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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:51:33 UTC

Update Date

2023-02-21 17:28:09 UTC

HMDB ID

HMDB0040326

Secondary Accession Numbers

HMDB40326

Metabolite Identification

Common Name

7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one

Description

7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety. 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one has been detected, but not quantified in, green vegetables. This could make 7-hydroxy-2,5-dimethyl-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 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one.

Structure

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


  Mrv0541 05061311452D          

 14 15  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  3  2  0  0  0  0
  7  2  1  0  0  0  0
  7  4  2  0  0  0  0
  8  3  1  0  0  0  0
  8  5  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
 14  7  1  0  0  0  0
 14 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040326

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(=O)C2=C(O1)C=C(O)C=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O3/c1-6-3-8(12)5-10-11(6)9(13)4-7(2)14-10/h3-5,12H,1-2H3

> <INCHI_KEY>
CRNGFKXWIYTEPH-UHFFFAOYSA-N

> <FORMULA>
C11H10O3

> <MOLECULAR_WEIGHT>
190.1953

> <EXACT_MASS>
190.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
19.620761858396516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-2,5-dimethyl-4H-chromen-4-one

> <ALOGPS_LOGP>
2.08

> <JCHEM_LOGP>
2.081409337

> <ALOGPS_LOGS>
-2.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.293805634819407

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.646187819530617

> <JCHEM_PKA_STRONGEST_BASIC>
-5.336338824895852

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
54.12930000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
altechromone A

> <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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   4.620   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       6.668   2.310   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    6    8                                                       
CONECT    4    7    9                                                       
CONECT    5    8   10                                                       
CONECT    6    1    3   11                                                  
CONECT    7    2    4   14                                                  
CONECT    8    3    5   12                                                  
CONECT    9    4   11   13                                                  
CONECT   10    5   11   14                                                  
CONECT   11    6    9   10                                                  
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14    7   10                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Hydroxy-2,5-dimethylchromone	HMDB, MeSH
Altechromone a	MeSH

Chemical Formula

C₁₁H₁₀O₃

Average Molecular Weight

190.1953

Monoisotopic Molecular Weight

190.062994186

IUPAC Name

7-hydroxy-2,5-dimethyl-4H-chromen-4-one

Traditional Name

altechromone A

CAS Registry Number

38412-47-4

SMILES

CC1=CC(=O)C2=C(O1)C=C(O)C=C2C

InChI Identifier

InChI=1S/C11H10O3/c1-6-3-8(12)5-10-11(6)9(13)4-7(2)14-10/h3-5,12H,1-2H3

InChI Key

CRNGFKXWIYTEPH-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-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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: HMDB0040326)
Cytoplasm (HMDB: HMDB0040326)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040326)

Source

Exogenous

Food

Food (HMDB: HMDB0040326)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0040326)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040326)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	258 - 260 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1805 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	1.41 g/L	ALOGPS
logP	2.08	ALOGPS
logP	2.08	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	6.65	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	54.13 m³·mol⁻¹	ChemAxon
Polarizability	19.62 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]+	142.976	31661259
DarkChem	[M-H]-	140.609	31661259
DeepCCS	[M+H]+	143.751	30932474
DeepCCS	[M-H]-	141.359	30932474
DeepCCS	[M-2H]-	175.378	30932474
DeepCCS	[M+Na]+	150.101	30932474
AllCCS	[M+H]+	137.4	32859911
AllCCS	[M+H-H2O]+	132.9	32859911
AllCCS	[M+NH4]+	141.6	32859911
AllCCS	[M+Na]+	142.9	32859911
AllCCS	[M-H]-	138.7	32859911
AllCCS	[M+Na-2H]-	138.8	32859911
AllCCS	[M+HCOO]-	139.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one	CC1=CC(=O)C2=C(O1)C=C(O)C=C2C	2729.1	Standard polar	33892256
7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one	CC1=CC(=O)C2=C(O1)C=C(O)C=C2C	1897.2	Standard non polar	33892256
7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one	CC1=CC(=O)C2=C(O1)C=C(O)C=C2C	1996.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one,1TMS,isomer #1	CC1=CC(=O)C2=C(C)C=C(O[Si](C)(C)C)C=C2O1	2034.8	Semi standard non polar	33892256
7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one,1TBDMS,isomer #1	CC1=CC(=O)C2=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C2O1	2296.8	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 - 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-01vp-0900000000-a036d1b9ea47c78224d5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one GC-MS (1 TMS) - 70eV, Positive	splash10-006t-5490000000-52ba85c89e3c5b36fc34	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxy-2,5-dimethyl-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 - 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one 10V, Positive-QTOF	splash10-0006-0900000000-70ea31c75536e8c9daf5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one 20V, Positive-QTOF	splash10-0006-0900000000-9bbf7cfa6cb6a51c1a8f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one 40V, Positive-QTOF	splash10-0089-4900000000-ecd64359cbd847a287aa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one 10V, Negative-QTOF	splash10-000i-0900000000-15d71c7eecb8f5143a90	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one 20V, Negative-QTOF	splash10-000i-0900000000-a52dc5d09d1ea13e8485	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one 40V, Negative-QTOF	splash10-000b-4900000000-70b112619cc0bc836e66	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one 10V, Positive-QTOF	splash10-0006-0900000000-7188fe6f113723eeef7f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one 20V, Positive-QTOF	splash10-0006-0900000000-33b0bef6302b4840013a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one 40V, Positive-QTOF	splash10-0ac9-6900000000-245ac32d3d1ac07b82c6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one 10V, Negative-QTOF	splash10-000i-0900000000-45febdcae9d40957ea03	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one 20V, Negative-QTOF	splash10-000i-0900000000-45febdcae9d40957ea03	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one 40V, Negative-QTOF	splash10-014i-9400000000-0caf48097bb501ebac03	2021-09-22	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

FDB020049

KNApSAcK ID

C00038203

Chemspider ID

4475859

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316891

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1882701

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 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one (HMDB0040326)

MOL for HMDB0040326 (7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one)

3D MOL for HMDB0040326 (7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one)

3D SDF for HMDB0040326 (7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one)

3D-SDF for HMDB0040326 (7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one)

PDB for HMDB0040326 (7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one)

3D PDB for HMDB0040326 (7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one)

SMILES for HMDB0040326 (7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one)

INCHI for HMDB0040326 (7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one)

Structure for HMDB0040326 (7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one)

3D Structure for HMDB0040326 (7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra