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

ID: ALA196586

PubChem CID: 44403672

Max Phase: Preclinical

Molecular Formula: C27H41NO4S

Molecular Weight: 475.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=C\c1csc(C)n1)[C@@H]1C[C@@H]2C[C@H]2CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)CCC(=O)O1

Standard InChI:  InChI=1S/C27H41NO4S/c1-16-8-7-9-20-13-21(20)14-23(17(2)12-22-15-33-19(4)28-22)32-24(29)10-11-27(5,6)26(31)18(3)25(16)30/h12,15-16,18,20-21,23,25,30H,7-11,13-14H2,1-6H3/b17-12+/t16-,18+,20+,21-,23-,25-/m0/s1

Standard InChI Key:  NOXUROOVJQOVMX-NCNOSHIYSA-N

Molfile:  

     RDKit          2D

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    3.6417   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1417   -1.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917    0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3417   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2000   -2.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2042   -1.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6292   -1.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5792   -0.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0667    0.2875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7792   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167    0.4083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9250   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7792    1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167   -0.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4125   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542    1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -0.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2768    1.2632    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -0.0100    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  0
  3 15  1  0
  4  6  1  0
  1  5  1  0
  6 10  1  0
  7  1  1  0
  8  9  1  0
  9 16  1  0
 10 11  2  0
  9 11  1  1
 12 22  1  0
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 15 21  1  0
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 17  8  1  0
 18  6  2  0
 19  3  2  0
 20 17  2  0
 21 23  1  0
 22 32  1  0
 23 17  1  0
 12 24  1  1
  2 25  1  6
 26  7  1  0
 27 11  1  0
 15 28  1  0
 15 29  1  0
 30 13  1  0
 31 26  1  0
 32 31  1  0
 22 33  1  6
  7  5  1  0
 14 13  1  0
  3  2  1  0
  7 34  1  1
  1 35  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA196586

   (1S,3S,10R,11S,12S,16R)-11-hydroxy-8,8,10,12-tetramethyl-3-[(E)-1-(2-methyl-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: 475.70

Molecular Weight (Monoisotopic): 475.2756

AlogP: 5.99

#Rotatable Bonds: 2

Polar Surface Area: 76.49

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.73

CX LogP: 5.96

CX LogD: 5.96

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.53

Np Likeness Score: 1.60

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