NP-MRD: Showing NP-Card for 2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one (NP0138409)

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Record Information

Version

1.0

Created at

2022-05-31 17:58:06 UTC

Updated at

2022-05-31 17:58:06 UTC

NP-MRD ID

NP0138409

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(R)-2,7-Dihydroxy-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 (R)-2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (R)-2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one has been detected, but not quantified in, cereals and cereal products and fats and oils. This could make (R)-2,7-dihydroxy-2H-1,4-benzoxazin-3(4H)-one a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241209182D          

 13 14  0  0  0  0            999 V2000
   -0.0394   -1.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0394   -0.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6818    0.2003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6818    1.0034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6818    0.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4045   -0.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4045   -1.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6818   -1.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6818   -2.2079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0394    2.2079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0394    1.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6818    1.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4045    1.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  2  0  0  0  0
  2  3  1  0  0  0  0
  2  5  2  0  0  0  0
  3 12  1  0  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138409

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1OC2=C(NC1=O)C=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C8H7NO4/c10-4-1-2-5-6(3-4)13-8(12)7(11)9-5/h1-3,8,10,12H,(H,9,11)

> <INCHI_KEY>
HDRDOKTYPONKPM-UHFFFAOYSA-N

> <FORMULA>
C8H7NO4

> <MOLECULAR_WEIGHT>
181.1455

> <EXACT_MASS>
181.037507717

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
16.391774036808876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.26

> <JCHEM_LOGP>
0.1623089316666665

> <ALOGPS_LOGS>
-0.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.20451258201855

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.307025961294023

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9381430068713845

> <JCHEM_POLAR_SURFACE_AREA>
78.78999999999999

> <JCHEM_REFRACTIVITY>
44.004400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.074  -1.873   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.074  -0.374   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.273   0.374   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       1.273   1.873   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.273   0.374   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.622  -0.374   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.622  -1.873   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.273  -2.622   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.273  -4.121   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.074   4.121   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.074   2.622   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.273   1.873   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.622   2.622   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3    5                                                  
CONECT    3    2   12                                                       
CONECT    4    5   11                                                       
CONECT    5    2    4    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    1    7    9                                                  
CONECT    9    8                                                            
CONECT   10   11                                                            
CONECT   11    4   10   12                                                  
CONECT   12    3   11   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₈H₇NO₄

Average Mass

181.1455 Da

Monoisotopic Mass

181.03751 Da

IUPAC Name

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

Traditional Name

2,7-dihydroxy-2,4-dihydro-1,4-benzoxazin-3-one

CAS Registry Number

69804-59-7

SMILES

OC1OC2=C(NC1=O)C=CC(O)=C2

InChI Identifier

InChI=1S/C8H7NO4/c10-4-1-2-5-6(3-4)13-8(12)7(11)9-5/h1-3,8,10,12H,(H,9,11)

InChI Key

HDRDOKTYPONKPM-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

Not Available

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
1-hydroxy-2-unsubstituted benzenoid
Oxazinane
Benzenoid
Carboxamide group
Hemiacetal
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Oxacycle
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organooxygen compound
Organic nitrogen 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	-0.26	ALOGPS
logP	0.16	ChemAxon
logS	-0.86	ALOGPS
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.79 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	44 m³·mol⁻¹	ChemAxon
Polarizability	16.39 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

HMDB0038054

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017265

KNApSAcK ID

Not Available

Chemspider ID

9249163

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11074014

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one (NP0138409)

MOL for NP0138409 (2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

3D MOL for NP0138409 (2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

3D SDF for NP0138409 (2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

3D-SDF for NP0138409 (2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

PDB for NP0138409 (2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

3D PDB for NP0138409 (2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

SMILES for NP0138409 (2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

INCHI for NP0138409 (2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

Structure for NP0138409 (2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)

3D Structure for NP0138409 (2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one)