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BGC0000429NRPS

skyllamycin A;skyllamycin B

Producing organism
Streptomyces sp. Acta 2897
Taxonomy
Bacteria›Actinomycetota›Actinomycetes›Kitasatosporales›Streptomycetaceae›Streptomyces
Biosynthetic class
NRPS (Type I)
Total steps
21
DOI
MIBiG entry
View on MIBiG ↗
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C75H94N12O201482.67 Da

Gene Cluster Map49 genes · 86,806 bp

AA20 kb86.8 kb visible · 86,806 bp total
Biosynthetic (core)
Biosynthetic (additional)
Regulatory
Transport
Unknown
Domains
KSKetosynthase (KS)
ATAcyltransferase (AT)
KRKetoreductase (KR)
CCondensation (C)
AAdenylation (A)
PCPPeptidyl carrier (PCP)
ACPAcyl carrier (ACP)
CnCOM N-term
TEThioesterase (TE)
EEpimerization (E)
A-OXAdenylation-oxidase
TgrTIGR01720

Pathway Graphsteps arranged in biosynthetic order

21 steps · 19 edges
Step 1
?
+2,4,6,8,10-dodeca…
Step 4
start
+Glutamic acid
Step 6
start
+Tyrosine
Step 2
sky5,sky27
Step 5
sky40,sky41
Step 7
sky37
Step 3
sky4,sky28
Step 8M1
sky29
+Threonine
Step 9M2
sky29
+Alanine
Step 10M3
sky29
+(β-methyl-asparti…
Step 11M4
sky29
+Glycine
Step 12M5
sky30
+phenylalanine
Step 13M6
sky30
+Proline
Step 14M7
sky30
Step 15M8
sky30
+Tryptophan
Step 16M9
sky31
+Glycine
Step 17M10
sky31
+Leucine
Step 18M11
sky31
+β-hydroxyleucine
Step 19TE
sky31
Step 20TE
sky31
Step 21TE
sky31
Starting stepIntermediateFinal product│ModuleLoadingTENo module│PKS stepNRPS stepTailoring/otherScroll to pan · Wheel to zoom

Biosynthetic Reactions21 steps

StepProduct IDEnzymeModuleSubstrateProduct SMILESNotes
1429-1?—
2,4,6,8,10-dodecapentaenoic acid
C/C=C/C=C/C=C/C=C/C=C/C(O)=O—
2429-2sky5,sky27—
429-1
from: 429-1
O=C(CO)/C=C/C=C/C=C\C=C\C=C/C—
3429-3sky4,sky28—
429-2
from: 429-2
O=C(CO)/C=C/C1=CC=CC=C1/C=C\C—
4429-4start—
Glutamic acid
OC(CC[C@@H](C(O)=O)N)=O—
5429-5sky40,sky41—
429-4
from: 429-4
O=C(O)[C@H]([C@H](N)C(O)=O)C—
6429-6start—
Tyrosine
N[C@H](C(O)=O)CC1=CC=C(O)C=C1—
7429-7sky37—
429-6
from: 429-6
N[C@H](C(O)=O)CC1=CC=C(OC)C=C1—
8429-8sky29M1
429-3;Threonine
from: 429-3
OC([C@@H](NC(/C=C/C1=C(C=CC=C1)/C=C\C)=O)[C@H](O)C)=O—
9429-9sky29M2
429-8;Alanine
from: 429-8
OC([C@H](C)NC([C@@H](NC(/C=C/C1=C(C=CC=C1)/C=C\C)=O)[C@H](O)C)=O)=O—
10429-10sky29M3
429-9;(β-methyl-aspartic acid/Aspartic acid)
from: 429-9
OC([C@H]([C@H]([R])C(O)=O)NC([C@H](C)NC([C@@H](NC(/C=C/C1=C(C=CC=C1)/C=C\C)=O)[C@H](O)C)=O)=O)=O—
11429-11sky29M4
429-10;Glycine
from: 429-10
OC(CNC([C@H]([C@H]([R])C(O)=O)NC([C@H](C)NC([C@@H](NC(/C=C/C1=C(C=CC=C1)/C=C\C)=O)[C@H](O)C)=O)=O)=O)=O—
12429-12sky30M5
429-11;phenylalanine
from: 429-11
OC([C@H](CC1=CC=CC=C1)NC(CNC([C@H]([C@H]([R])C(O)=O)NC([C@H](C)NC([C@@H](NC(/C=C/C2=C(C=CC=C2)/C=C\C)=O)[C@H](O)C)=O)=O)=O)=O)=O—
13429-13sky30M6
429-12;Proline
from: 429-12
OC([C@H]1N(C([C@H](CC2=CC=CC=C2)NC(CNC([C@H]([C@H]([R])C(O)=O)NC([C@H](C)NC([C@@H](NC(/C=C/C3=C(C=CC=C3)/C=C\C)=O)[C@H](O)C)=O)=O)=O)=O)=O)CCC1)=O—
14429-14sky30M7
429-13;429-7
from: 429-13, 429-7
OC([C@@H](NC([C@H]1N(C([C@H](CC2=CC=CC=C2)NC(CNC([C@H]([C@H]([R])C(O)=O)NC([C@H](C)NC([C@@H](NC(/C=C/C3=C(C=CC=C3)/C=C\C)=O)[C@H](O)C)=O)=O)=O)=O)=O)CCC1)=O)CC4=CC=C(OC)C=C4)=O—
15429-15sky30M8
429-14;Tryptophan
from: 429-14
OC([C@H](NC([C@@H](NC([C@H]1N(C([C@H](CC2=CC=CC=C2)NC(CNC([C@H]([C@H]([R])C(O)=O)NC([C@H](C)NC([C@@H](NC(/C=C/C3=C(C=CC=C3)/C=C\C)=O)[C@H](O)C)=O)=O)=O)=O)=O)CCC1)=O)CC4=CC=C(OC)C=C4)=O)CC5=CNC6=C5C=CC=C6)=O—
16429-16sky31M9
429-15;Glycine
from: 429-15
OC(CNC([C@H](NC([C@@H](NC([C@H]1N(C([C@H](CC2=CC=CC=C2)NC(CNC([C@H]([C@H]([R])C(O)=O)NC([C@H](C)NC([C@@H](NC(/C=C/C3=C(C=CC=C3)/C=C\C)=O)[C@H](O)C)=O)=O)=O)=O)=O)CCC1)=O)CC4=CC=C(OC)C=C4)=O)CC5=CNC6=C5C=CC=C6)=O)=O—
17429-17sky31M10
429-16;Leucine
from: 429-16
OC([C@H](NC(CNC([C@H](NC([C@@H](NC([C@H]1N(C([C@H](CC2=CC=CC=C2)NC(CNC([C@H]([C@H]([R])C(O)=O)NC([C@H](C)NC([C@@H](NC(/C=C/C3=C(C=CC=C3)/C=C\C)=O)[C@H](O)C)=O)=O)=O)=O)=O)CCC1)=O)CC4=CC=C(OC)C=C4)=O)CC5=CNC6=C5C=CC=C6)=O)=O)CC(C)C)=O—
18429-18sky31M11
429-17;β-hydroxyleucine
from: 429-17
OC([C@H](NC([C@H](NC(CNC([C@H](NC([C@@H](NC([C@H]1N(C([C@H](CC2=CC=CC=C2)NC(CNC([C@H]([C@H]([R])C(O)=O)NC([C@H](C)NC([C@@H](NC(/C=C/C3=C(C=CC=C3)/C=C\C)=O)[C@H](O)C)=O)=O)=O)=O)=O)CCC1)=O)CC4=CC=C(OC)C=C4)=O)CC5=CNC6=C5C=CC=C6)=O)=O)CC(C)C)=O)CC(C)C)=O—
19429-19sky31TE
429-18
from: 429-18
C/C=C\C1=C(/C=C/C(N[C@@H]([C@H](OC([C@@H]([C@@H](O)C(C)C)NC([C@H](N2)CC(C)C)=O)=O)C)C(N[C@@H](C)C(NC([C@H]([R])C(O)=O)C(NCC(N[C@@H]([C@H](C3=CC=CC=C3)O)C(N4[C@H](C(N[C@H](C(N[C@H](CC5=CNC6=C5C=CC=C6)C(NC(O)C2=O)=O)=O)[C@@H](O)C7=CC=C(OC)C=C7)=O)CCC4)=O)=O)=O)=O)=O)=O)C=CC=C1—
20429(1)sky31TE
429-18
from: 429-18
C/C=C\C1=C(/C=C/C(N[C@@H]([C@H](OC([C@@H]([C@@H](O)C(C)C)NC([C@H](N2)CC(C)C)=O)=O)C)C(N[C@@H](C)C(NC([C@H](C)C(O)=O)C(NCC(N[C@@H]([C@H](C3=CC=CC=C3)O)C(N4[C@H](C(N[C@H](C(N[C@H](CC5=CNC6=C5C=CC=C6)C(NC(O)C2=O)=O)=O)[C@@H](O)C7=CC=C(OC)C=C7)=O)CCC4)=O)=O)=O)=O)=O)=O)C=CC=C1—
21429(2)sky31TE
429-18
from: 429-18
C/C=C\C1=C(/C=C/C(N[C@@H]([C@H](OC([C@@H]([C@@H](O)C(C)C)NC([C@H](N2)CC(C)C)=O)=O)C)C(N[C@@H](C)C(NC(C([H])C(O)=O)C(NCC(N[C@@H]([C@H](C3=CC=CC=C3)O)C(N4[C@H](C(N[C@H](C(N[C@H](CC5=CNC6=C5C=CC=C6)C(NC(O)C2=O)=O)=O)[C@@H](O)C7=CC=C(OC)C=C7)=O)CCC4)=O)=O)=O)=O)=O)=O)C=CC=C1—
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