US9409931, 8

ID: ALA3926213

PubChem CID: 122463814

Max Phase: Preclinical

Molecular Formula: C27H38O6

Molecular Weight: 458.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C[C@@]23CC[C@@H]4[C@H]([C@H](C=C(CO)[C@@H](O)[C@]2(O)[C@H]1OC(=O)C1(C)CCCCC1)C3=O)C4(C)C

Standard InChI:  InChI=1S/C27H38O6/c1-15-13-26-11-8-18-19(24(18,2)3)17(21(26)30)12-16(14-28)20(29)27(26,32)22(15)33-23(31)25(4)9-6-5-7-10-25/h12-13,17-20,22,28-29,32H,5-11,14H2,1-4H3/t17-,18+,19-,20+,22-,26+,27-/m0/s1

Standard InChI Key:  TZUOGYWEVBTEEN-GEWCVNITSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  1  0  0  0  0  0999 V2000
   -4.7854    0.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6600    0.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3400    1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0800    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0100    2.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8100    3.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9800    2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5900    1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0400   -0.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0600   -1.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9600   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4174   -4.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5896   -4.2937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600   -2.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9723   -3.6552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6200   -1.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1880   -2.2771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2100   -1.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1832   -2.1598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6831   -3.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5033   -3.7940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6579   -4.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2578   -5.8474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1173   -3.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5922   -3.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5666   -4.1764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0662   -5.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5913   -5.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5900    0.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511    1.9313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    2.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4171    3.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3985    1.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  4  3  1  6
  4  5  1  0
  5  6  1  0
  7  6  1  1
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  1
 14 16  1  0
 16  4  1  0
 16 17  1  1
 16 18  1  0
 18  2  1  0
 18 19  1  1
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 22  1  0
  9 29  1  6
 29  4  1  0
 29 30  2  0
  8 31  1  1
 31  7  1  0
 31 32  1  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3926213

   ---

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: 458.60

Molecular Weight (Monoisotopic): 458.2668

AlogP: 3.09

#Rotatable Bonds: 3

Polar Surface Area: 104.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.14

CX Basic pKa: ┄

CX LogP: 3.12

CX LogD: 3.12

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.44

Np Likeness Score: 2.68

References

1.  (2016)  3-O-acyl-ingenol analogues, 

Source

Source(1):

• BindingDB Database