NP-MRD: Showing NP-Card for Medicagol (NP0047755)

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Record Information

Version

2.0

Created at

2022-03-17 20:45:26 UTC

Updated at

2022-03-17 20:45:26 UTC

NP-MRD ID

NP0047755

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Medicagol

Description

Medicagol belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, medicagol is considered to be a flavonoid lipid molecule. Medicagol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Medicagol has been detected, but not quantified in, several different foods, such as alfalfa, cereals and cereal products, pulses, herbs and spices, and chickpea. This could make medicagol a potential biomarker for the consumption of these foods. Medicagol is found in Cicer anatolicum, Cicer bijugum, Cicer canariensis, Cicer chorassanicum, Cicer cuneatum, Cicer echinospermum, Cicer judicum, Cicer macracanthum, Cicer nuristanicum, Cicer oxyodon, Cicer pinnatifidum, Cicer yamashitae, Cladrastis platycarpa, Cyclopia intermedia, Cyclopia sessiliflora, Dalbergia oliveri, Dalbergia stevensonii, Euchresta formosana, Euchresta japonica, Flemingia macrophylla, Galega officinalis, Maackia amurensis, Sophora chrysophylla, Sophora microphylla, Sophora moorcroftiana, Sophora tetraptera , Spatholobus suberectus, Sophora japonica and Trifolium pratense . Found in alfalfa (Medicago sativa) having viral leaf spot infectionsand is also from Cicer arietinum (chick pea) and Trifolium pratense (red clover).

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061307232D          

 22 26  0  0  0  0            999 V2000
   -0.4612   -0.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3618   -0.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618   -1.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5998   -1.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6578    0.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6116   -0.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8230   -0.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8230   -0.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9003   -1.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612   -1.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9293   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3283   -1.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3573   -0.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1072   -1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6460   -0.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7454   -2.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6460   -0.9397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2065   -2.8198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1035   -1.4996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1504   -0.1656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1541   -0.0603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9224   -2.1931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
  8  2  1  0  0  0  0
  9  4  2  0  0  0  0
 10  3  1  0  0  0  0
 10  8  2  0  0  0  0
 11  5  2  0  0  0  0
 11  9  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13 12  2  0  0  0  0
 14  9  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  2  0  0  0  0
 16 14  1  0  0  0  0
 17  7  1  0  0  0  0
 18 16  2  0  0  0  0
 19  6  1  0  0  0  0
 19 12  1  0  0  0  0
 20  6  1  0  0  0  0
 20 13  1  0  0  0  0
 21 11  1  0  0  0  0
 21 15  1  0  0  0  0
 22 10  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047755

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1)C1=C(C3=CC4=C(OCO4)C=C3O1)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H8O6/c17-7-1-2-8-10(3-7)22-16(18)14-9-4-12-13(20-6-19-12)5-11(9)21-15(8)14/h1-5,17H,6H2

> <INCHI_KEY>
URMVEUAWRUQHON-UHFFFAOYSA-N

> <FORMULA>
C16H8O6

> <MOLECULAR_WEIGHT>
296.2311

> <EXACT_MASS>
296.032087988

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.02475642612746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2,4(8),9,13(18),14,16-heptaen-20-one

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
2.324120111666666

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.117088387657561

> <JCHEM_PKA_STRONGEST_BASIC>
-4.198783131496715

> <JCHEM_POLAR_SURFACE_AREA>
78.13000000000001

> <JCHEM_REFRACTIVITY>
73.4055

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
medicagol

> <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      -0.861  -0.263   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.675  -0.156   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.675  -2.924   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.720  -2.995   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.828   0.083   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.475  -1.586   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.536  -1.647   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.536  -1.433   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.414  -2.179   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.861  -2.817   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.468  -0.640   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.079  -2.272   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.134  -0.733   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.933  -2.603   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.073  -1.326   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.258  -3.987   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.073  -1.754   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.119  -5.264   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.527  -2.799   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.614  -0.309   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.021  -0.113   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.722  -4.094   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    8                                                       
CONECT    3    7   10                                                       
CONECT    4    9   12                                                       
CONECT    5   11   13                                                       
CONECT    6   19   20                                                       
CONECT    7    1    3   17                                                  
CONECT    8    2   10   15                                                  
CONECT    9    4   11   14                                                  
CONECT   10    3    8   22                                                  
CONECT   11    5    9   21                                                  
CONECT   12    4   13   19                                                  
CONECT   13    5   12   20                                                  
CONECT   14    9   15   16                                                  
CONECT   15    8   14   21                                                  
CONECT   16   14   18   22                                                  
CONECT   17    7                                                            
CONECT   18   16                                                            
CONECT   19    6   12                                                       
CONECT   20    6   13                                                       
CONECT   21   11   15                                                       
CONECT   22   10   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-6H-[1,3]dioxolo[5,6]benzofuro[3,2-c][1]-benzopyran-6-one, 9ci	HMDB
3-Hydroxy-8,9-methylenedioxycoumestan	HMDB
7-Hydroxy-11,12-methylenedioxycoumestan	HMDB
7-Hydroxy-5',6'-methylenedioxybenzofurano[3',2':3,4]coumarin	HMDB

Chemical Formula

C₁₆H₈O₆

Average Mass

296.2311 Da

Monoisotopic Mass

296.03209 Da

IUPAC Name

16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2,4(8),9,13(18),14,16-heptaen-20-one

Traditional Name

medicagol

CAS Registry Number

1983-72-8

SMILES

OC1=CC2=C(C=C1)C1=C(C3=CC4=C(OCO4)C=C3O1)C(=O)O2

InChI Identifier

InChI=1S/C16H8O6/c17-7-1-2-8-10(3-7)22-16(18)14-9-4-12-13(20-6-19-12)5-11(9)21-15(8)14/h1-5,17H,6H2

InChI Key

URMVEUAWRUQHON-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cicer anatolicum	Plant	KNApSAcK
Cicer arietinum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cicer bijugum	Plant	KNApSAcK
Cicer canariensis	Plant	KNApSAcK
Cicer chorassanicum	Plant	KNApSAcK
Cicer cuneatum	Plant	KNApSAcK
Cicer echinospermum	Plant	KNApSAcK
Cicer judicum	Plant	KNApSAcK
Cicer macracanthum	Plant	KNApSAcK
Cicer nuristanicum	LOTUS Database	35616633
Cicer oxyodon	Plant	KNApSAcK
Cicer pinnatifidum	Plant	KNApSAcK
Cicer yamashitae	Plant	KNApSAcK
Cladrastis platycarpa	LOTUS Database	35616633
Cyclopia intermedia	LOTUS Database	35616633
Cyclopia sessiliflora	LOTUS Database	35616633
Dalbergia oliveri	Plant	KNApSAcK
Dalbergia stevensonii	Plant	KNApSAcK
Euchresta formosana	LOTUS Database	35616633
Euchresta japonica	LOTUS Database	35616633
Flemingia macrophylla	LOTUS Database	35616633
Galega officinalis	LOTUS Database	35616633
Maackia amurensis	LOTUS Database	35616633
Medicago sativa	FooDB	KNAPSACK
Sophora chrysophylla	LOTUS Database	35616633
Sophora microphylla	LOTUS Database	35616633
Sophora moorcroftiana	LOTUS Database	35616633
Sophora tetraptera	Plant	KNApSAcK
Spatholobus suberectus	LOTUS Database	35616633
Styphnolobium japonicum	Plant	KNApSAcK
Trifolium pratense	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Angular furanocoumarin
Furanocoumarin
Coumarin
Benzopyran
1-benzopyran
Benzodioxole
Benzofuran
Furopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Acetal
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090025 )

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	2.45	ALOGPS
logP	2.32	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.12	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	78.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.41 m³·mol⁻¹	ChemAxon
Polarizability	29.02 Å³	ChemAxon
Number of Rings	5	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

HMDB0033831

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011998

KNApSAcK ID

C00009760

Chemspider ID

4477641

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319322

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Medicagol (NP0047755)

MOL for NP0047755 (Medicagol)

3D MOL for NP0047755 (Medicagol)

3D SDF for NP0047755 (Medicagol)

3D-SDF for NP0047755 (Medicagol)

PDB for NP0047755 (Medicagol)

3D PDB for NP0047755 (Medicagol)

SMILES for NP0047755 (Medicagol)

INCHI for NP0047755 (Medicagol)

Structure for NP0047755 (Medicagol)

3D Structure for NP0047755 (Medicagol)