rac-(2S)-N-((1R)-2-amino-1-(4-(2-methylpentyloxy)phenyl)ethyl)-2-phenylpropanamide

Names and Identifiers

Canonical SMILES: CCCC(C)COc1ccc([C@H](CN)NC(=O)[C@@H](C)c2ccccc2)cc1

Standard InChI: InChI=1S/C23H32N2O2/c1-4-8-17(2)16-27-21-13-11-20(12-14-21)22(15-24)25-23(26)18(3)19-9-6-5-7-10-19/h5-7,9-14,17-18,22H,4,8,15-16,24H2,1-3H3,(H,25,26)/t17?,18-,22-/m0/s1

Standard InChI Key: FPSJEYDKDNQYJW-RBENRJQXSA-N

Alternative Forms

Parent:

ALA3403780
(2S)-N-((1R)-2-amino-1-(4-(2-methylpentyloxy)phenyl)ethyl)-2-phenylpropanamide
Alternative Forms:

ALA3403780
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Associated Targets(Human)

GPR88 Tchem Probable G-protein coupled receptor 88 (760 Activities)

Discover Target: GPR88

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

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

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: 368.52	Molecular Weight (Monoisotopic): 368.2464	AlogP: 4.42	#Rotatable Bonds: 10
Polar Surface Area: 64.35	Molecular Species: BASE	HBA: 3	HBD: 2
#RO5 Violations: ┄	HBA (Lipinski): 4	HBD (Lipinski): 3	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: 13.60	CX Basic pKa: 8.76	CX LogP: 4.53	CX LogD: 3.16
Aromatic Rings: 2	Heavy Atoms: 27	QED Weighted: 0.65	Np Likeness Score: -0.28

References

1. Dzierba CD, Bi Y, Dasgupta B, Hartz RA, Ahuja V, Cianchetta G, Kumi G, Dong L, Aleem S, Fink C, Garcia Y, Green M, Han J, Kwon S, Qiao Y, Wang J, Zhang Y, Liu Y, Zipp G, Liang Z, Burford N, Ferrante M, Bertekap R, Lewis M, Cacace A, Grace J, Wilson A, Nouraldeen A, Westphal R, Kimball D, Carson K, Bronson JJ, Macor JE.. (2015) Design, synthesis, and evaluation of phenylglycinols and phenyl amines as agonists of GPR88., 25 (7): [PMID:25690789] [10.1016/j.bmcl.2015.01.036]
2. (2012) Modulators of G-protein-coupled receptor 88,
3. Jin C, Decker AM, Langston TL.. (2017) Design, synthesis and pharmacological evaluation of 4-hydroxyphenylglycine and 4-hydroxyphenylglycinol derivatives as GPR88 agonists., 25 (2): [PMID:27956039] [10.1016/j.bmc.2016.11.058]
4. Rahman MT, Decker AM, Laudermilk L, Maitra R, Ma W, Ben Hamida S, Darcq E, Kieffer BL, Jin C.. (2021) Evaluation of Amide Bioisosteres Leading to 1,2,3-Triazole Containing Compounds as GPR88 Agonists: Design, Synthesis, and Structure-Activity Relationship Studies., 64 (16.0): [PMID:34387471] [10.1021/acs.jmedchem.1c01075]
5. Decker AM, Rahman MT, Kormos CM, Hesk D, Darcq E, Kieffer BL, Jin C.. (2023) Synthesis and pharmacological validation of a novel radioligand for the orphan GPR88 receptor., 80 [PMID:36587872] [10.1016/j.bmcl.2022.129120]

Source

Source(2):