(S)-N1-((S)-1-((S)-1-(2-amino-2-oxoethyl)-2-oxoazepan-3-ylamino)-3-cyclohexyl-1-oxopropan-2-yl)-2-((S)-5-guanidino-2-((S)-5-guanidino-2-((S)-5-oxopyrrolidine-2-carboxamido)pentanamido)pentanamido)pentanediamide

ID: ALA5285705

Max Phase: Preclinical

Molecular Formula: C39H67N15O9

Molecular Weight: 890.06

Associated Items:

Bioactivity Summary Target Summary Assay Summary

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES: N=C(N)NCCC[C@H](NC(=O)[C@@H]1CCC(=O)N1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC1CCCCC1)C(=O)N[C@H]1CCCCN(CC(N)=O)C1=O

Standard InChI: InChI=1S/C39H67N15O9/c40-29(55)15-13-26(35(61)53-28(20-22-8-2-1-3-9-22)36(62)52-27-10-4-5-19-54(37(27)63)21-30(41)56)51-33(59)24(12-7-18-47-39(44)45)49-32(58)23(11-6-17-46-38(42)43)50-34(60)25-14-16-31(57)48-25/h22-28H,1-21H2,(H2,40,55)(H2,41,56)(H,48,57)(H,49,58)(H,50,60)(H,51,59)(H,52,62)(H,53,61)(H4,42,43,46)(H4,44,45,47)/t23-,24-,25-,26-,27-,28-/m0/s1

Standard InChI Key: WTSWCLJTDBQZOR-QUQVWLGBSA-N

Molfile:

 
     RDKit          2D

 63 65  0  0  0  0  0  0  0  0999 V2000
    2.0110   -5.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7499   -6.4697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7499   -5.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6035   -8.1186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6035   -8.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900   -9.3572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3210   -9.3572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4633   -5.2310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1766   -5.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900   -4.4065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900   -5.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1766   -6.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900   -6.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900   -7.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7479   -2.7577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7479   -1.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0345   -1.5190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4613   -1.5190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6035   -5.6453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3210   -5.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0345   -6.4697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0345   -5.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3210   -4.4065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0345   -3.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0345   -3.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7479   -5.2310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4613   -5.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1789   -4.4065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1789   -5.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4613   -6.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1789   -6.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1789   -7.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8922   -8.1186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4613   -8.1186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8922   -5.6453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6056   -5.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3191   -6.4697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3191   -5.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0325   -5.2310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7501   -5.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6057   -4.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3359   -3.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0679   -4.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7959   -3.9925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8003   -3.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0703   -2.7218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3318   -3.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8771   -4.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0604   -4.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6894   -5.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2754   -5.6499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1472   -5.2006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4289   -5.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2180   -5.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5194   -6.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6873   -6.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1076   -6.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2958   -7.0363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8994   -6.7856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0451   -7.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6228   -8.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3763   -9.2731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4468   -8.2734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  8  1  0
 11 19  1  0
 22 26  1  0
 29 35  1  0
 38 39  1  0
  1  3  1  1
  3  2  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  8  9  1  0
  9 11  1  0
 11 10  2  0
  9 12  1  6
 12 13  1  0
 13 14  1  0
 14  4  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 19 20  1  0
 20 22  1  0
 22 21  2  0
 20 23  1  1
 23 24  1  0
 24 25  1  0
 25 15  1  0
 26 27  1  0
 27 29  1  0
 29 28  2  0
 27 30  1  6
 30 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 35 36  1  0
 36 38  1  0
 38 37  2  0
 40 39  1  1
 36 41  1  1
 41 42  1  0
 42 43  1  0
 42 47  1  0
 43 44  1  0
 44 45  1  0
 45 46  1  0
 46 47  1  0
  1 48  1  0
 48 49  1  0
 49 50  1  0
 50 51  1  0
 51  1  1  0
 50 52  2  0
 40 53  1  0
 53 54  1  0
 54 55  1  0
 40 56  1  0
 55 57  1  0
 56 58  1  0
 57 58  1  0
 56 59  2  0
 58 60  1  0
 60 61  1  0
 61 62  1  0
 61 63  2  0
M  END

Natural Product: No	Oral: No	Chemical Probe: No	Parenteral: No
Molecule Type:	Topical: No	First In Class: No	Black Box: No
Chirality: No	Availability: No	Prodrug: No

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 890.06	Molecular Weight (Monoisotopic): 889.5246	AlogP: -4.05	#Rotatable Bonds: 25
Polar Surface Area: 404.89	Molecular Species: BASE	HBA: 11	HBD: 14
#RO5 Violations: 3	HBA (Lipinski): 24	HBD (Lipinski): 18	#RO5 Violations (Lipinski): 3
CX Acidic pKa: 10.98	CX Basic pKa: 11.80	CX LogP: -6.41	CX LogD: -10.44
Aromatic Rings: ┄	Heavy Atoms: 63	QED Weighted: 0.02	Np Likeness Score: -0.09

References

1. Brust A, Croker DE, Colless B, Ragnarsson L, Andersson Å, Jain K, Garcia-Caraballo S, Castro J, Brierley SM, Alewood PF, Lewis RJ.. (2016) Conopeptide-Derived κ-Opioid Agonists (Conorphins): Potent, Selective, and Metabolic Stable Dynorphin A Mimetics with Antinociceptive Properties., 59 (6): [PMID:26859603] [10.1021/acs.jmedchem.5b00911]

(S)-N1-((S)-1-((S)-1-(2-amino-2-oxoethyl)-2-oxoazepan-3-ylamino)-3-cyclohexyl-1-oxopropan-2-yl)-2-((S)-5-guanidino-2-((S)-5-guanidino-2-((S)-5-oxopyrrolidine-2-carboxamido)pentanamido)pentanamido)pentanediamide

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Calculated Properties

References

Source