(2S,3S)-2-Amino-3-benzyloxy-succinic acid

ID: ALA475341

Chembl Id: CHEMBL475341

Cas Number: 1080022-24-7

PubChem CID: 4133412

Max Phase: Preclinical

Molecular Formula: C11H13NO5

Molecular Weight: 239.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(C(=O)O)C(OCc1ccccc1)C(=O)O

Standard InChI:  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)

Standard InChI Key:  BYOBCYXURWDEDS-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA475341

   2-Amino-3-phenylmethoxybutanedioic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 239.23

Molecular Weight (Monoisotopic): 239.0794

AlogP: 0.07

#Rotatable Bonds: 6

Polar Surface Area: 109.85

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.97

CX Basic pKa: 8.97

CX LogP: -2.08

CX LogD: -5.13

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.65

Np Likeness Score: 0.31

References

1. Shimamoto K, Shigeri Y, Yasuda-Kamatani Y, Lebrun B, Yumoto N, Nakajima T..  (2000)  Syntheses of optically pure beta-hydroxyaspartate derivatives as glutamate transporter blockers.,  10  (21): [PMID:11078189] [10.1016/s0960-894x(00)00487-x]

2. Boudker O, Ryan RM, Yernool D, Shimamoto K, Gouaux E..  (2007)  Coupling substrate and ion binding to extracellular gate of a sodium-dependent aspartate transporter.,  445  (7126): [PMID:17230192] [10.1038/nature05455]

3. Jensen AA, Erichsen MN, Nielsen CW, Stensbøl TB, Kehler J, Bunch L..  (2009)  Discovery of the first selective inhibitor of excitatory amino acid transporter subtype 1.,  52  (4): [PMID:19161278] [10.1021/jm8013458]

4. Sagot E, Jensen AA, Pickering DS, Pu X, Umberti M, Stensbøl TB, Nielsen B, Assaf Z, Aboab B, Bolte J, Gefflaut T, Bunch L..  (2008)  Chemo-enzymatic synthesis of (2S,4R)-2-amino-4-(3-(2,2-diphenylethylamino)-3-oxopropyl)pentanedioic acid: a novel selective inhibitor of human excitatory amino acid transporter subtype 2.,  51  (14): [PMID:18578477] [10.1021/jm800091e]

5. Liu N,Jensen AA,Bunch L.  (2020)  β-Indolyloxy Functionalized Aspartate Analogs as Inhibitors of the Excitatory Amino Acid Transporters (EAATs).,  11  (11): [PMID:33214831] [10.1021/acsmedchemlett.0c00342]

Source

Source(1):

• Scientific Literature