N-(1-Hydroxymethyl-2-methylsulfanylmethanesulfinyl-ethyl)-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acrylamide

ID: ALA2303630

Chembl Id: CHEMBL2303630

PubChem CID: 71718453

Max Phase: Phase

Molecular Formula: C13H19N3O5S2

Molecular Weight: 361.45

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Sparsomycin | NSC-59729 | U-19183 | SPARSOMYCIN|NSC-59729|CHEMBL2303630

Canonical SMILES:  CSC[S@@+]([O-])CC(CO)NC(=O)/C=C/c1c(C)[nH]c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C13H19N3O5S2/c1-8-10(12(19)16-13(20)14-8)3-4-11(18)15-9(5-17)6-23(21)7-22-2/h3-4,9,17H,5-7H2,1-2H3,(H,15,18)(H2,14,16,19,20)/b4-3+/t9?,23-/m0/s1

Standard InChI Key:  XKLZIVIOZDNKEQ-CKIHNWHUSA-N

Alternative Forms

1. Parent:

   

   ALA2303630

   SPARSOMYCIN

Molecule Features

Natural Product: No

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

Calculated Properties

Molecular Weight: 361.45

Molecular Weight (Monoisotopic): 361.0766

AlogP: -1.07

#Rotatable Bonds: 8

Polar Surface Area: 138.11

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.97

CX Basic pKa: ┄

CX LogP: -2.48

CX LogD: -2.49

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.34

Np Likeness Score: -0.40

References

1. Zemlicka J, Fernandez-Moyano MC, Ariatti M, Zurenko GE, Grady JE, Ballesta JP..  (1993)  Hybrids of antibiotics inhibiting protein synthesis. Synthesis and biological activity.,  36  (9): [PMID:8487260] [10.1021/jm00061a015]

2. Duke SS, Boots MR..  (1983)  Synthesis and biological evaluation of sparsomycin analogues.,  26  (11): [PMID:6415284] [10.1021/jm00365a003]

3. Santana L, González-Díaz H, Quezada E, Uriarte E, Yáñez M, Viña D, Orallo F..  (2008)  Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.,  51  (21): [PMID:18834112] [10.1021/jm800656v]

4. Zhou J, Bhattacharjee A, Chen S, Chen Y, Duffy E, Farmer J, Goldberg J, Hanselmann R, Ippolito JA, Lou R, Orbin A, Oyelere A, Salvino J, Springer D, Tran J, Wang D, Wu Y, Johnson G..  (2008)  Design at the atomic level: generation of novel hybrid biaryloxazolidinones as promising new antibiotics.,  18  (23): [PMID:18951792] [10.1016/j.bmcl.2008.10.014]

5. Schneider-Poetsch T, Ju J, Eyler DE, Dang Y, Bhat S, Merrick WC, Green R, Shen B, Liu JO..  (2010)  Inhibition of eukaryotic translation elongation by cycloheximide and lactimidomycin.,  6  (3): [PMID:20118940] [10.1038/nchembio.304]

6. Skripkin E, McConnell TS, DeVito J, Lawrence L, Ippolito JA, Duffy EM, Sutcliffe J, Franceschi F..  (2008)  R chi-01, a new family of oxazolidinones that overcome ribosome-based linezolid resistance.,  52  (10): [PMID:18663023] [10.1128/aac.01193-07]

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

8. Lee CK, Vince R..  (1978)  Effect of sparsomycin analogues on the puromycin-peptidyl transferase reaction on ribosomes.,  21  (2): [PMID:340693] [10.1021/jm00200a006]

9. Sala S, James PJC, Nealon GL, Fromont J, Gomez O, Vuong D, Lacey E, Flematti GR..  (2023)  Dendrillic Acids A and B: Nitrogenous, Rearranged Spongian Nor-Diterpenes from a Dendrilla sp. Marine Sponge.,  86  (3): [PMID:36926864] [10.1021/acs.jnatprod.2c01087]

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names