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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:44 UTC

Update Date

2023-02-21 17:19:39 UTC

HMDB ID

HMDB0030577

Secondary Accession Numbers

HMDB30577

Metabolite Identification

Common Name

1-Oxo-1H-2-benzopyran-3-carboxaldehyde

Description

1-Oxo-1H-2-benzopyran-3-carboxaldehyde, also known as 3-formylisocoumarin or artemidinal, belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1. Based on a literature review very few articles have been published on 1-Oxo-1H-2-benzopyran-3-carboxaldehyde.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   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       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    9                                                       
CONECT    5    7    8                                                       
CONECT    6    8   11                                                       
CONECT    7    3    5    9                                                  
CONECT    8    5    6   13                                                  
CONECT    9    4    7   10                                                  
CONECT   10    9   12   13                                                  
CONECT   11    6                                                            
CONECT   12   10                                                            
CONECT   13    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Formylisocoumarin	HMDB
Artemidinal	HMDB
Isocoumarin-3-carboxaldehyde	HMDB

Chemical Formula

C₁₀H₆O₃

Average Molecular Weight

174.1528

Monoisotopic Molecular Weight

174.031694058

IUPAC Name

1-oxo-1H-isochromene-3-carbaldehyde

Traditional Name

1-oxoisochromene-3-carbaldehyde

CAS Registry Number

34328-51-3

SMILES

O=CC1=CC2=CC=CC=C2C(=O)O1

InChI Identifier

InChI=1S/C10H6O3/c11-6-8-5-7-3-1-2-4-9(7)10(12)13-8/h1-6H

InChI Key

ALHVSADYXQWYJH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isocoumarins and derivatives

Sub Class

Not Available

Direct Parent

Isocoumarins and derivatives

Alternative Parents

Substituents

Isocoumarin
Benzopyran
2-benzopyran
Pyranone
Aryl-aldehyde
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Aldehyde
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: HMDB0030577)
Cytoplasm (HMDB: HMDB0030577)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030577)

Source

Endogenous

Endogenous (HMDB: HMDB0030577)

Plant

Plant (HMDB: HMDB0030577)

Exogenous

Food

Food (HMDB: HMDB0030577)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	178 - 179 °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	0.41 g/L	ALOGPS
logP	1.45	ALOGPS
logP	1.52	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.87 m³·mol⁻¹	ChemAxon
Polarizability	16.57 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	136.342	31661259
DarkChem	[M-H]-	133.002	31661259
DeepCCS	[M+H]+	134.893	30932474
DeepCCS	[M-H]-	131.549	30932474
DeepCCS	[M-2H]-	168.557	30932474
DeepCCS	[M+Na]+	143.954	30932474
AllCCS	[M+H]+	135.4	32859911
AllCCS	[M+H-H2O]+	130.8	32859911
AllCCS	[M+NH4]+	139.6	32859911
AllCCS	[M+Na]+	140.8	32859911
AllCCS	[M-H]-	134.2	32859911
AllCCS	[M+Na-2H]-	134.4	32859911
AllCCS	[M+HCOO]-	134.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Oxo-1H-2-benzopyran-3-carboxaldehyde	O=CC1=CC2=CC=CC=C2C(=O)O1	2575.7	Standard polar	33892256
1-Oxo-1H-2-benzopyran-3-carboxaldehyde	O=CC1=CC2=CC=CC=C2C(=O)O1	1601.2	Standard non polar	33892256
1-Oxo-1H-2-benzopyran-3-carboxaldehyde	O=CC1=CC2=CC=CC=C2C(=O)O1	1684.2	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 - 1-Oxo-1H-2-benzopyran-3-carboxaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-016r-1900000000-0816b6712acbbb250018	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Oxo-1H-2-benzopyran-3-carboxaldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Oxo-1H-2-benzopyran-3-carboxaldehyde 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 - 1-Oxo-1H-2-benzopyran-3-carboxaldehyde 10V, Negative-QTOF	splash10-00di-0900000000-2c694118e90a5c40146d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Oxo-1H-2-benzopyran-3-carboxaldehyde 20V, Negative-QTOF	splash10-00di-0900000000-8ee62ec19907092edffb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Oxo-1H-2-benzopyran-3-carboxaldehyde 40V, Negative-QTOF	splash10-004i-0900000000-3496fb394bdf2a026717	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Oxo-1H-2-benzopyran-3-carboxaldehyde 10V, Negative-QTOF	splash10-0002-0900000000-b5d5dc2c9b568bc3f334	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Oxo-1H-2-benzopyran-3-carboxaldehyde 20V, Negative-QTOF	splash10-0002-0900000000-03134310f0e93c9ac85a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Oxo-1H-2-benzopyran-3-carboxaldehyde 40V, Negative-QTOF	splash10-00kb-0900000000-ab7cfd02425cd39c8099	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Oxo-1H-2-benzopyran-3-carboxaldehyde 10V, Positive-QTOF	splash10-004i-0900000000-40f662a48682becd6b27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Oxo-1H-2-benzopyran-3-carboxaldehyde 20V, Positive-QTOF	splash10-004i-0900000000-afce505ec43ef2b717ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Oxo-1H-2-benzopyran-3-carboxaldehyde 40V, Positive-QTOF	splash10-0zir-3900000000-5f7e44ce8c6eb01a9159	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Oxo-1H-2-benzopyran-3-carboxaldehyde 10V, Positive-QTOF	splash10-004j-0900000000-38fd18204281fa0d10d4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Oxo-1H-2-benzopyran-3-carboxaldehyde 20V, Positive-QTOF	splash10-002b-0900000000-0a68ba3a48aa15e5f722	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Oxo-1H-2-benzopyran-3-carboxaldehyde 40V, Positive-QTOF	splash10-0ufr-5900000000-02de4c9c21fafd0dd1be	2021-09-23	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

FDB002467

KNApSAcK ID

C00054903

Chemspider ID

27021040

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12582097

PDB ID

Not Available

ChEBI ID

173471

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.. .

Enzymes

Enzyme Details

1. Carbonyl reductase [NADPH] 1

General function:: Involved in oxidoreductase activity
Specific function:: NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:: CBR1
Uniprot ID:: P16152
Molecular weight:: 30374.73

Reactions

1-Oxo-1H-2-benzopyran-3-carboxaldehyde → 3-(hydroxymethyl)-1H-isochromen-1-one	details

Showing metabocard for 1-Oxo-1H-2-benzopyran-3-carboxaldehyde (HMDB0030577)

MOL for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

3D MOL for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

3D SDF for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

3D-SDF for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

PDB for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

3D PDB for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

SMILES for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

INCHI for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

Structure for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

3D Structure for HMDB0030577 (1-Oxo-1H-2-benzopyran-3-carboxaldehyde)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

Reactions