(R)-7-[(6S,9R,12S)-6-sec-Butyl-9-(4-methoxy-benzyl)-5,8,11,14-tetraoxo-tetradecahydro-4a,7,10,13-tetraaza-benzocyclododecen-12-yl]-heptanoic acid hydroxyamide

ID: ALA1790593

PubChem CID: 56662148

Max Phase: Preclinical

Molecular Formula: C31H47N5O7

Molecular Weight: 601.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@H](C)[C@@H]1NC(=O)[C@@H](Cc2ccc(OC)cc2)NC(=O)[C@H](CCCCCCC(=O)NO)NC(=O)[C@H]2CCCCN2C1=O

Standard InChI:  InChI=1S/C31H47N5O7/c1-4-20(2)27-31(41)36-18-10-9-12-25(36)30(40)32-23(11-7-5-6-8-13-26(37)35-42)28(38)33-24(29(39)34-27)19-21-14-16-22(43-3)17-15-21/h14-17,20,23-25,27,42H,4-13,18-19H2,1-3H3,(H,32,40)(H,33,38)(H,34,39)(H,35,37)/t20-,23+,24-,25-,27+/m1/s1

Standard InChI Key:  IDNMSLGHIWCDPW-JNKSKZIFSA-N

Molfile:  

     RDKit          2D

 45 47  0  0  1  0  0  0  0  0999 V2000
   10.1042   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2542   -2.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6667   -0.9167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2167   -2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2542   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1917   -1.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7792   -2.7542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2167   -0.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3417   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6625   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7792   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1917   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5250   -1.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2042   -3.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7250   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1917   -0.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9167   -1.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0750   -0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7417   -3.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7417   -1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2167   -2.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7000   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6542   -0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8167   -0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9500   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9500    0.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7292   -2.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5292   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5292    0.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5125   -3.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4042   -0.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7167   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2125   -2.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2417   -1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7500   -0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6917    0.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7167   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2042   -2.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5500   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7167   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2042   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9500   -3.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7417   -1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1634   -3.6197    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1269   -0.3123    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  5  1  0
  4 10  1  0
  5  1  1  0
  6 11  1  0
  7  4  1  0
  8  3  1  0
  9  6  1  0
 10  2  1  0
 11  8  1  0
 12  7  1  0
 13  1  2  0
 14  4  2  0
 15 33  1  0
 16  8  2  0
 17  9  2  0
 11 18  1  1
 19 15  2  0
  5 20  1  0
 21 15  1  0
 22  2  1  0
 23 18  1  0
 24 29  2  0
 25 23  1  0
 26 23  2  0
 27 21  1  0
 28 25  2  0
 29 26  1  0
 10 30  1  0
 31 24  1  0
 12 32  1  6
 33 37  1  0
 34 20  1  0
 20 35  1  1
 36 31  1  0
 37 41  1  0
 38 32  1  0
 39 22  1  0
 40 38  1  0
 41 40  1  0
 42 39  1  0
 43 34  1  0
 30 42  1  0
  9 12  1  0
 28 24  1  0
 10 44  1  6
  5 45  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1790593

   7-[(3S,6R,9S,12R)-3-[(2R)-butan-2-yl]-6-[(4-methoxyphenyl)methyl]-2,5,8,11-tetraoxo-1,4,7,10-tetrazabicyclo[10.4.0]hexadecan-9-yl]-N-hydroxyheptanamide

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: 601.74

Molecular Weight (Monoisotopic): 601.3475

AlogP: 1.98

#Rotatable Bonds: 12

Polar Surface Area: 166.17

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.90

CX Basic pKa: ┄

CX LogP: 2.02

CX LogD: 2.00

Aromatic Rings: 1

Heavy Atoms: 43

QED Weighted: 0.14

Np Likeness Score: 0.84

References

1. Nishino N, Yoshikawa D, Watanabe LA, Kato T, Jose B, Komatsu Y, Sumida Y, Yoshida M..  (2004)  Synthesis and histone deacetylase inhibitory activity of cyclic tetrapeptides containing a retrohydroxamate as zinc ligand.,  14  (10): [PMID:15109626] [10.1016/j.bmcl.2004.03.018]

Source

Source(1):

• Scientific Literature