Salicylic acid

Relevant Data

Food Additives Approved in the United States:

Food Additives Approved by WHO:

General Information

Chemical nameSalicylic acid
CAS number69-72-7
COE number10165
JECFA number958
Flavouring typesubstances
FL No.08.112
MixtureNo
Purity of the named substance at least 95% unless otherwise specified
Reference bodyEFSA

From webgate.ec.europa.eu

Computed Descriptors

Download SDF
2D Structure
CID338
IUPAC Name2-hydroxybenzoic acid
InChIInChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
InChI KeyYGSDEFSMJLZEOE-UHFFFAOYSA-N
Canonical SMILESC1=CC=C(C(=C1)C(=O)O)O
Molecular FormulaC7H6O3
Wikipediasalicylate

From Pubchem

Computed Properties

Property Name Property Value
Molecular Weight138.122
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Complexity133.0
CACTVS Substructure Key Fingerprint A A A D c Y B g M A A A A A A A A A A A A A A A A A A A A A A A A A A w A A A A A A A A A A A B A A A A G g A A C A A A D A S A m A A w D o A A A g C I A i D S C A A C A A A k I A A I i A E G C M g I J z a C F R K A c U A l 4 B E I m Y e I y C C O A A A A A A A I A A A A A A A A A B A A A A A A A A A A A A = =
Topological Polar Surface Area57.5
Monoisotopic Mass138.032
Exact Mass138.032
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count10
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem

Food Additives Biosynthesis/Degradation

ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.6165
Human Intestinal AbsorptionHIA+0.9756
Caco-2 PermeabilityCaco2+0.8867
P-glycoprotein SubstrateNon-substrate0.7340
P-glycoprotein InhibitorNon-inhibitor0.9815
Non-inhibitor0.9937
Renal Organic Cation TransporterNon-inhibitor0.9167
Distribution
Subcellular localizationMitochondria0.8764
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7962
CYP450 2D6 SubstrateNon-substrate0.9233
CYP450 3A4 SubstrateNon-substrate0.7660
CYP450 1A2 InhibitorNon-inhibitor0.9517
CYP450 2C9 InhibitorNon-inhibitor0.7984
CYP450 2D6 InhibitorNon-inhibitor0.9659
CYP450 2C19 InhibitorNon-inhibitor0.7644
CYP450 3A4 InhibitorNon-inhibitor0.8675
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8525
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9631
Non-inhibitor0.9734
AMES ToxicityNon AMES toxic0.9829
CarcinogensNon-carcinogens0.8627
Fish ToxicityHigh FHMT0.7460
Tetrahymena Pyriformis ToxicityLow TPT0.7307
Honey Bee ToxicityHigh HBT0.7317
BiodegradationReady biodegradable0.8086
Acute Oral ToxicityIII0.7939
Carcinogenicity (Three-class)Non-required0.7871

From admetSAR

ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-1.6128LogS
Caco-2 Permeability1.0291LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.2160LD50, mol/kg
Fish Toxicity1.9177pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.3852pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of ExposureNone
Mechanism of ToxicitySalicylic acid directly and irreversibly inhibits the activity of both types of cyclo-oxygenases (COX-1 and COX-2) to decrease the formation of precursors of prostaglandins and thromboxanes from arachidonic acid. Salicylate may competitively inhibit prostaglandin formation. Salicylate's antirheumatic (nonsteroidal anti-inflammatory) actions are a result of its analgesic and anti-inflammatory mechanisms. Salicylic acid is a key ingredient in many skin-care products for the treatment of acne, psoriasis, calluses, corns, keratosis pilaris, and warts. It works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth. Because of its effect on skin cells, salicylic acid is used in several shampoos used to treat dandruff. Salicylic acid is also used as an active ingredient in gels which remove verrucas (plantar warts). Salicylic acid inhibits the oxidation of uridine-5-diphosphoglucose (UDPG) competitively with nicotinamide adenosine dinucleotide (NAD) and noncompetitively with UDPG. It also competitively inhibits the transferring of glucuronyl group of uridine-5-phosphoglucuronic acid (UDPGA) to the phenolic acceptor. The wound-healing retardation action of salicylates is probably due mainly to its inhibitory action on mucopolysaccharide synthesis.
MetabolismNone
Toxicity ValuesOral rat LD50: 891 mg/kg. Inhalation rat LC50: > 900 mg/m3/1hr. Irritation: skin rabbit: 500 mg/24H mild. Eye rabbit: 100 mg severe.
Lethal DoseNone
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNone
Health EffectsInvestigated as a mutagen and reproductive effector.
TreatmentNone
Reference
  1. Vane JR: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol. 1971 Jun 23;231(25):232-5.[5284360 ]
  2. Flower R, Gryglewski R, Herbaczynska-Cedro K, Vane JR: Effects of anti-inflammatory drugs on prostaglandin biosynthesis. Nat New Biol. 1972 Jul 26;238(82):104-6.[4505422 ]
  3. Schmook FP, Meingassner JG, Billich A: Comparison of human skin or epidermis models with human and animal skin in in-vitro percutaneous absorption. Int J Pharm. 2001 Mar 14;215(1-2):51-6.[11250091 ]
  4. Rutner M, Fitzek J, Jahnel-Kracht H, Otto J, Krause W: [Therapy of rheumatic disease with a hydroxyethylsalicylate gel. Results of 2 clinical studies of effectiveness and bioavailability]. Fortschr Med. 1995 Mar 20;113(8):111-3.[7759034 ]
  5. Khan AZ, Aarons L: A note on the use of salicylate saliva concentration in clinical pharmacokinetic studies. J Pharm Pharmacol. 1989 Oct;41(10):710-1.[2575150 ]
  6. Vila MM, Tubino M, de Oliveira Neto G: Determination of salicylate in blood serum by flow injection with immobilized salicylate hydroxylase. J AOAC Int. 2001 Sep-Oct;84(5):1363-9.[11601455 ]
  7. Zaugg S, Zhang X, Sweedler J, Thormann W: Determination of salicylate, gentisic acid and salicyluric acid in human urine by capillary electrophoresis with laser-induced fluorescence detection. J Chromatogr B Biomed Sci Appl. 2001 Mar 5;752(1):17-31.[11254191 ]
  8. Berkovitch M, Uziel Y, Greenberg R, Chen-Levy Z, Arcusin M, Marcus O, Pinto O, Evans S, Matias A, Lahat E: False-high blood salicylate levels in neonates with hyperbilirubinemia. Ther Drug Monit. 2000 Dec;22(6):757-61.[11128247 ]
  9. Goussis OS, Theodoropoulos TJ: Dilantin and salicylate effects on hepatic thyroxine bio-availability and dialyzable thyroxine. Horm Metab Res. 1990 Jun;22(6):342-4.[2379917 ]
  10. Benfeldt E, Serup J, Menne T: Microdialysis vs. suction blister technique for in vivo sampling of pharmacokinetics in the human dermis. Acta Derm Venereol. 1999 Sep;79(5):338-42.[10494706 ]
  11. Ndovi TT, Choi L, Caffo B, Parsons T, Baker S, Zhao M, Rohde C, Hendrix CW: Quantitative assessment of seminal vesicle and prostate drug concentrations by use of a noninvasive method. Clin Pharmacol Ther. 2006 Aug;80(2):146-58.[16890576 ]
  12. Kocoshis SA, Wong CT: Sodium salicylate and bile acid-induced colonic secretion in the rat. Ann Clin Lab Sci. 1991 May-Jun;21(3):197-204.[2064304 ]
  13. Owen SG, Francis HW, Roberts MS: Disappearance kinetics of solutes from synovial fluid after intra-articular injection. Br J Clin Pharmacol. 1994 Oct;38(4):349-55.[7833225 ]
  14. Quaranta A, Portalatini P, Camporeale M, Sallustio V: Effects of salicylates on evoked otoacoustic emissions and remote masking in humans. Audiology. 1999 May-Jun;38(3):174-9.[10437688 ]
  15. Yoshida NH, Roberts MS: Prediction of cathodal iontophoretic transport of various anions across excised skin from different vehicles using conductivity measurements. J Pharm Pharmacol. 1995 Nov;47(11):883-90.[8708980 ]
  16. Alanko K, Stubb S, Salo OP, Reitamo S: Suction blister fluid histamine in fixed drug eruption. Acta Derm Venereol. 1992;72(2):89-91.[1350413 ]
  17. Singh P, Anliker M, Smith GA, Zavortink D, Maibach HI: Transdermal iontophoresis and solute penetration across excised human skin. J Pharm Sci. 1995 Nov;84(11):1342-6.[8587053 ]
  18. Hazouard E, Grimbert M, Jonville-Berra AP, De Toffol MC, Legras A: [Salicylism and glaucoma: reciprocal augmentation of the toxicity of acetazolamide and acetylsalicylic acid]. J Fr Ophtalmol. 1999 Feb;22(1):73-5.[10221197 ]
  19. Pirola R, Bareggi SR, De Benedittis G: Determination of acetylsalicylic acid and salicylic acid in skin and plasma by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 1998 Feb 13;705(2):309-15.[9521569 ]
  20. Kunkel A, Watzig H: Pharmacokinetic investigations with direct injection of plasma samples: possible savings using capillary electrophoresis (CE). Arch Pharm (Weinheim). 1999 May;332(5):175-8.[10366903 ]
  21. Azaroual, Imbenotte M, Cartigny B, Lhermitte M, Vermeersch G: [Identification and quantification of exogenous metabolites in biological liquids with new development in NMR spectroscopy in one and two dimensions]. Acta Clin Belg Suppl. 1999;1:97-100.[10216993 ]
  22. Baggott JE, Morgan SL, Ha T, Vaughn WH, Hine RJ: Inhibition of folate-dependent enzymes by non-steroidal anti-inflammatory drugs. Biochem J. 1992 Feb 15;282 ( Pt 1):197-202.[1540135 ]

From T3DB

Taxonomic Classification

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassBenzoic acids and derivatives
Intermediate Tree NodesHydroxybenzoic acid derivatives - Salicylic acid and derivatives
Direct ParentSalicylic acids
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsSalicylic acid - Benzoic acid - Benzoyl - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Vinylogous acid - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.

From ClassyFire

Targets

Target Details

Prostaglandin G/H synthase 1

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 generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
References
  1. Vane JR: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol. 1971 Jun 23;231(25):232-5. [5284360 ]
Target Details

Prostaglandin G/H synthase 2

General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, phenotypic changes, resistance to apoptosis and tumor angiogenesis. In cancer cells, PTGS2 is a key step in the production of prostaglandin E2 (PGE2), which plays important roles in modulating motility, proliferation and resistance to apoptosis.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular Weight:
68995.625 Da
References
  1. Elvira C, Gallardo A, Lacroix N, Schacht E, San Roman J: Incorporation of salicylic acid derivatives to hydrophilic copolymer systems with biomedical applications. J Mater Sci Mater Med. 2001 Jun;12(6):535-42. [15348270 ]
Target Details

Aldo-keto reductase family 1 member C1

General Function:
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
Specific Function:
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:
AKR1C1
Uniprot ID:
Q04828
Molecular Weight:
36788.02 Da
References
  1. Dhagat U, Carbone V, Chung RP, Matsunaga T, Endo S, Hara A, El-Kabbani O: A salicylic acid-based analogue discovered from virtual screening as a potent inhibitor of human 20alpha-hydroxysteroid dehydrogenase. Med Chem. 2007 Nov;3(6):546-50. [18045204 ]
Target Details

Androgen receptor

General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

From T3DB