Bombasinol A

ID: ALA4096199

PubChem CID: 137655490

Max Phase: Preclinical

Molecular Formula: C21H24O6

Molecular Weight: 372.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)cc([C@@H]2OC[C@H]3[C@@H]2CO[C@H]3c2ccc(O)c(OC)c2)c1

Standard InChI:  InChI=1S/C21H24O6/c1-23-14-6-13(7-15(9-14)24-2)21-17-11-26-20(16(17)10-27-21)12-4-5-18(22)19(8-12)25-3/h4-9,16-17,20-22H,10-11H2,1-3H3/t16-,17-,20-,21-/m0/s1

Standard InChI Key:  MGDNKOAMJCAUJL-USNOLKROSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   10.3938   -5.7787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6360   -6.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6955   -6.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4866   -7.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9241   -6.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7911   -8.2269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2580   -7.5974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5474   -7.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5520   -4.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2748   -4.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9709   -4.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9457   -5.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2186   -6.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5241   -5.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8575   -4.3490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3029   -3.5801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6080   -3.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6314   -9.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9085   -9.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2112   -9.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2422   -8.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9648   -7.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6639   -8.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3822   -8.0173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0770   -8.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8851  -10.4226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5753  -10.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2821   -7.3011    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8985   -6.7029    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  5  1  0
  6  7  1  0
  6  8  1  0
  3  7  1  0
  4  8  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  9 14  2  0
  9 15  1  0
 16 17  1  0
 10 16  1  0
  2 12  1  6
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 18 23  2  0
 24 25  1  0
 23 24  1  0
 26 27  1  0
 19 26  1  0
  8 21  1  6
  4 28  1  1
  3 29  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4096199

   ---

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: 372.42

Molecular Weight (Monoisotopic): 372.1573

AlogP: 3.49

#Rotatable Bonds: 5

Polar Surface Area: 66.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.91

CX Basic pKa: ┄

CX LogP: 2.42

CX LogD: 2.42

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.87

Np Likeness Score: 1.02

References

1. Zhou D, Wei H, Jiang Z, Li X, Jiao K, Jia X, Hou Y, Li N..  (2017)  Natural potential neuroinflammatory inhibitors from Alhagi sparsifolia Shap.,  27  (4): [PMID:28073678] [10.1016/j.bmcl.2016.12.075]

Source

Source(1):

• Scientific Literature