(1S,2S,5S,6R,7R,8R,9R,12R)-5,6,12-tris(acetyloxy)-8-(benzoyloxy)-2-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl benzoate

ID: ALA2287545

PubChem CID: 76309238

Max Phase: Preclinical

Molecular Formula: C34H38O12

Molecular Weight: 638.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@H]1CC[C@](C)(O)[C@]23OC(C)(C)[C@H]([C@@H](OC(=O)c4ccccc4)[C@@H](OC(=O)c4ccccc4)[C@]12OC(C)=O)[C@H]3OC(C)=O

Standard InChI:  InChI=1S/C34H38O12/c1-19(35)41-24-17-18-32(6,40)34-27(42-20(2)36)25(31(4,5)46-34)26(43-29(38)22-13-9-7-10-14-22)28(33(24,34)45-21(3)37)44-30(39)23-15-11-8-12-16-23/h7-16,24-28,40H,17-18H2,1-6H3/t24-,25+,26+,27+,28+,32-,33+,34-/m0/s1

Standard InChI Key:  POKBFFWANFAPGO-WTPDSDAWSA-N

Molfile:  

     RDKit          2D

 46 50  0  0  0  0  0  0  0  0999 V2000
   19.6040   -2.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6040   -3.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2920   -3.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2920   -2.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9842   -2.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9811   -3.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6663   -3.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3586   -3.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3618   -2.6548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6725   -2.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9777   -1.8475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9698   -4.2409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3546   -4.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4139   -5.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1425   -4.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6747   -1.4203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3919   -1.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3940   -0.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1069   -1.4242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6615   -4.6772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9430   -5.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9383   -5.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1372   -5.2995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1123    0.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1149    1.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3993    1.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6798    1.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6808    0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2917   -4.6729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0808   -2.2464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7595   -1.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4736   -0.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3418   -0.3257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2909   -1.4160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7938   -2.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5128   -2.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7879   -3.4919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2246   -2.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9432   -2.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9495   -1.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2313   -1.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5158   -1.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5743   -1.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5732   -0.1767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8587   -1.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5734   -4.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  5 11  1  6
  6 12  1  1
  8 13  1  1
 12 13  1  0
 13 14  1  0
 13 15  1  0
 10 16  1  6
 16 17  1  0
 17 18  1  0
 17 19  2  0
  7 20  1  1
 20 21  1  0
 21 22  1  0
 21 23  2  0
 18 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 18  1  0
  3 29  1  1
  9 30  1  6
 11 31  1  0
 31 32  1  0
 31 33  2  0
  4 34  1  6
 30 35  1  0
 35 36  1  0
 35 37  2  0
 36 38  2  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 36  1  0
 34 43  1  0
 43 44  2  0
 43 45  1  0
  3 46  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2287545

   [(1S,2S,5S,6R,7R,8R,9R,12R)-5,6,12-triacetyloxy-7-benzoyloxy-2-hydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.01,6]dodecan-8-yl] benzoate

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: 638.67

Molecular Weight (Monoisotopic): 638.2363

AlogP: 3.33

#Rotatable Bonds: 7

Polar Surface Area: 160.96

Molecular Species: NEUTRAL

HBA: 12

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.68

CX Basic pKa: ┄

CX LogP: 3.66

CX LogD: 3.66

Aromatic Rings: 2

Heavy Atoms: 46

QED Weighted: 0.35

Np Likeness Score: 1.81

References

1. Gonzalez AG, Jimenez IA, Ravelo AG, Coll J, Gonzalez JA, Lloria J.  (1997)  Antifeedant activity of sesquiterpenes from celastraceae,  25  (6): [10.1016/S0305-1978(97)00035-5]

Source

Source(1):

• Scientific Literature