(3E,5E,11Z,16Z)-(7R,8S,10S,13S,14R,15S,20R,21S,22S)-8,10,14,20-tetrahydroxy-7,13,15,21-tetramethyl-22-((Z)-(S)-1-methyl-penta-2,4-dienyl)-oxacyclodocosa-3,5,11,16-tetraen-2-one

ID: ALA226985

PubChem CID: 16733270

Max Phase: Preclinical

Molecular Formula: C31H48O6

Molecular Weight: 516.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C/C=C\[C@H](C)[C@@H]1OC(=O)/C=C/C=C/[C@@H](C)[C@@H](O)C[C@H](O)/C=C\[C@H](C)[C@H](O)[C@@H](C)/C=C\CC[C@@H](O)[C@@H]1C

Standard InChI:  InChI=1S/C31H48O6/c1-7-8-13-24(5)31-25(6)27(33)16-11-9-15-22(3)30(36)23(4)18-19-26(32)20-28(34)21(2)14-10-12-17-29(35)37-31/h7-10,12-15,17-19,21-28,30-34,36H,1,11,16,20H2,2-6H3/b13-8-,14-10+,15-9-,17-12+,19-18-/t21-,22+,23+,24+,25+,26-,27-,28+,30-,31+/m1/s1

Standard InChI Key:  LJOAUXMVKKHPHN-LZCRJBGISA-N

Molfile:  

     RDKit          2D

 38 38  0  0  1  0  0  0  0  0999 V2000
    5.6500  -15.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6500  -16.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3620  -17.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0740  -16.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0740  -15.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3620  -15.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3620  -14.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0765  -14.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0765  -13.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7910  -13.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5054  -13.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2199  -13.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9344  -13.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6488  -13.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9344  -14.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2199  -14.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6488  -14.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3633  -14.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3633  -13.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0778  -13.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7923  -13.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5067  -13.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0778  -14.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6488  -15.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7873  -17.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5030  -16.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3620  -18.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7849  -18.0187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2162  -17.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5054  -15.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9319  -16.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6452  -17.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0250  -16.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7125  -16.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3958  -16.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7910  -14.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6475  -14.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5148  -15.2125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
  9 10  2  0
 19 20  2  0
  3  4  1  0
 20 21  1  0
 10 11  1  0
 21 22  2  0
  6  5  1  1
 18 23  1  6
 11 12  1  0
 17 24  1  0
  4 25  1  0
 12 13  1  0
 25 26  1  0
  6  7  1  0
  3 27  1  6
 13 14  1  1
 25 28  1  1
  1  2  2  0
 26 29  1  0
 13 15  1  0
 26 30  1  6
  7  8  1  0
 29 31  2  0
 15 16  1  1
 31 32  1  0
  1  6  1  0
 32 33  2  0
 15 17  1  0
 33 34  1  0
  8  9  1  0
 34 35  2  0
 34 24  1  0
 17 18  1  0
  8 36  1  6
  2  3  1  0
  7 37  1  6
 17 38  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA226985

   (3E,5E,7R,8S,10S,11Z,13S,14R,15S,16Z,20R,21S,22S)-22-[(2S,3Z)-hexa-3,5-dien-2-yl]-8,10,14,20-tetrahydroxy-7,13,15,21-tetramethyl-1-oxacyclodocosa-3,5,11,16-tetraen-2-one

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: 516.72

Molecular Weight (Monoisotopic): 516.3451

AlogP: 4.67

#Rotatable Bonds: 3

Polar Surface Area: 107.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.86

CX LogD: 4.86

Aromatic Rings: ┄

Heavy Atoms: 37

QED Weighted: 0.25

Np Likeness Score: 2.54

References

1. Jung WH, Harrison C, Shin Y, Fournier JH, Balachandran R, Raccor BS, Sikorski RP, Vogt A, Curran DP, Day BW..  (2007)  Total synthesis and biological evaluation of C16 analogs of (-)-dictyostatin.,  50  (13): [PMID:17542572] [10.1021/jm061385k]

Source

Source(1):

• Scientific Literature