(2R)-2-amino-3-{[5-(4-trifluoromethylphenyl)-10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-yl]sulfanyl}propanoic acid

ID: ALA3633365

Chembl Id: CHEMBL3633365

PubChem CID: 71748280

Max Phase: Preclinical

Molecular Formula: C25H22F3NO2S

Molecular Weight: 457.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CSC1(c2ccc(C(F)(F)F)cc2)c2ccccc2CCc2ccccc21)C(=O)O

Standard InChI:  InChI=1S/C25H22F3NO2S/c26-25(27,28)19-13-11-18(12-14-19)24(32-15-22(29)23(30)31)20-7-3-1-5-16(20)9-10-17-6-2-4-8-21(17)24/h1-8,11-14,22H,9-10,15,29H2,(H,30,31)/t22-/m0/s1

Standard InChI Key:  WBOSHVRLUFZOTA-QFIPXVFZSA-N

Alternative Forms

1. Parent:

   

   ALA3633365

   (2R)-2-amino-3-[[2-[4-(trifluoromethyl)phenyl]-2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenyl]sulfanyl]propanoic 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: 457.52

Molecular Weight (Monoisotopic): 457.1323

AlogP: 5.24

#Rotatable Bonds: 5

Polar Surface Area: 63.32

Molecular Species: ZWITTERION

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.17

CX Basic pKa: 9.12

CX LogP: 3.88

CX LogD: 3.87

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.55

Np Likeness Score: -0.04

References

1. Ogo N, Ishikawa Y, Sawada J, Matsuno K, Hashimoto A, Asai A..  (2015)  Structure-Guided Design of Novel l-Cysteine Derivatives as Potent KSP Inhibitors.,  6  (9): [PMID:26396688] [10.1021/acsmedchemlett.5b00221]

2. Fukai R,Ogo N,Ichida T,Yamane M,Sawada JI,Miyoshi N,Murakami H,Asai A.  (2021)  Design, synthesis, and evaluation of a novel prodrug, a S-trityl--cysteine derivative targeting kinesin spindle protein.,  215  [PMID:33640763] [10.1016/j.ejmech.2021.113288]

Source

Source(1):

• Scientific Literature