(S)-2-{(S)-2-[2-(3-Acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-3-methyl-butyrylamino}-pentanedioic acid 1-amide 5-{[3-(12-oxo-10,12-dihydro-isoindolo[1,2-b]quinazolin-8-ylcarbamoyl)-propyl]-amide}

ID: ALA174787

PubChem CID: 44386381

Max Phase: Preclinical

Molecular Formula: C47H58N8O12

Molecular Weight: 927.02

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)NC1C(OCc2ccccc2)OC(CO)C(O)C1OC(C)C(=O)N[C@H](C(=O)N[C@@H](CCC(=O)NCCCC(=O)Nc1ccc2c(c1)CN1C(=O)c3ccccc3C1=N2)C(N)=O)C(C)C

Standard InChI:  InChI=1S/C47H58N8O12/c1-25(2)38(54-44(62)26(3)66-41-39(50-27(4)57)47(67-35(23-56)40(41)60)65-24-28-11-6-5-7-12-28)45(63)53-34(42(48)61)18-19-36(58)49-20-10-15-37(59)51-30-16-17-33-29(21-30)22-55-43(52-33)31-13-8-9-14-32(31)46(55)64/h5-9,11-14,16-17,21,25-26,34-35,38-41,47,56,60H,10,15,18-20,22-24H2,1-4H3,(H2,48,61)(H,49,58)(H,50,57)(H,51,59)(H,53,63)(H,54,62)/t26?,34-,35?,38-,39?,40?,41?,47?/m0/s1

Standard InChI Key:  ANGLYMSGPVXRBY-AIEIXQCHSA-N

Molfile:  

     RDKit          2D

 67 72  0  0  1  0  0  0  0  0999 V2000
   -4.7708   -3.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4958   -4.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750   -4.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5958   -3.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9625    2.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5917    2.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8500   -5.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167    1.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1292   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2333   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3667    2.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -1.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9167    2.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000    0.3375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4208   -3.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1625    2.2958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2417    2.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7875    0.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1375   -4.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4125   -0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -1.8417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8042    1.5083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -3.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5750    1.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2167    0.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8708   -2.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7292    1.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6958   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4958   -2.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8833   -2.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0833   -2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4292    0.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4625   -3.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3250   -4.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5875    1.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833   -3.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375   -0.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792   -3.8000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0792    3.5833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -1.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042   -0.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -1.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5250    0.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7958   -3.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2417    3.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3917   -5.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9417   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7375    0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9500    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125   -1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4292    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792    1.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917   -0.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1500   -0.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5292   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6792   -2.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2125   -5.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4792   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3625   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7417   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1625   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  1  0
  5 16  1  0
  6  5  1  0
  7  2  1  0
  8  6  1  0
  9  4  1  0
 10  1  1  0
 11  5  1  0
 12 21  1  0
 13 17  1  0
 14 20  1  0
 15 10  1  0
 16 25  1  0
 17 11  1  0
 18 14  1  0
 19 15  1  0
 20 12  1  0
 21 24  1  0
 22  6  1  0
 23 24  1  0
 24 41  1  6
 25 18  1  0
 26 22  1  0
 27  4  2  0
 28  8  1  0
 29 30  1  0
 30 34  1  0
 31 44  1  0
 32 15  2  0
 33 12  2  0
 34 32  1  0
 35 18  2  0
 36 23  2  0
 37 19  2  0
 38 26  2  0
 39 29  2  0
 40 31  2  0
 41 46  1  0
 42 23  1  0
 43 11  1  0
 44 57  1  0
 20 45  1  1
 46 31  1  0
 47 28  1  0
 48 34  2  0
 49 17  1  0
 50  7  1  0
 51  9  1  0
 52 47  1  0
 53 49  1  0
 54 29  1  0
 55 26  1  0
 56 25  1  0
 57 62  1  0
 58 45  1  0
 59 45  1  0
 60 52  2  0
 61 52  1  0
 62 54  1  0
 63 50  2  0
 64 51  2  0
 65 60  1  0
 66 61  2  0
 67 66  1  0
  9  7  2  0
  3 19  1  0
 63 64  1  0
 48 37  1  0
  8 13  1  0
 65 67  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA174787

   (2S)-2-[[(2S)-2-[2-[5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-4-yl]oxypropanoylamino]-3-methylbutanoyl]amino]-N'-[4-oxo-4-[(12-oxo-10H-isoindolo[1,2-b]quinazolin-8-yl)amino]butyl]pentanediamide

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: 927.02

Molecular Weight (Monoisotopic): 926.4174

AlogP: 1.03

#Rotatable Bonds: 21

Polar Surface Area: 289.41

Molecular Species: NEUTRAL

HBA: 13

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 20

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.69

CX Basic pKa: 4.02

CX LogP: 0.10

CX LogD: 0.10

Aromatic Rings: 3

Heavy Atoms: 67

QED Weighted: 0.07

Np Likeness Score: 0.10

References

1. Dzierzbicka K, Trzonkowski P, Sewerynek P, Myśliwski A..  (2003)  Synthesis and cytotoxic activity of conjugates of muramyl and normuramyl dipeptides with batracylin derivatives.,  46  (6): [PMID:12620074] [10.1021/jm021067v]

Source

Source(1):

• Scientific Literature