(S)-2-((R)-2-((R)-2-acetamido-3-(4-hydroxyphenyl)propanamido)-3-(1H-indol-3-yl)propanamido)-N1-((8S,11S,17S,20S,21R)-8-((S)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-ylcarbamoyl)-17-benzyl-21-hydroxy-3-imino-11-isobutyl-10,13,16,19-tetraoxo-2,4,9,12,14,15,18-heptaazadocosan-20-yl)succinamide

ID: ALA3314224

Chembl Id: CHEMBL3314224

PubChem CID: 49787129

Max Phase: Preclinical

Molecular Formula: C64H83N17O13

Molecular Weight: 1298.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=N)NCCC[C@H](NC(=O)[C@H](CC(C)C)NC(=O)NNC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)[C@@H](Cc1ccc(O)cc1)NC(C)=O)[C@@H](C)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(N)=O

Standard InChI:  InChI=1S/C64H83N17O13/c1-34(2)26-48(57(88)73-46(20-13-25-69-63(67)68-5)56(87)74-47(55(66)86)29-39-32-70-44-18-11-9-16-42(39)44)78-64(94)81-80-61(92)50(27-37-14-7-6-8-15-37)77-62(93)54(35(3)82)79-60(91)52(31-53(65)85)76-59(90)51(30-40-33-71-45-19-12-10-17-43(40)45)75-58(89)49(72-36(4)83)28-38-21-23-41(84)24-22-38/h6-12,14-19,21-24,32-35,46-52,54,70-71,82,84H,13,20,25-31H2,1-5H3,(H2,65,85)(H2,66,86)(H,72,83)(H,73,88)(H,74,87)(H,75,89)(H,76,90)(H,77,93)(H,79,91)(H,80,92)(H3,67,68,69)(H2,78,81,94)/t35-,46+,47+,48+,49-,50+,51-,52+,54+/m1/s1

Standard InChI Key:  BDPDXFSIFWZPCE-PHOVXGMNSA-N

Alternative Forms

1. Parent:

   

   ALA3314224

   (2S)-2-[[(2R)-2-[[(2R)-2-acetamido-3-(4-hydroxyphenyl)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2S,3R)-1-[[(2S)-1-[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-5-[(N'-methylcarbamimidoyl)amino]-1-oxopentan-2-yl

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: 1298.47

Molecular Weight (Monoisotopic): 1297.6356

AlogP: ┄

#Rotatable Bonds: ┄

Polar Surface Area: ┄

Molecular Species: ┄

HBA: ┄

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): ┄

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: ┄

CX LogD: ┄

Aromatic Rings: ┄

Heavy Atoms: ┄

QED Weighted: ┄

Np Likeness Score: ┄

References

1. Asami T, Nishizawa N, Matsui H, Takatsu Y, Suzuki A, Kiba A, Terada M, Nishibori K, Nakayama M, Ban J, Matsumoto S, Tarui N, Ikeda Y, Yamaguchi M, Kusaka M, Ohtaki T, Kitada C..  (2014)  Physicochemically and pharmacokinetically stable nonapeptide KISS1 receptor agonists with highly potent testosterone-suppressive activity.,  57  (14): [PMID:24918545] [10.1021/jm5005489]

2. Nishizawa N, Takatsu Y, Kumano S, Kiba A, Ban J, Tsutsumi S, Matsui H, Matsumoto SI, Yamaguchi M, Ikeda Y, Kusaka M, Ohtaki T, Itoh F, Asami T..  (2016)  Design and Synthesis of an Investigational Nonapeptide KISS1 Receptor (KISS1R) Agonist, Ac-d-Tyr-Hydroxyproline (Hyp)-Asn-Thr-Phe-azaGly-Leu-Arg(Me)-Trp-NH2 (TAK-448), with Highly Potent Testosterone-Suppressive Activity and Excellent Water Solubility.,  59  (19): [PMID:27589480] [10.1021/acs.jmedchem.6b00379]

Source

Source(1):

• Scientific Literature