Cas no 87679-58-1 (rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid)

Technical Introduction: rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid is a chiral bicyclic amino acid derivative featuring a rigid octahydroindole scaffold. Its stereochemically defined structure (2S,3aR,7aS) makes it a valuable building block in asymmetric synthesis and medicinal chemistry, particularly for designing conformationally constrained peptides or peptidomimetics. The fused ring system enhances stability and influences secondary structure, offering advantages in drug discovery for targeting protein-protein interactions or enzyme active sites. Its high purity and defined stereochemistry ensure reproducibility in research applications. This compound is commonly utilized in the development of bioactive molecules, where stereocontrol and structural rigidity are critical for optimizing binding affinity and metabolic stability.
rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid structure
87679-58-1 structure
Product Name:rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid
CAS No:87679-58-1
MF:C9H15NO2
MW:169.220902681351
MDL:MFCD09952530
CID:708893
PubChem ID:7018901
Update Time:2025-08-03

rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid Chemical and Physical Properties

Names and Identifiers

    • 1H-Indole-2-carboxylicacid, octahydro-, (2R,3aS,7aR)-rel-
    • rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid
    • 1H-Indole-2-carboxylicacid,octahydro-,(2R,3aS,7aR)-rel-(9CI)
    • (2S,3aR,7aS)-rel-Octahydro-indole-2-carboxylic acid
    • 145438-94-4
    • rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid (~90%, contains cis)
    • rel-(2S, 3aR,7aS)-Octahydro-1H-indole-2-carboxylic Acid
    • (2S, 3aR,7aS)-rel-Octahydro-indole-2-carboxylic acid
    • (2S, 3aR,7aS)-Octahydro-indole-2-carboxylic acid
    • AKOS015854020
    • (2S,3AR,7aS)-rel-octahydro-1H-indole-2-carboxylicacid
    • CQYBNXGHMBNGCG-CSMHCCOUSA-N
    • 1H-Indole-2-carboxylic acid, octahydro-, (2S,3aR,7aS)-
    • DTXSID30427049
    • AS-49299
    • FD7165
    • BCP16126
    • MFCD09952530
    • (2S,3AR,7aS)-rel-octahydro-1H- indole-2-carboxylic acid
    • (2S,3aR,7aS) octahydro-1H-indole-2-carboxylic acid
    • (2S,3aR,7aS)-Octahydroindole-2-carboxylic acid
    • (2S,3ar,7as)-2,3,3a,4,5,6,7,7a-octahydro-1H-indole-2-carboxylic acid
    • L-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid
    • A808370
    • (2S,3aR,7aS)-octahydro-1H-indol-2-carboxylic acid
    • (2S,3aR,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-indol-1-ium-2-carboxylate
    • SCHEMBL497280
    • Q27464679
    • CS-0375707
    • (2S,3AR,7AS)-OCTAHYDRO-INDOLE-2-CARBOXYLIC ACID
    • 87679-58-1
    • (2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic acid
    • AM84415
    • (2S,3AR,7aS)-rel-octahydro-1H-indole-2-carboxylic acid
    • (2S,3aR,7aS)-perhydroindole-2-carboxylic acid
    • L-Octahydroindole-2-carboxylic acid
    • AC-28351
    • AKOS006284740
    • MDL: MFCD09952530
    • Inchi: 1S/C9H15NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h6-8,10H,1-5H2,(H,11,12)/t6-,7+,8+/m1/s1
    • InChI Key: CQYBNXGHMBNGCG-CSMHCCOUSA-N
    • SMILES: OC([C@@H]1C[C@H]2CCCC[C@@H]2N1)=O

Computed Properties

  • Exact Mass: 169.110278721g/mol
  • Monoisotopic Mass: 169.110278721g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 193
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 3
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -1
  • Topological Polar Surface Area: 49.3?2

Experimental Properties

  • Melting Point: >265°C (dec.)
  • Solubility: DMSO (Sparingly), Methanol (sparingly)

rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid Security Information

rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
TRC
O236901-5mg
rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid
87679-58-1
5mg
$ 236.00 2023-09-06
TRC
O236901-10mg
rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid
87679-58-1
10mg
$442.00 2023-05-17
TRC
O236901-25mg
rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid
87679-58-1
25mg
$ 972.00 2023-09-06
TRC
O236901-50mg
rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid
87679-58-1
50mg
$ 1851.00 2023-09-06
Ambeed
A482795-1g
(2S,3aR,7aS)-rel-Octahydro-1H-indole-2-carboxylic acid
87679-58-1 97%
1g
$839.0 2024-04-16
Chemenu
CM527129-1g
(2S,3aR,7aS)-rel-Octahydro-1H-indole-2-carboxylic acid
87679-58-1 97%
1g
$1117 2023-01-01
abcr
AB483466-250 mg
(2S,3AR,7aS)-rel-octahydro-1H- indole-2-carboxylic acid; .
87679-58-1
250mg
€595.80 2023-06-15
Key Organics Ltd
AS-49299-0.25g
(2s,3ar,7as)-rel-octahydro-1h- indole-2-carboxylic acid
87679-58-1 >95%
0.25g
£464.00 2025-02-08
eNovation Chemicals LLC
Y1126770-5g
(2S,3aR,7aS)-rel-Octahydro-indole-2-carboxylic acid
87679-58-1 95%
5g
$3805 2025-02-19
eNovation Chemicals LLC
Y1126770-1g
(2S,3aR,7aS)-rel-Octahydro-indole-2-carboxylic acid
87679-58-1 95%
1g
$950 2025-02-19

rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid Suppliers

Amadis Chemical Company Limited
Gold Member
Audited Supplier Audited Supplier
(CAS:87679-58-1)rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid
Order Number:A1185784
Stock Status:in Stock
Quantity:1g
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 01:58
Price ($):755.0

rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid Related Literature

Additional information on rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid

Latest Research on rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid (CAS: 87679-58-1) in Chemical Biology and Pharmaceutical Applications

rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid (CAS: 87679-58-1) is a structurally unique bicyclic amino acid derivative that has garnered significant attention in chemical biology and pharmaceutical research. This compound, characterized by its rigid octahydroindole scaffold, serves as a versatile building block for the synthesis of peptidomimetics and bioactive molecules. Recent studies have explored its potential in drug discovery, particularly in modulating protein-protein interactions and enhancing metabolic stability of peptide-based therapeutics.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the application of this compound in the design of selective protease inhibitors. Researchers utilized its constrained conformation to develop novel inhibitors targeting thrombin, achieving a 15-fold improvement in selectivity compared to linear peptide analogs. The CAS: 87679-58-1 scaffold was found to effectively mimic the β-turn structure in natural substrates, providing critical insights for structure-based drug design.

In neuropharmacology, recent investigations have focused on the compound's potential as a precursor for GABA receptor modulators. A team from MIT reported in ACS Chemical Neuroscience (2024) that derivatives of rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid showed promising activity as positive allosteric modulators of GABAA receptors, with improved blood-brain barrier penetration compared to classical benzodiazepines. These findings open new avenues for developing non-sedative anxiolytics.

The synthetic accessibility of this compound has also seen significant advancements. A 2024 Nature Protocols publication detailed an improved asymmetric synthesis route starting from commercially available starting materials, achieving 92% enantiomeric excess and 78% overall yield. This methodological breakthrough addresses previous challenges in large-scale production, making the compound more accessible for medicinal chemistry programs.

Emerging applications in targeted drug delivery systems have been reported in Advanced Drug Delivery Reviews (2023). Researchers functionalized the compound's carboxylic acid group to create pH-responsive drug conjugates, demonstrating enhanced tumor accumulation in mouse models. The rigid bicyclic structure was found to confer stability against enzymatic degradation while maintaining drug release properties.

Ongoing clinical trials (as of Q2 2024) are evaluating derivatives of this compound as potential treatments for fibrotic diseases. Preliminary results suggest that these molecules can effectively inhibit TGF-β signaling pathways with reduced off-target effects compared to current therapies. The unique spatial orientation of functional groups in the 87679-58-1 scaffold appears crucial for this selective inhibition.

Future research directions highlighted in recent review articles include exploring the compound's potential in PROTAC design and as a scaffold for covalent inhibitors. The presence of multiple modifiable positions offers opportunities for creating bifunctional molecules with tailored pharmacological properties. Computational studies predict that further optimization could yield compounds with improved binding kinetics and tissue distribution profiles.

Recommended suppliers
Amadis Chemical Company Limited
(CAS:87679-58-1)rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid
A1185784
Purity:99%
Quantity:1g
Price ($):755.0
Email