US9409931, 7

ID: ALA4113544

PubChem CID: 137662337

Max Phase: Preclinical

Molecular Formula: C28H40O5

Molecular Weight: 456.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=CC23C(=O)[C@@H](C=C(CO)[C@@H](O)[C@@H]2[C@H]1OC(=O)C1(C)CCCCC1)[C@H]1[C@@H](C[C@H]3C)C1(C)C

Standard InChI:  InChI=1S/C28H40O5/c1-15-13-28-16(2)11-19-20(26(19,3)4)18(24(28)31)12-17(14-29)22(30)21(28)23(15)33-25(32)27(5)9-7-6-8-10-27/h12-13,16,18-23,29-30H,6-11,14H2,1-5H3/t16-,18+,19-,20+,21-,22-,23+,28?/m1/s1

Standard InChI Key:  HFUSJJDLIQRQNC-DVDZDSMTSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  1  0  0  0  0  0999 V2000
   -2.0255    2.9094    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
   -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
   -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
    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
   -4.7854    0.8765    0.0000 C   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
  2  1  1  6
  2  3  1  0
  4  3  1  1
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  1
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 18  1  0
 14 25  1  0
 25 26  2  0
 26 27  1  0
 27  2  1  0
 13 27  1  6
 27 28  1  0
  6 28  1  6
 28 29  2  0
 25 30  1  0
  5 31  1  1
 31  4  1  0
 31 32  1  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4113544

   ---

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: 456.62

Molecular Weight (Monoisotopic): 456.2876

AlogP: 4.22

#Rotatable Bonds: 3

Polar Surface Area: 83.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.06

CX LogD: 4.06

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.49

Np Likeness Score: 2.24

References

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

Source

Source(1):

• BindingDB Database