(1R,3S,4R,7Z,11S,12S)-3-acetoxydolabella-7,18-dien-4,17-olide

ID: ALA2269164

PubChem CID: 76308653

Max Phase: Preclinical

Molecular Formula: C22H32O4

Molecular Weight: 360.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)[C@H]1CC[C@]2(C)C[C@H](OC(C)=O)[C@]3(C)CCC=C(CC[C@@H]12)C(=O)O3

Standard InChI:  InChI=1S/C22H32O4/c1-14(2)17-10-12-21(4)13-19(25-15(3)23)22(5)11-6-7-16(20(24)26-22)8-9-18(17)21/h7,17-19H,1,6,8-13H2,2-5H3/t17-,18+,19+,21-,22+/m1/s1

Standard InChI Key:  RHCIMJQERPEMOQ-SBOYYNGUSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   11.2435   -9.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9258   -8.8073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6863   -8.8059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9753  -10.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7325  -10.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5625  -10.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9549   -9.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3359   -8.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3957   -7.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6310   -7.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2638   -8.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4843   -8.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2931   -9.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9895   -9.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4142   -9.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8228   -7.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1640   -8.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0077   -9.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1905   -9.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4184  -10.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6936   -7.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3061   -6.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9344   -7.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7930   -6.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4681   -5.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6049   -6.3997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 14  4  1  0
  7  8  1  0
 15 13  1  0
 12 16  1  0
 16 17  1  0
 17 15  1  0
 15 18  1  1
 18 19  1  0
 18 20  2  0
 12 21  1  1
 10 22  1  6
  5  1  1  0
  2  9  1  0
  9 23  1  1
 22 24  1  0
 24 25  1  0
 24 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2269164

   [(1S,2S,4R,7S,8S)-1,4-dimethyl-16-oxo-7-prop-1-en-2-yl-15-oxatricyclo[9.3.2.04,8]hexadec-11-en-2-yl] acetate

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: 360.49

Molecular Weight (Monoisotopic): 360.2301

AlogP: 4.73

#Rotatable Bonds: 2

Polar Surface Area: 52.60

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.65

CX LogD: 4.65

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.53

Np Likeness Score: 2.99

References

1. del Carmen Ramrez M, Toscano RA, Arnason J, Omar S, Cerda-Garca-Rojas CM, Mata R.  (2000)  Structure, Conformation and Absolute Configuration of New Antifeedant Dolabellanes from Trichilia trifolia,  56  (29): [10.1016/S0040-4020(00)00423-3]

Source

Source(1):

• Scientific Literature