[(4R,6S)-8-Chloro-6-(2,3-dimethoxy-phenyl)-1-isopropyl-4H,6H-2,5-dioxa-3-aza-benzo[e]azulen-4-yl]-acetic acid

ID: ALA1778340

PubChem CID: 54583685

Max Phase: Preclinical

Molecular Formula: C24H24ClNO6

Molecular Weight: 457.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc([C@H]2O[C@H](CC(=O)O)c3noc(C(C)C)c3-c3ccc(Cl)cc32)c1OC

Standard InChI:  InChI=1S/C24H24ClNO6/c1-12(2)22-20-14-9-8-13(25)10-16(14)23(15-6-5-7-17(29-3)24(15)30-4)31-18(11-19(27)28)21(20)26-32-22/h5-10,12,18,23H,11H2,1-4H3,(H,27,28)/t18-,23-/m1/s1

Standard InChI Key:  WRADIXPKOCXFKO-WZONZLPQSA-N

Molfile:  

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   18.2018   -0.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.1318   -4.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0711   -0.3815    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.6509    0.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2349    1.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0256    1.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2327    2.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6493    1.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8617    0.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0267    0.9016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6095    1.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.4000    2.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA1778340

   [(4R,6S)-8-Chloro-6-(2,3-dimethoxy-phenyl)-1-isopropyl-4H,6H-2,5-dioxa-3-aza-benzo[e]azulen-4-yl]-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: 457.91

Molecular Weight (Monoisotopic): 457.1292

AlogP: 5.77

#Rotatable Bonds: 6

Polar Surface Area: 91.02

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.48

CX Basic pKa: ┄

CX LogP: 4.78

CX LogD: 1.96

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.50

Np Likeness Score: -0.03

References

1. Griebenow N, Buchmueller A, Kolkhof P, Schamberger J, Bischoff H..  (2011)  Identification of 4H,6H-[2]benzoxepino[4,5-c][1,2]oxazoles as novel squalene synthase inhibitors.,  21  (12): [PMID:21576018] [10.1016/j.bmcl.2011.04.092]

Source

Source(1):

• Scientific Literature