gerontoxanthone A

ID: ALA517514

PubChem CID: 11948658

Max Phase: Preclinical

Molecular Formula: C23H22O6

Molecular Weight: 394.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1Oc2cc3oc4c(O)c5c(cc4c(=O)c3c(O)c2C1(C)C)C=CC(C)(C)O5

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

Standard InChI Key:  YNHZDINWEJCMRF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    5.0378  -18.1549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0360  -16.5017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7515  -16.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7503  -17.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4634  -18.1525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4657  -16.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1833  -16.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1817  -17.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8940  -18.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8933  -16.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4657  -15.6702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8913  -15.6767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6106  -16.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6048  -17.7352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3889  -17.9960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8794  -17.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3983  -16.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7045  -17.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3229  -17.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3270  -16.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6203  -16.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9049  -16.9119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008  -17.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6121  -18.1522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4836  -18.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1003  -17.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0395  -18.9800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9803  -15.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1095  -16.2394    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
  5  8  1  0
  7  6  1  0
  2 20  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
  3  4  1  0
 16 18  1  0
 19 20  2  0
  7  8  2  0
 19  1  1  0
  8  9  1  0
  9 14  2  0
  1  4  2  0
 13 10  2  0
 19 24  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 10  7  1  0
 23 25  1  0
 23 26  1  0
  6 11  2  0
  1 27  1  0
  3  2  2  0
 17 28  1  0
 10 12  1  0
 17 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA517514

   GERONTOXANTHONE A

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: 4.60

#Rotatable Bonds: ┄

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: 8.25

CX Basic pKa: ┄

CX LogP: 4.94

CX LogD: 4.89

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.54

Np Likeness Score: 2.79

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. PubChem BioAssay data set, 

3. 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]

4. 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]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays