2-{2-[7-Chloro-5-(2,3-dimethoxy-phenyl)-1-(3-hydroxy-2,2-dimethyl-propyl)-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]oxazepin-3-yl]-acetylamino}-propionic acid

ID: ALA2112799

PubChem CID: 10918648

Max Phase: Preclinical

Molecular Formula: C27H33ClN2O8

Molecular Weight: 549.02

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc([C@H]2O[C@H](CC(=O)N[C@@H](C)C(=O)O)C(=O)N(CC(C)(C)CO)c3ccc(Cl)cc32)c1OC

Standard InChI:  InChI=1S/C27H33ClN2O8/c1-15(26(34)35)29-22(32)12-21-25(33)30(13-27(2,3)14-31)19-10-9-16(28)11-18(19)23(38-21)17-7-6-8-20(36-4)24(17)37-5/h6-11,15,21,23,31H,12-14H2,1-5H3,(H,29,32)(H,34,35)/t15-,21+,23+/m0/s1

Standard InChI Key:  JCHYHJUTOPKYNB-PNDGYVOYSA-N

Molfile:  

     RDKit          2D

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 17 36  1  6
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M  END

Alternative Forms

1. Parent:

   

   ALA2112799

   (2S)-2-[[(3R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]aminopropionic 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: 549.02

Molecular Weight (Monoisotopic): 548.1925

AlogP: 3.18

#Rotatable Bonds: 10

Polar Surface Area: 134.63

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.11

CX Basic pKa: ┄

CX LogP: 2.46

CX LogD: -1.00

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.41

Np Likeness Score: -0.31

References

1. Miki T, Kori M, Mabuchi H, Tozawa R, Nishimoto T, Sugiyama Y, Teshima K, Yukimasa H..  (2002)  Synthesis of novel 4,1-benzoxazepine derivatives as squalene synthase inhibitors and their inhibition of cholesterol synthesis.,  45  (20): [PMID:12238936] [10.1021/jm020234o]

2. Soltis, D A DA and 9 more authors.  1995-02-01  Expression, purification, and characterization of the human squalene synthase: use of yeast and baculoviral systems.  [PMID:7864626]

3. Cammerer, Simon B SB and 14 more authors.  2007-11  Quinuclidine derivatives as potential antiparasitics.  [PMID:17709461]

4. Song, Yongcheng and 11 more authors.  2009-02-26  Phosphonosulfonates are potent, selective inhibitors of dehydrosqualene synthase and staphyloxanthin biosynthesis in Staphylococcus aureus.  [PMID:19191557]

5. Lin, Fu-Yang and 7 more authors.  2012-05-10  Head-to-head prenyl tranferases: anti-infective drug targets.  [PMID:22486710]

Source

Source(1):

• Scientific Literature