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

ID: ALA435745

PubChem CID: 44403681

Max Phase: Preclinical

Molecular Formula: C29H43NO4

Molecular Weight: 469.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=C\c1ccc(C)cn1)[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/C29H43NO4/c1-18-10-11-24(30-17-18)14-20(3)25-16-23-15-22(23)9-7-8-19(2)27(32)21(4)28(33)29(5,6)13-12-26(31)34-25/h10-11,14,17,19,21-23,25,27,32H,7-9,12-13,15-16H2,1-6H3/b20-14+/t19-,21+,22+,23-,25-,27-/m0/s1

Standard InChI Key:  AKHKGBPWZBYJEX-PQWBVYKKSA-N

Molfile:  

     RDKit          2D

 36 38  0  0  1  0  0  0  0  0999 V2000
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    2.5750   -3.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2875   -3.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4250   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1292   -4.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1375   -3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8500   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5667   -3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -4.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4250   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9875   -3.8417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000   -3.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2792   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167   -5.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7042   -3.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542   -2.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7042   -2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542   -3.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2750   -2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9875   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8500   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -5.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542   -4.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0042   -0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2875   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4167   -2.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2151   -1.3247    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4250   -2.5992    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  1  0
  3 11  1  0
  1  4  1  0
  5  1  1  0
  6  7  1  0
  7 12  1  0
  7  8  1  1
  9 19  1  0
 10  8  2  0
 11 18  1  0
 12  1  1  0
 13  6  1  0
 14 16  2  0
 15  3  2  0
 16 10  1  0
 17 13  2  0
 18 20  1  0
 19 32  1  0
 20 13  1  0
 21 14  1  0
  9 22  1  1
 23 27  1  0
  2 24  1  6
 25 16  1  0
 26  5  1  0
 27 25  2  0
 28  8  1  0
 11 29  1  0
 11 30  1  0
 31 26  1  0
 32 31  1  0
 19 33  1  6
 34 23  1  0
  5  4  1  0
 23 21  2  0
  3  2  1  0
  5 35  1  1
  1 36  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA435745

   (1S,3S,10R,11S,12S,16R)-11-hydroxy-8,8,10,12-tetramethyl-3-[(E)-1-(5-methylpyridin-2-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: 469.67

Molecular Weight (Monoisotopic): 469.3192

AlogP: 5.92

#Rotatable Bonds: 2

Polar Surface Area: 76.49

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.05

CX LogP: 6.47

CX LogD: 6.47

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.54

Np Likeness Score: 1.49

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