(2S,4S,10R,11S,17S)-11-(R)-Hydroxy-8,8,10,12-tetramethyl-3-[1-methyl-2-(2-methylsulfanyl-thiazol-4-yl)-vinyl]-4-oxa-bicyclo[14.1.0]heptadecane-5,9-dione

ID: ALA196234

PubChem CID: 44403678

Max Phase: Preclinical

Molecular Formula: C27H41NO4S2

Molecular Weight: 507.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1nc(/C=C(\C)[C@@H]2C[C@@H]3C[C@H]3CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)CCC(=O)O2)cs1

Standard InChI:  InChI=1S/C27H41NO4S2/c1-16-8-7-9-19-13-20(19)14-22(17(2)12-21-15-34-26(28-21)33-6)32-23(29)10-11-27(4,5)25(31)18(3)24(16)30/h12,15-16,18-20,22,24,30H,7-11,13-14H2,1-6H3/b17-12+/t16-,18+,19+,20-,22-,24-/m0/s1

Standard InChI Key:  GKSHPMYFCJFEOO-PARXPCEFSA-N

Molfile:  

     RDKit          2D

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    1.8500    0.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3542    0.2708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7917    0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7000    2.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5542    0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917    1.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4042   -0.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4125    0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2750    1.6000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.8417    0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1250    0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417    1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -0.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6917    0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7000   -1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2750    0.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6167    1.0125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625    1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875   -0.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292    1.7208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917    2.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1250    1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792    2.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625    2.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2750    1.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0750    0.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4882    2.5764    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000    1.3050    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 14  1  0
  3  7  1  0
  4 15  1  0
  5  3  2  0
  1  6  1  0
  7 12  1  0
  8  1  1  0
  9 10  1  0
 10 16  1  0
 11 18  1  0
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 10 13  1  1
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 16  1  1  0
 17  9  1  0
 18  7  2  0
 19  4  2  0
 20 17  2  0
 21 24  1  0
 22  5  1  0
 23 32  1  0
 24 17  1  0
 14 25  1  1
  2 26  1  6
 27  8  1  0
 28 13  1  0
 15 29  1  0
 15 30  1  0
 31 27  1  0
 32 31  1  0
 23 33  1  6
 34 22  1  0
  8  6  1  0
 11  5  1  0
  4  2  1  0
  8 35  1  1
  1 36  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA196234

   (1S,3S,10R,11S,12S,16R)-11-hydroxy-8,8,10,12-tetramethyl-3-[(E)-1-(2-methylsulfanyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4-oxabicyclo[14.1.0]heptadecane-5,9-dione

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: 507.76

Molecular Weight (Monoisotopic): 507.2477

AlogP: 6.40

#Rotatable Bonds: 3

Polar Surface Area: 76.49

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 0.85

CX LogP: 7.14

CX LogD: 7.14

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.38

Np Likeness Score: 1.34

References

1. Nicolaou KC..  (2005)  Joys of molecules. 2. Endeavors in chemical biology and medicinal chemistry.,  48  (18): [PMID:16134928] [10.1021/jm050524f]

2. Nicolaou KC..  (2005)  Joys of molecules. 2. Endeavors in chemical biology and medicinal chemistry.,  48  (18): [PMID:16134928] [10.1021/jm050524f]

Source

Source(1):

• Scientific Literature