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InChI=1S/CH4O/c1-2/h2H,1H3
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ChEBI
> Main
CHEBI:623918 - nikkomycin Z
Main
ChEBI Ontology
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ChEBI Name
nikkomycin Z
ChEBI ID
CHEBI:623918
Definition
A uridine-based nucleoside-peptide antibiotic which inhibits fungal chitin biosynthesis by inhibiting chitin synthase.
Stars
This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs
CHEBI:109145, CHEBI:621961
Supplier Information
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Formula
C20H25N5O10
Net Charge
0
Average Mass
495.44000
Monoisotopic Mass
495.16014
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
InChIKey
WWJFFVUVFNBJTN-VHDFTHOZSA-N
SMILES
[H]
[C@@]
1(O[C@H]
([C@H]
(O)
[C@@H]
1O)
n1ccc(=O)
[nH]
c1=O)
[C@H]
(NC(=O)
[C@@H]
(N)
[C@H]
(C)
[C@H]
(O)
c1ccc(O)
cn1)
C(O)
=O
Roles Classification
Biological Role
(s):
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
nucleoside antibiotic
(via
nikkomycin
)
EC 2.4.1.16 (chitin synthase) inhibitor
A EC 2.4.1.* (hexosyltransferase) inhibitor that inhibits the action of chitin synthase (EC 2.4.1.16).
(via
nikkomycin
)
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
nikkomycin Z (
CHEBI:623918
)
has functional parent
uridine (
CHEBI:16704
)
nikkomycin Z (
CHEBI:623918
)
has role
antifungal agent (
CHEBI:35718
)
nikkomycin Z (
CHEBI:623918
)
is a
nikkomycin (
CHEBI:59668
)
Synonyms
Sources
(2
S
)-
{[(2
S
,3
S
,4
S
)-
2-
amino-
4-
hydroxy-
4-
(5-
hydroxypyridin-
2-
yl)-
3-
methylbutanoyl]amino}-
5-
(2,4-
dioxo-
3,4-
dihydropyrimidin-
1(2
H
)-
yl)-
β-
D
-
allo
-
furanuronic acid
ChEBI
(2
S
)-
{[(2
S
,3
S
,4
S
)-
2-
amino-
4-
hydroxy-
4-
(5-
hydroxypyridin-
2-
yl)-
3-
methylbutanoyl]amino}[(2
R
,3
S
,4
R
,5
R
)-
5-
(2,4-
dioxo-
3,4-
dihydropyrimidin-
1(2
H
)-
yl)-
3,4-
dihydroxytetrahydrofuran-
2-
yl]acetic acid
ChEBI
Neopolyoxin C
ChemIDplus
Nikkomycin
ChemIDplus
Registry Numbers
Types
Sources
4303204
Reaxys Registry Number
Reaxys
59456-70-1
CAS Registry Number
ChemIDplus
Citations
Types
Sources
10888330
PubMed citation
ChEMBL
12205060
PubMed citation
Europe PMC
12729648
PubMed citation
ChEMBL
1992114
PubMed citation
ChEMBL
19930628
PubMed citation
Europe PMC
20931236
PubMed citation
Europe PMC
22203603
PubMed citation
Europe PMC
Last Modified
16 April 2012