(S)-2-{[(1S,2S)-3-(3,4-Dichloro-phenyl)-2-(2-fluoro-biphenyl-4-yl)-1-methyl-propylcarbamoyl]-methyl}-succinic acid

ID: ALA2115091

PubChem CID: 71452787

Max Phase: Preclinical

Molecular Formula: C28H26Cl2FNO5

Molecular Weight: 546.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)C[C@H](CC(=O)O)C(=O)O)[C@@H](Cc1ccc(Cl)c(Cl)c1)c1ccc(-c2ccccc2)c(F)c1

Standard InChI:  InChI=1S/C28H26Cl2FNO5/c1-16(32-26(33)14-20(28(36)37)15-27(34)35)22(11-17-7-10-23(29)24(30)12-17)19-8-9-21(25(31)13-19)18-5-3-2-4-6-18/h2-10,12-13,16,20,22H,11,14-15H2,1H3,(H,32,33)(H,34,35)(H,36,37)/t16-,20+,22+/m0/s1

Standard InChI Key:  NBRLADMQSZWKGO-SAWYMBPVSA-N

Molfile:  

     RDKit          2D

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    2.6054   -4.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0333   -2.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8914   -3.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4738   -2.7306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1878   -3.9707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.0437   -3.9707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6054   -0.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6054   -5.2108    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.1774   -1.9039    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.3297   -4.3841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3194   -0.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1774   -0.2505    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.7702   -2.7306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7473   -3.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635   -3.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1774   -5.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635   -5.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2505   -4.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2505   -5.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  2  0
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  4  1  1  0
  5 12  2  0
  6 10  1  0
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  8 14  1  0
  9  1  1  0
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 12 18  1  0
 13 15  1  0
 14  3  1  0
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  4 16  1  6
 17 25  2  0
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 20 16  1  0
 21  3  2  0
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 25 29  1  0
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 10 32  1  1
 33 23  2  0
 34 23  1  0
 35 34  2  0
 36 33  1  0
 37 35  1  0
  5  2  1  0
 17 11  1  0
 37 36  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2115091

   (2R)-2-[2-[[(2S,3S)-4-(3,4-dichlorophenyl)-3-(3-fluoro-4-phenylphenyl)butan-2-yl]amino]-2-oxoethyl]butanedioic 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: 546.42

Molecular Weight (Monoisotopic): 545.1172

AlogP: 6.20

#Rotatable Bonds: 11

Polar Surface Area: 103.70

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.85

CX Basic pKa: ┄

CX LogP: 6.06

CX LogD: 0.84

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.27

Np Likeness Score: -0.43

References

1. Iwasawa Y, Hayashi M, Nomoto T, Shibata J, Mitsuya M, Hirota K, Yonemoto M, Kamei T, Miura K, Tomimoto K.  (1995)  Synthesis and biological activity of J-104,118, a novel, potent inhibitor of squalene synthase,  5  (17): [10.1016/0960-894X(95)00339-U]

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