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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:52 UTC

Update Date

2023-02-21 17:22:51 UTC

HMDB ID

HMDB0032950

Secondary Accession Numbers

HMDB32950

Metabolite Identification

Common Name

5,7-Dihydroxy-4H-1-benzopyran-4-one

Description

5,7-Dihydroxy-4H-1-benzopyran-4-one belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety. 5,7-Dihydroxy-4H-1-benzopyran-4-one has been detected, but not quantified in, nuts and peanuts (Arachis hypogaea). This could make 5,7-dihydroxy-4H-1-benzopyran-4-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5,7-Dihydroxy-4H-1-benzopyran-4-one.

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   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   3.850   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  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1   13                                                       
CONECT    3    5    7                                                       
CONECT    4    5    8                                                       
CONECT    5    3    4   10                                                  
CONECT    6    1    9   11                                                  
CONECT    7    3    9   12                                                  
CONECT    8    4    9   13                                                  
CONECT    9    6    7    8                                                  
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
CONECT   13    2    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5,7-Dihydroxy-4-chromone	HMDB

Chemical Formula

C₉H₆O₄

Average Molecular Weight

178.1415

Monoisotopic Molecular Weight

178.02660868

IUPAC Name

5,7-dihydroxy-4H-chromen-4-one

Traditional Name

5,7-dihydroxychromone

CAS Registry Number

31721-94-5

SMILES

OC1=CC(O)=C2C(=O)C=COC2=C1

InChI Identifier

InChI=1S/C9H6O4/c10-5-3-7(12)9-6(11)1-2-13-8(9)4-5/h1-4,10,12H

InChI Key

NYCXYKOXLNBYID-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Chromones

Alternative Parents

Substituents

Chromone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

chromones (CHEBI:2007 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032950)
Cytoplasm (HMDB: HMDB0032950)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032950)

Source

Exogenous

Food

Food (HMDB: HMDB0032950)

Nut

Peanut (FooDB: FOOD00016)
Nuts (FooDB: FOOD00869)

Endogenous

Plant

Plant (HMDB: HMDB0032950)

Process

Not Available

Role

Biological role

Industrial application

Agriculture

Pesticide

Herbicide (HMDB: HMDB0032950)

Pesticide (HMDB: HMDB0032950)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	272 - 273 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	9932 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.67 g/L	ALOGPS
logP	1.33	ALOGPS
logP	1.71	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	6.66	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.25 m³·mol⁻¹	ChemAxon
Polarizability	16.16 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
DeepCCS	[M+H]+	136.361	30932474
DeepCCS	[M-H]-	133.944	30932474
DeepCCS	[M-2H]-	169.39	30932474
DeepCCS	[M+Na]+	144.087	30932474
AllCCS	[M+H]+	136.2	32859911
AllCCS	[M+H-H2O]+	131.6	32859911
AllCCS	[M+NH4]+	140.5	32859911
AllCCS	[M+Na]+	141.7	32859911
AllCCS	[M-H]-	132.7	32859911
AllCCS	[M+Na-2H]-	133.0	32859911
AllCCS	[M+HCOO]-	133.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,7-Dihydroxy-4H-1-benzopyran-4-one	OC1=CC(O)=C2C(=O)C=COC2=C1	3090.5	Standard polar	33892256
5,7-Dihydroxy-4H-1-benzopyran-4-one	OC1=CC(O)=C2C(=O)C=COC2=C1	1874.2	Standard non polar	33892256
5,7-Dihydroxy-4H-1-benzopyran-4-one	OC1=CC(O)=C2C(=O)C=COC2=C1	1901.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5,7-Dihydroxy-4H-1-benzopyran-4-one,1TMS,isomer #1	C[Si](C)(C)OC1=CC(O)=C2C(=O)C=COC2=C1	2055.7	Semi standard non polar	33892256
5,7-Dihydroxy-4H-1-benzopyran-4-one,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C=CO2	2003.8	Semi standard non polar	33892256
5,7-Dihydroxy-4H-1-benzopyran-4-one,2TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=COC2=C1	2115.2	Semi standard non polar	33892256
5,7-Dihydroxy-4H-1-benzopyran-4-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=COC2=C1	2320.5	Semi standard non polar	33892256
5,7-Dihydroxy-4H-1-benzopyran-4-one,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C=CO2	2280.7	Semi standard non polar	33892256
5,7-Dihydroxy-4H-1-benzopyran-4-one,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=COC2=C1	2590.2	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 - 5,7-Dihydroxy-4H-1-benzopyran-4-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fbi-0900000000-0e015842f454aa0638c0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7-Dihydroxy-4H-1-benzopyran-4-one GC-MS (2 TMS) - 70eV, Positive	splash10-05fr-5092000000-da38f37aa25e8f7acd22	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7-Dihydroxy-4H-1-benzopyran-4-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 - 5,7-Dihydroxy-4H-1-benzopyran-4-one 10V, Positive-QTOF	splash10-004i-0900000000-09c4b2c72dc5397e3945	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-4H-1-benzopyran-4-one 20V, Positive-QTOF	splash10-004i-0900000000-82245dd5a7d55f4b98d5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-4H-1-benzopyran-4-one 40V, Positive-QTOF	splash10-0j4i-5900000000-1fcc1aabfa0c3c154e4e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-4H-1-benzopyran-4-one 10V, Negative-QTOF	splash10-004i-0900000000-356b9d14818ca0075682	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-4H-1-benzopyran-4-one 20V, Negative-QTOF	splash10-004i-0900000000-2ad0d1c422297e701ee5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-4H-1-benzopyran-4-one 40V, Negative-QTOF	splash10-0ugi-6900000000-bef39397b77521da9117	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-4H-1-benzopyran-4-one 10V, Positive-QTOF	splash10-004i-0900000000-268d2373aed653cef90c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-4H-1-benzopyran-4-one 20V, Positive-QTOF	splash10-004i-0900000000-268d2373aed653cef90c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-4H-1-benzopyran-4-one 40V, Positive-QTOF	splash10-000l-6900000000-b24f7e4e93c22b6c5b8d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-4H-1-benzopyran-4-one 10V, Negative-QTOF	splash10-004i-0900000000-0c76ac6afb0914fb6c47	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-4H-1-benzopyran-4-one 20V, Negative-QTOF	splash10-004i-0900000000-0c76ac6afb0914fb6c47	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-4H-1-benzopyran-4-one 40V, Negative-QTOF	splash10-014r-9600000000-5d8503d7877669a23f8a	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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+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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281343

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1832611

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 5,7-Dihydroxy-4H-1-benzopyran-4-one (HMDB0032950)

MOL for HMDB0032950 (5,7-Dihydroxy-4H-1-benzopyran-4-one)

3D MOL for HMDB0032950 (5,7-Dihydroxy-4H-1-benzopyran-4-one)

3D SDF for HMDB0032950 (5,7-Dihydroxy-4H-1-benzopyran-4-one)

3D-SDF for HMDB0032950 (5,7-Dihydroxy-4H-1-benzopyran-4-one)

PDB for HMDB0032950 (5,7-Dihydroxy-4H-1-benzopyran-4-one)

3D PDB for HMDB0032950 (5,7-Dihydroxy-4H-1-benzopyran-4-one)

SMILES for HMDB0032950 (5,7-Dihydroxy-4H-1-benzopyran-4-one)

INCHI for HMDB0032950 (5,7-Dihydroxy-4H-1-benzopyran-4-one)

Structure for HMDB0032950 (5,7-Dihydroxy-4H-1-benzopyran-4-one)

3D Structure for HMDB0032950 (5,7-Dihydroxy-4H-1-benzopyran-4-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra