ID: ALA268477

Max Phase: Preclinical

Molecular Formula: C30H33NO4

Molecular Weight: 471.60

Molecule Type: Small molecule

Representations

Synonyms (1): AP-227
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCC/C(CC1CCc2c(cccc2OCC(=O)O)C1)=N\OC(c1ccccc1)c1ccccc1

Standard InChI:  InChI=1S/C30H33NO4/c1-2-10-26(31-35-30(23-11-5-3-6-12-23)24-13-7-4-8-14-24)20-22-17-18-27-25(19-22)15-9-16-28(27)34-21-29(32)33/h3-9,11-16,22,30H,2,10,17-21H2,1H3,(H,32,33)/b31-26+

Standard InChI Key:  XNRBBSJYERPMMB-GKPLWNPISA-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: 471.60

Molecular Weight (Monoisotopic): 471.2410

AlogP: 6.61

#Rotatable Bonds: 11

Polar Surface Area: 68.12

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.04

CX Basic pKa: 3.11

CX LogP: 7.16

CX LogD: 4.36

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.25

Np Likeness Score: -0.09

References

1. Hamanaka N, Takahashi K, Nagao Y, Torisu K, Takada H, Tokumoto H, Kondo K.  (1995)  Molecular design of novel PGI2 agonists without PG skeleton. II,  5  (10): [10.1016/0960-894X(95)00168-S]

2. Hamanaka N, Takahashi K, Nagao Y, Torisu K, Shigeoka S, Hamada S, Kato H, Tokumoto H, Kondo K.  (1995)  Pharmacological evaluation of combined PGI2 agonists/thromboxane synthase inhibitors. I,  5  (10): [10.1016/0960-894X(95)00171-O]

3. Tsubaki K, Taniguchi K, Tabuchi S, Okitsu O, Hattori K, Seki J, Sakane K, Tanaka H..  (2000)  A novel pyridazinone derivative as a nonprostanoid PGI2 agonist.,  10  (24): [PMID:11133092] [10.1016/s0960-894x(00)00571-0]

4. Hattori K, Okitsu O, Tabuchi S, Taniguchi K, Nishio M, Koyama S, Seki J, Sakane K..  (2005)  Discovery of new diphenyloxazole derivatives containing a pyrrolidine ring: orally active prostacyclin mimetics. Part 2.,  15  (13): [PMID:15935660] [10.1016/j.bmcl.2005.04.042]

5. Hattori K, Tanaka A, Okitsu O, Tabuchi S, Taniguchi K, Nishio M, Koyama S, Higaki M, Seki J, Sakane K..  (2005)  Discovery of diphenylcarbamate derivatives as highly potent and selective IP receptor agonists: orally active prostacyclin mimetics. Part 3.,  15  (12): [PMID:15914004] [10.1016/j.bmcl.2005.04.047]

Source

Source(1):

• Scientific Literature