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Chemistry

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Also known as: Nafithromycin [inn], 75f74y2r70, 1691240-78-4, Wck 4873, Chembl4297519, Unii-75f74y2r70
Molecular Formula
C42H62N6O11S
Molecular Weight
859.0  g/mol
InChI Key
RLFCSBSRGRJFRO-QAOQTAGDSA-N
FDA UNII
75F74Y2R70

Nafithromycin
1 2D Structure

Nafithromycin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S,2R,5R,7R,8R,9R,11R,13R,14S,15R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-4,6,12,16-tetraoxo-N'-[(1S)-1-(5-pyridin-2-yl-1,3,4-thiadiazol-2-yl)ethoxy]-3,17-dioxabicyclo[12.3.0]heptadecane-15-carboximidamide
2.1.2 InChI
InChI=1S/C42H62N6O11S/c1-13-28-42(9)30(29(39(53)58-42)35(43)47-59-25(7)36-45-46-37(60-36)26-16-14-15-17-44-26)22(4)31(49)20(2)19-41(8,54-12)34(23(5)32(50)24(6)38(52)56-28)57-40-33(51)27(48(10)11)18-21(3)55-40/h14-17,20-25,27-30,33-34,40,51H,13,18-19H2,1-12H3,(H2,43,47)/t20-,21-,22-,23+,24-,25+,27+,28-,29-,30+,33-,34-,40+,41-,42-/m1/s1
2.1.3 InChI Key
RLFCSBSRGRJFRO-QAOQTAGDSA-N
2.1.4 Canonical SMILES
CCC1C2(C(C(C(=O)C(CC(C(C(C(=O)C(C(=O)O1)C)C)OC3C(C(CC(O3)C)N(C)C)O)(C)OC)C)C)C(C(=O)O2)C(=NOC(C)C4=NN=C(S4)C5=CC=CC=N5)N)C
2.1.5 Isomeric SMILES
CC[C@@H]1[C@@]2([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H](C(=O)[C@H](C(=O)O1)C)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)OC)C)C)[C@@H](C(=O)O2)/C(=N/O[C@@H](C)C4=NN=C(S4)C5=CC=CC=N5)/N)C
2.2 Other Identifiers
2.2.1 UNII
75F74Y2R70
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Wck 4873

2.3.2 Depositor-Supplied Synonyms

1. Nafithromycin [inn]

2. 75f74y2r70

3. 1691240-78-4

4. Wck 4873

5. Chembl4297519

6. Unii-75f74y2r70

7. (3r,31z,3as,4r,6r,8r,9r,10r,12r,15r,15as)-15-ethyl-8-methoxy-4,6,8,10,12,15a-hexamethyl-2,5,11,13-tetraoxo-n'-((1s)-1-(5-(pyridin-2-yl)-1,3,4-thiadiazol-2-yl)ethoxy)-9-((3,4,6-trideoxy-3-(dimethylamino)-.beta.-d-xylohexopyranosyl)oxy)tetradecahydro-2h-furo(2,3-c)oxacyclotetradecine-3-carboximidamide

8. (3r,31z,3as,4r,6r,8r,9r,10r,12r,15r,15as)-15-ethyl-8-methoxy-4,6,8,10,12,15a-hexamethyl-2,5,11,13-tetraoxo-n'-((1s)-1-(5-(pyridin-2-yl)-1,3,4-thiadiazol-2-yl)ethoxy)-9-((3,4,6-trideoxy-3-(dimethylamino)-beta-d-xylohexopyranosyl)oxy)tetradecahydro-2

9. 2h-furo(2,3-c)oxacyclotetradecin-3-carboximidamide, 15-ethyltetradecahydro-8-methoxy-4,6,8,10,12,15a-hexamethyl-2,5,11,13-tetraoxo-n'-((1s)-1-(5-(2-pyridinyl)-1,3,4-thiadiazol-2-yl)ethoxy)-9-((3,4,6-trideoxy-3-(dimethylamino)-.beta.-d-xylo-hexopyranosyl)oxy)-, (c(z),3r,3as,4r,6r,8r,9r,10r,12r,15r,15as)-

10. 2h-furo(2,3-c)oxacyclotetradecin-3-carboximidamide, 15-ethyltetradecahydro-8-methoxy-4,6,8,10,12,15a-hexamethyl-2,5,11,13-tetraoxo-n'-((1s)-1-(5-(2-pyridinyl)-1,3,4-thiadiazol-2-yl)ethoxy)-9-((3,4,6-trideoxy-3-(dimethylamino)-beta-d-xylo-hexopyrano

2.4 Create Date
2016-02-16
3 Chemical and Physical Properties
Molecular Weight 859.0 g/mol
Molecular Formula C42H62N6O11S
XLogP34.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count17
Rotatable Bond Count10
Exact Mass858.41972799 g/mol
Monoisotopic Mass858.41972799 g/mol
Topological Polar Surface Area252 Ų
Heavy Atom Count60
Formal Charge0
Complexity1580
Isotope Atom Count0
Defined Atom Stereocenter Count15
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


Protein Synthesis Inhibitors

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)


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