ID: ALA59765

Max Phase: Preclinical

Molecular Formula: C23H28ClNO4

Molecular Weight: 417.93

Molecule Type: Small molecule

Representations

Synonyms (1): FK-175
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCOC(=O)COc1ccc2c(c1)C[C@@H](NC[C@H](O)c1cccc(Cl)c1)CCC2

Standard InChI:  InChI=1S/C23H28ClNO4/c1-2-28-23(27)15-29-21-10-9-16-5-4-8-20(12-18(16)13-21)25-14-22(26)17-6-3-7-19(24)11-17/h3,6-7,9-11,13,20,22,25-26H,2,4-5,8,12,14-15H2,1H3/t20-,22-/m0/s1

Standard InChI Key:  QFMUIHJMDMGJAY-UNMCSNQZSA-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: 417.93

Molecular Weight (Monoisotopic): 417.1707

AlogP: 3.85

#Rotatable Bonds: 8

Polar Surface Area: 67.79

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.81

CX LogP: 4.33

CX LogD: 1.98

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.50

Np Likeness Score: -0.79

References

1. Kordik CP, Reitz AB..  (1999)  Pharmacological treatment of obesity: therapeutic strategies.,  42  (2): [PMID:9925722] [10.1021/jm980521l]

2. Imanishi M, Tomishima Y, Itou S, Hamashima H, Nakajima Y, Washizuka K, Sakurai M, Matsui S, Imamura E, Ueshima K, Yamamoto T, Yamamoto N, Ishikawa H, Nakano K, Unami N, Hamada K, Matsumura Y, Takamura F, Hattori K..  (2008)  Discovery of a novel series of biphenyl benzoic acid derivatives as potent and selective human beta3-adrenergic receptor agonists with good oral bioavailability. Part I.,  51  (6): [PMID:18307290] [10.1021/jm701324c]

3. Imanishi M, Itou S, Washizuka K, Hamashima H, Nakajima Y, Araki T, Tomishima Y, Sakurai M, Matsui S, Imamura E, Ueshima K, Yamamoto T, Yamamoto N, Ishikawa H, Nakano K, Unami N, Hamada K, Matsumura Y, Takamura F, Hattori K..  (2008)  Discovery of a novel series of biphenyl benzoic acid derivatives as highly potent and selective human beta3 adrenergic receptor agonists with good oral bioavailability. Part II.,  51  (13): [PMID:18553954] [10.1021/jm8000345]

4. Imanishi M, Nakajima Y, Tomishima Y, Hamashima H, Washizuka K, Sakurai M, Matsui S, Imamura E, Ueshima K, Yamamoto T, Yamamoto N, Ishikawa H, Nakano K, Unami N, Hamada K, Matsumura Y, Takamura F, Hattori K..  (2008)  Discovery of a novel series of benzoic acid derivatives as potent and selective human beta3 adrenergic receptor agonists with good oral bioavailability. 3. Phenylethanolaminotetraline (PEAT) skeleton containing biphenyl or biphenyl ether moiety.,  51  (15): [PMID:18651730] [10.1021/jm800222k]

Source

Source(1):

• Scientific Literature