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Showing NP-Card for 4-Acetyl-2(3H)-benzoxazolone (NP0049683)

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Record Information
Version2.0
Created at2022-03-17 21:16:25 UTC
Updated at2022-03-17 21:16:25 UTC
NP-MRD IDNP0049683
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Acetyl-2(3H)-benzoxazolone
Description4-Acetyl-2(3H)-benzoxazolone, also known as 4-acetylbenzoxazolin-2-one, belongs to the class of organic compounds known as benzoxazolones. These are organic compounds containing a benzene fused to an oxazole ring (a five-member aliphatic ring with three carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group. 4-Acetyl-2(3H)-benzoxazolone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-Acetyl-2(3H)-benzoxazolone is found, on average, in the highest concentration within corns. 4-Acetyl-2(3H)-benzoxazolone has also been detected, but not quantified in, cereals and cereal products and fats and oils. 4-Acetyl-2(3H)-benzoxazolone is found in Zea mays. This could make 4-acetyl-2(3H)-benzoxazolone a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049683 (4-Acetyl-2(3H)-benzoxazolone)


  Mrv0541 05061311592D          

 13 14  0  0  0  0            999 V2000
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  5  2  0  0  0  0
 12  9  2  0  0  0  0
 13  7  1  0  0  0  0
 13  9  1  0  0  0  0
M  END
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3D MOL for NP0049683 (4-Acetyl-2(3H)-benzoxazolone)

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3D SDF for NP0049683 (4-Acetyl-2(3H)-benzoxazolone)

  Mrv0541 05061311592D          

 13 14  0  0  0  0            999 V2000
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  5  2  0  0  0  0
 12  9  2  0  0  0  0
 13  7  1  0  0  0  0
 13  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049683

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=C2NC(=O)OC2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H7NO3/c1-5(11)6-3-2-4-7-8(6)10-9(12)13-7/h2-4H,1H3,(H,10,12)

> <INCHI_KEY>
FZAQRVWPQCXSPC-UHFFFAOYSA-N

> <FORMULA>
C9H7NO3

> <MOLECULAR_WEIGHT>
177.1568

> <EXACT_MASS>
177.042593095

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
16.787523706067653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-acetyl-2,3-dihydro-1,3-benzoxazol-2-one

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
0.8892741373333333

> <ALOGPS_LOGS>
-1.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.030300628038276

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.085136509124213

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6283331028838406

> <JCHEM_POLAR_SURFACE_AREA>
55.400000000000006

> <JCHEM_REFRACTIVITY>
46.667

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-acetyl-3H-1,3-benzoxazol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0049683 (4-Acetyl-2(3H)-benzoxazolone)
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PDB for NP0049683 (4-Acetyl-2(3H)-benzoxazolone)
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       6.258   6.693   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       3.590   6.693   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.320   2.843   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    3    4                                                       
CONECT    3    2    6                                                       
CONECT    4    2    7                                                       
CONECT    5    1    6   11                                                  
CONECT    6    3    5    8                                                  
CONECT    7    4    8   13                                                  
CONECT    8    6    7   10                                                  
CONECT    9   10   12   13                                                  
CONECT   10    8    9                                                       
CONECT   11    5                                                            
CONECT   12    9                                                            
CONECT   13    7    9                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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3D PDB for NP0049683 (4-Acetyl-2(3H)-benzoxazolone)
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SMILES for NP0049683 (4-Acetyl-2(3H)-benzoxazolone)
CC(=O)C1=C2NC(=O)OC2=CC=C1
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INCHI for NP0049683 (4-Acetyl-2(3H)-benzoxazolone)
InChI=1S/C9H7NO3/c1-5(11)6-3-2-4-7-8(6)10-9(12)13-7/h2-4H,1H3,(H,10,12)
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Synonyms
ValueSource
4-Acetylbenzoxazolin-2-oneHMDB
Chemical FormulaC9H7NO3
Average Mass177.1568 Da
Monoisotopic Mass177.04259 Da
IUPAC Name4-acetyl-2,3-dihydro-1,3-benzoxazol-2-one
Traditional Name4-acetyl-3H-1,3-benzoxazol-2-one
CAS Registry Number70735-79-4
SMILES
CC(=O)C1=C2NC(=O)OC2=CC=C1
InChI Identifier
InChI=1S/C9H7NO3/c1-5(11)6-3-2-4-7-8(6)10-9(12)13-7/h2-4H,1H3,(H,10,12)
InChI KeyFZAQRVWPQCXSPC-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Zea maysLOTUS Database
Zea mays L.FooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoxazolones. These are organic compounds containing a benzene fused to an oxazole ring (a five-member aliphatic ring with three carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzoxazoles  
Sub ClassBenzoxazolones  
Direct ParentBenzoxazolones  
Alternative Parents
Substituents
  • Benzoxazolone
    • 

  • Acetophenone
    • 

  • Aryl alkyl ketone
    • 

  • Aryl ketone
    • 

  • Benzenoid
    • 

  • Azole
    • 

  • Oxazole
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous amide
    • 

  • Ketone
    • 

  • Oxacycle
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.02ALOGPS
logP0.89ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)9.09ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.4 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.67 m³·mol⁻¹ChemAxon
Polarizability16.79 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040612  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020403  
KNApSAcK IDNot Available
Chemspider ID8165361  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9989779  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available