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(1S,2R,3S,4R,5R,6R)-2-amino-3-(2,5-dichlorobenzyloxy)-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid ID: ALA3979475
PubChem CID: 134152341
Max Phase: Preclinical
Molecular Formula: C15H15Cl2NO6
Molecular Weight: 376.19
Molecule Type: Small molecule
This compound is available for customization.
Associated Items:
Names and Identifiers Canonical SMILES: N[C@]1(C(=O)O)[C@@H]2[C@@H](C(=O)O)[C@@H]2[C@@H](O)[C@H]1OCc1cc(Cl)ccc1Cl
Standard InChI: InChI=1S/C15H15Cl2NO6/c16-6-1-2-7(17)5(3-6)4-24-12-11(19)8-9(13(20)21)10(8)15(12,18)14(22)23/h1-3,8-12,19H,4,18H2,(H,20,21)(H,22,23)/t8-,9-,10-,11+,12+,15+/m0/s1
Standard InChI Key: SGCNJDYPITVHEN-AFJGUQMISA-N
Molfile:
RDKit 2D
26 28 0 0 0 0 0 0 0 0999 V2000
12.8893 -9.5752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.3115 -8.9974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.1000 -9.7867 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
12.8002 -8.3434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.3243 -7.6759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11.5376 -8.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11.5476 -7.9215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.8336 -8.3222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.0164 -8.3123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.6165 -7.5997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
9.5993 -9.0150 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
12.5834 -6.9009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
13.6173 -8.3515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
14.0329 -7.6479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.8501 -7.6560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.6787 -9.3637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
12.6778 -10.3645 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
11.5397 -7.1030 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
11.5315 -9.5545 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
15.2495 -8.3702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.0659 -8.3786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.4823 -7.6745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.0764 -6.9603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.2613 -6.9554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.8324 -9.0729 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
16.4895 -6.2553 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 1
3 2 1 0
6 2 1 0
2 4 1 0
4 5 1 0
5 7 1 0
7 6 1 0
8 7 1 0
6 8 1 0
8 9 1 1
9 10 2 0
9 11 1 0
5 12 1 1
4 13 1 1
13 14 1 0
14 15 1 0
1 16 1 0
1 17 2 0
7 18 1 1
6 19 1 1
15 20 2 0
20 21 1 0
21 22 2 0
22 23 1 0
23 24 2 0
24 15 1 0
20 25 1 0
23 26 1 0
M END Associated Targets(Human) Molecule Features Natural Product: NoOral: NoChemical Probe: NoParenteral: NoMolecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: NoChirality: NoAvailability: NoProdrug: No
Drug Indications MESH ID MESH Heading EFO IDs EFO Terms Max Phase for Indication References
Mechanisms of Action Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References
Calculated Properties Molecular Weight: 376.19Molecular Weight (Monoisotopic): 375.0276AlogP: 0.98#Rotatable Bonds: 5Polar Surface Area: 130.08Molecular Species: ZWITTERIONHBA: 5HBD: 4#RO5 Violations: ┄HBA (Lipinski): 7HBD (Lipinski): 5#RO5 Violations (Lipinski): ┄CX Acidic pKa: 1.60CX Basic pKa: 8.87CX LogP: -1.44CX LogD: -4.66Aromatic Rings: 1Heavy Atoms: 24QED Weighted: 0.60Np Likeness Score: 0.34
References 1. Dressman BA, Tromiczak EG, Chappell MD, Tripp AE, Quimby SJ, Vetman T, Fivush AM, Matt J, Jaramillo C, Li R, Khilevich A, Blanco MJ, Smith SC, Carpintero M, de Diego JE, Barberis M, García-Cerrada S, Soriano JF, Schkeryantz JM, Witkin JM, Wafford KA, Seidel W, Britton T, Overshiner CD, Li X, Wang XS, Heinz BA, Catlow JT, Swanson S, Bedwell D, Ornstein PL, Mitch CH.. (2016) Novel bicyclo[3.1.0]hexane analogs as antagonists of metabotropic glutamate 2/3 receptors for the treatment of depression., 26 (23): [PMID:27836401 ] [10.1016/j.bmcl.2016.10.067 ]