(1R,3E,7Z,11S,12S)-dolabella-3,7,18-trien-17-oic acid methyl ester

ID: ALA2269163

PubChem CID: 21597138

Max Phase: Preclinical

Molecular Formula: C21H32O2

Molecular Weight: 316.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)[C@H]1CC[C@]2(C)C/C=C(\C)CC/C=C(\C(=O)OC)CC[C@@H]12

Standard InChI:  InChI=1S/C21H32O2/c1-15(2)18-12-14-21(4)13-11-16(3)7-6-8-17(20(22)23-5)9-10-19(18)21/h8,11,18-19H,1,6-7,9-10,12-14H2,2-5H3/b16-11+,17-8-/t18-,19+,21+/m1/s1

Standard InChI Key:  XZYWMVMURJJIFG-BAOOVMHGSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    6.5846   -9.0901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4374   -8.4702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8499   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1849   -7.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1560   -9.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4200   -9.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2552   -7.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5193   -7.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2606   -8.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6325   -9.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0426   -7.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4126   -8.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2302   -8.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3656   -7.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6312   -6.9933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0271   -9.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2021   -9.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417   -9.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7291   -6.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6474   -6.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8732   -9.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8803  -10.3291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1695  -10.7477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  1  0
  8  3  1  0
  3  4  1  0
  4  2  1  0
 12  5  2  0
  5  6  1  0
 11  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
 10  6  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  2  0
  2 16  1  1
 16 17  1  0
 16 18  2  0
  8 19  1  1
 15 20  1  0
  5 21  1  0
 21 22  1  0
 21  1  2  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2269163

   methyl (1S,3aR,5E,9Z,12aS)-3a,6-dimethyl-1-prop-1-en-2-yl-2,3,4,7,8,11,12,12a-octahydro-1H-cyclopenta[11]annulene-10-carboxylate

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: 316.49

Molecular Weight (Monoisotopic): 316.2402

AlogP: 5.60

#Rotatable Bonds: 2

Polar Surface Area: 26.30

Molecular Species: ┄

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.75

CX LogD: 5.75

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.49

Np Likeness Score: 2.74

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