NP-MRD: Showing NP-Card for 7-Acetyloxy-2-methylisoflavone (NP0056495)

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Record Information

Version

2.0

Created at

2022-04-28 02:15:56 UTC

Updated at

2022-04-28 02:15:56 UTC

NP-MRD ID

NP0056495

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-Acetyloxy-2-methylisoflavone

Description

7-Acetoxy-2-methylisoflavone belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, 7-acetoxy-2-methylisoflavone is considered to be a flavonoid lipid molecule. 7-Acetoxy-2-methylisoflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 7-Acetoxy-2-methylisoflavone has been detected, but not quantified in, herbs and spices and tea. 7-Acetyloxy-2-methylisoflavone is found in Glycyrrhiza glabra . This could make 7-acetoxy-2-methylisoflavone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -6.5666    2.2950   -0.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1077    2.1117   -0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3343    2.8396   -1.4310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5395    1.2379    0.1411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1604    1.0689    0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4374    1.9722    1.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0864    1.7378    1.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4422    0.6557    0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9102    0.4236    0.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5549    1.2469    1.4565 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4821   -0.6660    0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9082   -0.9166    0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3820   -1.3216    1.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7184   -1.5928    1.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6051   -1.4616    0.6318 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1015   -1.0516   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7680   -0.7780   -0.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7081   -1.5239   -0.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2929   -2.7169   -1.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5662   -1.2642   -0.7026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1653   -0.2367   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5158    0.0017   -0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7807    3.2649   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0583    2.2159    0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9930    1.5185   -1.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9284    2.8212    1.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4918    2.4419    1.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6948   -1.4406    2.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1104   -1.9181    2.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6641   -1.6776    0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7925   -0.9433   -1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3900   -0.4540   -1.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226   -2.5163   -2.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1813   -3.0954   -0.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5405   -3.5497   -1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0537   -0.7306   -0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 22  5  1  0
 17 12  1  0
 21  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  7 27  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
 22 36  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
M  END

  Mrv0541 02241218532D          

 22 24  0  0  0  0            999 V2000
    1.4433   -0.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417   -0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7008   -1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433   -0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7008    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7008    1.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433    2.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1859    2.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    2.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1859    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433    1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408    2.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1033   -1.4433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1033   -2.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458   -2.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433   -2.6808    0.0000 O   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
  2 16  1  0  0  0  0
  3  4  2  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6 19  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0056495

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H14O4/c1-11-17(13-6-4-3-5-7-13)18(20)15-9-8-14(22-12(2)19)10-16(15)21-11/h3-10H,1-2H3

> <INCHI_KEY>
DPIAJERHFDBLPT-UHFFFAOYSA-N

> <FORMULA>
C18H14O4

> <MOLECULAR_WEIGHT>
294.3014

> <EXACT_MASS>
294.089208936

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.366685098649697

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-4-oxo-3-phenyl-4H-chromen-7-yl acetate

> <ALOGPS_LOGP>
3.66

> <JCHEM_LOGP>
3.1469020390000004

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.352820389165702

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
82.69170000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-4-oxo-3-phenylchromen-7-yl 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       2.694  -0.384   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.308   0.384   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.078  -0.384   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.078  -1.924   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.308  -2.694   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.694  -1.924   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.694  -0.384   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.308   0.384   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.308   1.924   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.694   4.234   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.080   5.004   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.312   4.234   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.312   2.694   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.080   1.924   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.694   2.694   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.308   1.924   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.078   2.694   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.076   4.234   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.926  -2.694   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.926  -4.234   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.312  -5.004   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.694  -5.004   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    3    7    9                                                  
CONECT    9    8   17                                                       
CONECT   10   11   15                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   10   14   16                                                  
CONECT   16    2   15   17                                                  
CONECT   17    9   16   18                                                  
CONECT   18   17                                                            
CONECT   19    6   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
7-Acetyloxy-2-methylisoflavone	HMDB
2-Methyl-4-oxo-3-phenyl-4H-chromen-7-yl acetic acid	Generator

Chemical Formula

C₁₈H₁₄O₄

Average Mass

294.3014 Da

Monoisotopic Mass

294.08921 Da

IUPAC Name

2-methyl-4-oxo-3-phenyl-4H-chromen-7-yl acetate

Traditional Name

2-methyl-4-oxo-3-phenylchromen-7-yl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H14O4/c1-11-17(13-6-4-3-5-7-13)18(20)15-9-8-14(22-12(2)19)10-16(15)21-11/h3-10H,1-2H3

InChI Key

DPIAJERHFDBLPT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Glycyrrhiza glabra	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Isoflavone
Chromone
Benzopyran
1-benzopyran
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Carboxylic acid ester
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050003 )

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	3.66	ALOGPS
logP	3.15	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.69 m³·mol⁻¹	ChemAxon
Polarizability	31.37 Å³	ChemAxon
Number of Rings	3	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

HMDB0029364

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000431

KNApSAcK ID

C00009395

Chemspider ID

235753

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

268208

PDB ID

Not Available

ChEBI ID

486616

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 7-Acetyloxy-2-methylisoflavone (NP0056495)

MOL for NP0056495 (7-Acetyloxy-2-methylisoflavone)

3D MOL for NP0056495 (7-Acetyloxy-2-methylisoflavone)

3D SDF for NP0056495 (7-Acetyloxy-2-methylisoflavone)

3D-SDF for NP0056495 (7-Acetyloxy-2-methylisoflavone)

PDB for NP0056495 (7-Acetyloxy-2-methylisoflavone)

3D PDB for NP0056495 (7-Acetyloxy-2-methylisoflavone)

SMILES for NP0056495 (7-Acetyloxy-2-methylisoflavone)

INCHI for NP0056495 (7-Acetyloxy-2-methylisoflavone)

Structure for NP0056495 (7-Acetyloxy-2-methylisoflavone)

3D Structure for NP0056495 (7-Acetyloxy-2-methylisoflavone)