N-[(S)-1-{3-[4-(3-Amino-propylamino)-butylamino]-propylcarbamoyl}-2-(4-hydroxy-phenyl)-ethyl]-butyramide

ID: ALA16117

Chembl Id: CHEMBL16117

Cas Number: 115976-93-7

PubChem CID: 159548

Max Phase: Preclinical

Molecular Formula: C23H41N5O3

Molecular Weight: 435.61

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Philanthotoxin-343 | Philanthotoxin 343|Philanthotoxin-343|115976-93-7|Phtx 343|CHEMBL16117|CHEBI:34920|PHILANTHOTOXIN 343 TRIS-TRIFLUOROACETATE|N-[(2S)-1-[3-[4-(3-aminopropylamino)butylamino]propylamino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]butanamide|PhTX-343|AC1Q5PFY|VS3BZ5F9WP|(S)-Philanthotoxin 343|PhTX-343 TFA|SCHEMBL8391460|DTXSID20921884|N-[1-{3-[4-(3-Amino-propylamino)-butylamino]-propylcarbamoyl}-2-(4-hydroxy-phenyl)-ethyl]-butyramide|BDBM50094298|AKOS040753555|Q27116321|(alphaS)-N-[3-Show More⌵

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

Standard InChI:  InChI=1S/C23H41N5O3/c1-2-7-22(30)28-21(18-19-8-10-20(29)11-9-19)23(31)27-17-6-16-26-14-4-3-13-25-15-5-12-24/h8-11,21,25-26,29H,2-7,12-18,24H2,1H3,(H,27,31)(H,28,30)/t21-/m0/s1

Standard InChI Key:  DTWANULJDRVTFI-NRFANRHFSA-N

Alternative Forms

1. Parent:

   

   ALA16117

   PHILANTHOTOXIN 343

2. Alternative Forms:

   

   ALA16117

   N-[(2S)-1-[3-[4-(3-aminopropylamino)butylamino]propylamino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]butanamide;hydrochloride

Molecule Features

Natural Product: Yes

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: 435.61

Molecular Weight (Monoisotopic): 435.3209

AlogP: 1.03

#Rotatable Bonds: 18

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: 9.41

CX Basic pKa: 10.76

CX LogP: -1.01

CX LogD: -5.97

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.19

Np Likeness Score: -0.04

References

1. Strømgaard K, Mellor IR, Andersen K, Neagoe I, Pluteanu F, Usherwood PN, Krogsgaard-Larsen P, Jaroszewski JW..  (2002)  Solid-phase synthesis and pharmacological evaluation of analogues of PhTX-12-A potent and selective nicotinic acetylcholine receptor antagonist.,  12  (8): [PMID:11934578] [10.1016/s0960-894x(02)00120-8]

2. Strømgaard K, Brier TJ, Andersen K, Mellor IR, Saghyan A, Tikhonov D, Usherwood PN, Krogsgaard-Larsen P, Jaroszewski JW..  (2000)  Solid-phase synthesis and biological evaluation of a combinatorial library of philanthotoxin analogues.,  43  (23): [PMID:11087577] [10.1021/jm000220n]

3. Jørgensen MR, Olsen CA, Mellor IR, Usherwood PN, Witt M, Franzyk H, Jaroszewski JW..  (2005)  The effects of conformational constraints and steric bulk in the amino acid moiety of philanthotoxins on AMPAR antagonism.,  48  (1): [PMID:15634001] [10.1021/jm049906w]

4. Fleming JJ, England PM..  (2010)  Developing a complete pharmacology for AMPA receptors: a perspective on subtype-selective ligands.,  18  (4): [PMID:20096591] [10.1016/j.bmc.2009.12.072]

5. Frølund S, Bella A, Kristensen AS, Ziegler HL, Witt M, Olsen CA, Strømgaard K, Franzyk H, Jaroszewski JW..  (2010)  Assessment of structurally diverse philanthotoxin analogues for inhibitory activity on ionotropic glutamate receptor subtypes: discovery of nanomolar, nonselective, and use-dependent antagonists.,  53  (20): [PMID:20873775] [10.1021/jm100886h]

6. Eldefrawi AT, Eldefrawi ME, Konno K, Mansour NA, Nakanishi K, Oltz E, Usherwood PN..  (1988)  Structure and synthesis of a potent glutamate receptor antagonist in wasp venom.,  85  (13): [PMID:2838850] [10.1073/pnas.85.13.4910]

7. 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