S-[4-[(6R,9R,12R,16S)-9-ethyl-6,12-diisopropyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetrazacyclohexadec-16-yl]but-3-enyl] ethanethioate

ID: ALA3628318

PubChem CID: 122193363

Max Phase: Preclinical

Molecular Formula: C25H40N4O7S

Molecular Weight: 540.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H]1NC(=O)[C@@H](C(C)C)NC(=O)C[C@@H](/C=C/CCSC(C)=O)OC(=O)CNC(=O)[C@@H](C(C)C)NC1=O

Standard InChI:  InChI=1S/C25H40N4O7S/c1-7-18-23(33)29-21(14(2)3)24(34)26-13-20(32)36-17(10-8-9-11-37-16(6)30)12-19(31)28-22(15(4)5)25(35)27-18/h8,10,14-15,17-18,21-22H,7,9,11-13H2,1-6H3,(H,26,34)(H,27,35)(H,28,31)(H,29,33)/b10-8+/t17-,18-,21-,22-/m1/s1

Standard InChI Key:  DURCZQKZLVCYBZ-YXJNUVQQSA-N

Molfile:  

     RDKit          2D

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    0.0000    3.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9304    4.6604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0029    5.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5517   -1.4712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0444    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7184   -2.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3542    0.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1028    1.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6037    1.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3523    2.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8531    2.6104    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6018    3.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8018    3.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0001    4.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9455    2.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1005    3.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  4  5  2  0
  5  2  1  0
  5  1  1  0
  2  6  1  6
  6  7  1  0
  6  8  1  0
  3  9  1  0
  9 10  2  0
  1 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  1  6
 15 17  1  0
 16 18  1  0
 16 19  1  0
 17 20  1  0
 17 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
  9 26  1  0
 26 27  1  0
 27 24  1  0
 27 28  1  6
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 11 36  1  6
 36 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3628318

   ---

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: 540.68

Molecular Weight (Monoisotopic): 540.2618

AlogP: 0.82

#Rotatable Bonds: 7

Polar Surface Area: 159.77

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.59

CX Basic pKa: ┄

CX LogP: 0.72

CX LogD: 0.72

Aromatic Rings: ┄

Heavy Atoms: 37

QED Weighted: 0.21

Np Likeness Score: 1.78

References

1. Ni M, Esposito E, Raj VP, Muzi L, Zunino F, Zuco V, Cominetti D, Penco S, Dal Pozzo A..  (2015)  New macrocyclic analogs of the natural histone deacetylase inhibitor FK228; design, synthesis and preliminary biological evaluation.,  23  (21): [PMID:26481659] [10.1016/j.bmc.2015.10.004]

Source

Source(1):

• Scientific Literature