3-[N-(3-Phenylpropyl)amino]-4-methylbenzhydroxamic acid

ID: ALA4099064

PubChem CID: 137661848

Max Phase: Preclinical

Molecular Formula: C17H20N2O2

Molecular Weight: 284.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(=O)NO)cc1NCCCc1ccccc1

Standard InChI:  InChI=1S/C17H20N2O2/c1-13-9-10-15(17(20)19-21)12-16(13)18-11-5-8-14-6-3-2-4-7-14/h2-4,6-7,9-10,12,18,21H,5,8,11H2,1H3,(H,19,20)

Standard InChI Key:  KVQDENKEOQLMNA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   17.3742  -13.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3731  -14.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0811  -14.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7908  -14.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7879  -13.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0793  -12.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6650  -14.5791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4991  -14.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5004  -15.3953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2062  -14.1684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9145  -14.5759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6664  -12.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9577  -14.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2496  -14.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5422  -14.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8412  -14.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1422  -14.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4416  -14.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4437  -15.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1521  -15.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8498  -15.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
  1 12  1  0
  7 13  1  0
 13 14  1  0
 14 15  1  0
 16 15  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099064

   ---

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: 284.36

Molecular Weight (Monoisotopic): 284.1525

AlogP: 3.16

#Rotatable Bonds: 6

Polar Surface Area: 61.36

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: 4.21

CX LogP: 3.26

CX LogD: 3.26

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.43

Np Likeness Score: -1.18

References

1. Heimburg T, Kolbinger FR, Zeyen P, Ghazy E, Herp D, Schmidtkunz K, Melesina J, Shaik TB, Erdmann F, Schmidt M, Romier C, Robaa D, Witt O, Oehme I, Jung M, Sippl W..  (2017)  Structure-Based Design and Biological Characterization of Selective Histone Deacetylase 8 (HDAC8) Inhibitors with Anti-Neuroblastoma Activity.,  60  (24): [PMID:29190092] [10.1021/acs.jmedchem.7b01447]

Source

Source(1):

• Scientific Literature