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BGC0001452PKS

Sipanmycin

Producing organism
Streptomyces sp. CS149
Taxonomy
Bacteria›Actinomycetota›Actinomycetes›Kitasatosporales›Streptomycetaceae›Streptomyces
Biosynthetic class
PKS (Unknown)
Total steps
38
DOI
MIBiG entry
View on MIBiG ↗

Gene Cluster Map36 genes · 93,434 bp

KS20 kb93.4 kb visible · 93,434 bp total
Biosynthetic (core)
Biosynthetic (additional)
Regulatory
Transport
Unknown
Domains
KSKetosynthase (KS)
ATAcyltransferase (AT)
DHDehydratase (DH)
EREnoylreductase (ER)
KRKetoreductase (KR)
ACPAcyl carrier protein (ACP)
ACPAcyl carrier (ACP)
AAdenylation (A)
ACPAcyl carrier (ACP)
TEThioesterase (TE)
DnDocking N-term
DcDocking C-term
AmTAminotransferase I/II
NADNAD-binding

Pathway Graphsteps arranged in biosynthetic order

38 steps · 41 edges
Step 1
Start
+α-glutamic acid
Step 16
Start
+L-Valine/L-Isoleu…
Step 24
Start
+UDP-N-GlcNAc
Step 28
Start
+Glc-1-P
Step 2
sipL4
Step 17
?
Step 25
sipS2
Step 29
sipS7
Step 3
sipL3
Step 18
sipIB1
Step 26
sipS3
Step 30
sipS6
Step 4
sipL1;sipL6
Step 19
SipIB2
Step 27
sipS1
Step 31
sipS10
Step 5
sipL7
Step 20
?
Step 32
sipS11
Step 6Load
sipL2;sipP1
Step 21
sipIB3
Step 33
sipS5a
Step 7M1
sipP1
+Methylmalonyl-CoA
Step 34
sipS13
Step 8M2
sipP1
+Malonyl-CoA
Step 35
sipS8
Step 9M3
sipP2
+Methylmalonyl-CoA
Step 10M4
sipP2
+Malonyl-CoA
Step 11M5
sipP2
+Malonyl-CoA
Step 12M6
sipP4
+Methylmalonyl-CoA
Step 13M7
sipP3
+Malonyl-CoA
Step 14M8
sipP3
+Malonyl-CoA
Step 15M9
sipP3
+Methylmalonyl-CoA
Step 22M10
sipP3
Step 23TE
sipP3, (sipL5, sipO1)
Step 36
(sipS4, sipS15), (sipS1…
Step 37
(sipS4, sipS15), (sipS1…
Step 38
(sipS4, sipS15), (sipS1…
Starting stepIntermediateFinal product│ModuleLoadingTENo module│PKS stepNRPS stepTailoring/otherScroll to pan · Wheel to zoom

Biosynthetic Reactions38 steps

StepProduct IDEnzymeModuleSubstrateProduct SMILESNotes
11452-1Start—
α-glutamic acid
O=C([C@@H](CCC(O)=O)N)O—
21452-2sipL4—
1452-1
from: 1452-1
O=C(CC(N)CC(O)=O)O—
31452-3sipL3—
1452-2
from: 1452-2
C[C@@H](N)CC(O)=O—
41452-4sipL1;sipL6—
1452-3
from: 1452-3
C[C@@H](N)CC(O)=O—
51452-5sipL7—
1452-4
from: 1452-4
C[C@@H](NC([R])=O)CC(O)=O—
61452-6sipL2;sipP1Loading
1452-5
from: 1452-5
O=C(C[C@H](C)NC([R])=O)O—
71452-7sipP1M1
1452-6;Methylmalonyl-CoA
from: 1452-6
C[C@H](NC([R])=O)C/C=C(C)/C(O)=O—
81452-8sipP1M2
1452-7;Malonyl-CoA
from: 1452-7
C[C@H](NC([R])=O)C/C=C(C)/C=C/C(O)=O—
91452-9sipP2M3
1452-8;Methylmalonyl-CoA
from: 1452-8
C[C@H](NC([R])=O)C/C=C(C)/C=C/C=C(C)/C(O)=O—
101452-10sipP2M4
1452-9;Malonyl-CoA
from: 1452-9
C[C@H](NC([R])=O)C/C=C(C)/C=C/C=C(C)/C=C/C(O)=O—
111452-11sipP2M5
1452-10;Malonyl-CoA
from: 1452-10
C[C@H](NC([R])=O)C/C=C(C)/C=C/C=C(C)/C=C/C=C\C(O)=O—
121452-12sipP4M6
1452-11;Methylmalonyl-CoA
from: 1452-11
C[C@H](NC([R])=O)C/C=C(C)/C=C/C=C(C)/C=C/C=C\[C@H](O)[C@@H](C)C(O)=O—
131452-13sipP3M7
1452-12;Malonyl-CoA
from: 1452-12
C[C@H](NC([R])=O)C/C=C(C)/C=C/C=C(C)/C=C/C=C\[C@H](O)[C@@H](C)/C=C/C(O)=O—
141452-14sipP3M8
1452-13;Malonyl-CoA
from: 1452-13
C[C@H](NC([R])=O)C/C=C(C)/C=C/C=C(C)/C=C/C=C\[C@H](O)[C@@H](C)/C=C/C=C/C(O)=O—
151452-15sipP3M9
1452-14;Methylmalonyl-CoA
from: 1452-14
C[C@H](NC([R])=O)C/C=C(C)/C=C/C=C(C)/C=C/C=C\[C@H](O)[C@@H](C)/C=C/C=C/C=C(C)/C(O)=O—
161452-16Start—
L-Valine/L-Isoleucine
[R*]C[C@H](C)[C@H](N)C(O)=O—
171452-17?—
1452-16
from: 1452-16
[R*]C[C@H](C)C([R])=O—
181452-18sipIB1—
1452-17
from: 1452-17
[R*]C[C@H](C)C(CC([R])=O)=O—
191452-19SipIB2—
1452-18
from: 1452-18
[R*]C[C@H](C)[C@@H](O)CC([R])=O—
201452-20?—
1452-19
from: 1452-19
[R*]C[C@H](C)/C=C/C([R])=O—
211452-21sipIB3—
1452-20
from: 1452-20
[R*]C[C@H](C)CC(C(O)=O)C([R])=O—
221452-22sipP3M10
1452-15;1452-21
from: 1452-15, 1452-21
C[C@H](NC([R])=O)C/C=C(C)/C=C/C=C(C)/C=C/C=C\[C@H](O)[C@@H](C)/C=C/C=C/C=C(C)/C=C(C[C@@H](C)C[R*])/C(O)=O—
231452-23sipP3, (sipL5, sipO1)TE
1452-22
from: 1452-22
CC(/C=C/C=C\[C@H](O)[C@@](O)(C)/C=C/C=C/C=C(C)/C=C1\C[C@@H](C)C[R])=C\C=C\C(C)=C\C[C@H](C)NC1=O—
241452-24Start—
UDP-N-GlcNAc
O[C@H]1[C@H](O)[C@@H](NC(C)=O)[C@@H]([R])O[C@@H]1CO—
251452-25sipS2—
1452-24
from: 1452-24
O[C@H]1[C@H](O)[C@@H](NC(C)=O)[C@@H]([R])O[C@@H]1C(O)=O—
261452-26sipS3—
1452-25
from: 1452-25
O[C@H]1[C@H](O)[C@@H](NC(C)=O)[C@@H]([R])OC1—
271452-27sipS1—
1452-26
from: 1452-26
O[C@H]1[C@H](O)[C@@H](N)[C@@H]([R])OC1—
281452-28Start—
Glc-1-P
O[C@H]1[C@H](O)[C@@H](O)[C@@H]([R])O[C@@H]1CO—
291452-29sipS7—
1452-28
from: 1452-28
O[C@H]1[C@H](O)[C@@H](O)[C@@H]([R])O[C@@H]1CO—
301452-30sipS6—
1452-29
from: 1452-29
O[C@H]([C@@H](O)[C@@H]([R])O[C@@H]1C)C1=O—
311452-31sipS10—
1452-30
from: 1452-30
C[C@H]1O[C@H]([R])CC(C1=O)=O—
321452-32sipS11—
1452-31
from: 1452-31
C[C@H]1O[C@H]([R])C[C@@H](O)C1=O—
331452-33sipS5a—
1452-32
from: 1452-32
C[C@H]1O[C@H]([R])C[C@@H](O)[C@@H]1N—
341452-34sipS13—
1452-33
from: 1452-33
C[C@H]1O[C@H]([R])C[C@@H](O)[C@@H]1N(C)C—
351452-35sipS8—
1452-34
from: 1452-34
C[C@H]1O[C@H]([R])C[C@](O)(C)[C@@H]1N(C)C—
361452-36(sipS4, sipS15), (sipS14, sipS9, sipO2)—
1452-23;1452-27;1452-35
from: 1452-23, 1452-27, 1452-35
CC(/C=C/C=C\[C@H](O[C@H]1[C@H](N)[C@@H](O)[C@H](O[C@H]2C[C@](O)(C)[C@H](N(C)C)[C@@H](C)O2)CO1)[C@@](O)(C)/C=C/C=C/C=C(C)/C=C3\C[C@@H](C)C[R])=C\C=C\C(C)=C\C[C@H](C)NC3=O—
371452(1)(sipS4, sipS15), (sipS14, sipS9, sipO2)—
1452-23;1452-27;1452-35
from: 1452-23, 1452-27, 1452-35
CC(/C=C/C=C\[C@H](O[C@H]1[C@H](N)[C@@H](O)[C@H](O[C@H]2C[C@](O)(C)[C@H](N(C)C)[C@@H](C)O2)CO1)[C@@](O)(C)/C=C/C=C/C=C(C)/C=C3\CC(C)C[H])=C\C=C\C(C)=C\C[C@H](C)NC3=O—
381452(2)(sipS4, sipS15), (sipS14, sipS9, sipO2)—
1452-23;1452-27;1452-35
from: 1452-23, 1452-27, 1452-35
CC(/C=C/C=C\[C@H](O[C@H]1[C@H](N)[C@@H](O)[C@H](O[C@H]2C[C@](O)(C)[C@H](N(C)C)[C@@H](C)O2)CO1)[C@@](O)(C)/C=C/C=C/C=C(C)/C=C3\C[C@@H](C)CC)=C\C=C\C(C)=C\C[C@H](C)NC3=O—
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