(1S,4S,5S,6R,9S,10R,12R,14R)-4-(benzyloxy)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-15-one

ID: ALA3105088

PubChem CID: 76331997

Max Phase: Preclinical

Molecular Formula: C27H34O5

Molecular Weight: 438.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C[C@]23C(=O)[C@@H](C=C(CO)[C@@H](O)[C@]2(O)[C@H]1OCc1ccccc1)[C@H]1[C@@H](C[C@H]3C)C1(C)C

Standard InChI:  InChI=1S/C27H34O5/c1-15-12-26-16(2)10-20-21(25(20,3)4)19(23(26)30)11-18(13-28)22(29)27(26,31)24(15)32-14-17-8-6-5-7-9-17/h5-9,11-12,16,19-22,24,28-29,31H,10,13-14H2,1-4H3/t16-,19+,20-,21+,22-,24+,26+,27+/m1/s1

Standard InChI Key:  BKWJKDPWUAXVGB-WSHSHGDFSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
   11.2457   -2.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2886   -1.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6629   -2.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9621   -0.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2118   -3.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9667   -3.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5929   -3.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8120   -4.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5003   -2.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0190   -3.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4446   -3.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8922   -2.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7497   -1.4676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2196   -3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1680   -4.4608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0383   -4.2814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5979   -4.7971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0675   -4.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8660   -4.4496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5729   -0.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7289   -1.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0366   -1.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5230   -1.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7212   -0.2130    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5989   -2.3245    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7240   -0.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2963   -1.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3572   -2.8545    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3621   -4.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0767   -5.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2700   -5.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9845   -6.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5051   -6.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3147   -6.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5965   -5.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
 22  3  1  0
 21  4  1  0
  2  4  1  0
  5  1  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  5  8  1  0
  9 10  2  0
 10 11  1  0
  5 11  1  0
  1  9  1  6
  3 12  1  0
  1 12  1  0
 12 13  2  0
 10 14  1  0
 11 15  1  1
  5 16  1  1
  8 17  1  1
  7 18  1  0
 18 19  1  0
  2 20  1  6
 22 21  1  0
 23 22  1  0
 21 23  1  0
 21 24  1  6
 22 25  1  6
 23 26  1  0
 23 27  1  0
  3 28  1  1
 15 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3105088

   (1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-4-phenylmethoxytetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-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: 438.56

Molecular Weight (Monoisotopic): 438.2406

AlogP: 3.04

#Rotatable Bonds: 4

Polar Surface Area: 86.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.16

CX Basic pKa: ┄

CX LogP: 2.66

CX LogD: 2.66

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.63

Np Likeness Score: 2.70

References

1. Grue-Sørensen G, Liang X, Månsson K, Vedsø P, Dahl Sørensen M, Soor A, Stahlhut M, Bertelsen M, Engell KM, Högberg T..  (2014)  Synthesis, biological evaluation and SAR of 3-benzoates of ingenol for treatment of actinic keratosis and non-melanoma skin cancer.,  24  (1): [PMID:24332494] [10.1016/j.bmcl.2013.11.073]

Source

Source(1):

• Scientific Literature