Getiacaulein

ID: ALA467590

Chembl Id: CHEMBL467590

Cas Number: 15402-27-4

PubChem CID: 5281634

Max Phase: Preclinical

Molecular Formula: C15H12O6

Molecular Weight: 288.25

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Getiacaulein | Gentiacaulein|15402-27-4|2,6-dimethoxyxanthone|2,8-dihydroxy-1,6-dimethoxyxanthone|Getiacaulein|NSC661743|2,8-dihydroxy-1,6-dimethoxyxanthen-9-one|MLS000563494|CHEBI:5313|2,8-Dihydroxy-1,6-dimethoxy-9H-xanthen-9-one|2,8-dihydroxy-1,6-dimethoxy-xanthen-9-one|AC1NQYS1|CHEMBL467590|DTXSID10415161|BDBM174835|HMS2227I16|HMS3338N03|1,7-dihydroxy-3,8-dimethoxyxanthone|NSC-661743|SMR000232301|US9114126, 2027BA1|Q27106712

Canonical SMILES:  COc1cc(O)c2c(=O)c3c(OC)c(O)ccc3oc2c1

Standard InChI:  InChI=1S/C15H12O6/c1-19-7-5-9(17)12-11(6-7)21-10-4-3-8(16)15(20-2)13(10)14(12)18/h3-6,16-17H,1-2H3

Standard InChI Key:  WYOSCUWDVFHQFY-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA467590

   GETIACAULEIN

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: 288.25

Molecular Weight (Monoisotopic): 288.0634

AlogP: 2.37

#Rotatable Bonds: 2

Polar Surface Area: 89.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.27

CX Basic pKa:

CX LogP: 2.69

CX LogD: 2.63

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.70

Np Likeness Score: 1.48

References

1. Isakovic A, Jankovic T, Harhaji L, Kostic-Rajacic S, Nikolic Z, Vajs V, Trajkovic V..  (2008)  Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.,  16  (10): [PMID:18406151] [10.1016/j.bmc.2008.03.069]

2. PubChem BioAssay data set, 

3.  (2015)  Na/K-ATPase ligands, ouabain antagonists, assays and uses thereof, 

4. Tripathi AC, Upadhyay S, Paliwal S, Saraf SK..  (2018)  Privileged scaffolds as MAO inhibitors: Retrospect and prospects.,  145  [PMID:29335210] [10.1016/j.ejmech.2018.01.003]

5. Santos CMM, Freitas M, Fernandes E..  (2018)  A comprehensive review on xanthone derivatives as α-glucosidase inhibitors.,  157  [PMID:30282319] [10.1016/j.ejmech.2018.07.073]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• BindingDB Database