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Showing metabocard for Acetaminophen (HMDB0001859)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-22 10:57:58 UTC
Update Date2023-02-21 17:15:50 UTC
HMDB IDHMDB0001859
Secondary Accession Numbers
  • HMDB01859
Metabolite Identification
Common NameAcetaminophen
DescriptionThe excellent tolerability of therapeutic doses of paracetamol (acetaminophen) is a major factor in the very wide use of the drug. The major problem in the use of paracetamol is its hepatotoxicity after an overdose. Hepatotoxicity has also been reported after therapeutic doses, but critical analysis indicates that most patients with alleged toxicity from therapeutic doses have taken overdoses. Importantly, prospective studies indicate that therapeutic doses of paracetamol are an unlikely cause of hepatotoxicity in patients who ingest moderate to large amounts of alcohol (PMID: 15733027 ). Single doses of paracetamol are effective analgesics for acute postoperative pain and give rise to few adverse effects (PMID: 14974073 ). Acetaminophen (AAP) overdose and the resulting hepatotoxicity is an important clinical problem. In addition, AAP is widely used as a prototype hepatotoxin to study mechanisms of chemical-induced cell injury and to test the hepatoprotective potential of new drugs and herbal medicines. Because of its importance, the mechanisms of AAP-induced liver cell injury have been extensively investigated and controversially discussed for many years (PMID: 16863451 ).
Structure
Data?1676999750
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001859 (Acetaminophen)

316
  Mrv1652305271900012D          

 11 11  0  0  0  0            999 V2000
    2.3645   -2.1409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.1591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.1591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    2.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2 10  2  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  2  0  0  0  0
  7  9  2  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
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3D MOL for HMDB0001859 (Acetaminophen)

HMDB0001859
     RDKit          3D
Acetaminophen
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.7382    0.4326    0.6352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2723    0.6463    0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0104    1.7737   -0.1813 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3401   -0.3693    0.5185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0355   -0.2646    0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6706    0.8237   -0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0494    0.8405   -0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8326   -0.2426   -0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1870   -0.2371   -0.5073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2140   -1.3517    0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8686   -1.3690    0.5087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2074    1.3948    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8406   -0.3083    1.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2486    0.0509   -0.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7108   -1.2625    0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1261    1.7122   -0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5331    1.7154   -0.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7103    0.5147   -0.8854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7774   -2.2641    0.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3638   -2.2356    0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  6 16  1  0
  7 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
M  END
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3D SDF for HMDB0001859 (Acetaminophen)

316
  Mrv1652305271900012D          

 11 11  0  0  0  0            999 V2000
    2.3645   -2.1409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.1591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.1591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    2.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2 10  2  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  2  0  0  0  0
  7  9  2  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001859

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NC1=CC=C(O)C=C1

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

> <INCHI_KEY>
RZVAJINKPMORJF-UHFFFAOYSA-N

> <FORMULA>
C8H9NO2

> <MOLECULAR_WEIGHT>
151.1626

> <EXACT_MASS>
151.063328537

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.521685397961242

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(4-hydroxyphenyl)acetamide

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
0.9073908616666664

> <ALOGPS_LOGS>
-1.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.653657748938226

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.464366400804778

> <JCHEM_PKA_STRONGEST_BASIC>
-4.362180897047582

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
42.901900000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetaminophen

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001859 (Acetaminophen)

HMDB0001859
     RDKit          3D
Acetaminophen
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.7382    0.4326    0.6352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2723    0.6463    0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0104    1.7737   -0.1813 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3401   -0.3693    0.5185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0355   -0.2646    0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6706    0.8237   -0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0494    0.8405   -0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8326   -0.2426   -0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1870   -0.2371   -0.5073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2140   -1.3517    0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8686   -1.3690    0.5087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2074    1.3948    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8406   -0.3083    1.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2486    0.0509   -0.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7108   -1.2625    0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1261    1.7122   -0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5331    1.7154   -0.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7103    0.5147   -0.8854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7774   -2.2641    0.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3638   -2.2356    0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  6 16  1  0
  7 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
M  END
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PDB for HMDB0001859 (Acetaminophen)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 316                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       4.414  -3.996   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.081   2.164   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       4.414   2.164   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.414   0.624   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.747  -0.146   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.080  -0.146   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747  -1.686   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080  -1.686   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -2.456   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747   2.934   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747   4.474   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3    4   10                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6    9                                                       
CONECT    9    1    7    8                                                  
CONECT   10    2    3   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0001859 (Acetaminophen)

COMPND    HMDB0001859
HETATM    1  C1  UNL     1       3.738   0.433   0.635  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.272   0.646   0.295  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.010   1.774  -0.181  1.00  0.00           O  
HETATM    4  N1  UNL     1       1.340  -0.369   0.518  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.035  -0.265   0.236  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.671   0.824  -0.290  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.049   0.840  -0.540  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.833  -0.243  -0.266  1.00  0.00           C  
HETATM    9  O2  UNL     1      -4.187  -0.237  -0.507  1.00  0.00           O  
HETATM   10  C7  UNL     1      -2.214  -1.352   0.265  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.869  -1.369   0.509  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.207   1.395   0.917  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.841  -0.308   1.436  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.249   0.051  -0.264  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.711  -1.262   0.925  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.126   1.712  -0.531  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.533   1.715  -0.957  1.00  0.00           H  
HETATM   18  H7  UNL     1      -4.710   0.515  -0.885  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.777  -2.264   0.512  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.364  -2.236   0.927  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3    4
CONECT    4    5   15
CONECT    5    6    6   11
CONECT    6    7   16
CONECT    7    8    8   17
CONECT    8    9   10
CONECT    9   18
CONECT   10   11   11   19
CONECT   11   20
END
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SMILES for HMDB0001859 (Acetaminophen)

CC(=O)NC1=CC=C(O)C=C1
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INCHI for HMDB0001859 (Acetaminophen)

InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
4'-HydroxyacetanilideChEBI
4-(Acetylamino)phenolChEBI
4-AcetamidophenolChEBI
AcenolChEBI
AcetaminofenChEBI
AcetaminopheneChEBI
APAPChEBI
N-Acetyl-p-aminophenolChEBI
p-AcetamidophenolChEBI
p-AcetaminophenolChEBI
p-AcetylaminophenolChEBI
p-HydroxyacetanilideChEBI
p-HydroxyphenolacetamideChEBI
PanadolChEBI
ParacetamolumChEBI
TylenolChEBI
ParacetamolKegg
4-AcetaminophenolHMDB
4-HydroxyacetanilideHMDB
4-Hydroxyanilid kyseliny octoveHMDB
a-PerHMDB
A.F. anacinHMDB
AbenolHMDB
AbensanilHMDB
AbrolHMDB
AbroletHMDB
AcamolHMDB
Accu-tapHMDB
AcephenHMDB
AcertolHMDB
Aceta elixirHMDB
Aceta tabletsHMDB
AcetagesicHMDB
AcetalginHMDB
Acetaminophen unisertsHMDB
AcetamolHMDB
AcetofenHMDB
ActaminHMDB
Actamin extraHMDB
Actamin superHMDB
Actifed plusHMDB
Actimol chewable tabletsHMDB
Actimol children's suspensionHMDB
Actimol infants' suspensionHMDB
Actimol junior strength capletsHMDB
ActronHMDB
AfebrinHMDB
AfebrylHMDB
AferadolHMDB
AlgesidalHMDB
AlginaHMDB
AlgomolHMDB
AlgotropylHMDB
AllayHMDB
alpha-PerHMDB
AlpinyHMDB
AlpinylHMDB
AlvedonHMDB
AmadilHMDB
AminofenHMDB
Aminofen maxHMDB
Anacin-3HMDB
Anacin-3 extra strengthHMDB
Anadin dla dzieciHMDB
AnaflonHMDB
AnalterHMDB
AnapapHMDB
AndoxHMDB
AnelixHMDB
AnexsiaHMDB
Anexsia 10/660HMDB
Anexsia 5/325HMDB
Anexsia 7.5/325HMDB
Anexsia 7.5/650HMDB
AnhibaHMDB
AnoquanHMDB
Anti-algosHMDB
AntidolHMDB
ApacetHMDB
Apacet capsulesHMDB
Apacet elixirHMDB
Apacet extra strength capletsHMDB
Apacet extra strength tabletsHMDB
Apacet regular strength tabletsHMDB
ApadonHMDB
ApamidHMDB
ApamideHMDB
ApitrelalHMDB
Apo-acetaminophenHMDB
ArfenHMDB
AsetamHMDB
AsomalHMDB
AspacHMDB
Aspirin free anacin maximum strength capletsHMDB
Aspirin free anacin maximum strength gel capletsHMDB
Aspirin free anacin maximum strength tabletsHMDB
Aspirin-free anacinHMDB
Aspirin-free excedrin capletsHMDB
AsplinHMDB
Atasol capletsHMDB
Atasol dropsHMDB
Atasol forte capletsHMDB
Atasol forte tabletsHMDB
Atasol oral solutionHMDB
Atasol tabletsHMDB
AtralidonHMDB
BabikanHMDB
BacetamolHMDB
BancapHMDB
Bancap HCHMDB
BanesinHMDB
Bayer select allergy-sinusHMDB
Bayer select head coldHMDB
Bayer select headache painHMDB
Bayer select maximum strength headache pain relief formulaHMDB
Bayer select menstrual multi-symptomHMDB
Bayer select sinus pain reliefHMDB
Ben-u-ronHMDB
BenmyoHMDB
Bickie-molHMDB
BiocetamolHMDB
BucetHMDB
ButalbitalHMDB
ButapapHMDB
CadafenHMDB
CalapolHMDB
CalmanticoldHMDB
CalpolHMDB
Capital with codeineHMDB
CaptinHMDB
CausalonHMDB
CefalexHMDB
CetadolHMDB
Children'S acetaminophen elixir dropsHMDB
Children'S acetaminophen oral solutionHMDB
Children'S tylenol chewableHMDB
Claradol codeineHMDB
ClixodyneHMDB
CO-GesicHMDB
COD-Acamol forteHMDB
CodabrolHMDB
CodalginHMDB
CodapaneHMDB
CodicetHMDB
CodisalHMDB
Codisal forteHMDB
CodolipraneHMDB
Codral pain reliefHMDB
CofamolHMDB
ConacetolHMDB
Contac cough & sore throat formulaHMDB
Contra-schmerz pHMDB
CoricidinHMDB
Coricidin DHMDB
Coricidin sinusHMDB
CosutoneHMDB
Croix blancheHMDB
CuponolHMDB
CuradonHMDB
CurpolHMDB
CustodialHMDB
Dapa X-SHMDB
DarocetHMDB
DarvocetHMDB
Darvocet-N 50HMDB
DatrilHMDB
Datril extra-strengthHMDB
DaygripHMDB
DemiletsHMDB
DeminofenHMDB
DemocylHMDB
DemogripalHMDB
DesfebreHMDB
DhamolHMDB
DHC PlusHMDB
Dial-a-gesicHMDB
Dial-alpha-gesicHMDB
DimindolHMDB
DiroxHMDB
DisprolHMDB
Dol-stopHMDB
DolcorHMDB
DolefinHMDB
DolegrippinHMDB
Dolene ap-65HMDB
DolgesicHMDB
DolipraneHMDB
DolkoHMDB
DolofuginHMDB
DoloreductHMDB
DolorfugHMDB
Dolorol forteHMDB
DolorstopHMDB
DolotecHMDB
DolproneHMDB
DorocoffHMDB
DresanHMDB
Dristan cold no drowsinessHMDB
DristancitoHMDB
DuracetamolHMDB
Duradyne DHCHMDB
DurapanHMDB
DymadonHMDB
Dymadon coHMDB
Dymadon forteHMDB
DypapHMDB
EcosetolHMDB
ElixodyneHMDB
EmpracetHMDB
EndeconHMDB
EnelfaHMDB
EnerilHMDB
EsgicHMDB
Esgic-plusHMDB
Eu-medHMDB
ExcedrinHMDB
Excedrin capletsHMDB
Excedrin extra strength capletsHMDB
ExcipainHMDB
ExdolHMDB
Exdol strongHMDB
FanalgicHMDB
FarmadolHMDB
FebranineHMDB
FebrectalHMDB
FebrectolHMDB
FebrexHMDB
FebricetHMDB
FebridolHMDB
FebrilixHMDB
FebrinHMDB
FebrinolHMDB
Febro-gesicHMDB
FebrolinHMDB
FemcetHMDB
FendonHMDB
FensumHMDB
FepanilHMDB
Feverall junior strengthHMDB
Feverall sprinkle caps junior strengthHMDB
FevorHMDB
FinimalHMDB
FiniwehHMDB
FioricetHMDB
FluparmolHMDB
Fortalidon pHMDB
Freka-cetamolHMDB
Gattaphen THMDB
GelocatilHMDB
GelupraneHMDB
Genapap children's elixirHMDB
Genapap children's tabletsHMDB
Genapap extra strength capletsHMDB
Genapap extra strength tabletsHMDB
Genapap regular strength tabletsHMDB
Genebs extra strength capletsHMDB
Genebs regular strength tabletsHMDB
Genebs X-traHMDB
Geralgine-pHMDB
Gripin bebeHMDB
GrippostadHMDB
GynospasmineHMDB
HedexHMDB
Helon NHMDB
HomoolanHMDB
Hy-phenHMDB
Hycomine compoundHMDB
HydrocetHMDB
IldamolHMDB
InalgexHMDB
InfadropsHMDB
Infants' feverallHMDB
Influbene NHMDB
InjectapapHMDB
IntensinHMDB
JanupapHMDB
Junior disprolHMDB
KataprinHMDB
Kinder finimalHMDB
KorumHMDB
Kratofin simplexHMDB
LabamolHMDB
LekadolHMDB
LemgripHMDB
LemsipHMDB
LestempHMDB
LiquagesicHMDB
Liquigesic coHMDB
LiquiprinHMDB
Liquiprin children's elixirHMDB
Liquiprin infants" dropsHMDB
LonaridHMDB
Lonarid monoHMDB
Lorcet-HDHMDB
LortabHMDB
LupocetHMDB
LytecaHMDB
Lyteca syrupHMDB
MagnidolHMDB
Malex NHMDB
MalgisHMDB
MalidensHMDB
MaxadolHMDB
Medigesic plusHMDB
Medinol paediatricHMDB
MedocodeneHMDB
Melabon infantilHMDB
MexalenHMDB
Midol maximum strengthHMDB
Midol PM night time formulaHMDB
Midol regular strengthHMDB
Midol teen formulaHMDB
Migraleve yellowHMDB
MinafenHMDB
MinosetHMDB
MiralginHMDB
MomentumHMDB
mono PraecimedHMDB
MultinHMDB
N-(4-Hydroxyphenyl)acetamideHMDB
N-Acetyl-4-aminophenolHMDB
NaldegesicHMDB
NAPAHMDB
NapafenHMDB
NapapHMDB
NaprinolHMDB
NealgylHMDB
NebsHMDB
Neo-fepramolHMDB
NeoCitranHMDB
NeodolHMDB
NeodolitoHMDB
NeopapHMDB
NeotrendHMDB
NeuridonHMDB
New cortal for childrenHMDB
NilnOcenHMDB
NinaHMDB
NO-FebrilHMDB
NobedonHMDB
NodolexHMDB
NoralHMDB
NorcetHMDB
NorcoHMDB
O-AcetaminophenolHMDB
OltylHMDB
OralganHMDB
Oraphen-PDHMDB
OrtensanHMDB
OxycetHMDB
OxycocetHMDB
Oxycodone 2.5/apap 500HMDB
Oxycodone 5/apap 500HMDB
p-(Acetylamino)phenolHMDB
PacecoHMDB
PacemoHMDB
PacemolHMDB
PacetHMDB
PacimolHMDB
PaedialgonHMDB
PaedolHMDB
PainexHMDB
PaldesicHMDB
PamolHMDB
PanaceteHMDB
PanadeineHMDB
Panadeine coHMDB
PanadieneHMDB
Panado-coHMDB
Panado-co capletsHMDB
Panadol extra strengthHMDB
Panadol junior strength capletsHMDB
Panadol maximum strength capletsHMDB
Panadol maximum strength tabletsHMDB
PanaleveHMDB
PanamaxHMDB
PanasorbHMDB
PanasorbeHMDB
PanetsHMDB
PanexHMDB
PanodilHMDB
PanofenHMDB
PantalginHMDB
Papa-deine #3HMDB
Papa-deine #4HMDB
Para-suppoHMDB
Para-tabsHMDB
ParacemolHMDB
ParacenolHMDB
ParacetHMDB
Paracetamol alHMDB
Paracetamol antipanin pHMDB
Paracetamol basicsHMDB
Paracetamol BCHMDB
Paracetamol DCHMDB
Paracetamol dr. schmidgallHMDB
Paracetamol fecofarHMDB
Paracetamol genericonHMDB
Paracetamol hanselerHMDB
Paracetamol harkleyHMDB
Paracetamol heumannHMDB
Paracetamol hexalHMDB
Paracetamol italfarmacoHMDB
Paracetamol nycomedHMDB
Paracetamol PBHMDB
Paracetamol raffoHMDB
Paracetamol ratiopharmHMDB
Paracetamol roschHMDB
Paracetamol saarHMDB
Paracetamol smithkline beechamHMDB
Paracetamol stadaHMDB
Paracetamol von CTHMDB
Paracetamol winthropHMDB
ParacetamoleHMDB
ParacetamoloHMDB
ParacetanolHMDB
ParacetolHMDB
ParacinHMDB
ParacodHMDB
ParacodolHMDB
ParadorHMDB
ParadropsHMDB
ParakaptonHMDB
ParakeHMDB
ParalenHMDB
ParaliefHMDB
ParalinkHMDB
ParalyocHMDB
ParamolHMDB
ParamolanHMDB
ParanoxHMDB
ParapanHMDB
ParasedolHMDB
ParasinHMDB
ParaspenHMDB
ParcetolHMDB
ParelanHMDB
ParmolHMDB
ParogalHMDB
ParomaHMDB
PasolindHMDB
Pasolind NHMDB
PCM Paracetamol lichtensteinHMDB
Pe-tamHMDB
PediapirinHMDB
PediatrixHMDB
PedricHMDB
PercocetHMDB
Percocet-5HMDB
Percocet-demiHMDB
Percogesic with codeineHMDB
Perdolan monoHMDB
PhenaphenHMDB
Phenaphen capletsHMDB
Phenaphen w/codeineHMDB
PhendonHMDB
PhenipirinHMDB
PhogoglandinHMDB
PhrenilinHMDB
Phrenilin forteHMDB
PinexHMDB
PiraminHMDB
PirinasolHMDB
PlicetHMDB
PolmofenHMDB
PredimolHMDB
PredualitoHMDB
Prestwick_13HMDB
ProdolHMDB
PromptHMDB
ProntinaHMDB
PropacetHMDB
Propacet 100HMDB
Proval #3HMDB
PuernolHMDB
PulmofenHMDB
Pyregesic-CHMDB
PyrigesicHMDB
PyrinazineHMDB
PyromedHMDB
Quiet worldHMDB
RedutempHMDB
RelivHMDB
RemedolHMDB
Rhinex D-lay tabletsHMDB
RivalgylHMDB
RobigesicHMDB
Robitussin night reliefHMDB
Rockamol plusHMDB
RounoxHMDB
RoxicetHMDB
Roxicet 5/500HMDB
RoxiloxHMDB
RubieMolHMDB
RubophenHMDB
RupemolHMDB
SalzoneHMDB
SanicetHMDB
SanicopyrineHMDB
ScanolHMDB
ScentalgylHMDB
Scherzatabletten rezeptur 534HMDB
SchmerzexHMDB
SedalitoHMDB
SedapapHMDB
SemolacinHMDB
ServigesicHMDB
SeskamolHMDB
SetakopHMDB
SetamolHMDB
SetolHMDB
SifenolHMDB
SinasprilHMDB
Sine-OFF sinus medicine capletsHMDB
SinedolHMDB
SinmolHMDB
SinubidHMDB
SK-ApapHMDB
Snaplets-FRHMDB
Spalt fur die nachtHMDB
Spalt NHMDB
ST Joseph aspirin-freeHMDB
ST Joseph aspirin-free for childrenHMDB
St. joseph cold tablets for childrenHMDB
St. joseph fever reducerHMDB
StanbackHMDB
StopainHMDB
Sudafed severe cold formulaHMDB
Sudafed sinusHMDB
SunethetonHMDB
SupacHMDB
Supadol monoHMDB
SupofenHMDB
SuppapHMDB
Suppap-120HMDB
Suppap-325HMDB
Suppap-650HMDB
Supramol-mHMDB
Synalgos-DC-aHMDB
TabalginHMDB
TachiprinaHMDB
TalacenHMDB
Tapanol extra strength capletsHMDB
Tapanol extra strength tabletsHMDB
TaparHMDB
Tavist allergy/sinus/headacheHMDB
TazamolHMDB
TemloHMDB
TempanalHMDB
TempraHMDB
Tempra capletsHMDB
Tempra chewable tabletsHMDB
Tempra d.sHMDB
Tempra dropsHMDB
Tempra syrupHMDB
TenconHMDB
TermacetHMDB
TermalginHMDB
TermalgineHMDB
TermofrenHMDB
TheraFluHMDB
TibinideHMDB
TibizideHMDB
TiffyHMDB
TisinHMDB
TisiodrazidaHMDB
TitralganHMDB
TizideHMDB
Tocris-1706HMDB
Toximer pHMDB
TralgonHMDB
Treupel monHMDB
Treupel NHMDB
TreuphadolHMDB
TriadHMDB
Triaminic sore throat formulaHMDB
TriaprinHMDB
TricotonHMDB
TussapapHMDB
TycoletHMDB
TYLHMDB
Tylenol allergy sinusHMDB
Tylenol arthritis extended reliefHMDB
Tylenol capletsHMDB
Tylenol children's chewable tabletsHMDB
Tylenol children's elixirHMDB
Tylenol children's suspension liquidHMDB
Tylenol dropsHMDB
Tylenol elixirHMDB
Tylenol extra strength adult liquid pain relieverHMDB
Tylenol extra strength capletsHMDB
Tylenol extra strength gelcapsHMDB
Tylenol extra strength tabletsHMDB
Tylenol gelcapsHMDB
Tylenol infants dropsHMDB
Tylenol infants" suspension dropsHMDB
Tylenol junior strength capletsHMDB
Tylenol junior strength chewable tabletsHMDB
Tylenol regular strength capletsHMDB
Tylenol regular strength tabletsHMDB
Tylenol tabletsHMDB
TylexHMDB
Tylex CDHMDB
TylolHMDB
TyloxHMDB
Tylox-325HMDB
TymolHMDB
UltracetHMDB
UpsanolHMDB
UtraginHMDB
ValadolHMDB
ValgesicHMDB
ValorinHMDB
Valorin extraHMDB
VanquishHMDB
VeralginaHMDB
VermidonHMDB
VerpolHMDB
Viclor richetHMDB
VicodinHMDB
Vicodin esHMDB
Vicodin HPHMDB
VipsHMDB
VirufluHMDB
VivimedHMDB
VolpanHMDB
WygesicHMDB
ZatinolHMDB
ZolbenHMDB
AcetacoHMDB
Anacin3HMDB
N-(4-Hydroxyphenyl)acetanilideHMDB
AcetominophenHMDB
HydroxyacetanilideHMDB
AcetamidophenolHMDB
Anacin 3HMDB
Chemical FormulaC8H9NO2
Average Molecular Weight151.1626
Monoisotopic Molecular Weight151.063328537
IUPAC NameN-(4-hydroxyphenyl)acetamide
Traditional Nameacetaminophen
CAS Registry Number103-90-2
SMILES
CC(=O)NC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
InChI KeyRZVAJINKPMORJF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-2-unsubstituted benzenoids
Direct Parent1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Health effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial applicationEnvironmental role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point170 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility14 mg/mL at 25 °CNot Available
LogP0.46SANGSTER (1994)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-McLean134.1630932474
[M+H]+McLean132.0130932474
[M+H]+Not Available129.689http://allccs.zhulab.cn/database/detail?ID=AllCCS00000732
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.15 g/LALOGPS
logP0.51ALOGPS
logP0.91ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity42.9 m³·mol⁻¹ChemAxon
Polarizability15.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.49531661259
DarkChem[M-H]-131.6931661259
AllCCS[M+H]+132.33832859911
AllCCS[M-H]-130.96432859911
DeepCCS[M+H]+133.95130932474
DeepCCS[M-H]-130.27230932474
DeepCCS[M-2H]-167.80230932474
DeepCCS[M+Na]+143.3430932474
AllCCS[M+H]+132.332859911
AllCCS[M+H-H2O]+127.932859911
AllCCS[M+NH4]+136.532859911
AllCCS[M+Na]+137.732859911
AllCCS[M-H]-131.032859911
AllCCS[M+Na-2H]-132.432859911
AllCCS[M+HCOO]-133.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AcetaminophenCC(=O)NC1=CC=C(O)C=C12387.6Standard polar33892256
AcetaminophenCC(=O)NC1=CC=C(O)C=C11639.3Standard non polar33892256
AcetaminophenCC(=O)NC1=CC=C(O)C=C11736.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Acetaminophen,1TMS,isomer #1CC(=O)NC1=CC=C(O[Si](C)(C)C)C=C11767.1Semi standard non polar33892256
Acetaminophen,1TMS,isomer #2CC(=O)N(C1=CC=C(O)C=C1)[Si](C)(C)C1634.8Semi standard non polar33892256
Acetaminophen,2TMS,isomer #1CC(=O)N(C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C1606.6Semi standard non polar33892256
Acetaminophen,2TMS,isomer #1CC(=O)N(C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C1679.1Standard non polar33892256
Acetaminophen,2TMS,isomer #1CC(=O)N(C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C1765.5Standard polar33892256
Acetaminophen,1TBDMS,isomer #1CC(=O)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12039.0Semi standard non polar33892256
Acetaminophen,1TBDMS,isomer #2CC(=O)N(C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C1910.8Semi standard non polar33892256
Acetaminophen,2TBDMS,isomer #1CC(=O)N(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2105.8Semi standard non polar33892256
Acetaminophen,2TBDMS,isomer #1CC(=O)N(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2148.6Standard non polar33892256
Acetaminophen,2TBDMS,isomer #1CC(=O)N(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2053.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Acetaminophen GC-MS (2 TMS)splash10-0a4i-4971200000-17e6e1373f10ba4ec1382014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetaminophen EI-B (Non-derivatized)splash10-0a4i-1900000000-df97f74a81da3a46a6972017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetaminophen EI-B (Non-derivatized)splash10-0a4i-4900000000-ef277124e1b50b5f010e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetaminophen CI-B (Non-derivatized)splash10-0udi-0900000000-7aa6a54b74b345d91e372017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetaminophen GC-MS (Non-derivatized)splash10-0a4i-4971200000-17e6e1373f10ba4ec1382017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetaminophen GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-3900000000-070b8ab49f93898e0aa42017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetaminophen GC-MS (1 TMS) - 70eV, Positivesplash10-05gl-8930000000-76d6dca6afdf5945dba12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetaminophen GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-4900000000-ffdd0f8a1e6e450fc1622014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen LC-ESI-ITFT , negative-QTOFsplash10-0zfr-0900000000-125e44ce332576a1e1552017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen LC-ESI-ITFT , negative-QTOFsplash10-0udi-0900000000-7e46df4b4b653c90c2582017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen LC-ESI-ITFT , negative-QTOFsplash10-0udi-0900000000-bb6e34d2d574a249d7212017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen LC-ESI-ITFT , negative-QTOFsplash10-0udi-0900000000-2f45dd7efce38361f8062017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen LC-ESI-ITFT , negative-QTOFsplash10-0pb9-0900000000-e48b48d64b6b985ab4552017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0900000000-b72b0e33fd35512fe6de2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0900000000-97bcaa95f26159307d032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen LC-ESI-ITFT , negative-QTOFsplash10-0udi-0900000000-c50b4b79792e2c2e68f92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen LC-ESI-ITFT , negative-QTOFsplash10-0udi-0900000000-7e46df4b4b653c90c2582017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen LC-ESI-ITFT , negative-QTOFsplash10-0udi-0900000000-2b07cd2813d3f23e88f12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen LC-ESI-ITFT , negative-QTOFsplash10-0pb9-0900000000-5b92f09589afe838f23a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0900000000-f0ca5ff6526b9f0050342017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen LC-ESI-ITFT , negative-QTOFsplash10-0udi-0900000000-7e45ef71674dcdde90682017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen 15V, Negative-QTOFsplash10-0a4i-0900000000-f6d6bd9ad3bc874fabd52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen 35V, Negative-QTOFsplash10-0a4i-0900000000-7ec733f46e03a5a79fc42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen 30V, Negative-QTOFsplash10-0udi-0900000000-bb6e34d2d574a249d7212021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen 45V, Negative-QTOFsplash10-0udi-0900000000-2f45dd7efce38361f8062021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen 30V, Negative-QTOFsplash10-0udi-0900000000-7e46df4b4b653c90c2582021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen 35V, Negative-QTOFsplash10-0zfr-0900000000-125e44ce332576a1e1552021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen 60V, Negative-QTOFsplash10-0pb9-0900000000-e48b48d64b6b985ab4552021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen 75V, Negative-QTOFsplash10-0a4i-0900000000-b72b0e33fd35512fe6de2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen 45V, Negative-QTOFsplash10-0udi-0900000000-2b07cd2813d3f23e88f12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen 90V, Negative-QTOFsplash10-0a4i-0900000000-97bcaa95f26159307d032021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen 60V, Negative-QTOFsplash10-0pb9-0900000000-5b92f09589afe838f23a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen 75V, Negative-QTOFsplash10-0a4i-0900000000-f0ca5ff6526b9f0050342021-09-20HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • All Tissues
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified11 +/- 6 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified5.3 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified11.1 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified33.5 +/- 22.3 uMAdult (>18 years old)BothHeart Transplant details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified50.71 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB00316
Phenol Explorer Compound IDNot Available
FooDB IDFDB022713
KNApSAcK IDC00044491
Chemspider ID1906
KEGG Compound IDC06804
BioCyc IDCPD-7669
BiGG IDNot Available
Wikipedia LinkAcetaminophen
METLIN ID6353
PubChem Compound1983
PDB IDNot Available
ChEBI ID46195
Food Biomarker OntologyNot Available
VMH IDACMP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. de Morais SM, Uetrecht JP, Wells PG: Decreased glucuronidation and increased bioactivation of acetaminophen in Gilbert's syndrome. Gastroenterology. 1992 Feb;102(2):577-86. [PubMed:1732127 ]
  2. Muldrew KL, James LP, Coop L, McCullough SS, Hendrickson HP, Hinson JA, Mayeux PR: Determination of acetaminophen-protein adducts in mouse liver and serum and human serum after hepatotoxic doses of acetaminophen using high-performance liquid chromatography with electrochemical detection. Drug Metab Dispos. 2002 Apr;30(4):446-51. [PubMed:11901099 ]
  3. Bales JR, Nicholson JK, Sadler PJ: Two-dimensional proton nuclear magnetic resonance "maps" of acetaminophen metabolites in human urine. Clin Chem. 1985 May;31(5):757-62. [PubMed:3987005 ]
  4. van der Marel CD, Anderson BJ, Pluim MA, de Jong TH, Gonzalez A, Tibboel D: Acetaminophen in cerebrospinal fluid in children. Eur J Clin Pharmacol. 2003 Aug;59(4):297-302. Epub 2003 Jul 4. [PubMed:12845506 ]
  5. Watari N, Iwai M, Kaneniwa N: Pharmacokinetic study of the fate of acetaminophen and its conjugates in rats. J Pharmacokinet Biopharm. 1983 Jun;11(3):245-72. [PubMed:6644552 ]
  6. Kunkel A, Watzig H: Micellar electrokinetic capillary chromatography as a powerful tool for pharmacological investigations without sample pretreatment: a precise technique providing cost advantages and limits of detection to the low nanomolar range. Electrophoresis. 1999 Sep;20(12):2379-89. [PubMed:10499329 ]
  7. Vanbinst R, Koenig J, Di Fazio V, Hassoun A: Bile analysis of drugs in postmortem cases. Forensic Sci Int. 2002 Aug 14;128(1-2):35-40. [PubMed:12208019 ]
  8. Quattrone AJ, Putnam RS: A single liquid-chromatographic procedure for therapeutic monitoring of theophylline, acetaminophen, or ethosuximide. Clin Chem. 1981 Jan;27(1):129-32. [PubMed:7004665 ]
  9. Smilgin Z, Drozdzik M, Gawronska-Szklarz B, Wojcicki J, Tustanowski S, Gornik W: [Pharmacokinetics of acetaminophen in individuals occupationally exposed to polyvinyl chloride modified with plasticizers]. Med Pr. 1993;44(5):423-9. [PubMed:8107555 ]
  10. Griener JC, Msall ME, Cooke RE, Corcoran GB: Noninvasive determination of acetaminophen disposition in Down's syndrome. Clin Pharmacol Ther. 1990 Nov;48(5):520-8. [PubMed:2146059 ]
  11. Mohammadi M, Mohebbi MR, Naderi F: CSF Glucose Concentrations in Infants with Febrile Convulsions and the Possible Effect of Acetaminophen. Indian Pediatr. 2003 Dec;40(12):1183-6. [PubMed:14722369 ]
  12. Munsterhjelm E, Munsterhjelm NM, Niemi TT, Ylikorkala O, Neuvonen PJ, Rosenberg PH: Dose-dependent inhibition of platelet function by acetaminophen in healthy volunteers. Anesthesiology. 2005 Oct;103(4):712-7. [PubMed:16192763 ]
  13. Findlay JW, DeAngelis RL, Kearney MF, Welch RM, Findlay JM: Analgesic drugs in breast milk and plasma. Clin Pharmacol Ther. 1981 May;29(5):625-33. [PubMed:7214793 ]
  14. Lifshitz M, Weinstein O, Gavrilov V, Rosenthal G, Lifshitz T: Acetaminophen (paracetamol) levels in human tears. Ther Drug Monit. 1999 Oct;21(5):544-6. [PubMed:10519453 ]
  15. Bailey DN: Relative binding of acetaminophen, lidocaine, phenobarbital, phenytoin, quinidine, and theophylline to human tissues in vitro. J Anal Toxicol. 1997 Jan-Feb;21(1):1-4. [PubMed:9013284 ]
  16. Gandia P, Bareille MP, Saivin S, Le-Traon AP, Lavit M, Guell A, Houin G: Influence of simulated weightlessness on the oral pharmacokinetics of acetaminophen as a gastric emptying probe in man: a plasma and a saliva study. J Clin Pharmacol. 2003 Nov;43(11):1235-43. [PubMed:14551178 ]
  17. Graham GG, Scott KF, Day RO: Tolerability of paracetamol. Drug Saf. 2005;28(3):227-40. [PubMed:15733027 ]
  18. Barden J, Edwards J, Moore A, McQuay H: Single dose oral paracetamol (acetaminophen) for postoperative pain. Cochrane Database Syst Rev. 2004;(1):CD004602. [PubMed:14974073 ]
  19. Jaeschke H: Role of inflammation in the mechanism of acetaminophen-induced hepatotoxicity. Expert Opin Drug Metab Toxicol. 2005 Oct;1(3):389-97. [PubMed:16863451 ]
  20. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details
1. Prostaglandin G/H synthase 2
General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
Enzyme Details
2. Prostaglandin G/H synthase 1
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
Enzyme Details
3. Cytochrome P450 2E1
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
Enzyme Details
4. Cytochrome P450 1A2
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915