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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:07 UTC

Update Date

2023-02-21 17:22:56 UTC

HMDB ID

HMDB0032990

Secondary Accession Numbers

HMDB32990

Metabolite Identification

Common Name

7-Hydroxy-6-methyl-2H-1-benzopyran-2-one

Description

7-Hydroxy-6-methyl-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. 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one has been detected, but not quantified in, herbs and spices. This could make 7-hydroxy-6-methyl-2H-1-benzopyran-2-one a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 7-Hydroxy-6-methyl-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       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   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       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    3    7                                                       
CONECT    3    2   10                                                       
CONECT    4    6    7                                                       
CONECT    5    8    9                                                       
CONECT    6    1    4    8                                                  
CONECT    7    2    4    9                                                  
CONECT    8    5    6   11                                                  
CONECT    9    5    7   13                                                  
CONECT   10    3   12   13                                                  
CONECT   11    8                                                            
CONECT   12   10                                                            
CONECT   13    9   10                                                       
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
6-Methylumbelliferone	HMDB
7-Hydroxy-6-methylcoumarin	HMDB

Chemical Formula

C₁₀H₈O₃

Average Molecular Weight

176.1687

Monoisotopic Molecular Weight

176.047344122

IUPAC Name

7-hydroxy-6-methyl-2H-chromen-2-one

Traditional Name

7-hydroxy-6-methylchromen-2-one

CAS Registry Number

53811-56-6

SMILES

CC1=CC2=C(OC(=O)C=C2)C=C1O

InChI Identifier

InChI=1S/C10H8O3/c1-6-4-7-2-3-10(12)13-9(7)5-8(6)11/h2-5,11H,1H3

InChI Key

QWQWBHZHRMHXOC-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

7-hydroxycoumarin
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
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: HMDB0032990)
Cytoplasm (HMDB: HMDB0032990)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032990)

Source

Exogenous

Exogenous (HMDB: HMDB0032990)

Food

Food (HMDB: HMDB0032990)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0032990)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032990)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	247 - 248 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	9776 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	2.85 g/L	ALOGPS
logP	2.02	ALOGPS
logP	1.99	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	8.15	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	48.57 m³·mol⁻¹	ChemAxon
Polarizability	17.5 Å³	ChemAxon
Number of Rings	2	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]+	139.692	31661259
DarkChem	[M-H]-	136.928	31661259
DeepCCS	[M+H]+	138.25	30932474
DeepCCS	[M-H]-	135.855	30932474
DeepCCS	[M-2H]-	171.073	30932474
DeepCCS	[M+Na]+	145.52	30932474
AllCCS	[M+H]+	135.0	32859911
AllCCS	[M+H-H2O]+	130.4	32859911
AllCCS	[M+NH4]+	139.3	32859911
AllCCS	[M+Na]+	140.6	32859911
AllCCS	[M-H]-	135.2	32859911
AllCCS	[M+Na-2H]-	135.5	32859911
AllCCS	[M+HCOO]-	135.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7-Hydroxy-6-methyl-2H-1-benzopyran-2-one	CC1=CC2=C(OC(=O)C=C2)C=C1O	2951.0	Standard polar	33892256
7-Hydroxy-6-methyl-2H-1-benzopyran-2-one	CC1=CC2=C(OC(=O)C=C2)C=C1O	1734.0	Standard non polar	33892256
7-Hydroxy-6-methyl-2H-1-benzopyran-2-one	CC1=CC2=C(OC(=O)C=C2)C=C1O	1937.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7-Hydroxy-6-methyl-2H-1-benzopyran-2-one,1TMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C)OC(=O)C=C2	1989.1	Semi standard non polar	33892256
7-Hydroxy-6-methyl-2H-1-benzopyran-2-one,1TBDMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)OC(=O)C=C2	2247.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one EI-B (Non-derivatized)	splash10-002b-7900000000-14647595b20b9b27acdd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one EI-B (Non-derivatized)	splash10-002b-7900000000-14647595b20b9b27acdd	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-0900000000-a84a7219482a3e9f2344	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-4690000000-18e07247af0bb5cec62f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxy-6-methyl-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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one 10V, Positive-QTOF	splash10-004i-0900000000-30b162d9f815f2ad4931	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one 20V, Positive-QTOF	splash10-004i-0900000000-5c78e67bbadc81e5b352	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one 40V, Positive-QTOF	splash10-0a59-3900000000-738e1c7c456df0db9126	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one 10V, Negative-QTOF	splash10-004i-0900000000-80e6a45b583d34488fa7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one 20V, Negative-QTOF	splash10-004i-0900000000-68fd6f59274aa175e6e5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one 40V, Negative-QTOF	splash10-057i-3900000000-228efad55ffd18a97e4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one 10V, Positive-QTOF	splash10-004i-0900000000-00ffe2c25b8beb0eeaa0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one 20V, Positive-QTOF	splash10-004i-0900000000-c8fe15b4a3eb24aafcad	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one 40V, Positive-QTOF	splash10-057i-4900000000-56decb7e705479d61e3a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one 10V, Negative-QTOF	splash10-004i-0900000000-693f8014c5adb398a51a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one 20V, Negative-QTOF	splash10-004i-0900000000-f4f0a0d7b45ce84dce49	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one 40V, Negative-QTOF	splash10-0fi1-2900000000-6fe64d6ce6d6b0eeb7a7	2021-09-25	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

FDB010979

KNApSAcK ID

C00057431

Chemspider ID

4550448

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5412913

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1832751

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

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

Showing metabocard for 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one (HMDB0032990)

MOL for HMDB0032990 (7-Hydroxy-6-methyl-2H-1-benzopyran-2-one)

3D MOL for HMDB0032990 (7-Hydroxy-6-methyl-2H-1-benzopyran-2-one)

3D SDF for HMDB0032990 (7-Hydroxy-6-methyl-2H-1-benzopyran-2-one)

3D-SDF for HMDB0032990 (7-Hydroxy-6-methyl-2H-1-benzopyran-2-one)

PDB for HMDB0032990 (7-Hydroxy-6-methyl-2H-1-benzopyran-2-one)

3D PDB for HMDB0032990 (7-Hydroxy-6-methyl-2H-1-benzopyran-2-one)

SMILES for HMDB0032990 (7-Hydroxy-6-methyl-2H-1-benzopyran-2-one)

INCHI for HMDB0032990 (7-Hydroxy-6-methyl-2H-1-benzopyran-2-one)

Structure for HMDB0032990 (7-Hydroxy-6-methyl-2H-1-benzopyran-2-one)

3D Structure for HMDB0032990 (7-Hydroxy-6-methyl-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