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Showing NP-Card for n-(2-hydroxyphenyl)ethanimidic acid (NP0303978)

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Record Information
Version2.0
Created at2022-09-10 18:45:01 UTC
Updated at2022-09-10 18:45:02 UTC
NP-MRD IDNP0303978
Secondary Accession NumbersNone
Natural Product Identification
Common Namen-(2-hydroxyphenyl)ethanimidic acid
Description2'-Hydroxyacetanilide, also known as 2-(acetylamino)phenol or acet-O-aminofenol, belongs to the class of organic compounds known as acetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group. n-(2-hydroxyphenyl)ethanimidic acid is found in Huperzia serrata and Streptomyces xanthophaeus. n-(2-hydroxyphenyl)ethanimidic acid was first documented in 2014 (PMID: 24370547). 2'-Hydroxyacetanilide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0303978 (n-(2-hydroxyphenyl)ethanimidic acid)


  Mrv1652310161916352D          

 11 11  0  0  0  0            999 V2000
   -1.4289    2.4750    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 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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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  3  1  0  0  0  0
  6  1  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  4  0  0  0
 10  6  1  0  0  0  0
 11  8  1  0  0  0  0
M  END
Download

3D MOL for NP0303978 (n-(2-hydroxyphenyl)ethanimidic acid)

     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
    2.2928    0.5216   -0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9256   -0.8006    0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9600   -1.6516    0.8201 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7298   -1.2113    0.6209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4248   -0.4477    0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7516    0.6521    1.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8720    1.3804    0.7438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6591    1.0430   -0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3256   -0.0521   -1.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2066   -0.7899   -0.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729   -1.8991   -1.5890 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3881    1.0897   -0.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8216    1.1337    0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0060    0.3960   -0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7690   -1.3223    1.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1089    0.8745    1.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151    2.2370    1.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5349    1.6295   -0.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461   -0.3145   -1.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0751   -2.4686   -1.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
 11 20  1  0
M  END
Download

3D SDF for NP0303978 (n-(2-hydroxyphenyl)ethanimidic acid)


  Mrv1652310161916352D          

 11 11  0  0  0  0            999 V2000
   -1.4289    2.4750    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 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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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  3  1  0  0  0  0
  6  1  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  4  0  0  0
 10  6  1  0  0  0  0
 11  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303978

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)=NC1=CC=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C8H9NO2/c1-6(10)9-7-4-2-3-5-8(7)11/h2-5,11H,1H3,(H,9,10)

> <INCHI_KEY>
ADVGKWPZRIDURE-UHFFFAOYSA-N

> <FORMULA>
C8H9NO2

> <MOLECULAR_WEIGHT>
151.1626

> <EXACT_MASS>
151.063328537

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.44510713370702

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(2-hydroxyphenyl)ethanimidic acid

> <ALOGPS_LOGP>
1.06

> <JCHEM_LOGP>
2.2848475319999997

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.452380443769908

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.440115190832708

> <JCHEM_PKA_STRONGEST_BASIC>
-0.032141795613778945

> <JCHEM_POLAR_SURFACE_AREA>
52.82000000000001

> <JCHEM_REFRACTIVITY>
43.657

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(2-hydroxyphenyl)ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0303978 (n-(2-hydroxyphenyl)ethanimidic acid)

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PDB for NP0303978 (n-(2-hydroxyphenyl)ethanimidic acid)
HEADER    PROTEIN                                 16-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-OCT-19         0                                  
HETATM    1  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   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  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    8                                                       
CONECT    6    1    9   10                                                  
CONECT    7    4    8    9                                                  
CONECT    8    5    7   11                                                  
CONECT    9    6    7                                                       
CONECT   10    6                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0303978 (n-(2-hydroxyphenyl)ethanimidic acid)
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SMILES for NP0303978 (n-(2-hydroxyphenyl)ethanimidic acid)
CC(O)=NC1=CC=CC=C1O
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INCHI for NP0303978 (n-(2-hydroxyphenyl)ethanimidic acid)
InChI=1S/C8H9NO2/c1-6(10)9-7-4-2-3-5-8(7)11/h2-5,11H,1H3,(H,9,10)
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View in JSmol
Synonyms
ValueSource
2-(Acetylamino)phenolChEBI
2-(N-Acetylamino)phenolChEBI
2-AcetaminophenolChEBI
2-HydroxyacetanilideChEBI
Acet-O-aminofenolChEBI
N-(2-Hydroxyphenyl)acetamideChEBI
N-Acetyl-2-aminophenolChEBI
N-Acetyl-O-aminophenolChEBI
O-(Acetylamino)phenolChEBI
O-AcetamidophenolChEBI
O-AcetaminophenolChEBI
O-AcetylaminofenolChEBI
O-HydroxyacetanilideChEBI
2-AcetamidophenolHMDB
2’-hydroxyacetanilideHMDB
HPAAHMDB
2'-HydroxyacetanilideHMDB, ChEBI
Chemical FormulaC8H9NO2
Average Mass151.1626 Da
Monoisotopic Mass151.06333 Da
IUPAC NameN-(2-hydroxyphenyl)ethanimidic acid
Traditional NameN-(2-hydroxyphenyl)ethanimidic acid
CAS Registry NumberNot Available
SMILES
CC(O)=NC1=CC=CC=C1O
InChI Identifier
InChI=1S/C8H9NO2/c1-6(10)9-7-4-2-3-5-8(7)11/h2-5,11H,1H3,(H,9,10)
InChI KeyADVGKWPZRIDURE-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Huperzia serrataLOTUS Database
Streptomyces xanthophaeusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassAnilides  
Direct ParentAcetanilides  
Alternative Parents
Substituents
  • Acetanilide
    • 

  • N-acetylarylamine
    • 

  • N-arylamide
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Acetamide
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxamide group
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP1.06ALOGPS
logP2.28ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)5.44ChemAxon
pKa (Strongest Basic)-0.032ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.82 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.66 m³·mol⁻¹ChemAxon
Polarizability15.45 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0061919  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB093735  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11972  
PDB IDNot Available
ChEBI ID143107  
Good Scents IDNot Available
References
General References
  1. Dierkes G, Weiss T, Modick H, Kafferlein HU, Bruning T, Koch HM: N-Acetyl-4-aminophenol (paracetamol), N-acetyl-2-aminophenol and acetanilide in urine samples from the general population, individuals exposed to aniline and paracetamol users. Int J Hyg Environ Health. 2014 Apr-May;217(4-5):592-9. doi: 10.1016/j.ijheh.2013.11.005. Epub 2013 Dec 6. [PubMed:24370547  ] 
  2. LOTUS database [Link]