NP-MRD: Showing NP-Card for 5,7-Dimethoxycoumarin (NP0047503)

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Record Information

Version

2.0

Created at

2022-03-17 20:41:16 UTC

Updated at

2022-03-17 20:41:16 UTC

NP-MRD ID

NP0047503

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7-Dimethoxycoumarin

Description

Citropten, also known as limettin or omphamurrayin, belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Citropten is an extremely weak basic (essentially neutral) compound (based on its pKa). Citropten is a natural organic compound with the molecular formula C11H10O4. Outside of the human body, Citropten has been detected, but not quantified in, a few different foods, such as citrus, lemons, and limes. 5,7-Dimethoxycoumarin is found in Boenninghausenia albiflora, Bupleurum salicifolium, Citrus bergamia, Citrus medica, Citrus trifoliata, Dinosperma melanophloium, Edgeworthia chrysantha, Heracleum mantegazzianum, Melicope borbonica, Metrodorea nigra and Toddalia asiatica. This could make citropten a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061306492D          

 15 16  0  0  0  0            999 V2000
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    2.8579    2.4750    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
  4  3  2  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 11  4  1  0  0  0  0
 12 11  2  0  0  0  0
 13  1  1  0  0  0  0
 13  7  1  0  0  0  0
 14  2  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047503

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2C=CC(=O)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O4/c1-13-7-5-9(14-2)8-3-4-11(12)15-10(8)6-7/h3-6H,1-2H3

> <INCHI_KEY>
NXJCRELRQHZBQA-UHFFFAOYSA-N

> <FORMULA>
C11H10O4

> <MOLECULAR_WEIGHT>
206.1947

> <EXACT_MASS>
206.057908808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.36190716820778

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dimethoxy-2H-chromen-2-one

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
1.4680170839999995

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5508691816281095

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
54.475000000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
limettin

> <JCHEM_VEBER_RULE>
0

$$$$

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       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3    4    8                                                       
CONECT    4    3   11                                                       
CONECT    5    7    9                                                       
CONECT    6    7   10                                                       
CONECT    7    5    6   13                                                  
CONECT    8    3    9   10                                                  
CONECT    9    5    8   14                                                  
CONECT   10    6    8   15                                                  
CONECT   11    4   12   15                                                  
CONECT   12   11                                                            
CONECT   13    1    7                                                       
CONECT   14    2    9                                                       
CONECT   15   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
57-Dimethoxycoumarin	HMDB
5, 7-Dimethoxycoumarin	HMDB
5,7-Dimethoxy-2-benzopyrone	HMDB
5,7-Dimethoxy-2H-1-benzo-pyran-2-one	HMDB
5,7-Dimethoxy-2H-1-benzopyran-2-one	HMDB
5,7-Dimethoxy-2H-chromen-2-one	HMDB
5,7-Dimethoxy-coumarin	HMDB
5,7-Dimethoxycoumarin	HMDB
5,7-Dimethyloxy-2H-1-benzopyran-2-one	HMDB
Citraptene	HMDB
Citroptene	HMDB
Limetin	HMDB
Limettin	HMDB
Omphamurrayin	HMDB
Citropten	MeSH

Chemical Formula

C₁₁H₁₀O₄

Average Mass

206.1947 Da

Monoisotopic Mass

206.05791 Da

IUPAC Name

5,7-dimethoxy-2H-chromen-2-one

Traditional Name

limettin

CAS Registry Number

487-06-9

SMILES

COC1=CC(OC)=C2C=CC(=O)OC2=C1

InChI Identifier

InChI=1S/C11H10O4/c1-13-7-5-9(14-2)8-3-4-11(12)15-10(8)6-7/h3-6H,1-2H3

InChI Key

NXJCRELRQHZBQA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Boenninghausenia albiflora	LOTUS Database	35616633
Bupleurum salicifolium	LOTUS Database	35616633
Citrus aurantiifolia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus bergamia	LOTUS Database	35616633
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus medica	LOTUS Database	35616633
Citrus trifoliata	LOTUS Database	35616633
Dinosperma melanophloium	LOTUS Database	35616633
Edgeworthia chrysantha	LOTUS Database	35616633
Heracleum mantegazzianum	LOTUS Database	35616633
Melicope borbonica	LOTUS Database	35616633
Metrodorea nigra	LOTUS Database	35616633
Toddalia asiatica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.79	ALOGPS
logP	1.47	ChemAxon
logS	-2.7	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	2	ChemAxon
Refractivity	54.48 m³·mol⁻¹	ChemAxon
Polarizability	20.36 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

External Links

HMDB ID

HMDB0032952

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010938

KNApSAcK ID

Not Available

Chemspider ID

2673

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Citropten

METLIN ID

Not Available

PubChem Compound

2775

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5,7-Dimethoxycoumarin (NP0047503)

MOL for NP0047503 (5,7-Dimethoxycoumarin)

3D MOL for NP0047503 (5,7-Dimethoxycoumarin)

3D SDF for NP0047503 (5,7-Dimethoxycoumarin)

3D-SDF for NP0047503 (5,7-Dimethoxycoumarin)

PDB for NP0047503 (5,7-Dimethoxycoumarin)

3D PDB for NP0047503 (5,7-Dimethoxycoumarin)

SMILES for NP0047503 (5,7-Dimethoxycoumarin)

INCHI for NP0047503 (5,7-Dimethoxycoumarin)

Structure for NP0047503 (5,7-Dimethoxycoumarin)

3D Structure for NP0047503 (5,7-Dimethoxycoumarin)