2-epi-16-deoxysarcophine

ID: ALA560225

Max Phase: Preclinical

Molecular Formula: C20H30O2

Molecular Weight: 302.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C2CC/C(C)=C/CC[C@]3(C)O[C@H]3CC/C(C)=C\[C@H]2OC1

Standard InChI:  InChI=1S/C20H30O2/c1-14-6-5-11-20(4)19(22-20)10-8-15(2)12-18-17(9-7-14)16(3)13-21-18/h6,12,18-19H,5,7-11,13H2,1-4H3/b14-6+,15-12-/t18-,19+,20+/m1/s1

Standard InChI Key:  OQGXDKRHMBRZCS-CAPKMUHJSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    7.2343  -26.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5439  -26.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6665  -25.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9074  -25.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6149  -24.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9142  -24.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8519  -23.9163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6737  -23.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9685  -23.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5707  -23.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2729  -22.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7912  -26.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6006  -23.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2333  -23.5083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8708  -23.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6079  -25.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8252  -25.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6411  -25.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9281  -25.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2895  -24.6324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0490  -26.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0956  -26.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8875  -25.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500  -22.3792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  0
  1  2  1  0
  7 13  1  0
  2  3  2  0
 10 14  1  0
  8 14  1  0
  3  4  1  0
  8 15  1  6
 16 17  1  0
 16  5  1  0
  4  6  1  0
  5  7  2  0
  6  8  1  0
  7  9  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
  8 10  1  0
  1 21  1  0
 21 17  1  0
  9 11  1  0
 18 22  1  0
 10 11  1  0
 16 23  1  6
 10 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA560225

   ---

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: 5.11

#Rotatable Bonds: ┄

Polar Surface Area: 21.76

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.34

CX LogD: 4.34

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.46

Np Likeness Score: 3.33

References

1. Yu BZ, Kaimal R, Bai S, El Sayed KA, Tatulian SA, Apitz RJ, Jain MK, Deng R, Berg OG..  (2009)  Effect of guggulsterone and cembranoids of Commiphora mukul on pancreatic phospholipase A(2): role in hypocholesterolemia.,  72  (1): [PMID:19102680] [10.1021/np8004453]

2. Hassan HM, Sallam AA, Mohammed R, Hifnawy MS, Youssef DT, El Sayed KA..  (2011)  Semisynthetic analogues of the marine cembranoid sarcophine as prostate and breast cancer migration inhibitors.,  19  (16): [PMID:21775154] [10.1016/j.bmc.2011.06.060]

Source

Source(1):

• Scientific Literature