ID: ALA502135

Max Phase: Approved

Molecular Formula: C5H10O5

Molecular Weight: 150.13

Molecule Type: Small molecule

Representations

Synonyms (3): Xylose | FEMA NO. 3606 | NSC-122762
Synonyms from Alternative Forms(3):

Trade Names(2): Xylo-pfan | Xylose

Canonical SMILES:  OC1OC[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1

Standard InChI Key:  SRBFZHDQGSBBOR-IOVATXLUSA-N

Molecule Features

Natural Product: Yes

Oral: Yes

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: 150.13

Molecular Weight (Monoisotopic): 150.0528

AlogP: -2.58

#Rotatable Bonds: 0

Polar Surface Area: 90.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.31

CX Basic pKa:

CX LogP: -2.30

CX LogD: -2.30

Aromatic Rings: 0

Heavy Atoms: 10

QED Weighted: 0.30

Np Likeness Score: 2.51

References

1. Anderson RA, Oswald C, Zaneveld LJ..  (1981)  Inhibition of human acrosin by monosaccharides and related compounds: structure-activity relationships.,  24  (11): [PMID:7031247] [10.1021/jm00143a005]

2. Hadwiger P, Mayr P, Tauss A, Stütz AE, Nidetzky B..  (1999)  Binding and catalysis by yeast aldose reductase: a substrate-analog approach with new aldose derivatives.,  9  (12): [PMID:10397501] [10.1016/s0960-894x(99)00255-3]

3. Cavezza A, Boulle C, Guéguiniat A, Pichaud P, Trouille S, Ricard L, Dalko-Csiba M..  (2009)  Synthesis of Pro-Xylane: a new biologically active C-glycoside in aqueous media.,  19  (3): [PMID:19135365] [10.1016/j.bmcl.2008.12.037]

4. Gruzman A, Shamni O, Ben Yakir M, Sandovski D, Elgart A, Alpert E, Cohen G, Hoffman A, Katzhendler Y, Cerasi E, Sasson S..  (2008)  Novel D-xylose derivatives stimulate muscle glucose uptake by activating AMP-activated protein kinase alpha.,  51  (24): [PMID:19049348] [10.1021/jm8008713]

5. Lairson LL, Watts AG, Wakarchuk WW, Withers SG..  (2006)  Using substrate engineering to harness enzymatic promiscuity and expand biological catalysis.,  2  (12): [PMID:17057723] [10.1038/nchembio828]

6. PubChem BioAssay data set, 

7. Kruhlak NL, Choi SS, Contrera JF, Weaver JL, Willard JM, Hastings KL, Sancilio LF..  (2008)  Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.,  18  (2): [PMID:20020916] [10.1080/15376510701857262]

8. Unpublished dataset, 

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

10. PubChem BioAssay data set, 

11. Ndombera FT, VanHecke GC, Nagi S, Ahn YH..  (2016)  Carbohydrate-based inducers of cellular stress for targeting cancer cells.,  26  (5): [PMID:26832785] [10.1016/j.bmcl.2016.01.063]

12. 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]

13. Sakoguchi H,Yoshihara A,Shintani T,Okuma K,Izumori K,Sato M.  (2016)  Growth inhibitory effect of D-arabinose against the nematode Caenorhabditis elegans: Discovery of a novel bioactive monosaccharide.,  26  (3.0): [PMID:26791015] [10.1016/j.bmcl.2016.01.007]

Source

Source(5):

• Scientific Literature
• PubChem BioAssays
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• SARS-CoV-2 Screening Data 2020-21