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BGC0000021PKS

Apoptolidin

Producing organism
Amycolatopsis sp. FU40
Taxonomy
Bacteria›Actinomycetota›Actinomycetes›Pseudonocardiales›Pseudonocardiaceae›Amycolatopsis
Biosynthetic class
PKS (Unknown)
Total steps
31
DOI
MIBiG entry
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apoptolidin
C58H96O211128.64 Da

Gene Cluster Map39 genes · 115,746 bp

20 kb115.7 kb visible · 115,746 bp total
Biosynthetic (core)
Biosynthetic (additional)
Regulatory
Unknown
Domains
KSKetosynthase (KS)
ATAcyltransferase (AT)
DHDehydratase (DH)
EREnoylreductase (ER)
KRKetoreductase (KR)
ACPAcyl carrier protein (ACP)
ACPAcyl carrier (ACP)
TEThioesterase (TE)
DnDocking N-term
DcDocking C-term
FkFkbH-like
MTMethyltransferase
NADNAD-binding

Pathway Graphsteps arranged in biosynthetic order

31 steps · 32 edges
Step 1
Start
+1,3-BPG
Step 21
Start
+4-O-L-methyl-L-rh…
Step 2
apoE;apoJ
Step 23
(apoH3;apoH4), apoM1
Step 24
apoH1
Step 3
apoK
Step 25
apoH2
Step 26
apoH3;apoH4
Step 27
apoM2
Step 4
apoI
Step 28
?
Step 29
apoH3;apoH4
Step 5
apoM2
Step 6Load
apoS1
Inactive: KR
Step 7M1
apoS1
+Malonyl-CoA
Inactive: DH
Step 8M2
apoS1
+Methylmalonyl-CoA
Step 9M3
apoS1
+Methylmalonyl-CoA
Step 10M4
apoS2
+Malonyl-CoA
Inactive: DH, KR
Step 11M5
apoS3;apoS4
+Malonyl-CoA
Step 12M6
apoS5
+Malonyl-CoA
Step 13M7
apoS5
+Malonyl-CoA
Step 14M8
apoS5
+Methylmalonyl-CoA
Step 15M9
apoS6
+Malonyl-CoA
Step 16M10
apoS6
+Methylmalonyl-CoA
Step 17M11
apoS7
+Methylmalonyl-CoA
Step 18M12
apoS7
+Methylmalonyl-CoA
Step 19M13
apoS8
+Methylmalonyl-CoA
Step 20TE
apoS8
Step 22
?
Step 30
apoGT1;apoGT3
Step 31
(apoM1;apoM3;apoM4), (a…
Starting stepIntermediateFinal product│ModuleLoadingTENo module│PKS stepNRPS stepTailoring/otherScroll to pan · Wheel to zoom

Biosynthetic Reactions31 steps

StepProduct IDEnzymeModuleSubstrateProduct SMILESNotes
121-1Start—
1,3-BPG
OP([O-])(OC([C@H](O)COP(O)([O-])=O)=O)=O—
221-2apoE;apoJ—
21-1
from: 21-1
O=C(O)[C@H](O)CO—
321-3apoK—
21-2
from: 21-2
O=C(O)[C@H](O)C([H])=O—
421-4apoI—
21-3
from: 21-3
O=C(O)[C@H](O)C([O-])=O—
521-5apoM2—
21-4
from: 21-4
O=C(O)[C@H](OC)C([O-])=O—
621-6apoS1Loading
21-5
from: 21-5
O=C(O)COC{'Inactive': ['KR']}
721-7apoS1M1
21-6;Malonyl-CoA
from: 21-6
COC[C@H](O)CC(O)=O{'Inactive': ['DH']}
821-8apoS1M2
21-7;Methylmalonyl-CoA
from: 21-7
O[C@H](C[C@@H](O)[C@H](C)C(O)=O)C[O]—
921-9apoS1M3
21-8;Methylmalonyl-CoA
from: 21-8
O[C@H](C[C@@H](O)[C@H](C)[C@H](O)[C@H](C(O)=O)C)COC—
1021-10apoS2M4
21-9;Malonyl-CoA
from: 21-9
O[C@H](C[C@@H](O)[C@H](C)[C@H](O)[C@H](C(CC(O)=O)=O)C)COC{'Inactive': ['DH', 'KR']}
1121-11apoS3;apoS4M5
21-10;Malonyl-CoA
from: 21-10
O[C@H](C[C@@H](O)[C@H](C)[C@H](O)[C@H](C(C[C@@H](O)CC(O)=O)=O)C)COC—
1221-12apoS5M6
21-11;Malonyl-CoA
from: 21-11
O[C@H](C[C@@H](O)[C@H](C)[C@H](O)[C@H](C(C[C@@H](O)C[C@H](O)CC(O)=O)=O)C)C[O]—
1321-13apoS5M7
21-12;Malonyl-CoA
from: 21-12
O[C@H](C[C@@H](O)[C@H](C)[C@H](O)[C@H](C(C[C@@H](O)C[C@H](O)CCCC(O)=O)=O)C)COC—
1421-14apoS5M8
21-13;Methylmalonyl-CoA
from: 21-13
O[C@H](C[C@@H](O)[C@H](C)[C@H](O)[C@H](C(C[C@@H](O)C[C@H](O)CCC/C=C(C)/C(O)=O)=O)C)COC—
1521-15apoS6M9
21-14;Malonyl-CoA
from: 21-14
O[C@H](C[C@@H](O)[C@H](C)[C@H](O)[C@H](C(C[C@@H](O)C[C@H](O)CCC/C=C(C)/C=C/C(O)=O)=O)C)COC—
1621-16apoS6M10
21-15;Methylmalonyl-CoA
from: 21-15
O[C@H](C[C@@H](O)[C@H](C)[C@H](O)[C@H](C(C[C@@H](O)C[C@H](O)CCC/C=C(C)/C=C/[C@@H](O)[C@H](C)C(O)=O)=O)C)COC—
1721-17apoS7M11
21-16;Methylmalonyl-CoA
from: 21-16
O[C@H](C[C@@H](O)[C@H](C)[C@H](O)[C@H](C(C[C@@H](O)C[C@H](O)CCC/C=C(C)/C=C/[C@@H](O)[C@H](C)/C=C(C)/C(O)=O)=O)C)COC—
1821-18apoS7M12
21-17;Methylmalonyl-CoA
from: 21-17
O[C@H](C[C@@H](O)[C@H](C)[C@H](O)[C@H](C(C[C@@H](O)C[C@H](O)CCC/C=C(C)/C=C/[C@@H](O)[C@H](C)/C=C(C)/C=C(C)/C(O)=O)=O)C)COC—
1921-19apoS8M13
21-18;Methylmalonyl-CoA
from: 21-18
O[C@H](C[C@@H](O)[C@H](C)[C@H](O)[C@H](C(C[C@@H](O)C[C@H](O)CCC/C=C(C)/C=C/[C@@H](O)[C@H](C)/C=C(C)/C=C(C)/C=C(C)/C(O)=O)=O)C)COC—
2021-20apoS8TE
21-19
from: 21-19
O[C@@H]([C@H](C)/C=C(C)/C=C(C)/C=C1\C)/C=C/C(C)=C/CCC[C@@H](O)C[C@@H](C[C@]2(O)O[C@@](C[C@@H](O)COC)([H])[C@H](C)[C@H](O)[C@H]2C)OC1=O—
2121-21Start—
4-O-L-methyl-L-rhamnose
[R][C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](C)O1—
2221-22?—
21-20
from: 21-20
[R][C@@H](O[C@@H]1C)[C@H](O)[C@@H](O)C1=O—
2321-23(apoH3;apoH4), apoM1—
21-21
from: 21-21
[R][C@@H]1[C@H](O)[C@@H](O)[C@H](OC)[C@@H](C)O1—
2421-24apoH1—
21-21
from: 21-21
[R][C@@H](O[C@@H]1C)CC(C1=O)=O—
2521-25apoH2—
21-23
from: 21-23
[R][C@@H](O[C@@H]1C)C[C@@H](O)C1=O—
2621-26apoH3;apoH4—
21-24
from: 21-24
[R][C@@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1—
2721-27apoM2—
21-24
from: 21-24
[R][C@@H](O[C@@H]1C)C[C@](C)(O)C1=O—
2821-28?—
21-26
from: 21-26
[R][C@@H]1CC(O)(C)C([C@H](C)O1)=O—
2921-29apoH3;apoH4—
21-27
from: 21-27
[R][C@@H]1CC(O)(C)[C@@H](O)[C@H](C)O1—
3021-30apoGT1;apoGT3—
21-20;21-23
from: 21-20, 21-23
COC[C@H](O)C[C@]1([H])[C@H](C)[C@H](O)[C@@H](C)[C@](O1)(O)C[C@@H](O2)C[C@H](O)CCC/C=C(C)/C=C/[C@@H](O[C@H]3O[C@@H](C)[C@H](OC)[C@@H](O)[C@@H]3O)[C@H](C)/C=C(C)/C=C(C)/C=C(C)/C2=O—
3121(apoM1;apoM3;apoM4), (apoGT1;apoGT3), apoP, apoGT2, (apoM1;apoM3;apoM4), ?—
21-20;21-26;21-29
from: 21-20, 21-26, 21-29
COC[C@H](O[C@@H]1O[C@@H](C)[C@H](O[C@H]2C[C@@H](OC)[C@H](O)[C@@H](C)O2)[C@](O)(C)C1)C[C@]3([H])[C@H](C)[C@H](O)[C@@H](C)[C@](O3)(O)C[C@@H](O4)C[C@H](O)CCC/C=C(C)/C=C/[C@@H](O[C@H]5O[C@@H](C)[C@H](OC)[C@@H](O)[C@@H]5O)[C@H](C)/C=C(C)/C=C(C)/C=C(C)/C4=O—
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