Indole-3-propionic acid
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MedKoo CAT#: 528306

CAS#: 830-96-6

Description: Indole-3-propionic acid, also known as IPA and SHP-622, is a beta-amyloid protein neurotoxicity inhibitor potentially for the treatment of Friedreich's ataxia. The administration of IPA significantly decreased the level of 4-hydroxy-2-nonenal, a marker of lipid peroxidation, in ischemic hippocampal homogenates compared with that in the vehicle-treated ischemic groups at various times after ischemia/reperfusion. In addition, immunostaining for 8-hydroxy-2'-deoxyguanosine showed DNA damage in pyramidal neurons in the ischemic CA1 was significantly lower in the IPA-treated ischemic groups than in the vehicle-treated ischemic groups. IPA may be used as a pharmacological agent to protect against iron-induced oxidative damage to membranes and, potentially, against carcinogenesis.

Chemical Structure

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Indole-3-propionic acid
CAS# 830-96-6
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 528306
Name: Indole-3-propionic acid
CAS#: 830-96-6
Chemical Formula: C11H11NO2
Exact Mass: 189.08
Molecular Weight: 189.214
Elemental Analysis: C, 69.83; H, 5.86; N, 7.40; O, 16.91

Price and Availability

Size Price Availability Quantity
5g USD 200
10g USD 350 2 Weeks
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Synonym: Indole-3-propionic acid; Indole 3 propionic acid; IPA; OX-1; OX 1; OX1; SHP-622; SHP 622; SHP622; VP-20629; VP20629; VP 20629

IUPAC/Chemical Name: 3-(1H-indol-3-yl)propanoic acid

InChi Key: GOLXRNDWAUTYKT-UHFFFAOYSA-N

InChi Code: InChI=1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14)

SMILES Code: O=C(O)CCC1=CNC2=C1C=CC=C2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: 3-Indolepropionic acid is shown to be a powerful antioxidant and has potential in the treatment for Alzheimer’s disease.
In vitro activity: It was found that IPA (indole-3-propionic acid) pretreatment effectively improved the inhibition of the receptor protein PXR and inflammatory proteins TLR4, MyD88, and NF-κB and inhibited the maturation of the ensuing gene IL-1β and the NLRP3 inflammasome (Figure 3E). These results suggest that IPA also alleviates inflammation by PXR activation in muscle cells, causing the inhibition of the NF-κB signaling pathway and the secretion of proinflammatory cytokines. Reference: Int J Mol Sci. 2021 Nov 18;22(22):12435. https://pubmed.ncbi.nlm.nih.gov/34830317/
In vivo activity: In addition, recipients of IPA (indole-3-propionic acid)-treated feces showed a higher 5-day survival rate and a lower level of proinflammatory cytokines (IL-1β, P < 0.021; TNF-α, P = 0.026) than those of saline-treated feces recipients. These findings suggest that the protective effect of IPA against sepsis was transferrable by gut microbiota. Reference: Microbiol Spectr. 2022 Jun 29;10(3):e0012522. https://pubmed.ncbi.nlm.nih.gov/35658593/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 158.55
DMSO 55.7 294.20
Ethanol 30.0 158.55
Wate 1.0 5.29

Preparing Stock Solutions

The following data is based on the product molecular weight 189.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Du L, Qi R, Wang J, Liu Z, Wu Z. Indole-3-Propionic Acid, a Functional Metabolite of Clostridium sporogenes, Promotes Muscle Tissue Development and Reduces Muscle Cell Inflammation. Int J Mol Sci. 2021 Nov 18;22(22):12435. doi: 10.3390/ijms222212435. PMID: 34830317; PMCID: PMC8619491. 2. Yisireyili M, Takeshita K, Saito S, Murohara T, Niwa T. Indole-3-propionic acid suppresses indoxyl sulfate-induced expression of fibrotic and inflammatory genes in proximal tubular cells. Nagoya J Med Sci. 2017 Nov;79(4):477-486. doi: 10.18999/nagjms.79.4.477. PMID: 29238104; PMCID: PMC5719207. 3. Fang H, Fang M, Wang Y, Zhang H, Li J, Chen J, Wu Q, He L, Xu J, Deng J, Liu M, Deng Y, Chen C. Indole-3-Propionic Acid as a Potential Therapeutic Agent for Sepsis-Induced Gut Microbiota Disturbance. Microbiol Spectr. 2022 Jun 29;10(3):e0012522. doi: 10.1128/spectrum.00125-22. Epub 2022 Jun 6. PMID: 35658593; PMCID: PMC9241804. 4. Liu F, Sun C, Chen Y, Du F, Yang Y, Wu G. Indole-3-propionic Acid-aggravated CCl4-induced Liver Fibrosis via the TGF-β1/Smads Signaling Pathway. J Clin Transl Hepatol. 2021 Dec 28;9(6):917-930. doi: 10.14218/JCTH.2021.00032. Epub 2021 May 17. PMID: 34966655; PMCID: PMC8666369.
In vitro protocol: 1. Du L, Qi R, Wang J, Liu Z, Wu Z. Indole-3-Propionic Acid, a Functional Metabolite of Clostridium sporogenes, Promotes Muscle Tissue Development and Reduces Muscle Cell Inflammation. Int J Mol Sci. 2021 Nov 18;22(22):12435. doi: 10.3390/ijms222212435. PMID: 34830317; PMCID: PMC8619491. 2. Yisireyili M, Takeshita K, Saito S, Murohara T, Niwa T. Indole-3-propionic acid suppresses indoxyl sulfate-induced expression of fibrotic and inflammatory genes in proximal tubular cells. Nagoya J Med Sci. 2017 Nov;79(4):477-486. doi: 10.18999/nagjms.79.4.477. PMID: 29238104; PMCID: PMC5719207.
In vivo protocol: 1. Fang H, Fang M, Wang Y, Zhang H, Li J, Chen J, Wu Q, He L, Xu J, Deng J, Liu M, Deng Y, Chen C. Indole-3-Propionic Acid as a Potential Therapeutic Agent for Sepsis-Induced Gut Microbiota Disturbance. Microbiol Spectr. 2022 Jun 29;10(3):e0012522. doi: 10.1128/spectrum.00125-22. Epub 2022 Jun 6. PMID: 35658593; PMCID: PMC9241804. 2. Liu F, Sun C, Chen Y, Du F, Yang Y, Wu G. Indole-3-propionic Acid-aggravated CCl4-induced Liver Fibrosis via the TGF-β1/Smads Signaling Pathway. J Clin Transl Hepatol. 2021 Dec 28;9(6):917-930. doi: 10.14218/JCTH.2021.00032. Epub 2021 May 17. PMID: 34966655; PMCID: PMC8666369.

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1: Köse M, Ritter K, Thiemke K, Gillard M, Kostenis E, Müller CE. Development of [(3)H]2-Carboxy-4,6-dichloro-1H-indole-3-propionic Acid ([(3)H]PSB-12150): A Useful Tool for Studying GPR17. ACS Med Chem Lett. 2014 Jan 16;5(4):326-30. doi: 10.1021/ml400399f. PubMed PMID: 24900835; PubMed Central PMCID: PMC4027623.

2: Hwang IK, Yoo KY, Li H, Park OK, Lee CH, Choi JH, Jeong YG, Lee YL, Kim YM, Kwon YG, Won MH. Indole-3-propionic acid attenuates neuronal damage and oxidative stress in the ischemic hippocampus. J Neurosci Res. 2009 Jul;87(9):2126-37. doi: 10.1002/jnr.22030. PubMed PMID: 19235887.

3: Karbownik M, Stasiak M, Zygmunt A, Zasada K, Lewiński A. Protective effects of melatonin and indole-3-propionic acid against lipid peroxidation, caused by potassium bromate in the rat kidney. Cell Biochem Funct. 2006 Nov-Dec;24(6):483-9. PubMed PMID: 16397908.

4: Karbownik M, Stasiak M, Zasada K, Zygmunt A, Lewinski A. Comparison of potential protective effects of melatonin, indole-3-propionic acid, and propylthiouracil against lipid peroxidation caused by potassium bromate in the thyroid gland. J Cell Biochem. 2005 May 1;95(1):131-8. PubMed PMID: 15723291.

5: Ostrowski M, Hetmann A, Jakubowska A. Indole-3-acetic acid UDP-glucosyltransferase from immature seeds of pea is involved in modification of glycoproteins. Phytochemistry. 2015 Sep;117:25-33. doi: 10.1016/j.phytochem.2015.05.023. PubMed PMID: 26057226.

6: Bendheim PE, Poeggeler B, Neria E, Ziv V, Pappolla MA, Chain DG. Development of indole-3-propionic acid (OXIGON) for Alzheimer's disease. J Mol Neurosci. 2002 Aug-Oct;19(1-2):213-7. Review. PubMed PMID: 12212784.

7: Karbownik M, Garcia JJ, Lewiński A, Reiter RJ. Carcinogen-induced, free radical-mediated reduction in microsomal membrane fluidity: reversal by indole-3-propionic acid. J Bioenerg Biomembr. 2001 Feb;33(1):73-8. PubMed PMID: 11460928.

8: Karbownik M, Reiter RJ, Garcia JJ, Cabrera J, Burkhardt S, Osuna C, Lewiński A. Indole-3-propionic acid, a melatonin-related molecule, protects hepatic microsomal membranes from iron-induced oxidative damage: relevance to cancer reduction. J Cell Biochem. 2001;81(3):507-13. PubMed PMID: 11255233.

9: Bajguz A, Piotrowska-Niczyporuk A. Synergistic effect of auxins and brassinosteroids on the growth and regulation of metabolite content in the green alga Chlorella vulgaris (Trebouxiophyceae). Plant Physiol Biochem. 2013 Oct;71:290-7. doi: 10.1016/j.plaphy.2013.08.003. PubMed PMID: 23994360.

10: Chyan YJ, Poeggeler B, Omar RA, Chain DG, Frangione B, Ghiso J, Pappolla MA. Potent neuroprotective properties against the Alzheimer beta-amyloid by an endogenous melatonin-related indole structure, indole-3-propionic acid. J Biol Chem. 1999 Jul 30;274(31):21937-42. PubMed PMID: 10419516.

11: Tolan D, Gandin V, Morrison L, El-Nahas A, Marzano C, Montagner D, Erxleben A. Oxidative Stress Induced by Pt(IV) Pro-drugs Based on the Cisplatin Scaffold and Indole Carboxylic Acids in Axial Position. Sci Rep. 2016 Jul 11;6:29367. doi: 10.1038/srep29367. PubMed PMID: 27404565; PubMed Central PMCID: PMC4941645.

12: Bosco R, Caser M, Vanara F, Scariot V. Development of a rapid LC-DAD/FLD method for the simultaneous determination of auxins and abscisic acid in plant extracts. J Agric Food Chem. 2013 Nov 20;61(46):10940-7. doi: 10.1021/jf4034305. PubMed PMID: 24134056.

13: Edwards N, Anderson CM, Gatfield KM, Jevons MP, Ganapathy V, Thwaites DT. Amino acid derivatives are substrates or non-transported inhibitors of the amino acid transporter PAT2 (slc36a2). Biochim Biophys Acta. 2011 Jan;1808(1):260-70. doi: 10.1016/j.bbamem.2010.07.032. PubMed PMID: 20691150; PubMed Central PMCID: PMC3000476.

14: Wang L, Wang M, Yan H, Yuan Y, Tian J. A new graphene oxide/polypyrrole foam material with pipette-tip solid-phase extraction for determination of three auxins in papaya juice. J Chromatogr A. 2014 Nov 14;1368:37-43. doi: 10.1016/j.chroma.2014.09.059. PubMed PMID: 25441342.

15: Mariani ME, Madoery RR, Fidelio GD. Auxins action on Glycine max secretory phospholipase A2 is mediated by the interfacial properties imposed by the phytohormones. Chem Phys Lipids. 2015 Jul;189:1-6. doi: 10.1016/j.chemphyslip.2015.05.003. PubMed PMID: 25987194.

16: Castillo G, Torrecillas A, Nogueiras C, Michelena G, Sánchez-Bravo J, Acosta M. Simultaneous quantification of phytohormones in fermentation extracts of Botryodiplodia theobromae by liquid chromatography-electrospray tandem mass spectrometry. World J Microbiol Biotechnol. 2014 Jul;30(7):1937-46. doi: 10.1007/s11274-014-1612-5. PubMed PMID: 24510403.

17: Tomasić A, Bertosa B, Tomić S, Soskić M, Magnus V. Binding behavior of amino acid conjugates of indole-3-acetic acid to immobilized human serum albumin. J Chromatogr A. 2007 Jun 22;1154(1-2):240-9. PubMed PMID: 17459401.

18: Simon S, Kubeš M, Baster P, Robert S, Dobrev PI, Friml J, Petrášek J, Zažímalová E. Defining the selectivity of processes along the auxin response chain: a study using auxin analogues. New Phytol. 2013 Dec;200(4):1034-48. doi: 10.1111/nph.12437. PubMed PMID: 23914741.

19: Jin SH, Ma XM, Han P, Wang B, Sun YG, Zhang GZ, Li YJ, Hou BK. UGT74D1 is a novel auxin glycosyltransferase from Arabidopsis thaliana. PLoS One. 2013 Apr 16;8(4):e61705. doi: 10.1371/journal.pone.0061705. Erratum in: PLoS One. 2013;8(8). doi:10.1371/annotation/457d7567-fc12-421c-9d79-880950ab10e1. PubMed PMID: 23613909; PubMed Central PMCID: PMC3628222.

20: Barkawi LS, Tam YY, Tillman JA, Pederson B, Calio J, Al-Amier H, Emerick M, Normanly J, Cohen JD. A high-throughput method for the quantitative analysis of indole-3-acetic acid and other auxins from plant tissue. Anal Biochem. 2008 Jan 15;372(2):177-88. PubMed PMID: 17889819.