Galangustin

ID: ALA2268880

PubChem CID: 14353377

Max Phase: Preclinical

Molecular Formula: C17H14O6

Molecular Weight: 314.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2cc(=O)c3c(O)cc(O)c(OC)c3o2)cc1

Standard InChI:  InChI=1S/C17H14O6/c1-21-10-5-3-9(4-6-10)14-8-12(19)15-11(18)7-13(20)16(22-2)17(15)23-14/h3-8,18,20H,1-2H3

Standard InChI Key:  MRQSJFKGZKPPNM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   21.9843  -16.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9832  -16.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6912  -17.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6894  -15.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3981  -16.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3969  -16.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1031  -17.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8150  -16.8574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8161  -16.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1054  -15.6232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1008  -18.0817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6929  -18.0841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2765  -15.6299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6870  -14.8123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9781  -14.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5230  -15.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2300  -16.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9382  -15.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9406  -14.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2289  -14.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5236  -14.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6488  -14.4128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6497  -13.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  7 11  2  0
  3 12  1  0
  1 13  1  0
  4 14  1  0
 14 15  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  9 16  1  0
 19 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2268880

   GALANGUSTIN

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: 314.29

Molecular Weight (Monoisotopic): 314.0790

AlogP: 2.89

#Rotatable Bonds: 3

Polar Surface Area: 89.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.10

CX Basic pKa: ┄

CX LogP: 2.69

CX LogD: 2.21

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.77

Np Likeness Score: 1.27

References

1. Castillo L, Díaz M, González-Coloma A, Rossini C..  (2013)  Differential activity against aphid settling of flavones obtained from Clytostoma callistegioides (Bignoniaceae),  47  [10.1016/j.indcrop.2012.09.012]

2. Bian J, Li T, Weng T, Wang J, Chen Y, Li Z..  (2017)  Synthesis, evaluation and quantitative structure-activity relationship (QSAR) analysis of Wogonin derivatives as cytotoxic agents.,  27  (4): [PMID:28117202] [10.1016/j.bmcl.2016.12.076]

3. Wang J, Li T, Zhao T, Wu T, Liu C, Ding H, Li Z, Bian J..  (2019)  Design of wogonin-inspired selective cyclin-dependent kinase 9 (CDK9) inhibitors with potent in vitro and in vivo antitumor activity.,  178  [PMID:31238183] [10.1016/j.ejmech.2019.06.024]

Source

Source(1):

• Scientific Literature