gerontoxanthone I

ID: ALA478791

Chembl Id: CHEMBL478791

PubChem CID: 14412270

Max Phase: Preclinical

Molecular Formula: C23H24O6

Molecular Weight: 396.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Gerontoxanthone I | gerontoxanthone I|MLS000697632|SMR000470960|CHEMBL478791|BDBM53423|cid_14412270|HMS2271P03|1,3,5,6-tetrahydroxy-4-(2-methylbut-3-en-2-yl)-2-(3-methylbut-2-enyl)-9-xanthenone|1,3,5,6-tetrahydroxy-4-(2-methylbut-3-en-2-yl)-2-(3-methylbut-2-enyl)xanthen-9-one|4-(1,1-dimethylallyl)-1,3,5,6-tetrahydroxy-2-(3-methylbut-2-enyl)xanthone|4-(2-methylbut-3-en-2-yl)-2-(3-methylbut-2-enyl)-1,3,5,6-tetrakis(oxidanyl)xanthen-9-one

Canonical SMILES:  C=CC(C)(C)c1c(O)c(CC=C(C)C)c(O)c2c(=O)c3ccc(O)c(O)c3oc12

Standard InChI:  InChI=1S/C23H24O6/c1-6-23(4,5)16-19(27)12(8-7-11(2)3)17(25)15-18(26)13-9-10-14(24)20(28)21(13)29-22(15)16/h6-7,9-10,24-25,27-28H,1,8H2,2-5H3

Standard InChI Key:  SHKQTNVZRNUENO-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA478791

   GERONTOXANTHONE I

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: 396.44

Molecular Weight (Monoisotopic): 396.1573

AlogP: 4.74

#Rotatable Bonds: 4

Polar Surface Area: 111.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.00

CX Basic pKa:

CX LogP: 5.81

CX LogD: 5.13

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.29

Np Likeness Score: 2.31

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 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(2):

• Scientific Literature
• PubChem BioAssays