Sibirolide A

ID: ALA3594185

PubChem CID: 122182496

Max Phase: Preclinical

Molecular Formula: C15H16O3

Molecular Weight: 244.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1[C@H]2C[C@H]2[C@]2(C)CC(=O)C3=C(C)C(=O)O[C@@H]3[C@@H]12

Standard InChI:  InChI=1S/C15H16O3/c1-6-8-4-9(8)15(3)5-10(16)11-7(2)14(17)18-13(11)12(6)15/h8-9,12-13H,1,4-5H2,2-3H3/t8-,9-,12-,13+,15+/m1/s1

Standard InChI Key:  WQYDDKKOUFICFB-UVBAXCRRSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    2.7140   -1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3947   -1.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7758   -3.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851   -2.9666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835   -2.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3692   -4.1760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710   -1.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4230    1.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7140    1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5957    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1381    1.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5957    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6401    0.8361    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4024   -1.7446    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8141   -2.0807    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 16  3  1  0
  2  1  1  0
  1 17  1  0
  2  3  1  0
  2  6  1  0
  3  4  1  0
  4  5  1  0
  5  7  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  6 10  1  0
  1 11  2  0
  9 12  2  0
  8 13  1  0
  5 14  2  0
  3 15  1  6
 17 16  1  0
 18 17  1  0
 16 18  1  0
 17 19  1  1
 16 20  1  1
  2 21  1  1
  6 22  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3594185

   ---

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: 244.29

Molecular Weight (Monoisotopic): 244.1099

AlogP: 2.03

#Rotatable Bonds: ┄

Polar Surface Area: 43.37

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.08

CX Basic pKa: ┄

CX LogP: 1.97

CX LogD: 1.97

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.48

Np Likeness Score: 2.88

References

1. Shi YS, Liu YB, Ma SG, Li Y, Qu J, Li L, Yuan SP, Hou Q, Li YH, Jiang JD, Yu SS..  (2015)  Bioactive Sesquiterpenes and Lignans from the Fruits of Xanthium sibiricum.,  78  (7): [PMID:26110443] [10.1021/np500951s]

Source

Source(1):

• Scientific Literature