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BGC0000353NRPS

tacrolimus

Producing organism
Streptomyces sp. MA6548
Taxonomy
Bacteria›Actinomycetota›Actinomycetes›Kitasatosporales›Streptomycetaceae›Streptomyces
Biosynthetic class
NRPS (Type I)
Total steps
18
DOI
MIBiG entry
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tacrolimus
C44H69NO12803.48 Da

Gene Cluster Map3 genes · 28,732 bp

CACCALERKSATDHKRKSATDHKRKSATDHKRKSATDH5 kb28.7 kb visible · 28,732 bp total
Biosynthetic (core)
Unknown
Domains
KSKetosynthase (KS)
ATAcyltransferase (AT)
DHDehydratase (DH)
EREnoylreductase (ER)
KRKetoreductase (KR)
ACPAcyl carrier protein (ACP)
ACPAcyl carrier (ACP)
CCondensation (C)
AAdenylation (A)
PCPPeptidyl carrier (PCP)
CALCoA-ligase (CAL)

Pathway Graphsteps arranged in biosynthetic order

18 steps · 17 edges
Step 1
start
+Chorismic acid
Step 15
Start
+L-Lysine
Step 2
fkbO
Step 16
STSU_RS31755
Step 3
?
Step 4Load
fkbB
Step 5M1
fkbB
+methylmalonyl-CoA
Step 6M2
fkbB
+methylmalonyl-CoA
Inactive: DH
Step 7M3
fkbB
+malonyl-CoA
Inactive: DH
Step 8M4
fkbB
+allylmalonyl-CoA
Inactive: KR, DH
Step 9M5
fkbC
+methylmalonyl-CoA
Step 10M6
fkbC
+methylmalonyl-CoA
Step 11M7
fkbA
+methoxymalonyl-ACP
Step 12M8
fkbA
+methoxymalonyl-ACP
Inactive: DH
Step 13M9
fkbA
+methylmalonyl-CoA
Step 14M10
fkbA
+malonyl-CoA
Step 17
STSU_RS31730
Step 18
STSU_RS31715, STSU_RS31…
Starting stepIntermediateFinal product│ModuleLoadingTENo module│PKS stepNRPS stepTailoring/otherScroll to pan · Wheel to zoom

Biosynthetic Reactions18 steps

StepProduct IDEnzymeModuleSubstrateProduct SMILESNotes
1353-1start—
Chorismic acid
O[C@@H]1C=CC(C(O)=O)=C[C@H]1OC(C(O)=O)=C—
2353-2fkbO—
353-1
from: 353-1
O[C@@H]1C=CC(C(O)=O)=C[C@H]1O—
3353-3?—
353-2
from: 353-2
O[C@@H]1CC=C(C[C@H]1O)C(O)=O—
4353-4fkbBLoading
353-3
from: 353-3
OC([C@H]1C[C@@H](O)[C@H](O)CC1)=O—
5353-5fkbBM1
353-4;methylmalonyl-CoA
from: 353-4
OC(/C(C)=C/[C@H]1C[C@@H](O)[C@H](O)CC1)=O—
6353-6fkbBM2
353-5;methylmalonyl-CoA
from: 353-5
OC([C@@H](C)[C@H](O)/C(C)=C/[C@H]1C[C@@H](O)[C@H](O)CC1)=O{'Inactive':['DH']}
7353-7fkbBM3
353-6;malonyl-CoA
from: 353-6
OC(C[C@H](O)[C@@H](C)[C@H](O)/C(C)=C/[C@H]1C[C@@H](O)[C@H](O)CC1)=O{'Inactive':['DH']}
8353-8fkbBM4
353-7;allylmalonyl-CoA
from: 353-7
OC([C@@H](CC=C)C(C[C@H](O)[C@@H](C)[C@H](O)/C(C)=C/[C@H]1C[C@@H](O)[C@H](O)CC1)=O)=O{'Inactive':['KR','DH']}
9353-9fkbCM5
353-8;methylmalonyl-CoA
from: 353-8
OC(/C(C)=C/[C@@H](CC=C)C(C[C@H](O)[C@@H](C)[C@H](O)/C(C)=C/[C@H]1C[C@@H](O)[C@H](O)CC1)=O)=O—
10353-10fkbCM6
353-9;methylmalonyl-CoA
from: 353-9
C[C@@H](C/C(C)=C/[C@@H](CC=C)C(C[C@H](O)[C@@H](C)[C@H](O)/C(C)=C/[C@H]1C[C@@H](O)[C@H](O)CC1)=O)C(O)=O—
11353-11fkbAM7
353-10;methoxymalonyl-ACP
from: 353-10
OC([C@@H](OC)C[C@@H](C)C/C(C)=C/[C@@H](CC=C)C(C[C@H](O)[C@@H](C)[C@H](O)/C(C)=C/[C@H]1C[C@@H](O)[C@H](O)CC1)=O)=O—
12353-12fkbAM8
353-11;methoxymalonyl-ACP
from: 353-11
OC([C@H](OC)[C@@H](O)[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@@H](CC=C)C(C[C@H](O)[C@@H](C)[C@H](O)/C(C)=C/[C@H]1C[C@@H](O)[C@H](O)CC1)=O)=O{'Inactive':['DH']}
13353-13fkbAM9
353-12;methylmalonyl-CoA
from: 353-12
OC([C@H](C)C[C@H](OC)[C@@H](O)[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@@H](CC=C)C(C[C@H](O)[C@@H](C)[C@H](O)/C(C)=C/[C@H]1C[C@@H](O)[C@H](O)CC1)=O)=O—
14353-14fkbAM10
353-13;malonyl-CoA
from: 353-13
O=C(CC([C@H](C)C[C@H](OC)[C@@H](O)[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@@H](CC=C)C(C[C@H](O)[C@@H](C)[C@H](O)/C(C)=C/[C@H]1C[C@@H](O)[C@H](O)CC1)=O)=O)O—
15353-15Start—
L-Lysine
[NH3+]C(C(O)=O)CCCCN—
16353-16STSU_RS31755—
353-15
from: 353-15
O=C(C1NCCCC1)O—
17353-17STSU_RS31730—
353-14;353-16
from: 353-14, 353-16
C/C([C@H]([C@H](C)[C@H](CC([C@H](CC=C)/C=C(C[C@@H](C[C@@H]([C@@]1([H])O[C@](CC(N2[C@H]3CCCC2)=O)(O)[C@H](C)C[C@@H]1OC)OC)C)\C)=O)O)OC3=O)=C\[C@H]4C[C@@H](O)[C@H](O)CC4—
18353STSU_RS31715, STSU_RS31720—
353-17
from: 353-17
C/C([C@H]([C@H](C)[C@H](CC([C@H](CC=C)/C=C(C[C@@H](C[C@@H]([C@@]1([H])O[C@](C(C(N2[C@H]3CCCC2)=O)=O)(O)[C@H](C)C[C@@H]1OC)OC)C)\C)=O)O)OC3=O)=C\[C@H]4C[C@@H](OC)[C@H](O)CC4—
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