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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: Neopolyoxin c, Nikkomycin, 59456-70-1, 9z22c3qqcj, Chembl35306, Chebi:623918

Molecular Formula

C₂₀H₂₅N₅O₁₀

Molecular Weight

495.4 g/mol

InChI Key

WWJFFVUVFNBJTN-VHDFTHOZSA-N

FDA UNII

9Z22C3QQCJ

Nikkomycin Z has been used in trials studying the treatment and basic science of Coccidioidomycosis.

1 2D Structure

Nikkomycin z

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-[[(2S,3S,4S)-2-amino-4-hydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutanoyl]amino]-2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid

2.1.2 InChI

InChI=1S/C20H25N5O10/c1-7(13(28)9-3-2-8(26)6-22-9)11(21)17(31)24-12(19(32)33)16-14(29)15(30)18(35-16)25-5-4-10(27)23-20(25)34/h2-7,11-16,18,26,28-30H,21H2,1H3,(H,24,31)(H,32,33)(H,23,27,34)/t7-,11-,12-,13-,14-,15+,16+,18+/m0/s1

2.1.3 InChI Key

WWJFFVUVFNBJTN-VHDFTHOZSA-N

2.1.4 Canonical SMILES

CC(C(C1=NC=C(C=C1)O)O)C(C(=O)NC(C2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)C(=O)O)N

2.1.5 Isomeric SMILES

C[C@H]([C@@H](C1=NC=C(C=C1)O)O)[C@@H](C(=O)N[C@@H]([C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)C(=O)O)N

2.2 Other Identifiers

2.2.1 UNII

9Z22C3QQCJ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Neopolyoxin C

2. Nikkomycin

2.3.2 Depositor-Supplied Synonyms

1. Neopolyoxin C

2. Nikkomycin

3. 59456-70-1

4. 9z22c3qqcj

5. Chembl35306

6. Chebi:623918

7. (2s)-2-[[(2s,3s,4s)-2-amino-4-hydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutanoyl]amino]-2-[(2r,3s,4r,5r)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic Acid

8. (2r)-2-[[(2s,3s,4s)-2-amino-4-hydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutanoyl]amino]-2-[(2r,3s,4r,5r)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic Acid

9. (2s)-{[(2s,3s,4s)-2-amino-4-hydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutanoyl]amino}-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-beta-d-allo-furanuronic Acid

10. (2s)-{[(2s,3s,4s)-2-amino-4-hydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutanoyl]amino}[(2r,3s,4r,5r)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-3,4-dihydroxyoxolan-2-yl]acetic Acid (non-preferred Name)

11. (2s)-{[(2s,3s,4s)-2-amino-4-hydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutanoyl]amino}[(2r,3s,4r,5r)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]acetic Acid

12. .beta.-d-allofuranuronic Acid, 5-[[(2s,3s,4s)-2-amino-4-hydroxy-4-(5-hydroxy-2-pyridinyl)-3-methyl-1-oxobutyl]amino]-1,5-dideoxy-1-(3,4-dihydro-2,4-dioxo-1(2h)-pyrimidinyl)-

13. Unii-9z22c3qqcj

14. Nikkomicin

15. Nikkomycin Z From Streptomyces Tendae

16. Nsc-601906

17. .beta.-d-allofuranuronic Acid, 5-(((2s,3s,4s)-2-amino-4-hydroxy-4-(5-hydroxy-2-pyridinyl)-3-methyl-1-oxobutyl)amino)-1,5-dideoxy-1-(3,4-dihydro-2,4-dioxo-1(2h)-pyrimidinyl)-

18. Bgi

19. Nsc 601906

20. Brn 0873216

21. Bdbm50089541

22. Db12939

23. Hy-19593

24. Cs-0015875

25. Q61718271

26. (2s)-2-[[(2s,3s,4s)-2-amino-4-hydroxy-4-(5-hydroxy-2-pyridyl)-3-methyl-butanoyl]amino]-2-[(2r,3s,4r,5r)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]acetic Acid

27. (r)-[(s)-(2s,3s,4s)-2-amino-4-hydroxy-4-(5-hydroxy-pyridin-2-yl)-3-methyl-butyrylamino]-[(3s,4r,5r)-5-(2,4-dioxo-3,4-dihydro-2h-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic Acid

28. (s)-[(2r,3r,4r)-2-amino-4-hydroxy-4-(5-hydroxy-pyridin-2-yl)-3-methyl-butyrylamino]-[(s)-5-(2,4-dioxo-3,4-dihydro-2h-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic Acid

29. (s)-[(2s,3s,4s)-2-amino-4-hydroxy-4-(5-hydroxy-pyridin-2-yl)-3-methyl-butyrylamino]-[(2r,3r,5r)-5-(2,4-dioxo-3,4-dihydro-2h-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic Acid

30. (s)-[(2s,3s,4s)-2-amino-4-hydroxy-4-(5-hydroxy-pyridin-2-yl)-3-methyl-butyrylamino]-[5-(2,4-dioxo-3,4-dihydro-2h-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic Acid

31. (s)-2-((2s,3s,4s)-2-amino-4-hydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutanamido)-2-((2r,3s,4r,5r)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl)acetic Acid

32. [(s)-(2s,3s,4s)-2-amino-4-hydroxy-4-(5-hydroxy-pyridin-2-yl)-3-methyl-butyrylamino]-[(2r,3s,4r,5r)-5-(2,4-dioxo-3,4-dihydro-2h-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic Acid

33. [(s)-2-amino-4-hydroxy-4-((1s,2s)-5-hydroxy-pyridin-2-yl)-3-methyl-butyrylamino]-[5-(2,4-dioxo-3,4-dihydro-2h-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic Acid

34. [2-amino-4-hydroxy-4-(5-hydroxy-pyridin-2-yl)-3-methyl-butyrylamino]-[5-(2,4-dioxo-3,4-dihydro-2h-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic Acid(nikkomycin Z)

35. Beta-d-allofuranuronic Acid, 5-((2-amino-4-hydroxy-4-(5-hydroxy-2-pyridinyl)-3-methyl-1-oxobutyl)amino)-1,5-dideoxy-1-(3,4-dihydro-2,4-dioxo-1(2h)-pyrimidinyl)-, (2s-(2r*,3r*,4r*))-

36. Nz

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₅N₅O₁₀
Molecular Weight	495.4 g/mol
XLogP3	-5.6
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	8
Exact Mass	495.16014201 g/mol
Monoisotopic Mass	495.16014201 g/mol
Topological Polar Surface Area	245 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	871
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

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