NP-MRD: Showing NP-Card for 2h-[1,3]dioxolo[4,5-h]chromen-8-one (NP0157698)

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Record Information

Version

2.0

Created at

2022-09-02 15:08:42 UTC

Updated at

2022-09-02 15:08:42 UTC

NP-MRD ID

NP0157698

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2h-[1,3]dioxolo[4,5-h]chromen-8-one

Description

8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one, also known as 7,8-methylenedioxycoumarin, 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). 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one has been detected, but not quantified in, green vegetables. 2h-[1,3]dioxolo[4,5-h]chromen-8-one is found in Artemisia dracunculus and Pterocaulon polystachyum. This could make 8H-1,3-dioxolo[4,5-H][1]benzopyran-8-one a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061310482D          

 14 16  0  0  0  0            999 V2000
    3.4766    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2150   -0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608    0.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640   -0.2691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558   -0.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 12  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157698

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1OC2=C(C=CC3=C2OCO3)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H6O4/c11-8-4-2-6-1-3-7-10(9(6)14-8)13-5-12-7/h1-4H,5H2

> <INCHI_KEY>
OZRUEXJYRHKIJC-UHFFFAOYSA-N

> <FORMULA>
C10H6O4

> <MOLECULAR_WEIGHT>
190.1522

> <EXACT_MASS>
190.02660868

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
17.67080279877326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2H,8H-[1,3]dioxolo[4,5-h]chromen-8-one

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
1.4065930829999997

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.781088895813049

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
47.31550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2H-[1,3]dioxolo[4,5-h]chromen-8-one

> <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       6.490   3.388   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.840   2.127   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.950   3.340   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.651   0.818   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.614   0.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.301   2.079   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.222   1.983   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.923  -0.539   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.573   0.722   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.034   0.674   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.735  -1.848   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.727   1.616   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.039  -0.502   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       7.384  -0.587   0.000  0.00  0.00           O+0
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5   12   13                                                       
CONECT    6    1    2    9                                                  
CONECT    7    3   10   12                                                  
CONECT    8    4   11   14                                                  
CONECT    9    6   10   14                                                  
CONECT   10    7    9   13                                                  
CONECT   11    8                                                            
CONECT   12    5    7                                                       
CONECT   13    5   10                                                       
CONECT   14    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END

View in JSmol

Synonyms

Value	Source
7,8-Methylenedioxycoumarin	HMDB
8H-1,3-Dioxolo[4,5-H][1]benzopyran-8-one, 9ci	HMDB

Chemical Formula

C₁₀H₆O₄

Average Mass

190.1522 Da

Monoisotopic Mass

190.02661 Da

IUPAC Name

2H,8H-[1,3]dioxolo[4,5-h]chromen-8-one

Traditional Name

2H-[1,3]dioxolo[4,5-h]chromen-8-one

CAS Registry Number

Not Available

SMILES

O=C1OC2=C(C=CC3=C2OCO3)C=C1

InChI Identifier

InChI=1S/C10H6O4/c11-8-4-2-6-1-3-7-10(9(6)14-8)13-5-12-7/h1-4H,5H2

InChI Key

OZRUEXJYRHKIJC-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Artemisia dracunculus	LOTUS Database	35616633
Pterocaulon polystachyum	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
Benzodioxole
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Acetal
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	1.21	ALOGPS
logP	1.41	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Basic)	-4.8	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	0	ChemAxon
Refractivity	47.32 m³·mol⁻¹	ChemAxon
Polarizability	17.67 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

HMDB0039045

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018542

KNApSAcK ID

Not Available

Chemspider ID

11497732

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13704003

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2h-[1,3]dioxolo[4,5-h]chromen-8-one (NP0157698)

MOL for NP0157698 (2h-[1,3]dioxolo[4,5-h]chromen-8-one)

3D MOL for NP0157698 (2h-[1,3]dioxolo[4,5-h]chromen-8-one)

3D SDF for NP0157698 (2h-[1,3]dioxolo[4,5-h]chromen-8-one)

3D-SDF for NP0157698 (2h-[1,3]dioxolo[4,5-h]chromen-8-one)

PDB for NP0157698 (2h-[1,3]dioxolo[4,5-h]chromen-8-one)

3D PDB for NP0157698 (2h-[1,3]dioxolo[4,5-h]chromen-8-one)

SMILES for NP0157698 (2h-[1,3]dioxolo[4,5-h]chromen-8-one)

INCHI for NP0157698 (2h-[1,3]dioxolo[4,5-h]chromen-8-one)

Structure for NP0157698 (2h-[1,3]dioxolo[4,5-h]chromen-8-one)

3D Structure for NP0157698 (2h-[1,3]dioxolo[4,5-h]chromen-8-one)