Methyl abieta-8,13(15)-dien-18-oate

ID: ALA550421

Cas Number: 19402-34-7

PubChem CID: 11716678

Max Phase: Preclinical

Molecular Formula: C21H32O2

Molecular Weight: 316.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@]1(C)CCC[C@]2(C)C3=C(CC[C@@H]12)CC(=C(C)C)CC3

Standard InChI:  InChI=1S/C21H32O2/c1-14(2)15-7-9-17-16(13-15)8-10-18-20(17,3)11-6-12-21(18,4)19(22)23-5/h18H,6-13H2,1-5H3/t18-,20-,21-/m1/s1

Standard InChI Key:  VFNUXJRDTGGNPS-HMXCVIKNSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    9.1276   -6.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1276   -7.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8386   -8.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8386   -6.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5543   -6.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5554   -7.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2670   -8.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9821   -7.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2648   -6.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9836   -6.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6969   -6.5217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6977   -5.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9789   -5.2799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2593   -5.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5462   -6.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5462   -8.5802    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4086   -5.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1199   -5.6927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4082   -4.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0444   -8.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2507   -8.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4599   -9.5401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8361   -9.1812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0433   -9.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  2  3  1  0
  5 15  1  1
  5  9  1  0
  6 16  1  6
  6  7  1  0
 12 17  2  0
  7  8  1  0
 17 18  1  0
  8 10  1  0
 17 19  1  0
  9 10  2  0
  3 20  1  6
  3  6  1  0
  3 21  1  0
  5  4  1  0
 20 22  2  0
  5  6  1  0
 20 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA550421

   Methyl (1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-ylidene-3,4,5,6,8,9,10,10a-octahydro-2H-phenanthrene-1-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: 5.58

#Rotatable Bonds: 1

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: 5.01

CX LogD: 5.01

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.47

Np Likeness Score: 2.67

References

1. González MA, Correa-Royero J, Agudelo L, Mesa A, Betancur-Galvis L..  (2009)  Synthesis and biological evaluation of abietic acid derivatives.,  44  (6): [PMID:19217699] [10.1016/j.ejmech.2009.01.014]

Source

Source(1):

• Scientific Literature