ID: ALA253582

Max Phase: Approved

Molecular Formula: C12H22O11

Molecular Weight: 342.30

Molecule Type: Small molecule

Representations

Synonyms (4): Sucrose | GNE-410 | NSC-406942 | S-67F
Synonyms from Alternative Forms(4):

Canonical SMILES:  OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C12H22O11/c13-1-4-6(16)8(18)9(19)11(21-4)23-12(3-15)10(20)7(17)5(2-14)22-12/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11-,12+/m1/s1

Standard InChI Key:  CZMRCDWAGMRECN-UGDNZRGBSA-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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 342.30

Molecular Weight (Monoisotopic): 342.1162

AlogP: -5.40

#Rotatable Bonds: 5

Polar Surface Area: 189.53

Molecular Species: NEUTRAL

HBA: 11

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.84

CX Basic pKa:

CX LogP: -4.53

CX LogD: -4.53

Aromatic Rings: 0

Heavy Atoms: 23

QED Weighted: 0.24

Np Likeness Score: 2.14

References

1. Janusz JM, Young PA, Blum RB, Riley CM..  (1990)  High-potency dipeptide sweeteners. 2. L-aspartylfuryl-, thienyl-, and imidazolylglycine esters.,  33  (6): [PMID:2342061] [10.1021/jm00168a022]

2. Lüllmann H, Timmermans PB, Weikert GM, Ziegler A..  (1980)  Accumulation of drugs by guinea pig isolated atria. Quantitative correlations.,  23  (5): [PMID:7381857] [10.1021/jm00179a017]

3. Levin VA..  (1980)  Relationship of octanol/water partition coefficient and molecular weight to rat brain capillary permeability.,  23  (6): [PMID:7392035] [10.1021/jm00180a022]

4. 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]

5. Baert B, Deconinck E, Van Gele M, Slodicka M, Stoppie P, Bodé S, Slegers G, Vander Heyden Y, Lambert J, Beetens J, De Spiegeleer B..  (2007)  Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds.,  15  (22): [PMID:17827020] [10.1016/j.bmc.2007.07.050]

6. Sanderson L, Khan A, Thomas S..  (2007)  Distribution of suramin, an antitrypanosomal drug, across the blood-brain and blood-cerebrospinal fluid interfaces in wild-type and P-glycoprotein transporter-deficient mice.,  51  (9): [PMID:17576845] [10.1128/aac.00372-07]

7. Hamburger MO, Cordell GA..  (1987)  A direct bioautographic tlc assay for compounds possessing antibacterial activity.,  50  (1): [PMID:3110376] [10.1021/np50049a003]

8. Du-Cuny L, Song Z, Moses S, Powis G, Mash EA, Meuillet EJ, Zhang S..  (2009)  Computational modeling of novel inhibitors targeting the Akt pleckstrin homology domain.,  17  (19): [PMID:19734051] [10.1016/j.bmc.2009.08.022]

9. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]

10. Mazimba O, Majinda RR, Modibedi C, Masesane IB, Cencič A, Chingwaru W..  (2011)  Tylosema esculentum extractives and their bioactivity.,  19  (17): [PMID:21813280] [10.1016/j.bmc.2011.07.006]

11. PubChem BioAssay data set, 

12. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

13. Fernandes C, Oliveira L, Tiritan ME, Leitao L, Pozzi A, Noronha-Matos JB, Correia-de-Sá P, Pinto MM..  (2012)  Synthesis of new chiral xanthone derivatives acting as nerve conduction blockers in the rat sciatic nerve.,  55  [PMID:22819594] [10.1016/j.ejmech.2012.06.049]

14. Unpublished dataset, 

15. PubChem BioAssay data set, 

16. PubChem BioAssay data set, 

17. PubChem BioAssay data set, 

18. Kim KH, Kim CS, Park YJ, Moon E, Choi SU, Lee JH, Kim SY, Lee KR..  (2014)  Anti-inflammatory and antitumor phenylpropanoid sucrosides from the seeds of Raphanus sativus.,  25  (1): [PMID:25466198] [10.1016/j.bmcl.2014.11.001]

19. Mahon BP, Lomelino CL, Ladwig J, Rankin GM, Driscoll JM, Salguero AL, Pinard MA, Vullo D, Supuran CT, Poulsen SA, McKenna R..  (2015)  Mapping Selective Inhibition of the Cancer-Related Carbonic Anhydrase IX Using Structure-Activity Relationships of Glucosyl-Based Sulfamates.,  58  (16): [PMID:26203869] [10.1021/acs.jmedchem.5b00845]

20.  (2008)  T1R hetero-oligomeric taste receptors, cell lines that express said receptors, and taste compounds, 

21. British National Formulary (72nd edition), 

22. Lomelino CL, Murray AB, Supuran CT, McKenna R..  (2018)  Sweet Binders: Carbonic Anhydrase IX in Complex with Sucralose.,  9  (7): [PMID:30034596] [10.1021/acsmedchemlett.8b00100]

23. Unpublished dataset, 

24. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

25. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]

26. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

27. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

28. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

29. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

30. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(10):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• Gene Expression Atlas Compounds
• Patent Bioactivity Data
• British National Formulary
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6