{(S)-6-[(Diphenylcarbamoyloxy)-methyl]-6-hydroxy-5,6,7,8-tetrahydro-naphthalen-1-yloxy}-acetic acid

ID: ALA426829

PubChem CID: 44402739

Max Phase: Preclinical

Molecular Formula: C26H25NO6

Molecular Weight: 447.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)COc1cccc2c1CC[C@@](O)(COC(=O)N(c1ccccc1)c1ccccc1)C2

Standard InChI:  InChI=1S/C26H25NO6/c28-24(29)17-32-23-13-7-8-19-16-26(31,15-14-22(19)23)18-33-25(30)27(20-9-3-1-4-10-20)21-11-5-2-6-12-21/h1-13,31H,14-18H2,(H,28,29)/t26-/m0/s1

Standard InChI Key:  UZJAIYJXBYWENR-SANMLTNESA-N

Molfile:  

     RDKit          2D

 33 36  0  0  1  0  0  0  0  0999 V2000
    6.0417    5.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7625    5.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792    4.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792    5.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292    5.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917    4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042    5.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500    2.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1875    5.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7625    4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417    6.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7625    3.4208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667    4.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4750    5.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7625    1.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042    4.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167    5.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500    3.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292    1.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000    6.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7625    5.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500    5.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500    4.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1875    5.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4667    6.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542    4.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4792    4.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1750    7.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542    3.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4875    3.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9000    5.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7750    3.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8917    6.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  6  1  0
  4  9  1  0
  5  1  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
  9  7  1  0
 10  3  2  0
 11  1  2  0
 12 10  1  0
 13  2  1  0
 14  2  1  0
 15  8  2  0
 16  7  1  0
 17  5  1  0
 18 12  1  0
 19  8  1  0
  7 20  1  1
 21  4  2  0
 22 21  1  0
 23 10  1  0
 24 14  2  0
 25 14  1  0
 26 13  2  0
 27 13  1  0
 28 25  2  0
 29 26  1  0
 30 27  2  0
 31 24  1  0
 32 30  1  0
 33 28  1  0
  4  3  1  0
 31 33  2  0
 29 32  2  0
 22 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA426829

   2-[[(6S)-6-(diphenylcarbamoyloxymethyl)-6-hydroxy-7,8-dihydro-5H-naphthalen-1-yl]oxy]acetic 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: 447.49

Molecular Weight (Monoisotopic): 447.1682

AlogP: 4.34

#Rotatable Bonds: 7

Polar Surface Area: 96.30

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.68

CX Basic pKa: ┄

CX LogP: 4.46

CX LogD: 1.15

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.56

Np Likeness Score: -0.01

References

1. 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