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

ID: ALA2269165

PubChem CID: 15450496

Max Phase: Preclinical

Molecular Formula: C20H30O2

Molecular Weight: 302.46

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)O)CC[C@@H]12

Standard InChI:  InChI=1S/C20H30O2/c1-14(2)17-11-13-20(4)12-10-15(3)6-5-7-16(19(21)22)8-9-18(17)20/h7,10,17-18H,1,5-6,8-9,11-13H2,2-4H3,(H,21,22)/b15-10+,16-7-/t17-,18+,20+/m1/s1

Standard InChI Key:  RSEPFMSDFDKJDO-CYWCEOHPSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    6.7411   -3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6331   -2.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417   -1.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3830   -2.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3260   -3.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5969   -3.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4338   -1.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7047   -2.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4486   -2.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8169   -3.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2136   -2.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5801   -2.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3900   -2.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5241   -1.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7968   -1.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2267   -3.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4095   -3.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6374   -4.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126   -1.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8128   -0.6953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0365   -3.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0435   -4.8165    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA2269165

   (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-carboxylic acid

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: 302.46

Molecular Weight (Monoisotopic): 302.2246

AlogP: 5.52

#Rotatable Bonds: 2

Polar Surface Area: 37.30

Molecular Species: ACID

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.95

CX Basic pKa: ┄

CX LogP: 5.37

CX LogD: 2.95

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.68

Np Likeness Score: 2.94

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