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Identification
NameArachidonic Acid
Accession NumberDB04557  (EXPT00409)
Typesmall molecule
Groupsexperimental
Description

An 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
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number506-32-1
WeightAverage: 304.4669
Monoisotopic: 304.240230268
Chemical FormulaC20H32O2
InChI KeyYZXBAPSDXZZRGB-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassFatty Acids and Conjugates
SubclassStraight Chain Fatty Acids
Direct parentStraight Chain Fatty Acids
Alternative parentsUnsaturated Fatty Acids; Polyamines; Enolates; Carboxylic Acids
Substituentsenolate; polyamine; carboxylic acid; carboxylic acid derivative
Classification descriptionThis compound belongs to the straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Acetaminophen Action PathwayDrug actionSMP00710
Acetylsalicylic Acid Action PathwayDrug actionSMP00083
Mefenamic Acid Action PathwayDrug actionSMP00109
Tiaprofenic Acid Action PathwayDrug actionSMP00705
Alpha Linolenic Acid and Linoleic Acid MetabolismMetabolicSMP00018
Salicylic Acid Action PathwayDrug actionSMP00709
Arachidonic Acid MetabolismMetabolicSMP00075
Suprofen Action PathwayDrug actionSMP00101
Bromfenac Action PathwayDrug actionSMP00102
Diflunisal Action PathwayDrug actionSMP00289
Valdecoxib Action PathwayDrug actionSMP00116
Celecoxib Action PathwayDrug actionSMP00096
Ketorolac Action PathwayDrug actionSMP00098
Sulindac Action PathwayDrug actionSMP00094
Antrafenine Action PathwayDrug actionSMP00693
Flurbiprofen Action PathwayDrug actionSMP00697
Nepafenac Action PathwayDrug actionSMP00702
Lumiracoxib Action PathwayDrug actionSMP00699
Salicylate-sodium Action PathwayDrug actionSMP00708
Tenoxicam Action PathwayDrug actionSMP00706
Oxaprozin Action PathwayDrug actionSMP00113
Meloxicam Action PathwayDrug actionSMP00106
Trisalicylate-choline Action PathwayDrug actionSMP00703
Magnesium salicylate Action PathwayDrug actionSMP00698
Lornoxicam Action PathwayDrug actionSMP00700
Rofecoxib Action PathwayDrug actionSMP00087
Naproxen Action PathwayDrug actionSMP00120
Fenoprofen Action PathwayDrug actionSMP00696
Tolmetin Action PathwayDrug actionSMP00704
Ibuprofen Action PathwayDrug actionSMP00086
Etodolac Action PathwayDrug actionSMP00084
Ketoprofen Action PathwayDrug actionSMP00085
Diclofenac Action PathwayDrug actionSMP00093
Indomethacin Action PathwayDrug actionSMP00104
Nabumetone Action PathwayDrug actionSMP00114
Antipyrine Action PathwayDrug actionSMP00692
Phenylbutazone Action PathwayDrug actionSMP00701
Piroxicam Action PathwayDrug actionSMP00077
Carprofen Action PathwayDrug actionSMP00694
Etoricoxib Action PathwayDrug actionSMP00695
Salsalate Action PathwayDrug actionSMP00707
Leukotriene C4 Synthesis DeficiencyDiseaseSMP00353
Fc Epsilon Receptor I Signaling in Mast CellsSignalingSMP00358
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9945
Blood Brain Barrier + 0.9539
Caco-2 permeable + 0.8371
P-glycoprotein substrate Non-substrate 0.5962
P-glycoprotein inhibitor I Non-inhibitor 0.9487
P-glycoprotein inhibitor II Non-inhibitor 0.8964
Renal organic cation transporter Non-inhibitor 0.9272
CYP450 2C9 substrate Non-substrate 0.7643
CYP450 2D6 substrate Non-substrate 0.8954
CYP450 3A4 substrate Non-substrate 0.6678
CYP450 1A2 substrate Inhibitor 0.9107
CYP450 2C9 substrate Non-inhibitor 0.8972
CYP450 2D6 substrate Non-inhibitor 0.9545
CYP450 2C19 substrate Non-inhibitor 0.9467
CYP450 3A4 substrate Non-inhibitor 0.9295
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9349
Ames test Non AMES toxic 0.9674
Carcinogenicity Non-carcinogens 0.6568
Biodegradation Ready biodegradable 0.811
Rat acute toxicity 1.3991 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9133
hERG inhibition (predictor II) Non-inhibitor 0.9103
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 solubility1.51e-04 g/lALOGPS
logP6.8ALOGPS
logP6.59ChemAxon
logS-6.3ALOGPS
pKa (strongest acidic)4.82ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area37.3ChemAxon
rotatable bond count14ChemAxon
refractivity99.95ChemAxon
polarizability37.37ChemAxon
number of rings0ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
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 ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC00219
PubChem Compound5312542
PubChem Substance46506683
BindingDB22319
ChEBI15843
ChEMBL
Therapeutic Targets DatabaseDNC000249
HETACD
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. 14 kDa fatty acid-binding protein

Kind: protein

Organism: Blood fluke

Pharmacological action: unknown

Components

Name UniProt ID Details
14 kDa fatty acid-binding protein P29498 Details

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
  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

2. Prostaglandin G/H synthase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Prostaglandin G/H synthase 1 P23219 Details

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
  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
  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

Enzymes

1. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

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

Carriers

1. Fatty acid-binding protein, adipocyte

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Fatty acid-binding protein, adipocyte P15090 Details

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
  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
  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

2. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: no

Components

Name UniProt ID Details
Serum albumin P02768 Details

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

3. Fatty acid-binding protein, intestinal

Kind: protein

Organism: Human

Pharmacological action: no

Components

Name UniProt ID Details
Fatty acid-binding protein, intestinal P12104 Details

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. Epub 2009 Apr 27. Pubmed

Transporters

1. Solute carrier organic anion transporter family member 2A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 2A1 Q92959 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:25