ID: ALA1088977

Max Phase: Preclinical

Molecular Formula: C15H22N6O5S

Molecular Weight: 398.45

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[S+](CC[C@H](N)C(=O)[O-])C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/t7-,8+,10+,11+,14+,27?/m0/s1

Standard InChI Key:  MEFKEPWMEQBLKI-AIRLBKTGSA-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: 398.45

Molecular Weight (Monoisotopic): 398.1372

AlogP: -3.26

#Rotatable Bonds: 7

Polar Surface Area: 185.46

Molecular Species: ZWITTERION

HBA: 11

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.71

CX Basic pKa: 9.41

CX LogP: -5.32

CX LogD: -5.32

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.34

Np Likeness Score: 0.91

References

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7. Hermann JC, Marti-Arbona R, Fedorov AA, Fedorov E, Almo SC, Shoichet BK, Raushel FM..  (2007)  Structure-based activity prediction for an enzyme of unknown function.,  448  (7155): [PMID:17603473] [10.1038/nature05981]

8. Dowden J, Hong W, Parry RV, Pike RA, Ward SG..  (2010)  Toward the development of potent and selective bisubstrate inhibitors of protein arginine methyltransferases.,  20  (7): [PMID:20219369] [10.1016/j.bmcl.2010.02.069]

9. Eustáquio AS, Pojer F, Noel JP, Moore BS..  (2008)  Discovery and characterization of a marine bacterial SAM-dependent chlorinase.,  4  (1): [PMID:18059261] [10.1038/nchembio.2007.56]

10. PubChem BioAssay data set, 

11. Ham YW, Humphreys DJ, Choi S, Dayton DL..  (2011)  Rational design of SAM analogues targeting SAM-II riboswitch aptamer.,  21  (17): [PMID:21531555] [10.1016/j.bmcl.2011.04.033]

12. Li J, Wei H, Zhou MM..  (2011)  Structure-guided design of a methyl donor cofactor that controls a viral histone H3 lysine 27 methyltransferase activity.,  54  (21): [PMID:21958314] [10.1021/jm201000j]

13. Joce C, White R, Stockley PG, Warriner S, Turnbull WB, Nelson A..  (2012)  Design, synthesis and in vitro evaluation of novel bivalent S-adenosylmethionine analogues.,  22  (1): [PMID:22137339] [10.1016/j.bmcl.2011.11.017]

14. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

15. Borchardt RT, Wu YS, Wu BS..  (1978)  Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 7. Role of the ribosyl moiety in enzymatic binding of S-adenosyl-L-homocysteine and S-adenosyl-L-methionine.,  21  (12): [PMID:722739] [10.1021/jm00210a026]

16. 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]

17. Iyamu ID, Huang R..  (2021)  Mechanisms and inhibitors of nicotinamide N-methyltransferase.,  12  (8.0): [PMID:34458733] [10.1039/D1MD00016K]

18. 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(3):

• Scientific Literature
• PubChem BioAssays
• Fraunhofer HDAC6