Indole-3-pyruvic acid - Moligand™,≥95% , CAS No.392-12-1

CAS: 392-12-1 Cat. No.: I184250 Molecular Weight: 203.20 Beilstein Registry Number: 172966 EC Number: 206-874-1

GRADE & PURITY Moligand™, ≥95%

Synonyms

3-(1H-indol-3-yl)-2-keto-propionic acid | NSC 88874 | 3-indol-3-yl-2-oxopropanoic acid | 1H-Indole-3-propanoic acid, alpha-oxo- | 3-(1H-indol-3-yl)-2-oxidanylidene-propanoic acid | 3-(1H-Indol-3-yl)-2-oxopropanoic acid | alpha-Oxo-1H-indole-3-propanoic ac

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

α-Keto analogue of tryptophan

Specifications

Synonyms

3-(1H-indol-3-yl)-2-keto-propionic acid | NSC 88874 | 3-indol-3-yl-2-oxopropanoic acid | 1H-Indole-3-propanoic acid, alpha-oxo- | 3-(1H-indol-3-yl)-2-oxidanylidene-propanoic acid | 3-(1H-Indol-3-yl)-2-oxopropanoic acid | alpha-Oxo-1H-indole-3-propanoic ac

Specifications & Purity

Moligand™, ≥95%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 488179556
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488179556
• Canonical Smiles: C1=CC=C2C(=C1)C(=CN2)CC(=O)C(=O)O
• IUPAC Name: 3-(1H-indol-3-yl)-2-oxopropanoic acid
• InChIKey: RSTKLPZEZYGQPY-UHFFFAOYSA-N
• INCHI: 1S/C11H9NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H,14,15)
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)CC(=O)C(=O)O
• WGK Germany: 3
• RTECS: NM1880000
• Molecular Weight: 203.20
• Beilstein: 172966
• Reaxy-Rn: 172966
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=172966&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Indoles and derivatives
      • Subclass Indolyl carboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Indoles and derivatives
• Subclass: Indolyl carboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Indolyl carboxylic acids and derivatives
• Alternative Parents: 3-alkylindoles Substituted pyrroles Benzenoids Alpha-keto acids and derivatives Heteroaromatic compounds Alpha-hydroxy ketones Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Indolyl carboxylic acid derivative - 3-alkylindole - Indole - Alpha-keto acid - Keto acid - Substituted pyrrole - Benzenoid - Alpha-hydroxy ketone - Pyrrole - Heteroaromatic compound - Ketone - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Azacycle - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. These are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
• External Descriptors: 2-oxo monocarboxylic acid - indol-3-yl carboxylic acid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

Discover Target: ALDH1A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KYAT1 Tbio Kynurenine--oxoglutarate transaminase I (96 Activities)

Discover Target: KYAT1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)

Discover Target: PIN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GNAS Tbio Guanine nucleotide-binding protein G(s), subunit alpha (103405 Activities)

Discover Target: GNAS

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

POLI Tchem DNA polymerase iota (116820 Activities)

Discover Target: POLI

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)

Discover Target: KDM4A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SMN1 Tchem Survival motor neuron protein (34246 Activities)

Discover Target: SMN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)

Discover Target: HPGD

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GMNN Tbio Geminin (128009 Activities)

Discover Target: GMNN

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

Discover Target: CBX1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BAZ2B Tchem Bromodomain adjacent to zinc finger domain protein 2B (56204 Activities)

Discover Target: BAZ2B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

Discover Target: MEN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RAN Tchem GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 (21853 Activities)

Discover Target: RAN

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KPNB1 Tbio Importin subunit beta-1/Snurportin-1 (25097 Activities)

Discover Target: KPNB1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

ampC Beta-lactamase AmpC (62480 Activities)

Discover Target: ampC

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Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Pseudomonas aeruginosa (123386 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Plasmodium falciparum (966862 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

Discover Target: Txnrd1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

pigA Heme oxygenase (252 Activities)

Discover Target: pigA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TGR Thioredoxin glutathione reductase (28579 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mapt Microtubule-associated protein tau (6 Activities)

Discover Target: Mapt

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

Discover Target: fba

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

Discover Target: ffp

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

hemO Biliverdin-producing heme oxygenase (120 Activities)

Discover Target: hemO

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: solubility in ethanol:light yellow to yellow,clear to slightly hazy,49.00 - 51.00 mg/ml
• Melt Point(°C): 215°C
• Molecular Weight: 203.190 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 203.058 Da
• Monoisotopic Mass: 203.058 Da
• Topological Polar Surface Area: 70.200 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 277.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Mengmeng Song, Xianjie Sheng, Genyi Ye, Zhuicheng Xu, Xinru Li, Tong Xie, Haishan Deng, An Kang.  (2022)  Selective enrichment of microbiota-derived tryptophan metabolites in mouse faeces based on molecularly imprinted solid-phase extraction for HPLC analysis.  JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS,      [PMID:35182828] [10.1016/j.jpba.2022.114641]

2. Lijun Yang, Tiantian Zhou, Zhiyi Zhang, Wei Qi, Mengfan Wang.  (2025)  Co-immobilization of LAAO and Pt NPs in HOFs: An enzyme-metal coupled catalysis for enhancing the one-pot synthesis of α-keto acid.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:40319982] [10.1016/j.ijbiomac.2025.143899]

3. Lihua Zhao, Lei Jin, Yunhe Fu, Bin Yang.  (2025)  Gut microbial metabolite indole-3-propionic acid inhibits inflammation and restores blood-milk barrier in S. aureus- induced mastitis by targeting aryl hydrocarbon receptor.  Frontiers in Microbiology,      [PMID:41170435] [10.3389/fmicb.2025.1645561]