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Showing metabocard for Acetophenone (HMDB0033910)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 18:41:07 UTC
Update Date2023-02-21 17:23:45 UTC
HMDB IDHMDB0033910
Secondary Accession Numbers
  • HMDB33910
Metabolite Identification
Common NameAcetophenone
DescriptionAcetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colourless, viscous liquid is a precursor to useful resins and fragrances. Acetophenone is found in chicory. Acetophenone is a flavouring ingredient used in fruit flavours. Acetophenone is a raw material for the synthesis of some pharmaceuticals and is also listed as an approved excipient by the U.S. FDA. In a 1994 report released by five top cigarette companies in the U.S., acetophenone was listed as one of the 599 additives to cigarettes.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0033910 (Acetophenone)

  Mrv1652303202019002D          

  9  9  0  0  0  0            999 V2000
    0.0000    2.4750    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
    1.4289    2.4750    0.0000 O   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
    1.4289    0.8250    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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  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  2  0  0  0  0
  4  9  1  0  0  0  0
M  END
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3D MOL for HMDB0033910 (Acetophenone)

HMDB0033910
     RDKit          3D
Acetophenone
 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.6594    0.5281   -0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6664   -0.5542   -0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0725   -1.7422   -0.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2309   -0.3212    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2678    0.9697    0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6413    1.1746    0.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5358    0.1158    0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325   -1.1689    0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6613   -1.3632    0.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8675    0.9064    0.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5990    0.1589   -0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3304    1.3856   -0.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4067    1.8293   -0.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    2.2014    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6058    0.2730    0.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7477   -1.9802    0.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3310   -2.4131    0.0269 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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3D SDF for HMDB0033910 (Acetophenone)

  Mrv1652303202019002D          

  9  9  0  0  0  0            999 V2000
    0.0000    2.4750    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
    1.4289    2.4750    0.0000 O   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
    1.4289    0.8250    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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  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  2  0  0  0  0
  4  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033910

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3

> <INCHI_KEY>
KWOLFJPFCHCOCG-UHFFFAOYSA-N

> <FORMULA>
C8H8O

> <MOLECULAR_WEIGHT>
120.1485

> <EXACT_MASS>
120.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.05282053698111

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-phenylethan-1-one

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
1.5308933346666667

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.099925039370238

> <JCHEM_PKA_STRONGEST_BASIC>
-7.3885191025078125

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
36.460800000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetophenone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0033910 (Acetophenone)

HMDB0033910
     RDKit          3D
Acetophenone
 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.6594    0.5281   -0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6664   -0.5542   -0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0725   -1.7422   -0.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2309   -0.3212    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2678    0.9697    0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6413    1.1746    0.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5358    0.1158    0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325   -1.1689    0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6613   -1.3632    0.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8675    0.9064    0.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5990    0.1589   -0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3304    1.3856   -0.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4067    1.8293   -0.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    2.2014    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6058    0.2730    0.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7477   -1.9802    0.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3310   -2.4131    0.0269 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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PDB for HMDB0033910 (Acetophenone)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   2.310   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for HMDB0033910 (Acetophenone)

COMPND    HMDB0033910
HETATM    1  C1  UNL     1      -2.659   0.528  -0.054  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.666  -0.554  -0.027  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.073  -1.742  -0.027  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.231  -0.321   0.001  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.268   0.970   0.002  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.641   1.175   0.029  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.536   0.116   0.054  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.033  -1.169   0.053  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.661  -1.363   0.026  1.00  0.00           C  
HETATM   10  H1  UNL     1      -2.867   0.906   0.979  1.00  0.00           H  
HETATM   11  H2  UNL     1      -3.599   0.159  -0.516  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.330   1.386  -0.709  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.407   1.829  -0.017  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.009   2.201   0.029  1.00  0.00           H  
HETATM   15  H6  UNL     1       3.606   0.273   0.075  1.00  0.00           H  
HETATM   16  H7  UNL     1       2.748  -1.980   0.073  1.00  0.00           H  
HETATM   17  H8  UNL     1       0.331  -2.413   0.027  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    4
CONECT    4    5    5    9
CONECT    5    6   13
CONECT    6    7    7   14
CONECT    7    8   15
CONECT    8    9    9   16
CONECT    9   17
END
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SMILES for HMDB0033910 (Acetophenone)

CC(=O)C1=CC=CC=C1
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INCHI for HMDB0033910 (Acetophenone)

InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC8H8O
Average Molecular Weight120.1485
Monoisotopic Molecular Weight120.057514878
IUPAC Name1-phenylethan-1-one
Traditional Nameacetophenone
CAS Registry Number98-86-2
SMILES
CC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3
InChI KeyKWOLFJPFCHCOCG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Acetophenone
  • Aryl alkyl ketone
  • Benzoyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationEnvironmental roleBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point20 °CNot Available
Boiling Point202.00 to 203.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility6.13 mg/mL at 25 °CNot Available
LogP1.58Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Breath
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAsthma details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease 		details
Associated Disorders and Diseases
Disease References
Asthma
  1. van de Kant KD, van Berkel JJ, Jobsis Q, Lima Passos V, Klaassen EM, van der Sande L, van Schayck OC, de Jongste JC, van Schooten FJ, Derks E, Dompeling E, Dallinga JW: Exhaled breath profiling in diagnosing wheezy preschool children. Eur Respir J. 2013 Jan;41(1):183-8. doi: 10.1183/09031936.00122411. [PubMed:23277518 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Associated OMIM IDs
DrugBank IDDB04619
Phenol Explorer Compound IDNot Available
FooDB IDFDB012106
KNApSAcK IDC00002685
Chemspider ID7132
KEGG Compound IDC07113
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetophenone
METLIN IDNot Available
PubChem Compound7410
PDB IDAC0
ChEBI ID27632
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1000131
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gul HI, Ojanen T, Vepsalainen J, Gul M, Erciyas E, Hanninen O: Antifungal activity of some mono, bis and quaternary Mannich bases derived from acetophenone. Arzneimittelforschung. 2001 Jan;51(1):72-5. [PubMed:11215330 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .