3-(3'-Adamantan-1-yl-4'-cyanomethoxybiphenyl-4-yl)-Nhydroxyacrylamide

ID: ALA3235790

PubChem CID: 90654946

Max Phase: Preclinical

Molecular Formula: C27H27ClN2O2

Molecular Weight: 446.98

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CCc1ccc(-c2ccc(/C=C/C(=O)NO)cc2Cl)cc1C12CC3CC(CC(C3)C1)C2

Standard InChI:  InChI=1S/C27H27ClN2O2/c28-25-12-17(2-6-26(31)30-32)1-5-23(25)22-4-3-21(7-8-29)24(13-22)27-14-18-9-19(15-27)11-20(10-18)16-27/h1-6,12-13,18-20,32H,7,9-11,14-16H2,(H,30,31)/b6-2+

Standard InChI Key:  ZDEMAYQXILUXCI-QHHAFSJGSA-N

Molfile:  

     RDKit          2D

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    6.0913   -4.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0884   -4.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3730   -3.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7983   -3.6283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2270   -3.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2244   -2.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5033   -2.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7938   -2.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.0823   -2.7849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3614   -1.5510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7946   -2.3688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6472   -4.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1954   -3.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4041   -4.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6446   -3.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2012   -2.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4837   -2.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9532   -2.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3749   -5.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6591   -4.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5169   -4.8649    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9437   -5.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -6.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9423   -6.9316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1 28  2  0
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  2  3  1  0
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  4  1  1  0
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  6  7  1  0
  7  8  2  0
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  9 10  2  0
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  3  5  1  0
  8 11  1  0
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  1 17  1  0
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 20 22  1  0
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 22 17  1  0
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 20 23  1  0
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 24 25  1  0
 27 28  1  0
  6 29  1  0
 28 30  1  0
 30 31  1  0
 31 32  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA3235790

   (E)-3-[4-[3-(1-adamantyl)-4-(cyanomethyl)phenyl]-3-chlorophenyl]-N-hydroxyprop-2-enamide

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: 446.98

Molecular Weight (Monoisotopic): 446.1761

AlogP: 6.06

#Rotatable Bonds: 5

Polar Surface Area: 73.12

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.56

CX Basic pKa: ┄

CX LogP: 5.62

CX LogD: 5.62

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.33

Np Likeness Score: -0.15

References

1. Cincinelli R, Musso L, Giannini G, Zuco V, De Cesare M, Zunino F, Dallavalle S..  (2014)  Influence of the adamantyl moiety on the activity of biphenylacrylohydroxamic acid-based HDAC inhibitors.,  79  [PMID:24742384] [10.1016/j.ejmech.2014.04.021]

Source

Source(1):

• Scientific Literature