NP-MRD: Showing NP-Card for 4-Methylaesculetin (NP0046267)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 19:55:17 UTC

Updated at

2022-03-17 19:55:17 UTC

NP-MRD ID

NP0046267

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Methylaesculetin

Description

4-Methylaesculetin belongs to the class of organic compounds known as 6,7-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at positions 6 and 7 of the coumarin skeleton, respectively. 4-Methylaesculetin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-Methylaesculetin has been detected, but not quantified in, dills. This could make 4-methylaesculetin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309191702172D          

 14 15  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    1.4289    0.0000    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
    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
    2.1434   -1.2375    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
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
  9  6  2  0  0  0  0
 10  2  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13 10  2  0  0  0  0
 14  9  1  0  0  0  0
 14 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046267

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)OC2=C1C=C(O)C(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H8O4/c1-5-2-10(13)14-9-4-8(12)7(11)3-6(5)9/h2-4,11-12H,1H3

> <INCHI_KEY>
KVOJTUXGYQVLAJ-UHFFFAOYSA-N

> <FORMULA>
C10H8O4

> <MOLECULAR_WEIGHT>
192.17

> <EXACT_MASS>
192.042258738

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
18.356958434042703

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,7-dihydroxy-4-methyl-2H-chromen-2-one

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
1.475623577

> <ALOGPS_LOGS>
-1.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.25109934974998

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.879867262125235

> <JCHEM_PKA_STRONGEST_BASIC>
-6.266889551861909

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
49.79240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7-dihydroxy-4-methylcoumarin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-SEP-17         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    5   10                                                       
CONECT    3    6    7                                                       
CONECT    4    8    9                                                       
CONECT    5    1    2    6                                                  
CONECT    6    3    5    9                                                  
CONECT    7    3    8   11                                                  
CONECT    8    4    7   12                                                  
CONECT    9    4    6   14                                                  
CONECT   10    2   13   14                                                  
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13   10                                                            
CONECT   14    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
6,7-Dihydroxy-4-methylcoumarin	MeSH
DHMC-6,7	MeSH

Chemical Formula

C₁₀H₈O₄

Average Mass

192.1700 Da

Monoisotopic Mass

192.04226 Da

IUPAC Name

6,7-dihydroxy-4-methyl-2H-chromen-2-one

Traditional Name

6,7-dihydroxy-4-methylcoumarin

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)OC2=C1C=C(O)C(O)=C2

InChI Identifier

InChI=1S/C10H8O4/c1-5-2-10(13)14-9-4-8(12)7(11)3-6(5)9/h2-4,11-12H,1H3

InChI Key

KVOJTUXGYQVLAJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anethum graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6,7-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at positions 6 and 7 of the coumarin skeleton, respectively.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

6,7-dihydroxycoumarins

Alternative Parents

Substituents

6,7-dihydroxycoumarin
7-hydroxycoumarin
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
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	1.68	ALOGPS
logP	1.48	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	7.88	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	49.79 m³·mol⁻¹	ChemAxon
Polarizability	18.36 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

HMDB0136755

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003829

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319502

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-Methylaesculetin (NP0046267)

MOL for NP0046267 (4-Methylaesculetin)

3D MOL for NP0046267 (4-Methylaesculetin)

3D SDF for NP0046267 (4-Methylaesculetin)

3D-SDF for NP0046267 (4-Methylaesculetin)

PDB for NP0046267 (4-Methylaesculetin)

3D PDB for NP0046267 (4-Methylaesculetin)

SMILES for NP0046267 (4-Methylaesculetin)

INCHI for NP0046267 (4-Methylaesculetin)

Structure for NP0046267 (4-Methylaesculetin)

3D Structure for NP0046267 (4-Methylaesculetin)