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Showing NP-Card for 2-acetamidophenol (NP0332709)

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Record Information
Version2.0
Created at2024-03-21 17:34:58 UTC
Updated at2025-12-21 21:41:04 UTC
NP-MRD IDNP0332709
Natural Product DOIhttps://doi.org/10.57994/1970
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-acetamidophenol
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. 2-acetamidophenol was first documented in 1986 (PMID: 2868865). 2'-Hydroxyacetanilide is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 24370547) (PMID: 25663820) (PMID: 28474155) (PMID: 29790115) (PMID: 3508090).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0332709 (2-acetamidophenol )


  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 NP0332709 (2-acetamidophenol )

     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 NP0332709 (2-acetamidophenol )


  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>
NP0332709

> <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

$$$$
Download

3D-SDF for NP0332709 (2-acetamidophenol )

Download
PDB for NP0332709 (2-acetamidophenol )
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

Download
3D PDB for NP0332709 (2-acetamidophenol )
Download
SMILES for NP0332709 (2-acetamidophenol )
CC(O)=NC1=CC=CC=C1O
Download
INCHI for NP0332709 (2-acetamidophenol )
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
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)saranirathnayake@gmail.comThe University of QueenslandSarani Kankanamge2024-03-21View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)saranirathnayake@gmail.comThe University of QueenslandSarani Kankanamge2024-03-21View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)saranirathnayake@gmail.comThe University of QueenslandSarani Kankanamge2024-03-21View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)saranirathnayake@gmail.comThe University of QueenslandSarani Kankanamge2024-03-21View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)saranirathnayake@gmail.comThe University of QueenslandSarani Kankanamge2024-03-21View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)saranirathnayake@gmail.comThe University of QueenslandSarani Kankanamge2024-03-21View Spectrum
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
Streptomyces virginiae
      Not Available
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. Hanif F, Perveen K, Jawed H, Ahmed A, Malhi SM, Jamall S, Simjee SU: N-(2-hydroxyphenyl)acetamide (NA-2) and Temozolomide synergistically induce apoptosis in human glioblastoma cell line U87. Cancer Cell Int. 2014 Nov 30;14(1):133. doi: 10.1186/s12935-014-0133-5.  eCollection 2014. [PubMed:25663820  ] 
  3. Gul A, Kunwar B, Mazhar M, Perveen K, Simjee SU: N-(2-Hydroxyphenyl)acetamide: a Novel Suppressor of RANK/RANKL Pathway in Collagen-Induced Arthritis Model in Rats. Inflammation. 2017 Aug;40(4):1177-1190. doi: 10.1007/s10753-017-0561-1. [PubMed:28474155  ] 
  4. Siddiqui RA, Simjee SU, Kabir N, Ateeq M, Shah MR, Hussain SS: N-(2-hydroxyphenyl)acetamide and its gold nanoparticle conjugation prevent glycerol-induced acute kidney injury by attenuating inflammation and oxidative injury in mice. Mol Cell Biochem. 2019 Jan;450(1-2):43-52. doi: 10.1007/s11010-018-3371-3. Epub  2018 May 22. [PubMed:29790115  ] 
  5. Hamilton M, Kissinger PT: The metabolism of 2- and 3-hydroxyacetanilide. Determination of metabolic products by liquid chromatography/electrochemistry. Drug Metab Dispos. 1986 Jan-Feb;14(1):5-12. [PubMed:2868865  ] 
  6. Rottero AE, Kissinger P: Detection and identification of three thioether conjugates of 2-hydroxyacetanilide by liquid chromatography/electrochemistry. Biomed Chromatogr. 1987 Feb;2(1):24-9. doi: 10.1002/bmc.1130020108. [PubMed:3508090  ] 
  7. DOI: 10.1021/acs.jnatprod.4c00042
  8. PMID: 38517947