Record Information
Version1.0
Creation date2010-04-08 22:06:26 UTC
Update date2019-11-26 03:00:17 UTC
Primary IDFDB004879
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameOPC
DescriptionAripiprazole, also known as abilify or abilitat, belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group. Aripiprazole is a very strong basic compound (based on its pKa). Aripiprazole has been detected, but not quantified in, chinese cinnamons. This could make aripiprazole a potential biomarker for the consumption of these foods. Aripiprazole is a potentially toxic compound.
CAS Number129722-12-9
Structure
Thumb
Synonyms
SynonymSource
AbilifyChEBI
AbilitatChEBI
AripiprazolChEBI
AripiprazolumChEBI
7-(4-(4-(2,3-Dichlorophenyl)-1-piperazinyl)butyloxy)-3,4-dihydro-2(1H)-quinolinoneHMDB
Aripiprazolebiospider
Aripirazolebiospider
OPC 31manual
OPC-14597manual
Predicted Properties
PropertyValueSource
Water Solubility0.0078 g/LALOGPS
logP5.21ALOGPS
logP4.9ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)13.51ChemAxon
pKa (Strongest Basic)7.46ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.81 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity124.34 m³·mol⁻¹ChemAxon
Polarizability49.23 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC23H27Cl2N3O2
IUPAC name7-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy}-1,2,3,4-tetrahydroquinolin-2-one
InChI IdentifierInChI=1S/C23H27Cl2N3O2/c24-19-4-3-5-21(23(19)25)28-13-11-27(12-14-28)10-1-2-15-30-18-8-6-17-7-9-22(29)26-20(17)16-18/h3-6,8,16H,1-2,7,9-15H2,(H,26,29)
InChI KeyCEUORZQYGODEFX-UHFFFAOYSA-N
Isomeric SMILESClC1=CC=CC(N2CCN(CCCCOC3=CC4=C(CCC(=O)N4)C=C3)CC2)=C1Cl
Average Molecular Weight448.385
Monoisotopic Molecular Weight447.148032537
Classification
Description Belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPhenylpiperazines
Alternative Parents
Substituents
  • Phenylpiperazine
  • N-arylpiperazine
  • Tetrahydroquinolone
  • Quinolone
  • Tetrahydroquinoline
  • 1,2-dichlorobenzene
  • Tertiary aliphatic/aromatic amine
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Alkyl aryl ether
  • Halobenzene
  • Chlorobenzene
  • N-alkylpiperazine
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Tertiary amine
  • Tertiary aliphatic amine
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Ether
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point139-139.5 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSOPC, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0w4i-1490100000-261de3e19904b78dcdc2Spectrum
Predicted GC-MSOPC, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-3970100000-6b98b53e8175df39986e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0f72-0340900000-34d93478ad0d9f5cf2b02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-3970100000-6b98b53e8175df39986e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000b-0280900000-b9247c5494e58e66124c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-0190000000-f292c098f875dc5bf1032021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0130900000-09f4b35bcf7ec5b72e812016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-0691700000-856146a0ee910fc8c54b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-3950000000-13c06e4b3b715a51d3e42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0400900000-00ad2c66f6eb650acc112016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-2900400000-2f2ae13359ce2017c9792016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-5900000000-0638ccc974f117bcfc432016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000900000-80596c933df60e9bbd282021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0011900000-850b35a9d8f2a8e5dbe62021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-3920200000-00b90fd36a9ef68756de2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-ac7e0802ed0bc5c520a72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2000900000-2fd89cebd272760b74452021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03e9-6920100000-943ee90010dfdaceadee2021-09-24View Spectrum
NMRNot Available
ChemSpider ID54790
ChEMBL IDCHEMBL1112
KEGG Compound IDC12564
Pubchem Compound ID60795
Pubchem Substance IDNot Available
ChEBI ID31236
Phenol-Explorer IDNot Available
DrugBank IDDB01238
HMDB IDHMDB05042
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDOPC
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAripiprazole
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti-allergic50857 An agent that reduces or blocks allergic reactions, commonly used to manage symptoms of allergies, such as itching, sneezing, and inflammation, by inhibiting the release of histamine and other chemical mediators, providing relief in conditions like hay fever, asthma, and skin allergies.DUKE
Anti-anaphylactic52217 An agent that prevents or treats anaphylaxis, a severe allergic reaction. It plays a biological role in stabilizing mast cells and reducing histamine release. Therapeutically, it is used to manage allergic emergencies, with key medical applications including treatment of anaphylactic shock, asthma, and allergic rhinitis.DUKE
Anti-asthmatic49167 An agent that relieves bronchospasm and inflammation, commonly used to manage asthma symptoms, chronic obstructive pulmonary disease (COPD), and other respiratory disorders, improving lung function and overall respiratory health.DUKE
Anti-atherogenic38070 An agent that prevents or reduces the formation of atheromas (plaques) in arteries, thereby lowering the risk of cardiovascular disease. It inhibits the biological processes leading to atherosclerosis, and has therapeutic applications in managing hyperlipidemia, hypertension, and cardiovascular disease, with key medical uses including reducing inflammation and improving lipid profiles.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Antibiotic22582 An agent that inhibits the growth of or destroys microorganisms, particularly bacteria. Therapeutically, antibiotics are used to treat bacterial infections, such as pneumonia, tuberculosis, and skin infections, by targeting specific biochemical processes essential for microbial survival.DUKE
Anti-edemicAn agent that relieves or prevents edema, reducing abnormal fluid accumulation in tissues or the circulatory system, commonly used to treat conditions such as swelling, inflammation, and water retention.DUKE
Anti erythemic50177 An agent that reduces redness of the skin, often used to treat conditions like rosacea and eczema. It plays a biological role in inhibiting inflammation and dilating blood vessels, and has therapeutic applications in dermatology, with key medical uses including topical creams and ointments to alleviate skin redness and irritation.DUKE
Anti exudativeAn agent that reduces fluid or material leakage from cells and tissues, often caused by inflammation or injury, promoting healing and tissue repair, with therapeutic applications in managing edema, wounds, and inflammatory conditions.DUKE
Anti-gastriticAn agent that reduces stomach inflammation, protecting the gastric lining and relieving symptoms of gastritis, commonly used in managing ulcers, acid reflux, and gastrointestinal disorders.DUKE
Anti histaminic37956 An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis.DUKE
Anti HIV22587 An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti-obesity52217 An agent that reduces body weight, commonly used in managing obesity and related disorders, by regulating appetite, metabolism, and fat storage, with therapeutic applications in preventing chronic diseases such as diabetes and cardiovascular disease.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti radicularAn agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
CapillaritonicA flavonoid that strengthens capillaries, reducing permeability and fragility. It has anti-inflammatory and antioxidant properties, making it useful in treating conditions like hemorrhoids, varicose veins, and bruising. Therapeutically, capillaritonic is used to improve circulation, reduce swelling, and promote wound healing, commonly used in managing vascular disorders and preventing bleeding complications.DUKE
Hyaluronidase inhibitor23924 An agent that blocks the activity of hyaluronidase, an enzyme that breaks down hyaluronic acid. This inhibition helps maintain hyaluronic acid levels, reducing inflammation and improving tissue hydration, with therapeutic applications in ophthalmology, dermatology, and oncology, and key medical uses in treating dry eye, wrinkles, and certain cancers.DUKE
Immunomodulator50846 An agent that regulates the immune system, modifying its response to maintain balance. Therapeutically, it's used to treat autoimmune diseases, prevent transplant rejection, and manage chronic inflammatory conditions, such as rheumatoid arthritis and multiple sclerosis.DUKE
LipolyticAn agent that stimulates hydrolysis of fats into fatty acids and glycerol, playing a key biological role in fat metabolism. Therapeutically, lipolytics have applications in managing obesity and hypertriglyceridemia, with medical uses including weight loss and improving lipid profiles.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Sunscreen52217 A topical agent that blocks UV radiation, preventing skin damage and reducing the risk of skin cancer. Its therapeutic applications include protection against sunburn, photoaging, and photodermatoses. Key medical uses include prevention of melanoma, basal cell carcinoma, and squamous cell carcinoma, as well as management of photosensitive disorders.DUKE
Xanthine oxidase inhibitor35634 An agent that blocks xanthine oxidase, an enzyme involved in uric acid production, reducing inflammation and oxidative stress. Therapeutically, it's used to treat gout, hyperuricemia, and prevent kidney stones, with key applications in managing cardiovascular disease and improving kidney function.DUKE
Enzymes
NameGene NameUniProt ID
Alpha-2A adrenergic receptorADRA2AP08913
Alpha-2B adrenergic receptorADRA2BP18089
D(2) dopamine receptorDRD2P14416
D(4) dopamine receptorDRD4P21917
5-hydroxytryptamine receptor 7HTR7P34969
5-hydroxytryptamine receptor 1BHTR1BP28222
5-hydroxytryptamine receptor 1AHTR1AP08908
5-hydroxytryptamine receptor 6HTR6P50406
Histamine H1 receptorHRH1P35367
5-hydroxytryptamine receptor 3AHTR3AP46098
5-hydroxytryptamine receptor 1DHTR1DP28221
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).