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Identification
NameArachidonic Acid
Accession NumberDB04557  (EXPT00409)
TypeSmall Molecule
GroupsExperimental
DescriptionAn unsaturated, essential fatty acid. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. [PubChem]
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII27YG812J1I
CAS number506-32-1
WeightAverage: 304.4669
Monoisotopic: 304.240230268
Chemical FormulaC20H32O2
InChI KeyInChIKey=YZXBAPSDXZZRGB-CGRWFSSPSA-N
InChI
InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6+,10-9+,13-12+,16-15+
IUPAC Name
(5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoic acid
SMILES
CCCCC\C=C\C\C=C\C\C=C\C\C=C\CCCC(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Lornoxicam Action PathwayDrug actionSMP00700
Phenylbutazone Action PathwayDrug actionSMP00701
Salsalate Action PathwayDrug actionSMP00707
Acetaminophen Action PathwayDrug actionSMP00710
Ketorolac Action PathwayDrug actionSMP00098
Suprofen Action PathwayDrug actionSMP00101
Valdecoxib Action PathwayDrug actionSMP00116
Diflunisal Action PathwayDrug actionSMP00289
Leukotriene C4 Synthesis DeficiencyDiseaseSMP00353
Trisalicylate-choline Action PathwayDrug actionSMP00703
Arachidonic Acid MetabolismMetabolicSMP00075
Meloxicam Action PathwayDrug actionSMP00106
Mefenamic Acid Action PathwayDrug actionSMP00109
Fc Epsilon Receptor I Signaling in Mast CellsSignalingSMP00358
Magnesium salicylate Action PathwayDrug actionSMP00698
Nepafenac Action PathwayDrug actionSMP00702
Salicylate-sodium Action PathwayDrug actionSMP00708
Alpha Linolenic Acid and Linoleic Acid MetabolismMetabolicSMP00018
Etodolac Action PathwayDrug actionSMP00084
Ibuprofen Action PathwayDrug actionSMP00086
Diclofenac Action PathwayDrug actionSMP00093
Bromfenac Action PathwayDrug actionSMP00102
Antipyrine Action PathwayDrug actionSMP00692
Antrafenine Action PathwayDrug actionSMP00693
Fenoprofen Action PathwayDrug actionSMP00696
Flurbiprofen Action PathwayDrug actionSMP00697
Lumiracoxib Action PathwayDrug actionSMP00699
Tenoxicam Action PathwayDrug actionSMP00706
Salicylic Acid Action PathwayDrug actionSMP00709
Piroxicam Action PathwayDrug actionSMP00077
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9945
Blood Brain Barrier+0.9539
Caco-2 permeable+0.8371
P-glycoprotein substrateNon-substrate0.5962
P-glycoprotein inhibitor INon-inhibitor0.9487
P-glycoprotein inhibitor IINon-inhibitor0.8964
Renal organic cation transporterNon-inhibitor0.9272
CYP450 2C9 substrateNon-substrate0.7643
CYP450 2D6 substrateNon-substrate0.8954
CYP450 3A4 substrateNon-substrate0.6678
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.8972
CYP450 2D6 inhibitorNon-inhibitor0.9545
CYP450 2C19 inhibitorNon-inhibitor0.9467
CYP450 3A4 inhibitorNon-inhibitor0.9295
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9349
Ames testNon AMES toxic0.9674
CarcinogenicityNon-carcinogens0.6568
BiodegradationReady biodegradable0.811
Rat acute toxicity1.3991 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9133
hERG inhibition (predictor II)Non-inhibitor0.9103
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point-49.5 °CPhysProp
boiling point170 °C at 1.50E-01 mm HgPhysProp
logP6.98SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.000151 mg/mLALOGPS
logP6.8ALOGPS
logP6.59ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity99.95 m3·mol-1ChemAxon
Polarizability37.37 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-0036-9300000000-ae1de58ce6930b12084dView in MoNA
References
Synthesis Reference

Derek R. Buckle, “Arachidonic acid analogues, processes for their preparation and their use in medicine.” U.S. Patent US4699995, issued July, 1973.

US4699995
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AbirateroneThe metabolism of Arachidonic Acid can be decreased when combined with Abiraterone.
AmiodaroneThe metabolism of Arachidonic Acid can be decreased when combined with Amiodarone.
AprepitantThe metabolism of Arachidonic Acid can be increased when combined with Aprepitant.
CapecitabineThe metabolism of Arachidonic Acid can be decreased when combined with Capecitabine.
CarbamazepineThe metabolism of Arachidonic Acid can be increased when combined with Carbamazepine.
CeritinibThe serum concentration of Arachidonic Acid can be increased when it is combined with Ceritinib.
CholecalciferolThe metabolism of Arachidonic Acid can be decreased when combined with Cholecalciferol.
ClotrimazoleThe metabolism of Arachidonic Acid can be decreased when combined with Clotrimazole.
CyclosporineThe metabolism of Arachidonic Acid can be decreased when combined with Cyclosporine.
DabrafenibThe serum concentration of Arachidonic Acid can be decreased when it is combined with Dabrafenib.
DelavirdineThe metabolism of Arachidonic Acid can be decreased when combined with Delavirdine.
EfavirenzThe metabolism of Arachidonic Acid can be decreased when combined with Efavirenz.
EtravirineThe metabolism of Arachidonic Acid can be decreased when combined with Etravirine.
FloxuridineThe metabolism of Arachidonic Acid can be decreased when combined with Floxuridine.
FluconazoleThe metabolism of Arachidonic Acid can be decreased when combined with Fluconazole.
FluorouracilThe metabolism of Arachidonic Acid can be decreased when combined with Fluorouracil.
FluvastatinThe metabolism of Arachidonic Acid can be decreased when combined with Fluvastatin.
FluvoxamineThe metabolism of Arachidonic Acid can be decreased when combined with Fluvoxamine.
FosphenytoinThe metabolism of Arachidonic Acid can be increased when combined with Fosphenytoin.
GemfibrozilThe metabolism of Arachidonic Acid can be decreased when combined with Gemfibrozil.
IndinavirThe metabolism of Arachidonic Acid can be decreased when combined with Indinavir.
IrbesartanThe metabolism of Arachidonic Acid can be decreased when combined with Irbesartan.
KetoconazoleThe metabolism of Arachidonic Acid can be decreased when combined with Ketoconazole.
LeflunomideThe metabolism of Arachidonic Acid can be decreased when combined with Leflunomide.
LosartanThe metabolism of Arachidonic Acid can be decreased when combined with Losartan.
LovastatinThe metabolism of Arachidonic Acid can be decreased when combined with Lovastatin.
LumacaftorThe serum concentration of Arachidonic Acid can be decreased when it is combined with Lumacaftor.
MifepristoneThe serum concentration of Arachidonic Acid can be increased when it is combined with Mifepristone.
NicardipineThe metabolism of Arachidonic Acid can be decreased when combined with Nicardipine.
OmeprazoleThe metabolism of Arachidonic Acid can be decreased when combined with Omeprazole.
PhenobarbitalThe metabolism of Arachidonic Acid can be increased when combined with Phenobarbital.
PhenytoinThe metabolism of Arachidonic Acid can be increased when combined with Phenytoin.
PrimidoneThe metabolism of Arachidonic Acid can be increased when combined with Primidone.
PyrimethamineThe metabolism of Arachidonic Acid can be decreased when combined with Pyrimethamine.
QuinineThe metabolism of Arachidonic Acid can be decreased when combined with Quinine.
RifampicinThe metabolism of Arachidonic Acid can be increased when combined with Rifampicin.
RifapentineThe metabolism of Arachidonic Acid can be increased when combined with Rifapentine.
SecobarbitalThe metabolism of Arachidonic Acid can be increased when combined with Secobarbital.
SildenafilThe metabolism of Arachidonic Acid can be decreased when combined with Sildenafil.
SorafenibThe metabolism of Arachidonic Acid can be decreased when combined with Sorafenib.
SulfadiazineThe metabolism of Arachidonic Acid can be decreased when combined with Sulfadiazine.
SulfamethoxazoleThe metabolism of Arachidonic Acid can be decreased when combined with Sulfamethoxazole.
SulfisoxazoleThe metabolism of Arachidonic Acid can be decreased when combined with Sulfisoxazole.
TicagrelorThe metabolism of Arachidonic Acid can be decreased when combined with Ticagrelor.
TiclopidineThe metabolism of Arachidonic Acid can be decreased when combined with Ticlopidine.
TolbutamideThe metabolism of Arachidonic Acid can be decreased when combined with Tolbutamide.
TrimethoprimThe metabolism of Arachidonic Acid can be decreased when combined with Trimethoprim.
Valproic AcidThe metabolism of Arachidonic Acid can be decreased when combined with Valproic Acid.
ValsartanThe metabolism of Arachidonic Acid can be decreased when combined with Valsartan.
VoriconazoleThe metabolism of Arachidonic Acid can be decreased when combined with Voriconazole.
ZafirlukastThe metabolism of Arachidonic Acid can be decreased when combined with Zafirlukast.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
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. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Blood fluke
Pharmacological action
unknown
General Function:
Transporter activity
Specific Function:
May play a role in the transport of fatty acids. Binds various fatty acids, such as arachidonic, oleic, palmitic and linolenic acid (in vitro).
Gene Name:
Not Available
Uniprot ID:
P29498
Molecular Weight:
14847.73 Da
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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase 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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Mo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. [PubMed:20167001 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
no
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
References
  1. Petitpas I, Grune T, Bhattacharya AA, Curry S: Crystal structures of human serum albumin complexed with monounsaturated and polyunsaturated fatty acids. J Mol Biol. 2001 Dec 14;314(5):955-60. [PubMed:11743713 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Transporter activity
Specific Function:
Lipid transport protein in adipocytes. Binds both long chain fatty acids and retinoic acid. Delivers long-chain fatty acids and retinoic acid to their cognate receptors in the nucleus (By similarity).
Gene Name:
FABP4
Uniprot ID:
P15090
Molecular Weight:
14718.815 Da
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. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
no
General Function:
Transporter activity
Specific Function:
FABP are thought to play a role in the intracellular transport of long-chain fatty acids and their acyl-CoA esters. FABP2 is probably involved in triglyceride-rich lipoprotein synthesis. Binds saturated long-chain fatty acids with a high affinity, but binds with a lower affinity to unsaturated long-chain fatty acids. FABP2 may also help maintain energy homeostasis by functioning as a lipid sensor.
Gene Name:
FABP2
Uniprot ID:
P12104
Molecular Weight:
15207.165 Da
References
  1. Rowland A, Knights KM, Mackenzie PI, Miners JO: Characterization of the binding of drugs to human intestinal fatty acid binding protein (IFABP): potential role of IFABP as an alternative to albumin for in vitro-in vivo extrapolation of drug kinetic parameters. Drug Metab Dispos. 2009 Jul;37(7):1395-403. doi: 10.1124/dmd.109.027656. Epub 2009 Apr 27. [PubMed:19398502 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, as well as PGE1, PGE2 and PGF2A.
Gene Name:
SLCO2A1
Uniprot ID:
Q92959
Molecular Weight:
70043.33 Da
References
  1. Kanai N, Lu R, Satriano JA, Bao Y, Wolkoff AW, Schuster VL: Identification and characterization of a prostaglandin transporter. Science. 1995 May 12;268(5212):866-9. [PubMed:7754369 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:24