NP-MRD: Showing NP-Card for (R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (NP0049004)

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Record Information

Version

2.0

Created at

2022-03-17 21:05:36 UTC

Updated at

2022-03-17 21:05:36 UTC

NP-MRD ID

NP0049004

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one

Description

2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, also known as hmboa, 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-Hydroxy-7-methoxy-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-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one has been detected, but not quantified in, several different foods, such as hard wheats, oats, barley, wild rices, and fats and oils. (R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one is found in Zea mays. This could make 2-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309121709232D          

 14 15  0  0  0  0            999 V2000
   -2.1434   -1.2375    0.0000 C   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
   -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
    0.7145   -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
   -0.7145   -0.4125    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
    2.1434   -0.4125    0.0000 C   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
    2.1434   -1.2375    0.0000 C   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
    2.8579   -1.6500    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
  4  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
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049004

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(NC(=O)C(O)O2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO4/c1-13-5-2-3-6-7(4-5)14-9(12)8(11)10-6/h2-4,9,12H,1H3,(H,10,11)

> <INCHI_KEY>
NDEPTLCFICMYLH-UHFFFAOYSA-N

> <FORMULA>
C9H9NO4

> <MOLECULAR_WEIGHT>
195.1721

> <EXACT_MASS>
195.053157781

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.387282995955715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-7-methoxy-3,4-dihydro-2H-1,4-benzoxazin-3-one

> <ALOGPS_LOGP>
0.42

> <JCHEM_LOGP>
0.3082029876666664

> <ALOGPS_LOGS>
-0.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.02601353356227

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.060999242138859

> <JCHEM_PKA_STRONGEST_BASIC>
-4.637840909271957

> <JCHEM_POLAR_SURFACE_AREA>
67.79

> <JCHEM_REFRACTIVITY>
48.4867

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.99e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-7-methoxy-2,4-dihydro-1,4-benzoxazin-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-17         0                                  
HETATM    1  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -2.310   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  -2.310   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       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.667  -0.000   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12    5                                                       
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxy-7-methoxy-1,4-benzoxazin-3-one	HMDB
2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3-one	HMDB
Hmboa	HMDB

Chemical Formula

C₉H₉NO₄

Average Mass

195.1721 Da

Monoisotopic Mass

195.05316 Da

IUPAC Name

2-hydroxy-7-methoxy-3,4-dihydro-2H-1,4-benzoxazin-3-one

Traditional Name

2-hydroxy-7-methoxy-2,4-dihydro-1,4-benzoxazin-3-one

CAS Registry Number

17359-53-4

SMILES

COC1=CC2=C(NC(=O)C(O)O2)C=C1

InChI Identifier

InChI=1S/C9H9NO4/c1-13-5-2-3-6-7(4-5)14-9(12)8(11)10-6/h2-4,9,12H,1H3,(H,10,11)

InChI Key

NDEPTLCFICMYLH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Zea mays	LOTUS Database	35616633

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
Carboxamide group
Secondary carboxylic acid amide
Lactam
Hemiacetal
Oxacycle
Azacycle
Carboxylic acid derivative
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

a small molecule (CPD-6404 )

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	0.42	ALOGPS
logP	0.31	ChemAxon
logS	-0.99	ALOGPS
pKa (Strongest Acidic)	10.06	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.79 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48.49 m³·mol⁻¹	ChemAxon
Polarizability	18.39 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

HMDB0038055

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017266

KNApSAcK ID

Not Available

Chemspider ID

134162

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

152213

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (NP0049004)

MOL for NP0049004 ((R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one)

3D MOL for NP0049004 ((R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one)

3D SDF for NP0049004 ((R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one)

3D-SDF for NP0049004 ((R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one)

PDB for NP0049004 ((R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one)

3D PDB for NP0049004 ((R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one)

SMILES for NP0049004 ((R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one)

INCHI for NP0049004 ((R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one)

Structure for NP0049004 ((R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one)

3D Structure for NP0049004 ((R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one)