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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:09 UTC
HMDB IDHMDB0015196
Secondary Accession Numbers
  • HMDB15196
Metabolite Identification
Common NameAcetophenazine
DescriptionAcetophenazine is only found in individuals that have used or taken this drug.It is an antipsychotic drug of moderate-potency. It is used in the treatment of disorganized and psychotic thinking. It is also used to help treat false perceptions (e.g. hallucinations or delusions).Acetophenazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.
Structure
Data?1582753269
Synonyms
ValueSource
TindalHMDB
Acetophenazine, (Z)-2-maleate (1:2) saltHMDB
Acetophenazine, ion (1+)HMDB
Acetophenazine maleateHMDB
Chemical FormulaC23H29N3O2S
Average Molecular Weight411.56
Monoisotopic Molecular Weight411.198047877
IUPAC Name1-(10-{3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)ethan-1-one
Traditional Nameacetophenazine
CAS Registry Number2751-68-0
SMILES
CC(=O)C1=CC=C2SC3=C(C=CC=C3)N(CCCN3CCN(CCO)CC3)C2=C1
InChI Identifier
InChI=1S/C23H29N3O2S/c1-18(28)19-7-8-23-21(17-19)26(20-5-2-3-6-22(20)29-23)10-4-9-24-11-13-25(14-12-24)15-16-27/h2-3,5-8,17,27H,4,9-16H2,1H3
InChI KeyWNTYBHLDCKXEOT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Acetophenone
  • Aryl thioether
  • Tertiary aliphatic/aromatic amine
  • Aryl ketone
  • Aryl alkyl ketone
  • N-alkylpiperazine
  • Para-thiazine
  • 1,4-diazinane
  • Piperazine
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • 1,2-aminoalcohol
  • Ketone
  • Thioether
  • Azacycle
  • Alkanolamine
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Primary alcohol
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.06 g/LNot Available
LogP3.1Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.06 g/LALOGPS
logP10(3.48) g/LALOGPS
logP10(2.65) g/LChemAxon
logS10(-3.8) g/LALOGPS
pKa (Strongest Acidic)15.46ChemAxon
pKa (Strongest Basic)8.07ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.02 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity121.7 m³·mol⁻¹ChemAxon
Polarizability46.68 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+193.22731661259
DarkChem[M-H]-193.9431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AcetophenazineCC(=O)C1=CC=C2SC3=C(C=CC=C3)N(CCCN3CCN(CCO)CC3)C2=C14578.2Standard polar33892256
AcetophenazineCC(=O)C1=CC=C2SC3=C(C=CC=C3)N(CCCN3CCN(CCO)CC3)C2=C13509.0Standard non polar33892256
AcetophenazineCC(=O)C1=CC=C2SC3=C(C=CC=C3)N(CCCN3CCN(CCO)CC3)C2=C13529.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Acetophenazine,1TMS,isomer #1CC(=O)C1=CC=C2SC3=CC=CC=C3N(CCCN3CCN(CCO[Si](C)(C)C)CC3)C2=C13557.5Semi standard non polar33892256
Acetophenazine,1TBDMS,isomer #1CC(=O)C1=CC=C2SC3=CC=CC=C3N(CCCN3CCN(CCO[Si](C)(C)C(C)(C)C)CC3)C2=C13765.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Acetophenazine EI-B (Non-derivatized)splash10-0h2f-7962200000-29f2e9055979e0add70b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetophenazine EI-B (Non-derivatized)splash10-0h2f-7962200000-29f2e9055979e0add70b2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetophenazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-2349000000-75f8347d32e98e5870c42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetophenazine GC-MS (1 TMS) - 70eV, Positivesplash10-0gb9-4497700000-19170722c4cd954d36352017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetophenazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetophenazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetophenazine 10V, Positive-QTOFsplash10-03di-0216900000-65d7ee22f5883ea892672016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetophenazine 20V, Positive-QTOFsplash10-01wf-2629300000-b3894f918e8b27475eb12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetophenazine 40V, Positive-QTOFsplash10-0c3d-7953000000-80f19278e9466e5d33172016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetophenazine 10V, Negative-QTOFsplash10-03di-0005900000-d644bc2fd53c94c1fd762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetophenazine 20V, Negative-QTOFsplash10-0lxx-0189200000-8d67c1b2bf104d1d35782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetophenazine 40V, Negative-QTOFsplash10-0006-6791000000-4e91c776a81d776e96112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetophenazine 10V, Positive-QTOFsplash10-03di-0000900000-94a2b7e7b061d09294532021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetophenazine 20V, Positive-QTOFsplash10-03k9-0903800000-ddba95d3edbef216993e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetophenazine 40V, Positive-QTOFsplash10-000t-9606000000-223d2b11bec3cc5994582021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetophenazine 10V, Negative-QTOFsplash10-03di-0000900000-474df7b273d6c5e26ef62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetophenazine 20V, Negative-QTOFsplash10-03di-0005900000-c57eba79e8d178fc66422021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetophenazine 40V, Negative-QTOFsplash10-0006-0097000000-0aef515b0551c87a094b2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01063 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01063 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01063
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID16708
KEGG Compound IDC06807
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetophenazine
METLIN IDNot Available
PubChem Compound17676
PDB IDNot Available
ChEBI ID2401
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tam SW, Cook L: Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes. Proc Natl Acad Sci U S A. 1984 Sep;81(17):5618-21. [PubMed:6147851 ]
  2. Jones GL, Woodbury DM: Spin-label study of phenothiazine interactions with erythrocyte ghost membranes: a possible membrane-mediated antisickling action. J Pharmacol Exp Ther. 1978 Oct;207(1):203-11. [PubMed:702341 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular weight:
50618.9
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]
  4. Tam SW, Cook L: Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes. Proc Natl Acad Sci U S A. 1984 Sep;81(17):5618-21. [PubMed:6147851 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:
DRD1
Uniprot ID:
P21728
Molecular weight:
49292.8
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]