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3D SDF for NP0047504 (5-Geranyloxy-7-methoxycoumarin)

  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>
NP0047504

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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3D-SDF for NP0047504 (5-Geranyloxy-7-methoxycoumarin)
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PDB for NP0047504 (5-Geranyloxy-7-methoxycoumarin)
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

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3D PDB for NP0047504 (5-Geranyloxy-7-methoxycoumarin)
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SMILES for NP0047504 (5-Geranyloxy-7-methoxycoumarin)
COC1=CC(OC\C=C(/C)CCC=C(C)C)=C2C=CC(=O)OC2=C1
Download
INCHI for NP0047504 (5-Geranyloxy-7-methoxycoumarin)
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+
Download
View in JSmol
Synonyms
ValueSource
5-((3,7-Dimethyl-2,6-octadienyl)oxy)-7-methoxycoumarinHMDB
5-(Geranyloxy)-7-methoxycoumarinHMDB
5-(Geranyloxy)-herniarinHMDB
5-Geranoxy-7-methoxycoumarinHMDB
7-Methoxy-5-geranoxycoumarinHMDB
SAMEHMDB
5-Geranyloxy-7-methoxycoumarinMeSH
Chemical FormulaC20H24O4
Average Mass328.4022 Da
Monoisotopic Mass328.16746 Da
IUPAC Name5-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7-methoxy-2H-chromen-2-one
Traditional Name5-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7-methoxychromen-2-one
CAS Registry Number7380-39-4
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 KeyWXUOSNJWDJOHGW-XNTDXEJSSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Citrus aurantiifoliaFooDB
Citrus limonFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTerpene lactones  
Direct ParentTerpene 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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.5ALOGPS
logP4.49ChemAxon
logS-5.3ALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity97.4 m³·mol⁻¹ChemAxon
Polarizability37.09 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032954  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010940  
KNApSAcK IDNot Available
Chemspider ID4945553  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link5-Geranyloxy-7-methoxycoumarin  
METLIN IDNot Available
PubChem Compound6441377  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References