NP-MRD: Showing NP-Card for (3r)-6-(hydroxymethyl)-7,8-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one (NP0223968)

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Record Information

Version

2.0

Created at

2022-09-06 02:12:37 UTC

Updated at

2022-09-06 02:12:38 UTC

NP-MRD ID

NP0223968

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-6-(hydroxymethyl)-7,8-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

Description

(3R)-methyl-7,8-dimethoxy-6-(hydroxymethyl)dihydroisocoumarin 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. Based on a literature review very few articles have been published on (3r)-methyl-7,8-dimethoxy-6-(hydroxymethyl)dihydroisocoumarin.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062204122D          

 18 19  0  0  1  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   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
   -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
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   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
    0.0000    0.8250    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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  8 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223968

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(CO)C=C2C[C@@H](C)OC(=O)C2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O5/c1-7-4-8-5-9(6-14)11(16-2)12(17-3)10(8)13(15)18-7/h5,7,14H,4,6H2,1-3H3/t7-/m1/s1

> <INCHI_KEY>
CXNQIMXXPWGUDS-SSDOTTSWSA-N

> <FORMULA>
C13H16O5

> <MOLECULAR_WEIGHT>
252.266

> <EXACT_MASS>
252.099773615

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.07041140658923

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-6-(hydroxymethyl)-7,8-dimethoxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

> <JCHEM_LOGP>
1.1504940123333331

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.460734720966872

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0346746330490895

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
65.554

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-6-(hydroxymethyl)-7,8-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    9   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    8                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₆O₅

Average Mass

252.2660 Da

Monoisotopic Mass

252.09977 Da

IUPAC Name

(3R)-6-(hydroxymethyl)-7,8-dimethoxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

Traditional Name

(3R)-6-(hydroxymethyl)-7,8-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

CAS Registry Number

Not Available

SMILES

COC1=C(CO)C=C2C[C@@H](C)OC(=O)C2=C1OC

InChI Identifier

InChI=1S/C13H16O5/c1-7-4-8-5-9(6-14)11(16-2)12(17-3)10(8)13(15)18-7/h5,7,14H,4,6H2,1-3H3/t7-/m1/s1

InChI Key

CXNQIMXXPWGUDS-SSDOTTSWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Anisole
Alkyl aryl ether
Benzenoid
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
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
logP	1.15	ChemAxon
pKa (Strongest Acidic)	14.46	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	65.55 m³·mol⁻¹	ChemAxon
Polarizability	26.07 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

67173714

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132992971

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r)-6-(hydroxymethyl)-7,8-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one (NP0223968)

MOL for NP0223968 ((3r)-6-(hydroxymethyl)-7,8-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D MOL for NP0223968 ((3r)-6-(hydroxymethyl)-7,8-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D SDF for NP0223968 ((3r)-6-(hydroxymethyl)-7,8-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D-SDF for NP0223968 ((3r)-6-(hydroxymethyl)-7,8-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

PDB for NP0223968 ((3r)-6-(hydroxymethyl)-7,8-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D PDB for NP0223968 ((3r)-6-(hydroxymethyl)-7,8-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

SMILES for NP0223968 ((3r)-6-(hydroxymethyl)-7,8-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

INCHI for NP0223968 ((3r)-6-(hydroxymethyl)-7,8-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

Structure for NP0223968 ((3r)-6-(hydroxymethyl)-7,8-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)

3D Structure for NP0223968 ((3r)-6-(hydroxymethyl)-7,8-dimethoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one)