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

ID: ALA196779

Cas Number: 227951-89-5

PubChem CID: 9911469

Product Number: F610330, Order Now?

Max Phase: Preclinical

Molecular Formula: C26H25NO6

Molecular Weight: 447.49

Molecule Type: Small molecule

Names and Identifiers

Synonyms: FK-788 | FK-788|227951-89-5|UNII-LSJ4493RPW|LSJ4493RPW|FK 788|CHEMBL196779|GTPL5855|SCHEMBL6612986|DTXSID70945479|FK788|BDBM50167887|SB19698|A857154|Q27077300|(R)-2-(6-((diphenylcarbamoyloxy)methyl)-6-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yloxy)acetic acid|[(6-{[(Diphenylcarbamoyl)oxy]methyl}-6-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)oxy]acetic acid|{(R)-6-[(Diphenylcarbamoyloxy)-methyl]-6-hydroxy-5,6,7,8-tetrahydro-naphthalen-1-yloxy}-acetic acid|2-[[(6R)-6-(diphenylcarbamoyloxymethyl)-6-hydShow More⌵

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-/m1/s1

Standard InChI Key:  UZJAIYJXBYWENR-AREMUKBSSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  1  0  0  0  0  0999 V2000
    6.3917    1.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1042    1.4500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250    0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250    1.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792    1.4458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5417    0.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2500    1.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -1.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292    1.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1042    0.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875    2.6833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1042   -0.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1125    0.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8167    1.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1042   -2.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2542    0.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9625    1.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -1.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6792   -2.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417    2.2583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1042    1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917    1.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917    0.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5292    1.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8125    2.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4000    0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8250    0.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167    3.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4042   -0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8292   -0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2417    1.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1167   -1.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2417    2.7083    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  6
 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:

   

   ALA196779

   FK-788

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]

2. Takamura F, Tanaka A, Takasugi H, Taniguchi K, Nishio M, Seki J, Hattori K..  (2006)  Metabolism investigation leading to novel drug design 2: orally active prostacyclin mimetics. Part 5.,  16  (17): [PMID:16824754] [10.1016/j.bmcl.2006.06.033]

3. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of MMV (CH) - Pandemic Response Box,  [10.6019/CHEMBL4513161]

Source

Source(2):

• Scientific Literature
• CO-ADD antimicrobial screening data