NP-MRD: Showing NP-Card for 4-Methylumbelliferyl acetate (NP0047515)

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Record Information

Version

2.0

Created at

2022-03-17 20:41:28 UTC

Updated at

2022-03-17 20:41:28 UTC

NP-MRD ID

NP0047515

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Methylumbelliferyl acetate

Description

4-Methylumbelliferyl acetate, also known as 4-methyl-7-acetyloxy coumarin or 7-acetoxy-4-methylchromen-2-one, 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). 4-Methylumbelliferyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-Methylumbelliferyl acetate has been detected, but not quantified in, a few different foods, such as fenugreeks, green vegetables, and herbs and spices. This could make 4-methylumbelliferyl acetate a potential biomarker for the consumption of these foods. 4-Methylumbelliferyl acetate was first documented in 2002 (PMID: 11888210). An acetate ester consiting of umbelliferone carrying a 7-O-acetyl group (PMID: 23245880).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241214482D          

 16 17  0  0  0  0            999 V2000
   -4.6865    6.7842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9720    6.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2575    6.7842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5431    6.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5431    5.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8286    5.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1141    5.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1141    6.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3997    6.7842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3148    6.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0293    6.7842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3148    5.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3997    5.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3997    4.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8286    6.7842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9720    5.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 15  2  0  0  0  0
  4 15  1  0  0  0  0
  2 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047515

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1=CC=C2C(C)=CC(=O)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O4/c1-7-5-12(14)16-11-6-9(15-8(2)13)3-4-10(7)11/h3-6H,1-2H3

> <INCHI_KEY>
HXVZGASCDAGAPS-UHFFFAOYSA-N

> <FORMULA>
C12H10O4

> <MOLECULAR_WEIGHT>
218.2054

> <EXACT_MASS>
218.057908808

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
21.95338195692243

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methyl-2-oxo-2H-chromen-7-yl acetate

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
1.6900151946666662

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.734862938872942

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
56.963

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methylumbelliferyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -8.748  12.664   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -7.414  11.894   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.081  12.664   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.747  11.894   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.747  10.354   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.413   9.584   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.080  10.354   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.080  11.894   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.746  12.664   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.588  11.894   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.921  12.664   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.588  10.354   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.746   9.584   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.746   8.044   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.413  12.664   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.414  10.354   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13                                                            
CONECT   15    8    4                                                       
CONECT   16    2                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
4-Methyl-7-acetyloxy coumarin	ChEBI
7-(Acetyloxy)-4-methyl-2-benzopyrone	ChEBI
7-(Acetyloxy)-4-methyl-2H-1-benzopyran-2-one	ChEBI
7-Acetoxy-4-methylchromen-2-one	ChEBI
7-Acetoxy-4-methylcoumarin	ChEBI
beta-Methylumbelliferyl acetate	ChEBI
b-Methylumbelliferyl acetate	Generator
b-Methylumbelliferyl acetic acid	Generator
beta-Methylumbelliferyl acetic acid	Generator
Β-methylumbelliferyl acetate	Generator
Β-methylumbelliferyl acetic acid	Generator
4-Methylumbelliferyl acetic acid	Generator
7-Acetoxy-4-methyl-2H-1-benzopyran-2-one	HMDB
4-MUA	HMDB
7AMC	HMDB

Chemical Formula

C₁₂H₁₀O₄

Average Mass

218.2054 Da

Monoisotopic Mass

218.05791 Da

IUPAC Name

4-methyl-2-oxo-2H-chromen-7-yl acetate

Traditional Name

4-methylumbelliferyl acetate

CAS Registry Number

2747-05-9

SMILES

CC(=O)OC1=CC=C2C(C)=CC(=O)OC2=C1

InChI Identifier

InChI=1S/C12H10O4/c1-7-5-12(14)16-11-6-9(15-8(2)13)3-4-10(7)11/h3-6H,1-2H3

InChI Key

HXVZGASCDAGAPS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trigonella foenum-graecum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

acetate ester (CHEBI:17763 )
a small molecule (CPD-181 )

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	2.03	ALOGPS
logP	1.69	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	56.96 m³·mol⁻¹	ChemAxon
Polarizability	21.95 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

HMDB0032989

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010978

KNApSAcK ID

Not Available

Chemspider ID

359

KEGG Compound ID

C03837

BioCyc ID

CPD-181

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

366

PDB ID

Not Available

ChEBI ID

17763

Good Scents ID

Not Available

References

General References

Kordic S, Cummins I, Edwards R: Cloning and characterization of an S-formylglutathione hydrolase from Arabidopsis thaliana. Arch Biochem Biophys. 2002 Mar 15;399(2):232-8. doi: 10.1006/abbi.2002.2772. [PubMed:11888210 ]
Cunha E, Pinto PC, Carvalho JP, Saraiva ML: Automated carboxylesterase assay for the evaluation of ionic liquids' human toxicity. J Hazard Mater. 2013 Jan 15;244-245:563-9. doi: 10.1016/j.jhazmat.2012.10.045. Epub 2012 Nov 5. [PubMed:23245880 ]

Showing NP-Card for 4-Methylumbelliferyl acetate (NP0047515)

MOL for NP0047515 (4-Methylumbelliferyl acetate)

3D MOL for NP0047515 (4-Methylumbelliferyl acetate)

3D SDF for NP0047515 (4-Methylumbelliferyl acetate)

3D-SDF for NP0047515 (4-Methylumbelliferyl acetate)

PDB for NP0047515 (4-Methylumbelliferyl acetate)

3D PDB for NP0047515 (4-Methylumbelliferyl acetate)

SMILES for NP0047515 (4-Methylumbelliferyl acetate)

INCHI for NP0047515 (4-Methylumbelliferyl acetate)

Structure for NP0047515 (4-Methylumbelliferyl acetate)

3D Structure for NP0047515 (4-Methylumbelliferyl acetate)