gerontoxanthone B

ID: ALA478938

PubChem CID: 14259057

Max Phase: Preclinical

Molecular Formula: C23H22O6

Molecular Weight: 394.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(C)(C)c1c(O)cc2oc3c(O)c4c(cc3c(=O)c2c1O)C=CC(C)(C)O4

Standard InChI:  InChI=1S/C23H22O6/c1-6-22(2,3)16-13(24)10-14-15(18(16)26)17(25)12-9-11-7-8-23(4,5)29-20(11)19(27)21(12)28-14/h6-10,24,26-27H,1H2,2-5H3

Standard InChI Key:  LGFMLQQVQWNWFN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   14.9179  -18.5306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9161  -16.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6318  -17.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6306  -18.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3438  -18.5282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3461  -16.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0639  -17.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0623  -18.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7749  -18.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7742  -16.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3461  -16.0452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7722  -16.0517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4916  -17.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4858  -18.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2028  -18.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2069  -17.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5000  -16.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7845  -17.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7804  -18.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4918  -18.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3630  -18.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9796  -17.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9196  -19.3559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2001  -18.5244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2063  -16.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9159  -16.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6228  -17.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7909  -16.1584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6349  -16.8574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  3  6  1  0
  4  5  1  0
 15 16  2  0
  5  8  1  0
  7  6  1  0
  2 16  1  0
  3  4  1  0
  7  8  2  0
 15  1  1  0
 15 20  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
  8  9  1  0
 19 21  1  0
  9 14  2  0
 19 22  1  0
  1  4  2  0
  1 23  1  0
 13 10  2  0
 14 24  1  0
 10  7  1  0
 13 25  1  0
 25 26  1  0
  6 11  2  0
 25 27  1  0
  3  2  2  0
 25 28  1  0
 10 12  1  0
 26 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA478938

   GERONTOXANTHONE B

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: 394.42

Molecular Weight (Monoisotopic): 394.1416

AlogP: 4.71

#Rotatable Bonds: 2

Polar Surface Area: 100.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.27

CX Basic pKa: ┄

CX LogP: 5.29

CX LogD: 4.89

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: 2.66

References

1. Hou A, Fukai T, Shimazaki M, Sakagami H, Sun H, Nomura T..  (2001)  Benzophenones and xanthones with isoprenoid groups from Cudrania cochinchinensis.,  64  (1): [PMID:11170668] [10.1021/np000406p]

2. Nakashima K, Tanaka T, Murata H, Kaburagi K, Inoue M..  (2015)  Xanthones from the roots of Maclura cochinchinensis var. gerontogea and their retinoic acid receptor-α agonistic activity.,  25  (9): [PMID:25838141] [10.1016/j.bmcl.2015.02.075]

3. Nakashima KI, Ogiwara T, Hirai T, Tanaka T, Murata H, Kaburagi K, Fujii-Kuriyama Y, Hayashi H, Inoue M..  (2017)  Gerontoxanthone B from Maclura cochinchinensis var. gerontogea exhibits anti-inflammatory potential as an aryl hydrocarbon receptor agonist.,  25  (16): [PMID:28662965] [10.1016/j.bmc.2017.05.047]

4. Liu X, Shen J, Zhu K..  (2022)  Antibacterial activities of plant-derived xanthones.,  13  (2.0): [PMID:35308024] [10.1039/d1md00351h]

Source

Source(1):

• Scientific Literature