(S)-2-(2-(1H-Indol-3-yl)acetamido)-N1-(5-(3-(4-(3-aminopropylamino)butylamino)propanamido)pentyl)-succinamide

ID: ALA2178919

Cas Number: 114355-41-8

PubChem CID: 188869

Max Phase: Preclinical

Molecular Formula: C29H48N8O4

Molecular Weight: 572.76

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Nephila polyamine toxin-8 | CHEMBL2178919|114355-41-8|Nephilatoxin 8|DTXSID90921336|BDBM50399431|Butanediamide, N1-(5-((3-((4-((3-aminopropyl)amino)butyl)amino)-1-oxopropyl)amino)pentyl)-2-((1H-indol-3-ylacetyl)amino)-, (S)-|N~1~-(5-{[3-({4-[(3-Aminopropyl)amino]butyl}amino)-1-hydroxypropylidene]amino}pentyl)-2-{[1-hydroxy-2-(1H-indol-3-yl)ethylidene]amino}butanediimidic acid

Canonical SMILES:  NCCCNCCCCNCCC(=O)NCCCCCNC(=O)[C@H](CC(N)=O)NC(=O)Cc1c[nH]c2ccccc12

Standard InChI:  InChI=1S/C29H48N8O4/c30-12-8-15-32-13-6-7-14-33-18-11-27(39)34-16-4-1-5-17-35-29(41)25(20-26(31)38)37-28(40)19-22-21-36-24-10-3-2-9-23(22)24/h2-3,9-10,21,25,32-33,36H,1,4-8,11-20,30H2,(H2,31,38)(H,34,39)(H,35,41)(H,37,40)/t25-/m0/s1

Standard InChI Key:  ILUCYJIKJBTHOD-VWLOTQADSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2178919

   Nephilatoxin 8

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: 572.76

Molecular Weight (Monoisotopic): 572.3799

AlogP: 0.17

#Rotatable Bonds: 23

Polar Surface Area: 196.26

Molecular Species: BASE

HBA: 7

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.71

CX Basic pKa: 10.38

CX LogP: -1.59

CX LogD: -7.66

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.09

Np Likeness Score: -0.32

References

1. Lucas S, Poulsen MH, Nørager NG, Barslund AF, Bach TB, Kristensen AS, Strømgaard K..  (2012)  General synthesis of β-alanine-containing spider polyamine toxins and discovery of nephila polyamine toxins 1 and 8 as highly potent inhibitors of ionotropic glutamate receptors.,  55  (22): [PMID:23092360] [10.1021/jm301255m]

Source

Source(1):

• Scientific Literature