ID: ALA444122

Max Phase: Phase

Molecular Formula: C38H60O18

Molecular Weight: 804.88

Molecule Type: Small molecule

Representations

Synonyms (10): (-)-stevioside | .alpha.-g-sweet | Stevian 50 | Stevibioside | Stevioside | Steviosin | E-960 | FEMA NO. 4763 | INS NO.960 | INS-960
Synonyms from Alternative Forms(10):

Canonical SMILES:  C=C1C[C@@]23CC[C@H]4[C@@](C)(CCC[C@@]4(C)C(=O)O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H]2CC[C@]1(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C3

Standard InChI:  InChI=1S/C38H60O18/c1-16-11-37-9-5-20-35(2,7-4-8-36(20,3)34(50)55-32-29(49)26(46)23(43)18(13-40)52-32)21(37)6-10-38(16,15-37)56-33-30(27(47)24(44)19(14-41)53-33)54-31-28(48)25(45)22(42)17(12-39)51-31/h17-33,39-49H,1,4-15H2,2-3H3/t17-,18-,19-,20+,21+,22-,23-,24-,25+,26+,27+,28-,29-,30-,31+,32+,33+,35-,36-,37-,38+/m1/s1

Standard InChI Key:  UEDUENGHJMELGK-HYDKPPNVSA-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: 804.88

Molecular Weight (Monoisotopic): 804.3780

AlogP: -2.94

#Rotatable Bonds: 9

Polar Surface Area: 294.98

Molecular Species: NEUTRAL

HBA: 18

HBD: 11

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.84

CX Basic pKa:

CX LogP: -2.16

CX LogD: -2.16

Aromatic Rings: 0

Heavy Atoms: 56

QED Weighted: 0.06

Np Likeness Score: 1.88

References

1. DuBois GE, Dietrich PS, Lee JF, McGarraugh GV, Stephenson RA..  (1981)  Diterpenoid sweeteners. Synthesis and sensory evaluation of stevioside analogues nondegradable to steviol.,  24  (11): [PMID:7310801] [10.1021/jm00143a001]

2. DuBois GE, Stephenson RA..  (1985)  Diterpenoid sweeteners. Synthesis and sensory evaluation of stevioside analogues with improved organoleptic properties.,  28  (1): [PMID:3965718] [10.1021/jm00379a017]

3. Chang SF, Yang LM, Hsu FL, Hsu JY, Liaw JH, Lin SJ..  (2006)  Transformation of steviol-16alpha,17-epoxide by Streptomyces griseus and Cunninghamella bainieri.,  69  (10): [PMID:17067160] [10.1021/np0602564]

4. Takasaki M, Konoshima T, Kozuka M, Tokuda H, Takayasu J, Nishino H, Miyakoshi M, Mizutani K, Lee KH..  (2009)  Cancer preventive agents. Part 8: Chemopreventive effects of stevioside and related compounds.,  17  (2): [PMID:19131254] [10.1016/j.bmc.2008.11.077]

5. Akihisa T, Hamasaki Y, Tokuda H, Ukiya M, Kimura Y, Nishino H..  (2004)  Microbial transformation of isosteviol and inhibitory effects on Epstein-Barr virus activation of the transformation products.,  67  (3): [PMID:15043419] [10.1021/np030393q]

6. Melis MS..  (1992)  Renal excretion of stevioside in rats.,  55  (5): [PMID:1517741] [10.1021/np50083a024]

7. Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH..  (1991)  Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.,  54  (1): [PMID:1710653] [10.1021/np50073a012]

8. Ceunen S, Geuns JM..  (2013)  Steviol glycosides: chemical diversity, metabolism, and function.,  76  (6): [PMID:23713723] [10.1021/np400203b]

9. Ibrahim MA, Rodenburg DL, Alves K, Fronczek FR, McChesney JD, Wu C, Nettles BJ, Venkataraman SK, Jaksch F..  (2014)  Minor diterpene glycosides from the leaves of Stevia rebaudiana.,  77  (5): [PMID:24758242] [10.1021/np4009656]

10.  (2008)  T1R hetero-oligomeric taste receptors, cell lines that express said receptors, and taste compounds, 

11. Wang M, Li H, Xu F, Gao X, Li J, Xu S, Zhang D, Wu X, Xu J, Hua H, Li D..  (2018)  Diterpenoid lead stevioside and its hydrolysis products steviol and isosteviol: Biological activity and structural modification.,  156  [PMID:30059803] [10.1016/j.ejmech.2018.07.052]

12. Unpublished dataset, 

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• Patent Bioactivity Data