2-{3-[3-(3-Amino-propylamino)-propylamino]-propylamino}-N-[(5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-acetamide

ID: ALA4247400

PubChem CID: 145986243

Max Phase: Preclinical

Molecular Formula: C32H45N5O8

Molecular Weight: 627.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@@H]2c3cc4c(cc3[C@@H](NC(=O)CNCCCNCCCNCCCN)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1O

Standard InChI:  InChI=1S/C32H45N5O8/c1-41-25-12-19(13-26(42-2)31(25)39)28-20-14-23-24(45-18-44-23)15-21(20)30(22-17-43-32(40)29(22)28)37-27(38)16-36-11-5-10-35-9-4-8-34-7-3-6-33/h12-15,22,28-30,34-36,39H,3-11,16-18,33H2,1-2H3,(H,37,38)/t22-,28+,29-,30+/m0/s1

Standard InChI Key:  KZASBEFUPQBECK-GEYQZXRLSA-N

Molfile:  

     RDKit          2D

 47 51  0  0  0  0  0  0  0  0999 V2000
   22.3776  -16.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3758  -14.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0844  -14.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0832  -15.7782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7894  -16.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7917  -14.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6695  -15.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6707  -14.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8945  -14.7107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4136  -15.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8926  -16.0318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5025  -14.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5033  -15.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2818  -16.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7622  -15.3675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2805  -14.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7860  -17.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0758  -17.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0737  -18.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7810  -18.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4920  -18.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4906  -17.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7804  -19.4520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3649  -18.6306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6583  -18.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2003  -18.6309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2014  -19.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5350  -16.8070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7918  -13.7288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4995  -13.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4995  -12.5030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2072  -13.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9149  -13.3202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.6226  -13.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3303  -13.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0380  -13.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7457  -13.3203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4534  -13.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1611  -13.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8688  -13.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4951  -14.1399    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.4951  -16.5915    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   31.5766  -13.3203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.2843  -13.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9920  -13.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6997  -13.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4074  -13.3204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0
  1  4  2  0
  3  2  2  0
  2  8  1  0
  3  4  1  0
  3  6  1  0
  4  5  1  0
  5 13  1  0
 12  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 12 16  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
  5 17  1  6
 20 23  1  0
 19 24  1  0
 24 25  1  0
 21 26  1  0
 26 27  1  0
 14 28  2  0
  6 29  1  1
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 12 41  1  6
 13 42  1  1
 40 43  1  0
 43 44  1  0
 44 45  1  0
 45 46  1  0
 46 47  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4247400

   ---

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: 627.74

Molecular Weight (Monoisotopic): 627.3268

AlogP: 1.13

#Rotatable Bonds: 17

Polar Surface Area: 174.66

Molecular Species: BASE

HBA: 12

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.31

CX Basic pKa: 10.36

CX LogP: -1.72

CX LogD: -5.65

Aromatic Rings: 2

Heavy Atoms: 45

QED Weighted: 0.11

Np Likeness Score: 0.81

References

1. Oviatt AA, Kuriappan JA, Minniti E, Vann KR, Onuorah P, Minarini A, De Vivo M, Osheroff N..  (2018)  Polyamine-containing etoposide derivatives as poisons of human type II topoisomerases: Differential effects on topoisomerase IIα and IIβ.,  28  (17): [PMID:30006062] [10.1016/j.bmcl.2018.07.010]

Source

Source(1):

• Scientific Literature