gerontoxanthone H

ID: ALA514057

Cas Number: 125140-06-9

PubChem CID: 11211194

Max Phase: Preclinical

Molecular Formula: C23H24O5

Molecular Weight: 380.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Gerontoxanthone H | gerontoxanthone H|MLS000697646|2,6,8-trihydroxy-1,5-bis(3-methylbut-2-enyl)xanthen-9-one|SMR000470972|125140-06-9|CHEMBL514057|BDBM69606|cid_11211194|HMS2269B20|2,6,8-trihydroxy-1,5-bis(3-methylbut-2-enyl)xanthone|2,6,8-trihydroxy-1,5-bis(3-methylbut-2-enyl)-9-xanthenone|1,5-bis(3-methylbut-2-enyl)-2,6,8-tris(oxidanyl)xanthen-9-one

Canonical SMILES:  CC(C)=CCc1c(O)cc(O)c2c(=O)c3c(CC=C(C)C)c(O)ccc3oc12

Standard InChI:  InChI=1S/C23H24O5/c1-12(2)5-7-14-16(24)9-10-19-20(14)22(27)21-18(26)11-17(25)15(23(21)28-19)8-6-13(3)4/h5-6,9-11,24-26H,7-8H2,1-4H3

Standard InChI Key:  VGCAJFOJSSFOSL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    5.0569  -23.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0557  -24.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7706  -24.5860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7688  -22.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4841  -23.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4830  -24.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1959  -24.5836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1983  -22.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9158  -23.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9141  -24.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6264  -24.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3409  -24.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3386  -23.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6257  -22.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1983  -22.1016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6238  -22.1081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0558  -24.5813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7663  -22.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0506  -21.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0481  -20.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3324  -20.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7614  -20.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3423  -22.9335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6257  -25.4061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3398  -25.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3391  -26.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0532  -27.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6242  -27.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  0
 13 14  2  0
 14  9  1  0
  1  2  2  0
  8 15  2  0
  5  8  1  0
 14 16  1  0
  6  7  1  0
 12 17  1  0
  7 10  1  0
  4 18  1  0
  9  8  1  0
 18 19  1  0
  5  4  2  0
 19 20  2  0
  4  1  1  0
 20 21  1  0
  9 10  2  0
 20 22  1  0
  5  6  1  0
  1 23  1  0
 10 11  1  0
 11 24  1  0
 24 25  1  0
 11 12  2  0
 25 26  2  0
  2  3  1  0
 26 27  1  0
 12 13  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA514057

   GERONTOXANTHONE H

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: 380.44

Molecular Weight (Monoisotopic): 380.1624

AlogP: 5.08

#Rotatable Bonds: 4

Polar Surface Area: 90.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.36

CX Basic pKa: ┄

CX LogP: 6.16

CX LogD: 5.83

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.43

Np Likeness Score: 1.81

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. Jo YH, Shin B, Liu Q, Lee KY, Oh DC, Hwang BY, Lee MK..  (2014)  Antiproliferative prenylated xanthones and benzophenones from the roots of Cudrania tricuspidata in HSC-T6 cells.,  77  (11): [PMID:25322455] [10.1021/np5002797]

4. 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]

5. 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]

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

Source

Source(2):

• Scientific Literature
• PubChem BioAssays