N-((S)-1-(3-(((1R,2R)-2-((3-aminopropylamino)methyl)cyclopropyl)methylamino)propylamino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)butyramide

ID: ALA4531333

PubChem CID: 155546334

Max Phase: Preclinical

Molecular Formula: C24H41N5O3

Molecular Weight: 447.62

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)NCCCNC[C@@H]1C[C@H]1CNCCCN

Standard InChI:  InChI=1S/C24H41N5O3/c1-2-5-23(31)29-22(14-18-6-8-21(30)9-7-18)24(32)28-13-4-12-27-17-20-15-19(20)16-26-11-3-10-25/h6-9,19-20,22,26-27,30H,2-5,10-17,25H2,1H3,(H,28,32)(H,29,31)/t19-,20-,22-/m0/s1

Standard InChI Key:  AZKMTKVSVYHHAA-ONTIZHBOSA-N

Molfile:  

 
     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   14.5495  -17.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7539  -17.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4657  -17.5820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0420  -17.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3302  -17.9947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3302  -18.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6183  -19.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0420  -19.2246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9106  -18.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1988  -19.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0420  -16.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3302  -16.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3332  -15.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6222  -15.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9135  -15.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9161  -16.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6235  -16.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2011  -15.1180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1775  -17.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8894  -17.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5971  -17.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3089  -17.5820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0207  -17.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7539  -18.8160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7326  -17.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1439  -16.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2584  -17.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9692  -17.5719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6820  -17.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3928  -17.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1016  -17.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8124  -17.5647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  7  9  1  0
  9 10  1  0
  4 11  1  1
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 15 18  1  0
  3 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  2 24  2  0
 25 23  1  6
  1 25  1  0
 26  1  1  0
 25 26  1  0
  1 27  1  1
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4531333

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 447.62

Molecular Weight (Monoisotopic): 447.3209

AlogP: 0.89

#Rotatable Bonds: 17

Polar Surface Area: 128.51

Molecular Species: BASE

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.42

CX Basic pKa: 10.80

CX LogP: -1.19

CX LogD: -6.20

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.20

Np Likeness Score: 0.28

References

1. Kachel HS, Franzyk H, Mellor IR..  (2019)  Philanthotoxin Analogues That Selectively Inhibit Ganglionic Nicotinic Acetylcholine Receptors with Exceptional Potency.,  62  (13): [PMID:31244109] [10.1021/acs.jmedchem.9b00519]

Source

Source(1):

• Scientific Literature