(1S,3S,10R,11S,12S,16R)-11-Hydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-4-oxa-bicyclo[14.1.0]heptadecane-5,9-dione

ID: ALA194251

PubChem CID: 44403673

Max Phase: Preclinical

Molecular Formula: C28H43NO4S

Molecular Weight: 489.72

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C28H43NO4S/c1-17-9-8-11-28(7)15-21(28)14-23(18(2)13-22-16-34-20(4)29-22)33-24(30)10-12-27(5,6)26(32)19(3)25(17)31/h13,16-17,19,21,23,25,31H,8-12,14-15H2,1-7H3/b18-13+/t17-,19+,21+,23-,25-,28+/m0/s1

Standard InChI Key:  TXATZGFMRLDAFJ-QNXAMBSESA-N

Molfile:  

     RDKit          2D

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    5.0000    0.8583    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8500    0.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0042    2.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000    0.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250    0.5633    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 12  1  0
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 12 25  1  1
  1 26  1  1
  3 27  1  6
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  2  5  1  0
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  2 35  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA194251

   (1S,3S,10R,11S,12S,16R)-11-hydroxy-8,8,10,12,16-pentamethyl-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: 489.72

Molecular Weight (Monoisotopic): 489.2913

AlogP: 6.38

#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: 6.26

CX LogD: 6.26

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.49

Np Likeness Score: 1.71

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