ID: ALA538921

Max Phase: Preclinical

Molecular Formula: C27H30O17

Molecular Weight: 626.52

Molecule Type: Small molecule

Representations

Synonyms (1): Saponarin
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=c1cc(-c2ccc(O)cc2)oc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)c12

Standard InChI:  InChI=1S/C27H30O17/c28-6-12-15(32)18(35)20(37)26(41-12)43-24-17(34)14-10(31)5-11(8-1-3-9(30)4-2-8)40-23(14)25(22(24)39)44-27-21(38)19(36)16(33)13(7-29)42-27/h1-5,12-13,15-16,18-21,26-30,32-39H,6-7H2/t12-,13-,15-,16-,18+,19+,20-,21-,26+,27+/m1/s1

Standard InChI Key:  CSNXTSWTBUEIJB-PXJYGDGDSA-N

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

Properties

Molecular Weight: 626.52

Molecular Weight (Monoisotopic): 626.1483

AlogP: -3.07

#Rotatable Bonds: 7

Polar Surface Area: 289.66

Molecular Species: ACID

HBA: 17

HBD: 11

#RO5 Violations: 3

HBA (Lipinski): 17

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 6.35

CX Basic pKa:

CX LogP: -2.44

CX LogD: -3.51

Aromatic Rings: 3

Heavy Atoms: 44

QED Weighted: 0.12

Np Likeness Score: 1.49

References

1. Cos P, Ying L, Calomme M, Hu JP, Cimanga K, Van Poel B, Pieters L, Vlietinck AJ, Vanden Berghe D..  (1998)  Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers.,  61  (1): [PMID:9461655] [10.1021/np970237h]

2. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P..  (2012)  Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.,  20  (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]

3. Seo WD, Lee JH, Jia Y, Wu C, Lee SJ..  (2015)  Saponarin activates AMPK in a calcium-dependent manner and suppresses gluconeogenesis and increases glucose uptake via phosphorylation of CRTC2 and HDAC5.,  25  (22): [PMID:26471090] [10.1016/j.bmcl.2015.09.057]

Source

Source(1):

• Scientific Literature