2-((3S,6S,12S,E)-12-amino-3-methyl-5,13-dioxo-1-oxo-4-azacyclotridec-8-en-6-yl)-N-benzyl-N-(2-hydroxyethyl)acetamide

ID: ALA1213326

Cas Number: 1132653-86-1

PubChem CID: 25109984

Max Phase: Preclinical

Molecular Formula: C23H33N3O5

Molecular Weight: 431.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1COC(=O)[C@@H](N)CC/C=C/C[C@@H](CC(=O)N(CCO)Cc2ccccc2)C(=O)N1

Standard InChI:  InChI=1S/C23H33N3O5/c1-17-16-31-23(30)20(24)11-7-3-6-10-19(22(29)25-17)14-21(28)26(12-13-27)15-18-8-4-2-5-9-18/h2-6,8-9,17,19-20,27H,7,10-16,24H2,1H3,(H,25,29)/b6-3+/t17-,19-,20-/m0/s1

Standard InChI Key:  VFEYLGADIZPNOZ-RTLQKPCFSA-N

Molfile:  

     RDKit          2D

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   -1.9083   -2.3750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4833   -3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833   -2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958   -1.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9458   -3.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9458   -4.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6250    0.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9458   -5.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4833   -4.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083   -4.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3125    0.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833    0.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958   -4.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3375   -2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292   -6.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583   -6.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625   -6.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292   -6.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9458   -7.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  7  1  0
  4  5  1  0
  5 17  1  0
  6  3  1  0
  8  7  1  1
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  9  1  2  0
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 15 20  1  0
 16 15  2  0
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 13 18  1  1
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 27 19  2  0
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 24 13  1  0
 31 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1213326

   2-((3S,6S,12S,E)-12-Amino-3-methyl-5,13-dioxo-1-oxa-4-azacyclotridec-8-en-6-yl)-N-benzyl-N-(2-hydroxyethyl)acetamide

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: 431.53

Molecular Weight (Monoisotopic): 431.2420

AlogP: 1.13

#Rotatable Bonds: 6

Polar Surface Area: 121.96

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.39

CX LogP: 0.63

CX LogD: 0.34

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.46

Np Likeness Score: 0.18

References

1. 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]

2. 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]

Source

Source(1):

• Scientific Literature