Robotnikinin

ID: ALA473392

Cas Number: 1132653-79-2

PubChem CID: 25109985

Product Number: R346308, Order Now?

Max Phase: Preclinical

Molecular Formula: C25H27ClN2O4

Molecular Weight: 454.95

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Robotnikinin | Robotnikinin|1132653-79-2|CHEMBL473392|N-[(4-Chlorophenyl)methyl]-2-[(2R,6S,8E)-5,12-dioxo-2- phenyl-1-oxa-4-azacyclododec-8-en-6-yl]acetamide|N-(4-chlorobenzyl)-2-((2R,6S,E)-5,12-dioxo-2-phenyl-1-oxa-4-azacyclododec-8-en-6-yl)acetamide|N-[(4-chlorophenyl)methyl]-2-[(2R,6S,8E)-5,12-dioxo-2-phenyl-1-oxa-4-azacyclododec-8-en-6-yl]acetamide|SCHEMBL2187337|SCHEMBL2187345|DRDSZZCLAHXSAE-BQIDRLATSA-N|BDBM50249181|AKOS040747411|HY-100515|CS-0019654|BRD-K65111630-001-02-6|N-(4-chlorobenzyShow More⌵

Canonical SMILES:  O=C(C[C@@H]1C/C=C/CCC(=O)O[C@H](c2ccccc2)CNC1=O)NCc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C25H27ClN2O4/c26-21-13-11-18(12-14-21)16-27-23(29)15-20-9-5-2-6-10-24(30)32-22(17-28-25(20)31)19-7-3-1-4-8-19/h1-5,7-8,11-14,20,22H,6,9-10,15-17H2,(H,27,29)(H,28,31)/b5-2+/t20-,22-/m0/s1

Standard InChI Key:  DRDSZZCLAHXSAE-BQIDRLATSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -3.0812    0.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0842   -0.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3732   -0.5084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3718    1.1435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9303    1.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6473    2.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3712    1.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9373    1.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9654   -1.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0839    2.3873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6691   -0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9533   -0.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287   -0.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2249    0.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6650    0.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2570   -1.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2691   -2.5960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4634   -1.3691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -3.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4271   -3.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2948   -4.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072   -5.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4017   -5.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1245   -5.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1334   -4.2597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3906   -6.3138    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7952    1.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7910    1.9679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5041    2.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2200    1.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2183    1.1400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5045    0.7305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 16  1  0
  3 11  1  0
 16 17  1  0
 16 18  2  0
 12  9  1  1
 17 19  1  0
  1  2  1  0
 19 20  1  0
  7 10  2  0
 20 21  2  0
  1  4  1  0
 21 22  1  0
  2  3  1  0
 22 23  2  0
 11 12  1  0
 23 24  1  0
  4  7  1  0
 24 25  2  0
 25 20  1  0
 12 13  1  0
 23 26  1  0
  8  5  1  0
  1 27  1  1
 13 14  1  0
 27 28  2  0
 14  8  2  0
 28 29  1  0
  5  6  1  0
 29 30  2  0
 11 15  2  0
 30 31  1  0
  6  7  1  0
 31 32  2  0
 32 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA473392

   Robotnikinin

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: 454.95

Molecular Weight (Monoisotopic): 454.1659

AlogP: 4.10

#Rotatable Bonds: 5

Polar Surface Area: 84.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.61

CX LogD: 3.61

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.53

Np Likeness Score: 0.27

References

1. Mahindroo N, Punchihewa C, Fujii N..  (2009)  Hedgehog-Gli signaling pathway inhibitors as anticancer agents.,  52  (13): [PMID:19309080] [10.1021/jm801420y]

2. Peng LF, Stanton BZ, Maloof N, Wang X, Schreiber SL..  (2009)  Syntheses of aminoalcohol-derived macrocycles leading to a small-molecule binder to and inhibitor of Sonic Hedgehog.,  19  (22): [PMID:19819139] [10.1016/j.bmcl.2009.09.089]

3. Stanton BZ, Peng LF, Maloof N, Nakai K, Wang X, Duffner JL, Taveras KM, Hyman JM, Lee SW, Koehler AN, Chen JK, Fox JL, Mandinova A, Schreiber SL..  (2009)  A small molecule that binds Hedgehog and blocks its signaling in human cells.,  5  (3): [PMID:19151731] [10.1038/nchembio.142]

4. Heretsch P, Tzagkaroulaki L, Giannis A..  (2010)  Modulators of the hedgehog signaling pathway.,  18  (18): [PMID:20708941] [10.1016/j.bmc.2010.07.038]

5. Dockendorff C, Nagiec MM, Weïwer M, Buhrlage S, Ting A, Nag PP, Germain A, Kim HJ, Youngsaye W, Scherer C, Bennion M, Xue L, Stanton BZ, Lewis TA, Macpherson L, Palmer M, Foley MA, Perez JR, Schreiber SL..  (2012)  Macrocyclic Hedgehog Pathway Inhibitors: Optimization of Cellular Activity and Mode of Action Studies.,  3  (10): [PMID:23074541] [10.1021/ml300172p]

6. Marsault E, Peterson ML..  (2011)  Macrocycles are great cycles: applications, opportunities, and challenges of synthetic macrocycles in drug discovery.,  54  (7): [PMID:21381769] [10.1021/jm1012374]

7. Galperin I, Dempwolff L, Diederich WE, Lauth M..  (2019)  Inhibiting Hedgehog: An Update on Pharmacological Compounds and Targeting Strategies.,  62  (18): [PMID:30986059] [10.1021/acs.jmedchem.9b00188]

Source

Source(1):

• Scientific Literature