(3S,7S,10R,11S,12S,17S)-7,11-Dihydroxy-8,8,10,12-tetramethyl-3-[(E)-1-methyl-2-((S)-2-methyl-thiazol-4-yl)-vinyl]-4-oxa-bicyclo[14.1.0]heptadecane-5,9-dione

ID: ALA194867

PubChem CID: 9957284

Max Phase: Preclinical

Molecular Formula: C27H41NO5S

Molecular Weight: 491.69

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)[C@@H](O)CC(=O)O1

Standard InChI:  InChI=1S/C27H41NO5S/c1-15-8-7-9-19-11-20(19)12-22(16(2)10-21-14-34-18(4)28-21)33-24(30)13-23(29)27(5,6)26(32)17(3)25(15)31/h10,14-15,17,19-20,22-23,25,29,31H,7-9,11-13H2,1-6H3/b16-10+/t15-,17+,19-,20-,22-,23-,25-/m0/s1

Standard InChI Key:  VRYGQKIVLMBMGY-CDGZLMSPSA-N

Molfile:  

     RDKit          2D

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    0.7167   -3.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5875   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5667   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0625   -0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7125   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2292    0.7333    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417   -0.2716    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  9  1  0
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  9 29  1  0
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 16 24  1  1
 11 25  1  6
  2 26  1  0
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  3 28  1  6
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 23 34  1  6
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 17 18  1  0
  9 35  1  6
  4 36  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA194867

   (1S,3S,7S,10R,11S,12S,16S)-7,11-dihydroxy-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: 491.69

Molecular Weight (Monoisotopic): 491.2705

AlogP: 4.96

#Rotatable Bonds: 2

Polar Surface Area: 96.72

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.73

CX LogP: 4.88

CX LogD: 4.88

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.57

Np Likeness Score: 1.80

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