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

ID: ALA1778343

PubChem CID: 53354784

Max Phase: Preclinical

Molecular Formula: C30H33ClN2O7

Molecular Weight: 569.05

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc([C@H]2O[C@H](CC(=O)N3CCC(C(=O)O)CC3)c3noc(C(C)C)c3-c3ccc(Cl)cc32)c1OC

Standard InChI:  InChI=1S/C30H33ClN2O7/c1-16(2)27-25-19-9-8-18(31)14-21(19)28(20-6-5-7-22(37-3)29(20)38-4)39-23(26(25)32-40-27)15-24(34)33-12-10-17(11-13-33)30(35)36/h5-9,14,16-17,23,28H,10-13,15H2,1-4H3,(H,35,36)/t23-,28-/m1/s1

Standard InChI Key:  HSHHDCPKQVEASM-QDPGVEIFSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1778343

   1-{2-[(4R,6S)-8-Chloro-6-(2,3-dimethoxy-phenyl)-1-isopropyl-4H,6H-2,5-dioxa-3-aza-benzo[e]azulen-4-yl]-acetyl}-piperidine-4-carboxylic 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: 569.05

Molecular Weight (Monoisotopic): 568.1976

AlogP: 6.01

#Rotatable Bonds: 7

Polar Surface Area: 111.33

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.90

CX Basic pKa: ┄

CX LogP: 4.49

CX LogD: 1.28

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.37

Np Likeness Score: -0.44

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]

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