ID: ALA1208974

Max Phase: Preclinical

Molecular Formula: C9H18O9S2

Molecular Weight: 334.37

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  O=S(=O)([O-])O[C@@H](CO)[C@H](O)C[S@+]1C[C@@H](O)[C@H](O)[C@H]1CO

Standard InChI:  InChI=1S/C9H18O9S2/c10-1-7(18-20(15,16)17)5(12)3-19-4-6(13)9(14)8(19)2-11/h5-14H,1-4H2/t5-,6-,7+,8-,9+,19-/m1/s1

Standard InChI Key:  SOWRVDSZMRPKRG-YRPOCYRVSA-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: 334.37

Molecular Weight (Monoisotopic): 334.0392

AlogP: -4.10

#Rotatable Bonds: 7

Polar Surface Area: 167.58

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: -1.84

CX Basic pKa:

CX LogP: -6.69

CX LogD: -7.33

Aromatic Rings: 0

Heavy Atoms: 20

QED Weighted: 0.18

Np Likeness Score: 2.27

References

1. Tanabe G, Yoshikai K, Hatanaka T, Yamamoto M, Shao Y, Minematsu T, Muraoka O, Wang T, Matsuda H, Yoshikawa M..  (2007)  Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the alpha-glucosidase inhibitory activity.,  15  (11): [PMID:17416527] [10.1016/j.bmc.2006.10.014]

2. Minami Y, Kuriyama C, Ikeda K, Kato A, Takebayashi K, Adachi I, Fleet GW, Kettawan A, Okamoto T, Asano N..  (2008)  Effect of five-membered sugar mimics on mammalian glycogen-degrading enzymes and various glucosidases.,  16  (6): [PMID:18258441] [10.1016/j.bmc.2008.01.032]

3. Ozaki S, Oe H, Kitamura S..  (2008)  Alpha-glucosidase inhibitor from Kothala-himbutu (Salacia reticulata WIGHT).,  71  (6): [PMID:18547114] [10.1021/np070604h]

4. Nakamura S, Takahira K, Tanabe G, Morikawa T, Sakano M, Ninomiya K, Yoshikawa M, Muraoka O, Nakanishi I..  (2010)  Docking and SAR studies of salacinol derivatives as alpha-glucosidase inhibitors.,  20  (15): [PMID:20598536] [10.1016/j.bmcl.2010.06.059]

5. Mohan S, Sim L, Rose DR, Pinto BM..  (2010)  Probing the active-site requirements of human intestinal N-terminal maltase-glucoamylase: Synthesis and enzyme inhibitory activities of a six-membered ring nitrogen analogue of kotalanol and its de-O-sulfonated derivative.,  18  (22): [PMID:20970346] [10.1016/j.bmc.2010.09.059]

6. Xie W, Tanabe G, Akaki J, Morikawa T, Ninomiya K, Minematsu T, Yoshikawa M, Wu X, Muraoka O..  (2011)  Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors.,  19  (6): [PMID:21345683] [10.1016/j.bmc.2011.01.052]

7. Xie W, Tanabe G, Matsuoka K, Amer MF, Minematsu T, Wu X, Yoshikawa M, Muraoka O..  (2011)  Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor.,  19  (7): [PMID:21420866] [10.1016/j.bmc.2011.02.028]

8. Tanabe G, Otani T, Cong W, Minematsu T, Ninomiya K, Yoshikawa M, Muraoka O..  (2011)  Biological evaluation of 3'-O-alkylated analogs of salacinol, the role of hydrophobic alkyl group at 3' position in the side chain on the α-glucosidase inhibitory activity.,  21  (10): [PMID:21454075] [10.1016/j.bmcl.2011.02.109]

9. Jones K, Sim L, Mohan S, Kumarasamy J, Liu H, Avery S, Naim HY, Quezada-Calvillo R, Nichols BL, Pinto BM, Rose DR..  (2011)  Mapping the intestinal alpha-glucogenic enzyme specificities of starch digesting maltase-glucoamylase and sucrase-isomaltase.,  19  (13): [PMID:21669536] [10.1016/j.bmc.2011.05.033]

10. Tanabe G, Matsuoka K, Yoshinaga M, Xie W, Tsutsui N, A Amer MF, Nakamura S, Nakanishi I, Wu X, Yoshikawa M, Muraoka O..  (2012)  Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor. Part 2.,  20  (21): [PMID:23031648] [10.1016/j.bmc.2012.09.006]

11. Takashima K,Sakano M,Kinouchi E,Nakamura S,Marumoto S,Ishikawa F,Ninomiya K,Nakanishi I,Morikawa T,Tanabe G.  (2021)  Elongation of the side chain by linear alkyl groups increases the potency of salacinol, a potent α-glucosidase inhibitor from the Ayurvedic traditional medicine "Salacia," against human intestinal maltase.,  33  [PMID:33347966] [10.1016/j.bmcl.2020.127751]

Source

Source(1):

• Scientific Literature