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BGC0002430NRPS

Gausemycin A;Gausemycin B

Producing organism
Streptomyces kanamyceticus
Taxonomy
Bacteria›Actinomycetota›Actinomycetes›Kitasatosporales›Streptomycetaceae›Streptomyces
Biosynthetic class
NRPS (Type I);saccharide (None)
Total steps
35
DOI
MIBiG entry
View on MIBiG ↗
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Gene Cluster Map68 genes · 121,518 bp

20 kb121.5 kb visible · 121,518 bp total
Biosynthetic (core)
Biosynthetic (additional)
Regulatory
Transport
Unknown
Domains
KRKetoreductase (KR)
ACPAcyl carrier (ACP)
CCondensation (C)
AAdenylation (A)
PCPPeptidyl carrier (PCP)
ACPAcyl carrier (ACP)
CnCOM N-term
TEThioesterase (TE)
EEpimerization (E)
CALCoA-ligase (CAL)
AmTAminotransferase I/II
TauDTauD oxygenase
NADNAD-binding
TgrTIGR01720

Pathway Graphsteps arranged in biosynthetic order

35 steps · 34 edges
Step 1
Start
+Phenylalanine
Step 9
Start
+Tryptophan
Step 13
orf19;orf22
+6-methylheptanoic…
Step 30
Start
Step 2
orf26
Step 10
orf44, orf33
Step 14
orf20, orf21
Step 31
orf7, (orf2/orf6/orf55)
Step 3
orf16
Step 11
orf43
Step 15M1
gauA
+β-alanine
Step 32
orf10
Step 4
orf14, orf15
Step 12
orf42
Step 16M2
gauA
+Ornithine
Step 33
orf66
Step 5
orf13
Step 6
?
Step 7
orf26
Step 8
orf24
Step 17M3
gauA
Step 18M4
gauA, (orf25/orf41)
+Glutamic acid
Step 19M5
gauA
+Tyrosine
Step 20M6
gauA
Trans-AT
Step 21M7
gauA
+D-Leucine
Step 22M8
gauC
+Asparagine
Step 23M9
gauC
+Glycine
Step 24M10
gauC
+Serine
Step 25M11
gauC
+Glycine
Step 26M12
gauC
Step 27M13
gauC
+Alanine
Step 28M14
gauD
+Proline
Step 29TE
gauD
Step 34
orf17
Step 35
?
+2430(1), ?
Starting stepIntermediateFinal product│ModuleLoadingTENo module│PKS stepNRPS stepTailoring/otherScroll to pan · Wheel to zoom

Biosynthetic Reactions35 steps

StepProduct IDEnzymeModuleSubstrateProduct SMILESNotes
12430-1Start—
Phenylalanine
N[C@H](C(O)=O)CC1=CC=CC=C1—
22430-2orf26—
2430-1
from: 2430-1
O=C(C(O)=O)CC1=CC=CC=C1—
32430-3orf16—
2430-2
from: 2430-2
OC([C@](O)(CC(O)=O)CC1=CC=CC=C1)=O—
42430-4orf14, orf15—
2430-3
from: 2430-3
OC(C(C(O)C(O)=O)CC1=CC=CC=C1)=O—
52430-5orf13—
2430-4
from: 2430-4
OC(C(C(C(O)=O)=O)CC1=CC=CC=C1)=O—
62430-6?—
2430-5
from: 2430-5
O=C(C(O)=O)CCC1=CC=CC=C1—
72430-7orf26—
2430-6
from: 2430-6
OC([C@@H](N)CCC1=CC=CC=C1)=O—
82430-8orf24—
2430-7
from: 2430-7
OC([C@@H](N)CC(O)C1=CC=CC=C1)=O—
92430-9Start—
Tryptophan
N[C@H](C(O)=O)CC1=CNC2=C1C=CC=C2—
102430-10orf44, orf33—
2430-9
from: 2430-9
N[C@H](C(O)=O)CC1=CNC2=C1C=CC(Cl)=C2—
112430-11orf43—
2430-10
from: 2430-10
N[C@H](C(O)=O)CC(C1=C(NC=O)C=C(Cl)C=C1)=O—
122430-12orf42—
2430-11
from: 2430-11
N[C@H](C(O)=O)CC(C1=C(N)C=C(Cl)C=C1)=O—
132430-13orf19;orf22—
6-methylheptanoic acid
O=C(CCCCC(C)C)O—
142430-14orf20, orf21—
2430-13
from: 2430-13
OC(/C=C\C=C\C(C)C)=O—
152430-15gauAM1
2430-14;β-alanine
from: 2430-14
OC(CCNC(/C=C\C=C\C(C)C)=O)=O—
162430-16gauAM2
2430-15;Ornithine
from: 2430-15
OC([C@H](CCCN)NC(CCNC(/C=C\C=C\C(C)C)=O)=O)=O—
172430-17gauAM3
2430-16;2430-8
from: 2430-16, 2430-8
OC(C(CC(O)C1=CC=CC=C1)NC([C@H](CCCN)NC(CCNC(/C=C\C=C\C(C)C)=O)=O)=O)=O—
182430-18gauA, (orf25/orf41)M4
2430-17;Glutamic acid
from: 2430-17
OC(C(C(CC(O)=O)O)NC(C(CC(O)C1=CC=CC=C1)NC([C@H](CCCN)NC(CCNC(/C=C\C=C\C(C)C)=O)=O)=O)=O)=O—
192430-19gauAM5
2430-18;Tyrosine
from: 2430-18
OC([C@H](CC1=CC=C(O)C=C1)NC(C(C(CC(O)=O)O)NC(C(CC(O)C2=CC=CC=C2)NC([C@H](CCCN)NC(CCNC(/C=C\C=C\C(C)C)=O)=O)=O)=O)=O)=O—
202430-20gauAM6
2430-19
from: 2430-19
OC(C(C(N)C)NC([C@H](CC1=CC=C(O)C=C1)NC(C(C(CC(O)=O)O)NC(C(CC(O)C2=CC=CC=C2)NC([C@H](CCCN)NC(CCNC(/C=C\C=C\C(C)C)=O)=O)=O)=O)=O)=O)=O{'transAT': ['guaB', '2,3-di…
212430-21gauAM7
2430-20;D-Leucine
from: 2430-20
OC([C@@H](CC(C)C)NC(C(C(N)C)NC([C@H](CC1=CC=C(O)C=C1)NC(C(C(CC(O)=O)O)NC(C(CC(O)C2=CC=CC=C2)NC([C@H](CCCN)NC(CCNC(/C=C\C=C\C(C)C)=O)=O)=O)=O)=O)=O)=O)=O—
222430-22gauCM8
2430-21;Asparagine
from: 2430-21
OC([C@H](CC(O)=O)NC([C@@H](CC(C)C)NC(C(C(N)C)NC([C@H](CC1=CC=C(O)C=C1)NC(C(C(CC(O)=O)O)NC(C(CC(O)C2=CC=CC=C2)NC([C@H](CCCN)NC(CCNC(/C=C\C=C\C(C)C)=O)=O)=O)=O)=O)=O)=O)=O)=O—
232430-23gauCM9
2430-22;Glycine
from: 2430-22
OC(CNC([C@H](CC(O)=O)NC([C@@H](CC(C)C)NC(C(C(N)C)NC([C@H](CC1=CC=C(O)C=C1)NC(C(C(CC(O)=O)O)NC(C(CC(O)C2=CC=CC=C2)NC([C@H](CCCN)NC(CCNC(/C=C\C=C\C(C)C)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O—
242430-24gauCM10
2430-23;Serine
from: 2430-23
OC([C@H](CO)NC(CNC([C@H](CC(O)=O)NC([C@@H](CC(C)C)NC(C(C(N)C)NC([C@H](CC1=CC=C(O)C=C1)NC(C(C(CC(O)=O)O)NC(C(CC(O)C2=CC=CC=C2)NC([C@H](CCCN)NC(CCNC(/C=C\C=C\C(C)C)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O—
252430-25gauCM11
2430-24;Glycine
from: 2430-24
OC(CNC([C@H](CO)NC(CNC([C@H](CC(O)=O)NC([C@@H](CC(C)C)NC(C(C(N)C)NC([C@H](CC1=CC=C(O)C=C1)NC(C(C(CC(O)=O)O)NC(C(CC(O)C2=CC=CC=C2)NC([C@H](CCCN)NC(CCNC(/C=C\C=C\C(C)C)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O—
262430-26gauCM12
2430-25;2430-12
from: 2430-25, 2430-12
OC([C@H](CC(C1=C(N)C=C(Cl)C=C1)=O)NC(CNC([C@H](CO)NC(CNC([C@H](CC(O)=O)NC([C@@H](CC(C)C)NC(C(C(N)C)NC([C@H](CC2=CC=C(O)C=C2)NC(C(C(CC(O)=O)O)NC(C(CC(O)C3=CC=CC=C3)NC([C@H](CCCN)NC(CCNC(/C=C\C=C\C(C)C)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O—
272430-27gauCM13
2430-26;Alanine
from: 2430-26
C[C@@H](C(O)=O)NC([C@H](CC(C1=C(N)C=C(Cl)C=C1)=O)NC(CNC([C@H](CO)NC(CNC([C@H](CC(O)=O)NC([C@@H](CC(C)C)NC(C(C(N)C)NC([C@H](CC2=CC=C(O)C=C2)NC(C(C(CC(O)=O)O)NC(C(CC(O)C3=CC=CC=C3)NC([C@H](CCCN)NC(CCNC(/C=C\C=C\C(C)C)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O—
282430-28gauDM14
2430-27;Proline
from: 2430-27
C[C@@H](C(N1CCC[C@H]1C(O)=O)=O)NC([C@H](CC(C2=C(N)C=C(Cl)C=C2)=O)NC(CNC([C@H](CO)NC(CNC([C@H](CC(O)=O)NC([C@@H](CC(C)C)NC(C(C(N)C)NC([C@H](CC3=CC=C(O)C=C3)NC(C(C(CC(O)=O)O)NC(C(CC(O)C4=CC=CC=C4)NC([C@H](CCCN)NC(CCNC(/C=C\C=C\C(C)C)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O—
292430-29gauDTE
2430-28
from: 2430-28
O=C(C(C(C)NC1=O)NC([C@H](CC2=CC=C(O)C=C2)NC(C(C(O)CC(O)=O)NC(C(CC(C3=CC=CC=C3)O)NC([C@H](CCCN)NC(CCNC(/C=C\C=C\C(C)C)=O)=O)=O)=O)=O)=O)N[C@H](CC(C)C)C(N[C@H](C(NCC(N[C@H](C(NCC(N[C@H](C(N[C@@H](C)C(N4CCC[C@H]41)=O)=O)CC(C5=CC=C(Cl)C=C5N)=O)=O)=O)CO)=O)=O)CC(O)=O)=O—
302430-30Start—
OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H]([R])O1—
312430-31orf7, (orf2/orf6/orf55)—
2430-30
from: 2430-30
OC([C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H]([R])O1)=O—
322430-32orf10—
2430-31
from: 2430-31
[R][C@@H]1[C@H](O)[C@@H](O)[C@H](O)CO1—
332430-33orf66—
2430-32
from: 2430-32
[R][C@@H]1[C@H](O)[C@@H](O)[C@@H](O)CO1—
342430(1)orf17—
2430-29;2430-33
from: 2430-29, 2430-33
O=C(C(C(C)NC1=O)NC([C@H](CC2=CC=C(O[C@@H]([C@@H]([C@H]3O)O)OC[C@@H]3O)C=C2)NC(C(C(O)CC(O)=O)NC(C(CC(C4=CC=CC=C4)O)NC([C@H](CCCN)NC(CCNC(/C=C\C=C\C(C)C)=O)=O)=O)=O)=O)=O)N[C@H](CC(C)C)C(N[C@H](C(NCC(N[C@H](C(NCC(N[C@H](C(N[C@@H](C)C(N5CCC[C@H]51)=O)=O)CC(C6=CC=C(Cl)C=C6N)=O)=O)=O)CO)=O)=O)CC(O)=O)=O—
352430(2)?—
2430(1);?
O=C(C(C(C)NC1=O)NC([C@H](CC2=CC=C(O[C@@H]([C@@H]([C@H]3O)O)OC[C@@H]3O)C=C2)NC(C(C(O)CC(O)=O)NC(C(CC(C4=CC=CC=C4)O)NC([C@H](CCCNC(CCN)=O)NC(CCNC(/C=C\C=C\C(C)C)=O)=O)=O)=O)=O)=O)N[C@H](CC(C)C)C(N[C@H](C(NCC(N[C@H](C(NCC(N[C@H](C(N[C@@H](C)C(N5CCC[C@H]51)=O)=O)CC(C6=CC=C(Cl)C=C6N)=O)=O)=O)CO)=O)=O)CC(O)=O)=O—
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