N-hydroxy-2-((5-(3-nitrophenyl)furan-2-yl)methyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxamide

ID: ALA3338404

PubChem CID: 101882265

Max Phase: Preclinical

Molecular Formula: C21H19N3O5

Molecular Weight: 393.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NO)c1ccc2c(c1)CN(Cc1ccc(-c3cccc([N+](=O)[O-])c3)o1)CC2

Standard InChI:  InChI=1S/C21H19N3O5/c25-21(22-26)16-5-4-14-8-9-23(12-17(14)10-16)13-19-6-7-20(29-19)15-2-1-3-18(11-15)24(27)28/h1-7,10-11,26H,8-9,12-13H2,(H,22,25)

Standard InChI Key:  PMFDRULHDRRWFP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    2.2355   -2.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2344   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9424   -3.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9407   -2.3440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5277   -2.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275   -1.5272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8201   -2.7532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1123   -2.3447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6493   -2.7492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6481   -3.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3582   -3.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0740   -3.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0752   -2.7513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3606   -2.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7839   -2.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4906   -2.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5713   -3.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3702   -3.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7806   -3.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2352   -2.4216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5896   -2.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0679   -3.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8801   -3.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2150   -2.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7316   -2.1149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9211   -2.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0642   -1.3659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5831   -0.7054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8768   -1.2796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3 10  2  0
  9  4  2  0
  4  1  1  0
  1  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 16  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 19 21  1  0
 27 28  2  0
 27 29  1  0
 25 27  1  0
M  CHG  2  27   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3338404

   N-hydroxy-2-[[5-(3-nitrophenyl)furan-2-yl]methyl]-3,4-dihydro-1H-isoquinoline-7-carboxamide

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: 393.40

Molecular Weight (Monoisotopic): 393.1325

AlogP: 3.53

#Rotatable Bonds: 5

Polar Surface Area: 108.85

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.21

CX Basic pKa: 6.93

CX LogP: 3.09

CX LogD: 2.96

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.39

Np Likeness Score: -1.42

References

1. Tang G, Wong JC, Zhang W, Wang Z, Zhang N, Peng Z, Zhang Z, Rong Y, Li S, Zhang M, Yu L, Feng T, Zhang X, Wu X, Wu JZ, Chen L..  (2014)  Identification of a novel aminotetralin class of HDAC6 and HDAC8 selective inhibitors.,  57  (19): [PMID:25238284] [10.1021/jm5008962]

Source

Source(1):

• Scientific Literature