NP-MRD: Showing NP-Card for 4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one (NP0258056)

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Record Information

Version

2.0

Created at

2022-09-07 23:21:05 UTC

Updated at

2022-09-07 23:21:05 UTC

NP-MRD ID

NP0258056

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

Description

(-)-Trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one, also known as 3-methyl-4,8-dihydroxy-3,4-dihydroisocoumarin or 4,8-dihydroxy-3-methylbenzopyran-1-one, belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position (-)-trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (-)-trans-3,4-Dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one has been detected, but not quantified in, a few different foods, such as fats and oils, green vegetables, and herbs and spices. This could make (-)-trans-3,4-dihydro-4,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one a potential biomarker for the consumption of these foods. 4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one is found in Aspergillus melleus, Cephalotaxus mannii, Dinemasporium strigosum, Diplodia corticola, Durio zibethinus, Emericellopsis minima, Garcinia mangostana, Illigera luzonensis, Lasiodiplodia theobromae, Xylaria feejeensis and Xylaria longiana. An isochromane that is mellein bearing a hydroxy group at position 4.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061305292D          

 14 15  0  0  0  0            999 V2000
    5.0013    1.2375    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14  5  1  0  0  0  0
 14 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0258056

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(=O)C2=C(C=CC=C2O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O4/c1-5-9(12)6-3-2-4-7(11)8(6)10(13)14-5/h2-5,9,11-12H,1H3

> <INCHI_KEY>
STSOHAOGZMLWFR-UHFFFAOYSA-N

> <FORMULA>
C10H10O4

> <MOLECULAR_WEIGHT>
194.184

> <EXACT_MASS>
194.057908808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.53012692437463

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,8-dihydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

> <ALOGPS_LOGP>
0.92

> <JCHEM_LOGP>
1.6606248423333332

> <ALOGPS_LOGS>
-0.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.313602969278904

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.567712452623942

> <JCHEM_PKA_STRONGEST_BASIC>
-3.605892516568062

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
49.0001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.82e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

> <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       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   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       4.001  -0.770   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       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.668   3.850   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
HETATM   14  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    3    4                                                       
CONECT    3    2    6                                                       
CONECT    4    2    7                                                       
CONECT    5    1    9   14                                                  
CONECT    6    3    8    9                                                  
CONECT    7    4    8   11                                                  
CONECT    8    6    7   10                                                  
CONECT    9    5    6   12                                                  
CONECT   10    8   13   14                                                  
CONECT   11    7                                                            
CONECT   12    9                                                            
CONECT   13   10                                                            
CONECT   14    5   10                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
3-Methyl-4,8-dihydroxy-3,4-dihydroisocoumarin	ChEBI
4,8-Dihydroxy-3-methylbenzopyran-1-one	ChEBI
trans-4-Hydroxymellein	HMDB

Chemical Formula

C₁₀H₁₀O₄

Average Mass

194.1840 Da

Monoisotopic Mass

194.05791 Da

IUPAC Name

4,8-dihydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

Traditional Name

4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

CAS Registry Number

Not Available

SMILES

CC1OC(=O)C2=C(C=CC=C2O)C1O

InChI Identifier

InChI=1S/C10H10O4/c1-5-9(12)6-3-2-4-7(11)8(6)10(13)14-5/h2-5,9,11-12H,1H3

InChI Key

STSOHAOGZMLWFR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus melleus	LOTUS Database	35616633
Cephalotaxus mannii	LOTUS Database	35616633
Dinemasporium strigosum	LOTUS Database	35616633
Diplodia corticola	LOTUS Database	35616633
Durio zibethinus	LOTUS Database	35616633
Emericellopsis minima	LOTUS Database	35616633
Garcinia mangostana	LOTUS Database	35616633
Illigera luzonensis	LOTUS Database	35616633
Lasiodiplodia theobromae	LOTUS Database	35616633
Xylaria feejeensis	LOTUS Database	35616633
Xylaria longiana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

2-benzopyrans

Direct Parent

2-benzopyrans

Alternative Parents

Substituents

2-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organic oxygen compound
Organooxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.92	ALOGPS
logP	1.66	ChemAxon
logS	-0.71	ALOGPS
pKa (Strongest Acidic)	9.57	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	49 m³·mol⁻¹	ChemAxon
Polarizability	18.53 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

External Links

HMDB ID

HMDB0030765

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002698

KNApSAcK ID

C00000119

Chemspider ID

148269

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

169539

PDB ID

Not Available

ChEBI ID

141335

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one (NP0258056)

MOL for NP0258056 (4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D MOL for NP0258056 (4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D SDF for NP0258056 (4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D-SDF for NP0258056 (4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

PDB for NP0258056 (4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D PDB for NP0258056 (4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

SMILES for NP0258056 (4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

INCHI for NP0258056 (4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

Structure for NP0258056 (4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D Structure for NP0258056 (4,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)