3alpha-acetoxy-4alpha-hydroxy-11(13)-eudesmen-12-oic acid methyl ester

ID: ALA464281

PubChem CID: 15699305

Max Phase: Preclinical

Molecular Formula: C18H28O5

Molecular Weight: 324.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C(=O)OC)[C@@H]1CC[C@@]2(C)CC[C@@H](OC(C)=O)[C@@](C)(O)[C@@H]2C1

Standard InChI:  InChI=1S/C18H28O5/c1-11(16(20)22-5)13-6-8-17(3)9-7-15(23-12(2)19)18(4,21)14(17)10-13/h13-15,21H,1,6-10H2,2-5H3/t13-,14-,15-,17+,18+/m1/s1

Standard InChI Key:  CHDDYPARQRCBSM-WGMGUUHVSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    4.7083  -10.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7083  -11.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4204  -11.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4204  -10.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1324  -10.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1289  -11.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8376  -11.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5544  -11.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5580  -10.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8446  -10.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1250   -9.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1208  -12.2292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2666  -11.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2619  -12.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9834  -11.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9945  -11.8219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2794  -11.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5655  -11.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2782  -10.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0000  -12.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8250  -12.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6968  -11.8364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9893  -10.5949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6950  -12.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6 12  1  6
  1  2  1  0
  8 13  1  1
  1  4  1  0
 13 14  2  0
  2  3  1  0
 13 15  1  0
  3  6  1  0
  2 16  1  6
  5  4  1  0
 16 17  1  0
  5 10  1  0
 17 18  1  0
  6  7  1  0
 17 19  2  0
  7  8  1  0
  3 20  1  6
  8  9  1  0
  3 21  1  0
  9 10  1  0
  5  6  1  0
 15 22  1  0
 15 23  2  0
  5 11  1  1
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA464281

   methyl 2-[(2R,4aS,7R,8S,8aR)-7-acetyloxy-8-hydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoate

Molecule Features

Natural Product: Yes

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: 324.42

Molecular Weight (Monoisotopic): 324.1937

AlogP: 2.61

#Rotatable Bonds: 3

Polar Surface Area: 72.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.79

CX Basic pKa: ┄

CX LogP: 2.55

CX LogD: 2.55

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.64

Np Likeness Score: 2.73

References

1. Gu JQ, Gills JJ, Park EJ, Mata-Greenwood E, Hawthorne ME, Axelrod F, Chavez PI, Fong HH, Mehta RG, Pezzuto JM, Kinghorn AD..  (2002)  Sesquiterpenoids from Tithonia diversifolia with potential cancer chemopreventive activity.,  65  (4): [PMID:11975495] [10.1021/np010545m]

Source

Source(1):

• Scientific Literature