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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:23:52 UTC

Update Date

2023-02-21 17:26:51 UTC

HMDB ID

HMDB0039045

Secondary Accession Numbers

HMDB39045

Metabolite Identification

Common Name

8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one

Description

8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-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). 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one has been detected, but not quantified in, green vegetables. This could make 8H-1,3-dioxolo[4,5-H][1]benzopyran-8-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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>
HMDB0039045

> <DATABASE_NAME>
hmdb

> <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 View NMR Assignments View Stereo Labels

Synonyms

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

Chemical Formula

C₁₀H₆O₄

Average Molecular Weight

190.1522

Monoisotopic Molecular Weight

190.02660868

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

4361-93-7

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

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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039045)
Cytoplasm (HMDB: HMDB0039045)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039045)

Source

Exogenous

Food

Food (HMDB: HMDB0039045)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0039045)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039045)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	187 - 189 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.4 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.68	31661259
DarkChem	[M-H]-	138.153	31661259
DeepCCS	[M+H]+	140.289	30932474
DeepCCS	[M-H]-	137.894	30932474
DeepCCS	[M-2H]-	173.073	30932474
DeepCCS	[M+Na]+	147.543	30932474
AllCCS	[M+H]+	138.0	32859911
AllCCS	[M+H-H2O]+	133.4	32859911
AllCCS	[M+NH4]+	142.2	32859911
AllCCS	[M+Na]+	143.5	32859911
AllCCS	[M-H]-	137.5	32859911
AllCCS	[M+Na-2H]-	137.2	32859911
AllCCS	[M+HCOO]-	137.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one	O=C1OC2=C(C=CC3=C2OCO3)C=C1	2715.5	Standard polar	33892256
8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one	O=C1OC2=C(C=CC3=C2OCO3)C=C1	1737.0	Standard non polar	33892256
8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one	O=C1OC2=C(C=CC3=C2OCO3)C=C1	1854.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-2900000000-e584206f8357f666a382	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one 10V, Positive-QTOF	splash10-0006-0900000000-db67cc7b5ebaf8c5176f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one 20V, Positive-QTOF	splash10-0006-0900000000-89e2a08d7dbedd711bd9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one 40V, Positive-QTOF	splash10-03mj-0900000000-88d03b4e9ded7c62255c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one 10V, Negative-QTOF	splash10-000i-0900000000-6172c3ccdf57842e5faf	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one 20V, Negative-QTOF	splash10-000i-0900000000-d818cefd0f3eee2e4c52	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one 40V, Negative-QTOF	splash10-0002-0900000000-0c30853842131508a898	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one 10V, Positive-QTOF	splash10-0006-0900000000-64124938617c6e0bfdf8	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one 20V, Positive-QTOF	splash10-0006-0900000000-bd7814cd866b65acb03c	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one 40V, Positive-QTOF	splash10-03di-2900000000-08b70dcebcaf8c03b950	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one 10V, Negative-QTOF	splash10-000i-0900000000-949d3fd145cdfd4ccec2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one 20V, Negative-QTOF	splash10-03dr-0900000000-bc9e4ba5ff100873f534	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one 40V, Negative-QTOF	splash10-03di-1900000000-194073e5ceb70a6690ec	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

173903

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one (HMDB0039045)

MOL for HMDB0039045 (8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one)

3D MOL for HMDB0039045 (8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one)

3D SDF for HMDB0039045 (8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one)

3D-SDF for HMDB0039045 (8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one)

PDB for HMDB0039045 (8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one)

3D PDB for HMDB0039045 (8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one)

SMILES for HMDB0039045 (8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one)

INCHI for HMDB0039045 (8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one)

Structure for HMDB0039045 (8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one)

3D Structure for HMDB0039045 (8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra