ID: ALA99055

Max Phase: Preclinical

Molecular Formula: C23H22F6N4O2

Molecular Weight: 500.44

Molecule Type: Small molecule

Representations

Synonyms (1): L-741671
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=c1[nH]nc(CN2CCC[C@H](OCc3cc(C(F)(F)F)cc(C(F)(F)F)c3)[C@@H]2c2ccccc2)[nH]1

Standard InChI:  InChI=1S/C23H22F6N4O2/c24-22(25,26)16-9-14(10-17(11-16)23(27,28)29)13-35-18-7-4-8-33(12-19-30-21(34)32-31-19)20(18)15-5-2-1-3-6-15/h1-3,5-6,9-11,18,20H,4,7-8,12-13H2,(H2,30,31,32,34)/t18-,20-/m0/s1

Standard InChI Key:  ZUWHBRRBKKTMQO-ICSRJNTNSA-N

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

Properties

Molecular Weight: 500.44

Molecular Weight (Monoisotopic): 500.1647

AlogP: 5.06

#Rotatable Bonds: 6

Polar Surface Area: 74.01

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 5.87

CX Basic pKa: 7.03

CX LogP: 4.21

CX LogD: 4.14

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.46

Np Likeness Score: -0.81

References

1. Ladduwahetty T, Baker R, Cascieri MA, Chambers MS, Haworth K, Keown LE, MacIntyre DE, Metzger JM, Owen S, Rycroft W, Sadowski S, Seward EM, Shepheard SL, Swain CJ, Tattersall FD, Watt AP, Williamson DW, Hargreaves RJ..  (1996)  N-heteroaryl-2-phenyl-3-(benzyloxy)piperidines: a novel class of potent orally active human NK1 antagonists.,  39  (15): [PMID:8709125] [10.1021/jm9506534]

2. Takeuchi Y, Shands EF, Beusen DD, Marshall GR..  (1998)  Derivation of a three-dimensional pharmacophore model of substance P antagonists bound to the neurokinin-1 receptor.,  41  (19): [PMID:9733486] [10.1021/jm9700171]

3. Evers A, Klebe G..  (2004)  Successful virtual screening for a submicromolar antagonist of the neurokinin-1 receptor based on a ligand-supported homology model.,  47  (22): [PMID:15481976] [10.1021/jm0311487]

4. Wu YJ, Meanwell NA..  (2021)  Geminal Diheteroatomic Motifs: Some Applications of Acetals, Ketals, and Their Sulfur and Nitrogen Homologues in Medicinal Chemistry and Drug Design.,  64  (14.0): [PMID:34213340] [10.1021/acs.jmedchem.1c00790]

Source

Source(1):

• Scientific Literature