(6-{2-[(E)-Benzhydryloxyimino]-pentyl}-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid

ID: ALA268477

Chembl Id: CHEMBL268477

PubChem CID: 9847589

Max Phase: Preclinical

Molecular Formula: C30H33NO4

Molecular Weight: 471.60

Molecule Type: Small molecule

Names and Identifiers

Synonyms: AP-227 | CHEMBL268477|AP-227|AP227|BDBM50095205|(6-{2-[(E)-Benzhydryloxyimino]-pentyl}-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid|[6-(2-Benzhydryloxyimino-pentyl)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid

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

Alternative Forms

1. Parent:

   

   ALA268477

   AP-227

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: 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