7,11-dihydroxy-8,8,10,12,15a-pentamethyl-3-[1-methyl-2-(2-pyridyl)-(E)-1-ethenyl]perhydrooxireno[2,3-d]oxacyclohexadecine-5,9-dione

ID: ALA94599

PubChem CID: 11454608

Max Phase: Preclinical

Molecular Formula: C28H41NO6

Molecular Weight: 487.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=C\c1ccccn1)[C@@H]1C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1

Standard InChI:  InChI=1S/C28H41NO6/c1-17-10-9-12-28(6)23(35-28)15-21(18(2)14-20-11-7-8-13-29-20)34-24(31)16-22(30)27(4,5)26(33)19(3)25(17)32/h7-8,11,13-14,17,19,21-23,25,30,32H,9-10,12,15-16H2,1-6H3/b18-14+/t17-,19+,21-,22-,23-,25-,28+/m0/s1

Standard InChI Key:  SIBRPCAZMYQWFA-NJSQBWDTSA-N

Molfile:  

     RDKit          2D

 36 38  0  0  1  0  0  0  0  0999 V2000
    5.1250   -0.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -3.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4125   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5542   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -4.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7042   -2.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1250   -4.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9917   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -2.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -4.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -3.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5542   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4250   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9792   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4250   -1.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7000   -0.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -1.4192    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  6  1  0
  5 10  1  0
  6 14  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
 10 12  1  0
 11  3  1  0
 12  7  1  0
  9 13  1  1
 14 20  1  0
 15 13  2  0
 16  4  2  0
 17 19  2  0
 18  7  2  0
 19 15  1  0
 20 31  1  0
 21  2  1  0
 14 22  1  1
 10 23  1  6
  2 24  1  6
  5 25  1  0
  5 26  1  0
  6 27  1  6
 28 13  1  0
 29 21  1  0
 30 17  1  0
 31 29  1  0
 20 32  1  6
 33 19  1  0
 34 35  1  0
 35 33  2  0
  2  3  1  0
  5  4  1  0
 30 34  2  0
  3 36  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA94599

   (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-pyridin-2-ylprop-1-en-2-yl]-4,17-dioxabicyclo[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: 487.64

Molecular Weight (Monoisotopic): 487.2934

AlogP: 4.11

#Rotatable Bonds: 2

Polar Surface Area: 109.25

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.64

CX LogP: 4.12

CX LogD: 4.12

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.48

Np Likeness Score: 2.13

References

1. Altmann KH, Bold G, Caravatti G, Flörsheimer A, Guagnano V, Wartmann M..  (2000)  Synthesis and biological evaluation of highly potent analogues of epothilones B and D.,  10  (24): [PMID:11133086] [10.1016/s0960-894x(00)00555-2]

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

3. 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