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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

HMDB0032951

Secondary Accession Numbers

HMDB32951

Metabolite Identification

Common Name

4,7-Dihydroxy-2H-1-benzopyran-2-one

Description

4,7-Dihydroxy-2H-1-benzopyran-2-one belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. 4,7-Dihydroxy-2H-1-benzopyran-2-one has been detected, but not quantified in, several different foods, such as red tea, green vegetables, teas (Camellia sinensis), black tea, and herbs and spices. This could make 4,7-dihydroxy-2H-1-benzopyran-2-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4,7-Dihydroxy-2H-1-benzopyran-2-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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    6                                                       
CONECT    3    5    8                                                       
CONECT    4    7    9                                                       
CONECT    5    1    3   10                                                  
CONECT    6    2    7    8                                                  
CONECT    7    4    6   11                                                  
CONECT    8    3    6   13                                                  
CONECT    9    4   12   13                                                  
CONECT   10    5                                                            
CONECT   11    7                                                            
CONECT   12    9                                                            
CONECT   13    8    9                                                       
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
4,7-Dihydroxy-2H-chromen-2-one	HMDB
4,7-Dihydroxy-coumarin	HMDB
4,7-Dihydroxycoumarin	HMDB

Chemical Formula

C₉H₆O₄

Average Molecular Weight

178.1415

Monoisotopic Molecular Weight

178.02660868

IUPAC Name

4,7-dihydroxy-2H-chromen-2-one

Traditional Name

4,7-dihydroxychromen-2-one

CAS Registry Number

1983-81-9

SMILES

OC1=CC2=C(C=C1)C(O)=CC(=O)O2

InChI Identifier

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

InChI Key

CYSRKZFPSNZSCS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

7-hydroxycoumarins

Alternative Parents

Substituents

4-hydroxycoumarin
7-hydroxycoumarin
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032951)
Cytoplasm (HMDB: HMDB0032951)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032951)

Source

Exogenous

Exogenous (HMDB: HMDB0032951)

Food

Food (HMDB: HMDB0032951)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0032951)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032951)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	282 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	160000 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	4.36 g/L	ALOGPS
logP	1.22	ALOGPS
logP	0.73	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	6.18	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.42 m³·mol⁻¹	ChemAxon
Polarizability	16.25 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]+	136.841	31661259
DarkChem	[M-H]-	134.661	31661259
DeepCCS	[M+H]+	135.454	30932474
DeepCCS	[M-H]-	133.058	30932474
DeepCCS	[M-2H]-	168.66	30932474
DeepCCS	[M+Na]+	143.85	30932474
AllCCS	[M+H]+	135.9	32859911
AllCCS	[M+H-H2O]+	131.3	32859911
AllCCS	[M+NH4]+	140.2	32859911
AllCCS	[M+Na]+	141.4	32859911
AllCCS	[M-H]-	132.3	32859911
AllCCS	[M+Na-2H]-	132.5	32859911
AllCCS	[M+HCOO]-	132.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4,7-Dihydroxy-2H-1-benzopyran-2-one	OC1=CC2=C(C=C1)C(O)=CC(=O)O2	3276.7	Standard polar	33892256
4,7-Dihydroxy-2H-1-benzopyran-2-one	OC1=CC2=C(C=C1)C(O)=CC(=O)O2	1955.7	Standard non polar	33892256
4,7-Dihydroxy-2H-1-benzopyran-2-one	OC1=CC2=C(C=C1)C(O)=CC(=O)O2	2152.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4,7-Dihydroxy-2H-1-benzopyran-2-one,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(O)=CC(=O)OC2=C1	2126.5	Semi standard non polar	33892256
4,7-Dihydroxy-2H-1-benzopyran-2-one,1TMS,isomer #2	C[Si](C)(C)OC1=CC(=O)OC2=CC(O)=CC=C12	2067.6	Semi standard non polar	33892256
4,7-Dihydroxy-2H-1-benzopyran-2-one,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(O[Si](C)(C)C)=CC(=O)OC2=C1	2200.3	Semi standard non polar	33892256
4,7-Dihydroxy-2H-1-benzopyran-2-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(O)=CC(=O)OC2=C1	2361.4	Semi standard non polar	33892256
4,7-Dihydroxy-2H-1-benzopyran-2-one,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(=O)OC2=CC(O)=CC=C12	2325.5	Semi standard non polar	33892256
4,7-Dihydroxy-2H-1-benzopyran-2-one,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(O[Si](C)(C)C(C)(C)C)=CC(=O)OC2=C1	2675.4	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 - 4,7-Dihydroxy-2H-1-benzopyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ugr-0900000000-19c6b453b35face9ae17	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,7-Dihydroxy-2H-1-benzopyran-2-one GC-MS (2 TMS) - 70eV, Positive	splash10-00di-5392000000-da32f3c148f96fd1bdd5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,7-Dihydroxy-2H-1-benzopyran-2-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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4,7-Dihydroxy-2H-1-benzopyran-2-one LC-ESI-qTof , Positive-QTOF	splash10-000i-0900000000-9e91caf88a434806625d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4,7-Dihydroxy-2H-1-benzopyran-2-one , positive-QTOF	splash10-000i-0900000000-9e91caf88a434806625d	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,7-Dihydroxy-2H-1-benzopyran-2-one 10V, Negative-QTOF	splash10-004i-0900000000-12840024438b7d9eca2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,7-Dihydroxy-2H-1-benzopyran-2-one 20V, Negative-QTOF	splash10-004i-0900000000-eadb6c9145d0d0402628	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,7-Dihydroxy-2H-1-benzopyran-2-one 40V, Negative-QTOF	splash10-0553-4900000000-a539974280af2d549674	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,7-Dihydroxy-2H-1-benzopyran-2-one 10V, Negative-QTOF	splash10-004i-0900000000-0c76ac6afb0914fb6c47	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,7-Dihydroxy-2H-1-benzopyran-2-one 20V, Negative-QTOF	splash10-004i-0900000000-f908170c5f027e498f8f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,7-Dihydroxy-2H-1-benzopyran-2-one 40V, Negative-QTOF	splash10-066u-9500000000-b090a575cb55a1028e7e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,7-Dihydroxy-2H-1-benzopyran-2-one 10V, Positive-QTOF	splash10-004i-0900000000-1efab5ad003cf2848b11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,7-Dihydroxy-2H-1-benzopyran-2-one 20V, Positive-QTOF	splash10-004i-0900000000-0a97c784e28125af9553	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,7-Dihydroxy-2H-1-benzopyran-2-one 40V, Positive-QTOF	splash10-000i-4900000000-d66529871b6cfd6546e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,7-Dihydroxy-2H-1-benzopyran-2-one 10V, Positive-QTOF	splash10-004i-0900000000-268d2373aed653cef90c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,7-Dihydroxy-2H-1-benzopyran-2-one 20V, Positive-QTOF	splash10-004i-0900000000-bae91b98349be30a81c4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,7-Dihydroxy-2H-1-benzopyran-2-one 40V, Positive-QTOF	splash10-0pvi-3900000000-3b73fa4e7e86ed18bec3	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

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

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

FDB010937

KNApSAcK ID

C00055290

Chemspider ID

10255809

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54679630

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1447501

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. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

4,7-Dihydroxy-2H-1-benzopyran-2-one → 3,4,5-trihydroxy-6-[(7-hydroxy-2-oxo-2H-chromen-4-yl)oxy]oxane-2-carboxylic acid	details
4,7-Dihydroxy-2H-1-benzopyran-2-one → 3,4,5-trihydroxy-6-[(4-hydroxy-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic acid	details

Showing metabocard for 4,7-Dihydroxy-2H-1-benzopyran-2-one (HMDB0032951)

MOL for HMDB0032951 (4,7-Dihydroxy-2H-1-benzopyran-2-one)

3D MOL for HMDB0032951 (4,7-Dihydroxy-2H-1-benzopyran-2-one)

3D SDF for HMDB0032951 (4,7-Dihydroxy-2H-1-benzopyran-2-one)

3D-SDF for HMDB0032951 (4,7-Dihydroxy-2H-1-benzopyran-2-one)

PDB for HMDB0032951 (4,7-Dihydroxy-2H-1-benzopyran-2-one)

3D PDB for HMDB0032951 (4,7-Dihydroxy-2H-1-benzopyran-2-one)

SMILES for HMDB0032951 (4,7-Dihydroxy-2H-1-benzopyran-2-one)

INCHI for HMDB0032951 (4,7-Dihydroxy-2H-1-benzopyran-2-one)

Structure for HMDB0032951 (4,7-Dihydroxy-2H-1-benzopyran-2-one)

3D Structure for HMDB0032951 (4,7-Dihydroxy-2H-1-benzopyran-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions