NP-MRD: Showing NP-Card for 2,4-Dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one (NP0048831)

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Record Information

Version

2.0

Created at

2022-03-17 21:02:52 UTC

Updated at

2022-03-17 21:02:52 UTC

NP-MRD ID

NP0048831

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4-Dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one

Description

2,4-Dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one belongs to the class of organic compounds known as benzoxazinones. These are organic compounds containing a benzene fused to an oxazine ring (a six-member aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group. 2,4-Dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2,4-Dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one has been detected, but not quantified in, a few different foods, such as cereals and cereal products, corns, and fats and oils. This could make 2,4-dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061309512D          

 17 18  0  0  0  0            999 V2000
   -2.1434   -0.4125    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    0.0000    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
    0.7145   -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
   -0.7145   -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
    2.1434   -0.4125    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 N   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   -1.6500    0.0000 O   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
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15  1  1  0  0  0  0
 15  7  1  0  0  0  0
 16  2  1  0  0  0  0
 16  8  1  0  0  0  0
 17  6  1  0  0  0  0
 17 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048831

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C2N(O)C(=O)C(O)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO6/c1-15-7-3-5-6(4-8(7)16-2)17-10(13)9(12)11(5)14/h3-4,10,13-14H,1-2H3

> <INCHI_KEY>
VVCAIBZWJDJGJQ-UHFFFAOYSA-N

> <FORMULA>
C10H11NO6

> <MOLECULAR_WEIGHT>
241.1974

> <EXACT_MASS>
241.058637089

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
22.217016311967626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4-dihydroxy-6,7-dimethoxy-3,4-dihydro-2H-1,4-benzoxazin-3-one

> <ALOGPS_LOGP>
0.08

> <JCHEM_LOGP>
-0.21226000233333356

> <ALOGPS_LOGS>
-1.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.817397442113975

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.708413916972128

> <JCHEM_PKA_STRONGEST_BASIC>
-4.476245170694502

> <JCHEM_POLAR_SURFACE_AREA>
88.46000000000002

> <JCHEM_REFRACTIVITY>
54.9337

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4-dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3-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      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3    5    7                                                       
CONECT    4    6    8                                                       
CONECT    5    3    6   11                                                  
CONECT    6    4    5   17                                                  
CONECT    7    3    8   15                                                  
CONECT    8    4    7   16                                                  
CONECT    9   10   11   12                                                  
CONECT   10    9   13   17                                                  
CONECT   11    5    9   14                                                  
CONECT   12    9                                                            
CONECT   13   10                                                            
CONECT   14   11                                                            
CONECT   15    1    7                                                       
CONECT   16    2    8                                                       
CONECT   17    6   10                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
2,4-Dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one, 9ci	HMDB

Chemical Formula

C₁₀H₁₁NO₆

Average Mass

241.1974 Da

Monoisotopic Mass

241.05864 Da

IUPAC Name

2,4-dihydroxy-6,7-dimethoxy-3,4-dihydro-2H-1,4-benzoxazin-3-one

Traditional Name

2,4-dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3-one

CAS Registry Number

67467-45-2

SMILES

COC1=C(OC)C=C2N(O)C(=O)C(O)OC2=C1

InChI Identifier

InChI=1S/C10H11NO6/c1-15-7-3-5-6(4-8(7)16-2)17-10(13)9(12)11(5)14/h3-4,10,13-14H,1-2H3

InChI Key

VVCAIBZWJDJGJQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoxazinones. These are organic compounds containing a benzene fused to an oxazine ring (a six-member aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazines

Sub Class

Benzoxazinones

Direct Parent

Benzoxazinones

Alternative Parents

Substituents

Benzoxazinone
Benzomorpholine
Anisole
Alkyl aryl ether
Benzenoid
Oxazinane
Hemiacetal
Hydroxamic acid
Carboxylic acid derivative
Oxacycle
Azacycle
Ether
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
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	0.08	ALOGPS
logP	-0.21	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	7.71	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	54.93 m³·mol⁻¹	ChemAxon
Polarizability	22.22 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

HMDB0037548

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016630

KNApSAcK ID

Not Available

Chemspider ID

10280317

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14893473

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2,4-Dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one (NP0048831)

MOL for NP0048831 (2,4-Dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one)

3D MOL for NP0048831 (2,4-Dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one)

3D SDF for NP0048831 (2,4-Dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one)

3D-SDF for NP0048831 (2,4-Dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one)

PDB for NP0048831 (2,4-Dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one)

3D PDB for NP0048831 (2,4-Dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one)

SMILES for NP0048831 (2,4-Dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one)

INCHI for NP0048831 (2,4-Dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one)

Structure for NP0048831 (2,4-Dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one)

3D Structure for NP0048831 (2,4-Dihydroxy-6,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one)