DL-TBOA - Moligand™, ≥98%(HPLC) , Inhibitor of Excitatory amino acid transporter 1;Inhibitor of Excitatory amino acid transporter 2;Inhibitor of Excitatory amino acid transporter 3;Inhibitor of Excitatory amino acid transporter 4;Inhibitor of Excitatory a, Inhibitor of Excitatory amino acid transporter 1;Inhibitor of Excitatory amino acid transporter 2;Inhibitor of Excitatory amino acid transporter 3;Inhibitor of Excitatory amino acid transporter 4;Inhibitor of Excitatory amino acid transporter 5

CAS: 205309-81-5 Cat. No.: D286841 Molecular Weight: 239.23

GRADE & PURITY Moligand™, ≥98%(HPLC)

Synonyms

AKOS030606641 | HB0258 | C11H13NO5 | BT162587 | SR-01000597407-1 | (2S,3S)-2-amino-3-(benzyloxy)butanedioic acid | (2S,3S)-2-amino-3-(phenylmethoxy)butanedioic acid | BDBM50093753 | DL-TBOA ammonium | (2s,3s)-2-amino-3-benzyloxysuccinic acid | (2S,3S)-2-A

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

AKOS030606641 | HB0258 | C11H13NO5 | BT162587 | SR-01000597407-1 | (2S, 3S)-2-amino-3-(benzyloxy)butanedioic acid | (2S, 3S)-2-amino-3-(phenylmethoxy)butanedioic acid | BDBM50093753 | DL-TBOA ammonium | (2s, 3s)-2-amino-3-benzyloxysuccinic acid | (2S, 3S)-2-A

Specifications & Purity

Moligand™, ≥98%(HPLC)

Biochemical and Physiological Mechanisms

A competitive, non-transportable blocker of excitatory amino acid transporters (IC50values are 70, 6, and 6μM for EAAT1, EAAT2 and EAAT3 respectively). Also inhibits EAAT4 and EAAT5 (Kivalues are 4.4 and 3.2μM respectively). Displays high selectivity for

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Inhibitor of Excitatory amino acid transporter 1;Inhibitor of Excitatory amino acid transporter 2;Inhibitor of Excitatory amino acid transporter 3;Inhibitor of Excitatory amino acid transporter 4;Inhibitor of Excitatory amino acid transporter 5

Purity

≥98%(HPLC)

Names and Identifiers

• Canonical Smiles: C1=CC=C(C=C1)COC(C(C(=O)O)N)C(=O)O
• IUPAC Name: (2S,3S)-2-amino-3-phenylmethoxybutanedioic acid
• InChIKey: BYOBCYXURWDEDS-IUCAKERBSA-N
• INCHI: 1S/C11H13NO5/c12-8(10(13)14)9(11(15)16)17-6-7-4-2-1-3-5-7/h1-5,8-9H,6,12H2,(H,13,14)(H,15,16)/t8-,9-/m0/s1
• Isomeric SMILES: C1=CC=C(C=C1)CO[C@@H]([C@@H](C(=O)O)N)C(=O)O
• Molecular Weight: 239.23
• Reaxy-Rn: 11560807
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=11560807&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Aspartic acid and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Aspartic acid and derivatives
• Alternative Parents: L-alpha-amino acids Benzylethers Monosaccharides Dicarboxylic acids and derivatives Amino acids Dialkyl ethers Carboxylic acids Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Aspartic acid or derivatives - Alpha-amino acid - L-alpha-amino acid - Benzylether - Monocyclic benzene moiety - Dicarboxylic acid or derivatives - Monosaccharide - Benzenoid - Amino acid - Ether - Dialkyl ether - Carboxylic acid - Primary amine - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Amine - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Organic oxide - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as aspartic acid and derivatives. These are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
• External Descriptors: Not available

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)

SLC1A1 Tchem Excitatory amino acid transporter 3 (1 Activities)

Discover Target: SLC1A1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SLC1A7 Tchem Excitatory amino acid transporter 5 (1 Activities)

Discover Target: SLC1A7

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SLC1A3 Tchem Excitatory amino acid transporter 1 (1 Activities)

Discover Target: SLC1A3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SLC1A6 Tchem Excitatory amino acid transporter 4 (1 Activities)

Discover Target: SLC1A6

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SLC1A2 Tchem Excitatory amino acid transporter 2 (3 Activities)

Discover Target: SLC1A2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

GRIK3 Tclin Glutamate receptor ionotropic kainate 3 (50 Activities)

Discover Target: GRIK3

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

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

Discover Target: CYP2D6

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

SLC1A1 Tchem Excitatory amino acid transporter 3 (527 Activities)

Discover Target: SLC1A1

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

SLC1A3 Tchem Excitatory amino acid transporter 1 (586 Activities)

Discover Target: SLC1A3

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

GRIK1 Tclin Glutamate receptor ionotropic kainate 1 (340 Activities)

Discover Target: GRIK1

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

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

Discover Target: CYP1A2

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

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

Discover Target: CYP2C9

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

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

Discover Target: CYP2C19

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

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

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

Associated Targets(non-human)

Grik2 Glutamate receptor ionotropic kainate 2 (298 Activities)

Discover Target: Grik2

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

Slc1a2 Excitatory amino acid transporter 2 (39 Activities)

Discover Target: Slc1a2

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

Slc1a6 Excitatory amino acid transporter 4 (71 Activities)

Discover Target: Slc1a6

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

Grin1 Glutamate NMDA receptor (6467 Activities)

Discover Target: Grin1

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:DMSO, Max Conc. mg/mL: 23.92, Max Conc. mM: 100; Solvent:water, Max Conc. mg/mL: 1.2, Max Conc. mM: 5 with gentle warming
• Molecular Weight: 239.220 g/mol
• XLogP3: -2.400
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 239.079 Da
• Monoisotopic Mass: 239.079 Da
• Topological Polar Surface Area: 110.000 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 275.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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