NP-MRD: Showing NP-Card for methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylate (NP0282294)

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Record Information

Version

2.0

Created at

2022-09-09 09:04:32 UTC

Updated at

2022-09-09 09:04:32 UTC

NP-MRD ID

NP0282294

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylate

Description

Methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-5-carboxylate belongs to the class of organic compounds known as m-phthalate esters. These are ester derivatives of m-phthalic acids, which are based on a benzene 1,3-dicarboxylic acid skeleton. methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylate is found in Xylaria cubensis. Based on a literature review very few articles have been published on methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-5-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    3.5719   -1.8995   -0.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3953   -1.1243   -0.2967 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383    0.1601    0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4225    0.6674    0.6418 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1127    0.9173    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2045    2.2583    0.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1315    3.0902    0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1294    2.5681    0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2031    3.3942    0.2014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2551    1.2319   -0.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1244    0.4087   -0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369   -1.0187   -0.5424 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2946   -1.3568   -1.7619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6595   -1.5451   -0.3758 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0269   -1.6641    1.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5766   -0.6659   -0.9852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5198    0.6663   -0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5787    1.3673   -0.6198 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4757   -1.2576   -0.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5907   -2.5901    0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5701   -2.5859   -1.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009    2.6392    0.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1580    4.1279    0.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1127    3.2367   -0.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3285   -1.5856    0.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624   -1.8949   -2.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6799   -2.5371   -0.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1188   -1.3987    1.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4054   -2.6729    1.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8057   -0.9363    1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 11  5  1  0
 17 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
 12 25  1  1
 13 26  1  0
 14 27  1  6
 15 28  1  0
 15 29  1  0
 15 30  1  0
M  END


  Mrv1652309092211042D          

 18 19  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
    0.0000   -1.6500    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    1.4289    0.8250    0.0000 O   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
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0282294

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC=C(O)C2=C1C(O)C(C)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H12O6/c1-5-10(14)8-6(11(15)17-2)3-4-7(13)9(8)12(16)18-5/h3-5,10,13-14H,1-2H3

> <INCHI_KEY>
OIKSASBCRUAAKC-UHFFFAOYSA-N

> <FORMULA>
C12H12O6

> <MOLECULAR_WEIGHT>
252.222

> <EXACT_MASS>
252.063388106

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.847692708359034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-5-carboxylate

> <JCHEM_LOGP>
1.6641018063333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.035044807984793

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.64587015040956

> <JCHEM_PKA_STRONGEST_BASIC>
-3.73065280750198

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
61.025400000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   17                                                  
CONECT   11   10    5   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   10   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-5-carboxylic acid	Generator

Chemical Formula

C₁₂H₁₂O₆

Average Mass

252.2220 Da

Monoisotopic Mass

252.06339 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC=C(O)C2=C1C(O)C(C)OC2=O

InChI Identifier

InChI=1S/C12H12O6/c1-5-10(14)8-6(11(15)17-2)3-4-7(13)9(8)12(16)18-5/h3-5,10,13-14H,1-2H3

InChI Key

OIKSASBCRUAAKC-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
Xylaria cubensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-phthalate esters. These are ester derivatives of m-phthalic acids, which are based on a benzene 1,3-dicarboxylic acid skeleton.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

m-Phthalate esters

Alternative Parents

Substituents

Meta-phthalic acid ester
Meta_phthalic_acid
2-benzopyran
Isochromane
Benzopyran
1-hydroxy-2-unsubstituted benzenoid
Dicarboxylic acid or derivatives
Vinylogous acid
Methyl ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163064163

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylate (NP0282294)

MOL for NP0282294 (methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylate)

3D MOL for NP0282294 (methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylate)

3D SDF for NP0282294 (methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylate)

3D-SDF for NP0282294 (methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylate)

PDB for NP0282294 (methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylate)

3D PDB for NP0282294 (methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylate)

SMILES for NP0282294 (methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylate)

INCHI for NP0282294 (methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylate)

Structure for NP0282294 (methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylate)

3D Structure for NP0282294 (methyl 4,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylate)