2,4',6-trihydroxy-4-methoxy-benzophenone-2-O-beta-D-glucoside

ID: ALA2159665

Chembl Id: CHEMBL2159665

PubChem CID: 71451475

Max Phase: Preclinical

Molecular Formula: C20H22O10

Molecular Weight: 422.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Mahkoside A | Mahkoside A|CHEMBL2159665

Canonical SMILES:  COc1cc(O)c(C(=O)c2ccc(O)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1

Standard InChI:  InChI=1S/C20H22O10/c1-28-11-6-12(23)15(16(24)9-2-4-10(22)5-3-9)13(7-11)29-20-19(27)18(26)17(25)14(8-21)30-20/h2-7,14,17-23,25-27H,8H2,1H3/t14-,17-,18+,19-,20-/m1/s1

Standard InChI Key:  LCZPALDWQFYTCU-LWUBGYQZSA-N

Alternative Forms

1. Parent:

   

   ALA2159665

   MAHKOSIDE 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: 422.39

Molecular Weight (Monoisotopic): 422.1213

AlogP: -0.48

#Rotatable Bonds: 6

Polar Surface Area: 166.14

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.03

CX Basic pKa: ┄

CX LogP: 0.75

CX LogD: 0.14

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.33

Np Likeness Score: 1.54

References

1. Zhang SY, Zhang QH, Zhao W, Zhang X, Zhang Q, Bi YF, Zhang YB..  (2012)  Isolation, characterization and cytotoxic activity of benzophenone glucopyranosides from Mahkota Dewa (Phaleria macrocarpa (Scheff.) Boerl).,  22  (22): [PMID:23044367] [10.1016/j.bmcl.2012.09.038]

2. Abdel-Mageed WM, Bayoumi SA, Chen C, Vavricka CJ, Li L, Malik A, Dai H, Song F, Wang L, Zhang J, Gao GF, Lv Y, Liu L, Liu X, Sayed HM, Zhang L..  (2014)  Benzophenone C-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity.,  22  (7): [PMID:24613627] [10.1016/j.bmc.2014.02.014]

3. Nguyen HX, Do TN, Le TH, Nguyen MT, Nguyen NT, Esumi H, Awale S..  (2016)  Chemical Constituents of Mangifera indica and Their Antiausterity Activity against the PANC-1 Human Pancreatic Cancer Cell Line.,  79  (8): [PMID:27466882] [10.1021/acs.jnatprod.6b00381]

Source

Source(1):

• Scientific Literature