show all | hide all No of entries

Information on EC 5.2.1.8 - peptidylprolyl isomerase and Organism(s) Homo sapiens and UniProt Accession Q14318

for references in articles please use BRENDA:EC5.2.1.8
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
EC Tree
IUBMB Comments
The first type of this enzyme found proved to be the protein cyclophilin, which binds the immunosuppressant cyclosporin A. Other distinct families of the enzyme exist, one being FK-506 binding proteins (FKBP) and another that includes parvulin from Escherichia coli. The three families are structurally unrelated and can be distinguished by being inhibited by cyclosporin A, FK-506 and 5-hydroxy-1,4-naphthoquinone, respectively.
Specify your search results
Select one or more organisms in this record:
This record set is specific for:
Homo sapiens
UNIPROT: Q14318
Word Map
The taxonomic range for the selected organisms is: Homo sapiens
The enzyme appears in selected viruses and cellular organisms
Synonyms
12 kDa FKBP, 12.6 kDa FKBP, 13 kDa FKBP, 15 kDa FKBP, 19 kDa FK506-binding protein, 22 kDa FK506-binding protein, 25 kDa FKBP, 27 kDa membrane protein, 36 kDa FK506 binding protein, 40 kDa thylakoid lumen PPIase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
12 kDa FKBP
-
-
-
-
12.6 kDa FKBP
-
-
-
-
13 kDa FKBP
-
-
-
-
15 kDa FKBP
-
-
-
-
19 kDa FK506-binding protein
-
-
-
-
22 kDa FK506-binding protein
-
-
-
-
25 kDa FKBP
-
-
-
-
27 kDa membrane protein
-
-
-
-
36 kDa FK506 binding protein
-
-
-
-
40 kDa thylakoid lumen PPIase
-
-
-
-
40 kDa thylakoid lumen rotamase
-
-
-
-
51 kDa FK506-binding protein
-
-
-
-
52 kDa FK506 binding protein
-
-
-
-
54 kDa progesterone receptor-associated immunophilin
-
-
-
-
65 kDa FK506-binding protein
-
-
-
-
CGI-124
-
-
-
-
Chl-Mip
-
-
-
-
CPH
-
-
-
-
Cwc27
294725
-
Cyclophilin
Cyclophilin 18
-
-
-
-
Cyclophilin 33
-
-
-
-
Cyclophilin A
Cyclophilin B
Cyclophilin C
-
-
-
-
Cyclophilin cyp2
-
-
-
-
cyclophilin H
247
-
cyclophilin hCyp-18
247
-
Cyclophilin homolog
-
-
-
-
cyclophilin J
247
-
Cyclophilin ScCypA
-
-
-
-
Cyclophilin ScCypB
-
-
-
-
Cyclophilin-10
-
-
-
-
Cyclophilin-11
-
-
-
-
Cyclophilin-40
-
-
-
-
Cyclophilin-60
-
-
-
-
Cyclophilin-like protein Cyp-60
-
-
-
-
Cyclophilin-related protein
-
-
-
-
Cyclosporin A-binding protein
-
-
-
-
CYP-40
-
-
-
-
CYP-S1
-
-
-
-
Cyp18
247
-
Cyp3 PPIase
-
-
-
-
Cyp40
247
-
Estrogen receptor binding cyclophilin
-
-
-
-
FF1 antigen
-
-
-
-
FK506 binding protein 12
247
-
FKBP
-
-
-
-
FKBP 12
247
-
FKBP-12
-
-
-
-
FKBP-12.6
-
-
-
-
FKBP-13
-
-
-
-
FKBP-15
-
-
-
-
FKBP-19
-
-
-
-
FKBP-21
-
-
-
-
FKBP-22
-
-
-
-
FKBP-23
-
-
-
-
FKBP-25
-
-
-
-
FKBP-36
-
-
-
-
FKBP-51
-
-
-
-
FKBP-70
-
-
-
-
FKBP22
FKBP25
311451
-
FKBP3
311451
-
FKBP38
247
-
FKBP51
247
-
FKBP52
247
-
FKBP52 protein
-
-
-
-
FKBP54
-
-
-
-
FKBP59
-
-
-
-
FKBP65
-
-
-
-
FKBP65RS
-
-
-
-
h Par14
247
-
HBI
-
-
-
-
hCyP33
247
-
Histidine rich protein
-
-
-
-
hPar14
HSP binding immunophilin
-
-
-
-
HSP90-binding immunophilin
-
-
-
-
Immunophilin FKBP12
-
-
-
-
Immunophilin FKBP12.6
-
-
-
-
Immunophilin FKBP36
-
-
-
-
Immunophilin FKBP65
-
-
-
-
Isomerase, peptidylprolyl cis-trans
-
-
-
-
Macrolide binding protein
-
-
-
-
Macrophage infectivity potentiator
-
-
-
-
MtFK
-
-
-
-
NIMA-1
283181
-
Nucleolar proline isomerase
-
-
-
-
p17.7
-
-
-
-
P31
-
-
-
-
P54
-
-
-
-
p59 protein
-
-
-
-
Par14
Parvulin
Parvulin 14
-
-
-
-
parvulin1 4
247
-
Peptide bond isomerase
-
-
-
-
peptidyl prolyl isomerase-like protein 1
247
-
Peptidyl-prolyl cis-trans isomerase
peptidyl-prolyl cis-trans isomerase NIMA-interacting 1
247
-
Peptidyl-prolyl cis-trans isomerase plp
-
-
-
-
Peptidyl-prolyl cis-trans isomerase surA
-
-
-
-
peptidyl-prolyl cis/trans isomerase
247
-
Peptidyl-prolyl cis/trans isomerase EPVH
-
-
-
-
peptidyl-prolyl cis/trans isomerase NIMA-interacting 1
247
-
peptidyl-prolyl isomerase
peptidyl-prolyl isomerase 1
247
-
peptidylproline cis-trans-isomerase
247
-
Peptidylprolyl cis-trans isomerase
-
-
-
-
peptidylprolyl isomerase
247
-
PfCyP
-
-
-
-
Planta-induced rust protein 28
-
-
-
-
PpiA
294726
peptidyl-prolyl isomerase domain
PPIase
PPIase Pin1
-
-
-
-
PPIase Pin4
-
-
-
-
PpiB
294727
peptidyl-prolyl isomerase domain
PPIC
294728
peptidyl-prolyl isomerase domain
PpiD
294729
peptidyl-prolyl isomerase domain
PPIE
294730
peptidyl-prolyl isomerase domain
PPIF
294731
peptidyl-prolyl isomerase domain
PPIG
294732
peptidyl-prolyl isomerase domain
PPIH
294733
peptidyl-prolyl isomerase domain
PPIL1
247
-
PPWD1
247
-
Proline rotamase
-
-
-
-
prolyl-peptidyl isomerase
247
-
protein phosphatase 2A phosphatase activator
247
-
Proteins, cyclophilins
-
-
-
-
Proteins, specific or class, cyclophilins
-
-
-
-
PtpA
247
-
Rapamycin-binding protein
-
-
-
-
Rapamycin-selective 25 kDa immunophilin
-
-
-
-
Rotamase
-
-
-
-
Rotamase Pin1
-
-
-
-
Rotamase Pin4
-
-
-
-
Rotamase plp
-
-
-
-
S-cyclophilin
-
-
-
-
S1205-06
-
-
-
-
SCYLP
-
-
-
-
SDCCAG-10
SmCYP A
-
-
-
-
SmCYP B
-
-
-
-
Smp17.7
-
-
-
-
SP18
-
-
-
-
spliceosome-associated protein CWC27 homolog
294725
-
WHP
-
-
-
-
additional information
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
peptidylproline (omega=180) = peptidylproline (omega=0)
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
cis-trans-isomerization
-
-
SYSTEMATIC NAME
IUBMB Comments
Peptidylproline cis-trans-isomerase
The first type of this enzyme found [1] proved to be the protein cyclophilin, which binds the immunosuppressant cyclosporin A. Other distinct families of the enzyme exist, one being FK-506 binding proteins (FKBP) and another that includes parvulin from Escherichia coli. The three families are structurally unrelated and can be distinguished by being inhibited by cyclosporin A, FK-506 and 5-hydroxy-1,4-naphthoquinone, respectively.
CAS REGISTRY NUMBER
COMMENTARY hide
95076-93-0
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(cis)-Pro residue in HIF-1alpha
(trans)-Pro residue in HIF-1alpha
show the reaction diagram
-
-
-
-
r
(trans)-Pro190 of protein phosphatase 2A
(cis)-Pro190 of protein phosphatase 2A
show the reaction diagram
-
-
-
-
?
6-(dimethylamino)-2-naphthoyl-Ala-Ala-(cis)-Pro-Phe-4-nitroanilide
6-(dimethylamino)-2-naphthoyl-Ala-Ala-(trans)-Pro-Phe-4-nitroanilide
show the reaction diagram
-
-
-
?
acetyl-Ala-Ala-(cis)-Pro-Ala-Lys-NH2
acetyl-Ala-Ala-(trans)-Pro-Ala-Lys-NH2
show the reaction diagram
-
-
-
?
acetyl-Ala-Ala-Ser(PO3H2)-(cis)-Pro-Arg-NH-4-nitroanilide
acetyl-Ala-Ala-Ser(PO3H2)-(trans)-Pro-Arg-NH-4-nitroanilide
show the reaction diagram
-
-
-
?
Ala-Ala-(cis)-Pro-Ala
Ala-Ala-(trans)-Pro-Ala
show the reaction diagram
-
-
-
?
Ala-Glu-(cis)-Pro-Phe-4-nitroanilide
Ala-Glu-(trans)-Pro-Phe-4-nitroanilide
show the reaction diagram
-
-
-
-
?
Ala-Ser(PO3H2)-(cis)-Pro
Ala-Ser(PO3H2)-(trans)-Pro
show the reaction diagram
-
-
-
?
Ala-Ser(PO3H2)-(cis)-Pro-Arg
Ala-Ser(PO3H2)-(trans)-Pro-Arg
show the reaction diagram
-
-
-
?
amyloidbeta precursor protein
?
show the reaction diagram
-
interaction with Thr688
-
-
?
barstar C40A/C82A/P27A
?
show the reaction diagram
-
the mutant of barstar lacks complications arising from oxidation of Cys in wild-type or isomerization affecting the peptidyl-Pro27 bond. Refolding is comprised by several kinetically detectable folding phases. The slowest phase in refolding, the trans to cis isomerization of the Tyr47-Pro48 peptide bond being in cis conformation in the native state
-
?
cis-succinyl-Ala-Leu-Pro-Phe-p-nitroanilide
trans-succinyl-Ala-Leu-Pro-Phe-p-nitroanilide
show the reaction diagram
-
-
-
?
D-Glyceraldehyde 3-phosphate
Glycerone phosphate
show the reaction diagram
-
-
-
-
GFPRALPAWARPDYNPPLVE
?
show the reaction diagram
-
a synthetic peptide, named PepD2, corresponding to residues 304-323 of NS5A
-
-
?
hepatitis C virus NS5A protein
?
show the reaction diagram
interleukin-2 tyrosine kinase
?
show the reaction diagram
-
catalytic activity of interleukin-2 tyrosine kinase is inhibited by peptidylprolyl isomerase activity of cyclophilin A. Proline-dependent conformational switch within the interleukin-2 tyrosine kinase SH2 domain regulates substrate recognition and mediates regulatory interactions with the active site of cyclophilin A
-
?
N-succinyl-Ala-Ala-(cis)-Pro-Phe-4-nitroanilide
N-succinyl-Ala-Ala-(trans)-Pro-Phe-4-nitroanilide
show the reaction diagram
N-succinyl-Ala-Ala-(trans)-Pro-Phe-4-nitroanilide
N-succinyl-Ala-Ala-(cis)-Pro-Phe-4-nitroanilide
show the reaction diagram
N-succinyl-Ala-Glu-(cis)-Pro-Phe-p-nitroanilide
N-succinyl-Ala-Glu-(trans)-Pro-Phe-p-nitroanilide
show the reaction diagram
-
-
-
-
?
N-succinyl-Ala-Glu-(trans)-Pro-Phe-4-nitroanilide
N-succinyl-Ala-Glu-(cis)-Pro-Phe-4-nitroanilide
show the reaction diagram
-
-
-
-
?
peptidylproline (omega=180)
peptidylproline (omega=0)
show the reaction diagram
Phe-Phe-L-pSer-Pro-Arg-pNA
?
show the reaction diagram
-
-
-
-
?
phosphorylated pro-apoptotic Bcl-2-associated X protein
?
show the reaction diagram
protein tau
?
show the reaction diagram
-
interaction with Thr231 of tau in Alzheimer's disease
-
-
?
RNA polymerase II
?
show the reaction diagram
-
Pin1 modulates RNA polymerase II CTD domain during transcription cycles by interacting with numerous YSPTSPS heptapeptide repeats in the substrate protein
-
-
?
Ser(PO3H2)-(cis)-Pro-Arg
Ser(PO3H2)-(trans)-Pro-Arg
show the reaction diagram
-
-
-
?
Ser(PO3H2)-(cis)-Pro-Arg-NH-4-nitroanilide
Ser(PO3H2)-(trans)-Pro-Arg-NH-4-nitroanilide
show the reaction diagram
-
-
-
?
serine/threonine protein kinase B
?
show the reaction diagram
Suc-Ala-Ala-(trans)-Pro-Lys-p-nitroanilide
Suc-Ala-Ala-(cis)-Pro-Lys-p-nitroanilide
show the reaction diagram
-
-
-
-
?
Suc-Ala-Ala-(trans)-Pro-Phe-methylcoumarylamide
Suc-Ala-Ala-(cis)-Pro-Phe-methylcoumarylamide
show the reaction diagram
-
-
-
-
?
Suc-Ala-Ala-(trans)-Pro-Phe-p-nitroanilide
Suc-Ala-Ala-(cis)-Pro-Phe-p-nitroanilide
show the reaction diagram
-
-
-
-
?
suc-Ala-Glu-(cis)-Pro-Phe-4-nitroanilide
suc-Ala-Glu-(trans)-Pro-Phe-4-nitroanilide
show the reaction diagram
-
-
-
-
?
Suc-Ala-Glu-(trans)-Pro-Phe-p-nitroanilide
Suc-Ala-Glu-(cis)-Pro-Phe-p-nitroanilide
show the reaction diagram
-
-
-
-
?
Suc-Ala-Glu-Pro-Phe-4-nitroanilide
?
show the reaction diagram
-
-
-
-
?
Suc-Ala-Glu-Pro-Phe-7-amido-4-methylcoumarin
?
show the reaction diagram
-
-
-
-
?
succinyl-Ala-(cis)-Pro-Phe-NH-4-nitroanilide
succinyl-Ala-(trans)-Pro-Phe-NH-4-nitroanilide
show the reaction diagram
-
-
-
?
succinyl-Ala-Ala-(cis)-Pro-Phe-4-nitroanilide
succinyl-Ala-Ala-(trans)-Pro-Phe-4-nitroanilide
show the reaction diagram
-
-
-
?
succinyl-Ala-Ala-(cis)-Pro-Phe-NH-4-nitroanilide
succinyl-Ala-Ala-(trans)-Pro-Phe-NH-4-nitroanilide
show the reaction diagram
-
-
-
?
succinyl-Ala-Ala-(trans)-Pro-Arg-p-nitroanilide
succinyl-Ala-Ala-(cis)-Pro-Arg-p-nitroanilide
show the reaction diagram
-
-
-
r
succinyl-Ala-Ala-Pro-Phe 4-nitroanilide
succinyl-Ala-Ala-(trans)-Pro-Phe 4-nitroanilide
show the reaction diagram
-
-
-
-
-
Succinyl-Ala-Glu-(cis)-Pro-Phe 4-nitroanilide
Succinyl-Ala-Glu-(trans)-Pro-Phe 4-nitroanilide
show the reaction diagram
-
-
-
-
-
succinyl-Ala-Glu-(cis)-Pro-Phe-4-nitroanilide
succinyl-Ala-Glu-(trans)-Pro-Phe-4-nitroanilide
show the reaction diagram
-
-
-
-
?
succinyl-Ala-Glu-(trans)-Pro-Phe-4-nitroanilide
succinyl-Ala-Glu-(cis)-Pro-Phe-4-nitroanilide
show the reaction diagram
-
-
-
?
Succinyl-Ala-Gly-(cis)-Pro-Phe 4-nitroanilide
Succinyl-Ala-Gly-(trans)-Pro-Phe 4-nitroanilide
show the reaction diagram
-
-
-
-
-
succinyl-Ala-Gly-(cis)-Pro-Phe-4-nitroanilide
succinyl-Ala-Gly-(trans)-Pro-Phe-4-nitroanilide
show the reaction diagram
-
-
-
?
Succinyl-Ala-Leu-(cis)-Pro-Phe 4-nitroanilide
Succinyl-Ala-Leu-(trans)-Pro-Phe 4-nitroanilide
show the reaction diagram
-
-
-
-
-
Succinyl-Ala-Lys-(cis)-Pro-Phe 4-nitroanilide
Succinyl-Ala-Lys-(trans)-Pro-Phe 4-nitroanilide
show the reaction diagram
-
-
-
-
-
Succinyl-Ala-Phe-(cis)-Pro-Phe 4-nitroanilide
Succinyl-Ala-Phe-(trans)-Pro-Phe 4-nitroanilide
show the reaction diagram
-
-
-
-
-
succinyl-Ala-Phe-(cis)-Pro-Phe-4-nitroanilide
succinyl-Ala-Phe-(trans)-Pro-Phe-4-nitroanilide
show the reaction diagram
-
-
-
?
Succinyl-Ala-Val-(cis)-Pro-Phe 4-nitroanilide
Succinyl-Ala-Val-(trans)-Pro-Phe 4-nitroanilide
show the reaction diagram
-
-
-
-
Succinyl-Arg-Leu-(cis)-Pro-Phe 4-nitroanilide
Succinyl-Arg-Leu-(trans)-Pro-Phe 4-nitroanilide
show the reaction diagram
-
-
-
-
Succinyl-Leu-Leu-(cis)-Pro-Phe 4-nitroanilide
Succinyl-Leu-Leu-(trans)-Pro-Phe 4-nitroanilide
show the reaction diagram
-
-
-
-
Succinyl-Phe-Leu-(cis)-Pro-Phe 4-nitroanilide
Succinyl-Phe-Leu-(trans)-Pro-Phe 4-nitroanilide
show the reaction diagram
-
-
-
-
Succinyl-Ser-Leu-(cis)-Pro-Phe 4-nitroanilide
Succinyl-Ser-Leu-(trans)-Pro-Phe 4-nitroanilide
show the reaction diagram
-
-
-
-
Trp-Phe-Tyr-pSer-Pro-Arg-4-nitroanilide
?
show the reaction diagram
-
-
-
-
?
Trp-Phe-Tyr-Ser(PO3H2)-(cis)-Pro-Arg-4-nitroanilide
Trp-Phe-Tyr-Ser(PO3H2)-(trans)-Pro-Arg-4-nitroanilide
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
amyloidbeta precursor protein
?
show the reaction diagram
-
interaction with Thr688
-
-
?
hepatitis C virus NS5A protein
?
show the reaction diagram
-
nonstructural 5A protein, NS5A, from the JFH1 hepatitis C virus strain. Mutations in this domain are linked to cyclosporin A resistance
-
-
?
interleukin-2 tyrosine kinase
?
show the reaction diagram
-
catalytic activity of interleukin-2 tyrosine kinase is inhibited by peptidylprolyl isomerase activity of cyclophilin A. Proline-dependent conformational switch within the interleukin-2 tyrosine kinase SH2 domain regulates substrate recognition and mediates regulatory interactions with the active site of cyclophilin A
-
?
peptidylproline (omega=180)
peptidylproline (omega=0)
show the reaction diagram
-
-
-
-
?
phosphorylated pro-apoptotic Bcl-2-associated X protein
?
show the reaction diagram
-
Pin1 prevents activation of Bax, prevents Bax cleavage by calpain, and prevents Bax translocation to mitochondria
-
-
?
protein tau
?
show the reaction diagram
-
interaction with Thr231 of tau in Alzheimer's disease
-
-
?
RNA polymerase II
?
show the reaction diagram
-
Pin1 modulates RNA polymerase II CTD domain during transcription cycles by interacting with numerous YSPTSPS heptapeptide repeats in the substrate protein
-
-
?
serine/threonine protein kinase B
?
show the reaction diagram
-
-
-
-
?
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
-
stimulation
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1,2-dimethyl-1H-indol-3-yl)(5'-fluoro-2',4-dihydroxy-1,1'-biphenyl-3-yl)methanone
-
-
(1R)-1,3-diphenyl-1-propyl (2S)-1-(3,3-dimethyl-1,2-dioxopentyl)-2-piperidinecarboxylate
-
-
(1R)-1,3-diphenylpropyl 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
-
-
(1R)-1-cyclohexyl-3-phenylpropyl 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
-
-
(1R)-1-naphthalen-2-yl-3-phenylpropyl 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
-
-
(1R)-1-phenyl-3-(3,4,5-trimethoxyphenyl)propyl 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
-
-
(1R)-1-[3-(diethenylcarbamoyl)phenyl]-3-phenylpropyl 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
-
inhibition of FKBP12 cis-trans peptidylprolyl isomerase activity, but no activity in splenocyte mitogenesis assay for immunosuppression
(1R)-3-(1,3-benzodioxol-5-yl)-1-phenylpropyl 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
-
-
(1R)-3-(3,4-dimethoxyphenyl)-1-phenylpropyl 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
-
-
(1R)-3-cyclohexyl-1-phenylpropyl 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
-
-
(1R)-3-cyclohexyl-1-phenylpropyl 1-[cyclohexyl(oxo)acetyl]piperidine-2-carboxylate
-
-
(1R)-3-phenyl-1-[3-(phenylcarbonyl)phenyl]propyl 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
-
inhibition of FKBP12 cis-trans peptidylprolyl isomerase activity, but no activity in splenocyte mitogenesis assay for immunosuppression
(1R,5S)-1-(phenylsulfonyl)bicyclo[3.3.1]nonan-3-one
-
-
(1R,5S)-1-(phenylthio)bicyclo[3.3.1]nonan-3-one
-
-
(1S)-1,3-diphenylpropyl 1-(benzylsulfonyl)piperidine-2-carboxylate
-
-
(1S)-1-cyclohexyl-3-phenylpropyl (2R)-1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
-
-
(1S)-1-phenyl-3-(3,4,5-trimethoxyphenyl)propyl 1-(3,3-dimethylbutanoyl)piperidine-2-carboxylate
-
-
(2,5-dimethyl-1-benzofuran-3-yl)(2-hydroxy-5-iodophenyl)methanone
-
-
(2,5-dimethyl-1-benzofuran-3-yl)(2-hydroxy-5-methylphenyl)methanone
-
-
(2,5-dimethyl-1-benzofuran-3-yl)(3',4,5'-trihydroxy-1,1'-biphenyl-3-yl)methanone
-
-
(2,5-dimethyl-1-benzofuran-3-yl)(5'-fluoro-2',4-dihydroxy-1,1'-biphenyl-3-yl)methanone
-
-
(2,5-dimethyl-1-benzofuran-3-yl)[2-hydroxy-5-(trifluoromethyl)phenyl]methanone
-
-
(2,5-dimethyl-1-benzofuran-3-yl)[4-hydroxy-4'-(trifluoromethoxy)-1,1'-biphenyl-3-yl]methanone
-
-
(2-butyl-1-benzothiophen-3-yl)(5'-fluoro-2',4-dihydroxy-1,1'-biphenyl-3-yl)methanone
-
-
(24aS)-17,17-dimethylhexadecahydropyrido[2,1-c][1,9,4]dioxazacyclohenicosine-1,14,18,19(3H,21)-tetrone
-
-
(3S,26aR)-19,19-dimethyl-3-(2-phenylethyl)-12,13,14,15,18,19,24,25,26,26a-decahydro-3H,10H-4,8-(metheno)pyrido[2,1-c][1,9,17,4]trioxazacyclotricosine-1,16,20,21(11H,23H)-tetrone
-
-
(5'-fluoro-2',4-dihydroxy-1,1'-biphenyl-3-yl)(2-methyl-1-benzofuran-3-yl)methanone
-
-
(5'-fluoro-2',4-dihydroxy-1,1'-biphenyl-3-yl)(2-methyl-1-benzothiophen-3-yl)methanone
-
-
(5'-fluoro-2',4-dihydroxybiphenyl-3-yl)(2-methyl-1-benzofuran-3-yl)methanethione
-
-
(5'-fluoro-2',4-dihydroxybiphenyl-3-yl)(2-methyl-1-benzothiophen-3-yl)methanethione
-
-
(5'-fluoro-2',4-dimethoxybiphenyl-3-yl)(2-methyl-1-benzofuran-3-yl)methanethione
-
-
(5-bromo-2-hydroxyphenyl)(2,5-dimethyl-1-benzofuran-3-yl)methanone
-
-
(E)-2-(2-hydroxy-2-isobutylethy 1idene)-1-meth ylcyclopentane-(L)-tyrosylcarboxamide
-
-
(E)-6-phenylhexyl 3-(3,4-dihydroxyphenyl)acrylate
-
20 micorM, 15% residual activity
1-(1H-imidazol-2-ylthio)bicyclo[3.3.1]nonan-3-one
-
-
1-(2-phenylethyl)-4-pyridin-3-ylbutyl (2R)-1-[difluoro(3,4,5-trimethoxyphenyl)acetyl]piperidine-2-carboxylate
-
-
1-(3-hydroxyphenoxy)bicyclo[3.3.1]nonan-3-one
-
-
1-(phenylthio)bicyclo[3.3.1]nonan-3-one
-
-
1-(pyridin-3-ylthio)bicyclo[3.3.1]nonan-3-one
-
-
1-(pyridin-4-ylthio)bicyclo[3.3.1]nonan-3-one
-
-
1-benzyl-2-pyridin-3-ylethyl 1-[difluoro(3,4,5-trimethoxyphenyl)acetyl]-D-prolinate
-
-
1-benzyl-3-phenylpropyl 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
-
-
1-phenyl-3-pyridin-3-ylpropyl (2R)-1-[difluoro(3,4,5-trimethoxyphenyl)acetyl]piperidine-2-carboxylate
-
-
1-[(1R,10S)-3,8-dioxa-14-azabicyclo[8.3.1]tetradec-14-yl]-3,3-dimethyl-1-oxopentan-2-one
-
15,15-dimethyltetradecahydropyrido[2,1-c][1,9,4]dioxazacyclononadecine-1,12,16,17(3H,19H)-tetrone
-
-
2-(4-((2R)-2-[(1R,3R,5R)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl)-2,6-dioxopiperidin-1-yl)acetamide
-
competitive inhibition. Evaluation of cytotoxicity against cell lines L-929 fibroblasts and K-562 leukemic cells
2-oxo-2-[(1R,10S)-5-phenoxy-3,8-dioxa-14-azabicyclo[8.3.1]tetradec-14-yl]-1-(3,4,5-trimethoxyphenyl)ethanone
-
2-[(1R,10S)-3,8-dioxa-14-azabicyclo[8.3.1]tetradec-14-yl]-2-oxo-1-(3,4,5-trimethoxyphenyl)ethanone
-
3,5-dichloro-N-(3-[(2-naphthylacetyl)amino]phenyl)benzamide
-
-
3,5-dichloro-N-[3-([[(2,4-dibromophenyl)amino]carbonyl]amino)phenyl]benzamide
-
-
3,5-dichloro-N-[3-([[(3,5-dichlorophenyl)amino]carbonyl]amino)phenyl]benzamide
-
-
3,5-dichloro-N-[3-[(3,3-diphenylpropanoyl)amino]phenyl]benzamide
-
-
3,5-dichloro-N-[3-[([[4-(trifluoromethyl)phenyl]amino]carbonyl)amino]phenyl]benzamide
-
-
3-(3,4,5-trimethoxyphenyl)propyl (2R)-1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
-
-
3-(3,4,5-trimethoxyphenyl)propyl 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
-
-
3-(3,4,5-trimethoxyphenyl)propyl 1-(benzylsulfonyl)piperidine-2-carboxylate
-
-
3-phenyl-1-(2-pyridin-3-ylethyl)propyl 1-[difluoro(3,4,5-trimethoxyphenyl)acetyl]-D-prolinate
-
-
3-phenylpropyl 1-(2-hydroxy-3,3-dimethylpentanoyl)piperidine-2-carboxylate
-
-
4-phenyl-1-(2-pyridin-3-ylethyl)butyl (2R)-1-[difluoro(3,4,5-trimethoxyphenyl)acetyl]piperidine-2-carboxylate
-
-
4-phenyl-1-(3-pyridin-3-ylpropyl)butyl (2R)-1-[difluoro(3,4,5-trimethoxyphenyl)acetyl]piperidine-2-carboxylate
-
-
4-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]-2,6-piperidinedione
-
competitive inhibition. Evaluation of cytotoxicity against cell lines L-929 fibroblasts and K-562 leukemic cells
4-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]-2,6-piperidinedione-1-(4-ethyl butanoate)
-
competitive inhibition. Evaluation of cytotoxicity against cell lines L-929 fibroblasts and K-562 leukemic cells
4-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]-2,6-piperidinedione-1-(ethyl ethanoate)
-
competitive inhibition. Evaluation of cytotoxicity against cell lines L-929 fibroblasts and K-562 leukemic cells. Compound is able to significantly speed nerve regeneration in a rat sciatic nerve neurotomy model
5-hydroxy-1,4-naphthoquinone
-
i.e. juglone, 0.0057 mM, complete inactivation within 150 min, irreversible inhibition of the parvulin family of peptidyl-prolyl cis/trans isomerases, specific inhibition allows selective inactivation of these enzymes in presence of other peptidylprolyl isomerases, the inactivated parvulin contains two juglone molecules that are covalently bound to the side chains of Cys41 and Cys69, partial unfolding of the active site of the parvulins is thought to be the cause of the deterioration of peptidylprolyl isomerase activity
5-methoxy-1',3'dihydro-3H-spiro[1-benzofuran-2,2'-indene]-3-one
-
-
5-methoxy-2',3'-dihydro-3H-spiro[1-benzofuran-2,1'-indene]-3-one
-
-
5-methoxy-3H-spiro[1-benzofuran-2,1'-cyclopent[3]en]-3-one
-
-
Ac-Ala-GlyPSI(PO2Et-N)Pro-Phe-4-nitroanilide
-
transition-state analogue of peptidylprolyl isomerase activity of cyclophilin Cyp-18, Kd value 0.127 mM
Ac-beta-(3-benzothienyl)Ala-Thr(PO3H2)-piperidine-2-carboxylic acid-beta-(2-naphthyl)Ala-Gln-NH2
-
-
Ac-Lys(Nepsilon-biotinoyl)-Ala-Ala-(t-butyl)Phe-Thr(PO3H2)-(methyl)Ala-beta-(2-naphthyl)Ala-Gln-NH2
-
-
Ac-Lys(Nepsilon-biotinoyl)-Ala-Ala-(t-butyl)Phe-Thr(PO3H2)-Yaa-Zaa-Gln-NH2
-
-
Ac-Lys(Nepsilon-biotinoyl)-Ala-Ala-beta-(2-thienyl)Ala-Thr(PO3H2)-(methyl)Ala-beta-(2-naphthyl)Ala-Gln-NH2
-
-
Ac-Lys(Nepsilon-biotinoyl)-Ala-Ala-beta-(3-benzothienyl)Ala-D-Thr(PO3H2)-piperidine-2-carboxylic acid-beta-(2-naphthyl)Ala-Gln-NH2
-
-
Ac-Lys(Nepsilon-biotinoyl)-Ala-Ala-beta-(3-benzothienyl)Ala-Thr(PO3H2)-piperidine-2-carboxylic acid-beta-(2-naphthyl)Ala-Gln-NH2
-
-
Ac-Lys(Nepsilon-biotinoyl)-Ala-Ala-beta-cyclohexylAla-Thr(PO3H2)-(methyl)Ala-beta-(2-naphthyl)Ala-Gln-NH2
-
-
Ac-Lys(Nepsilon-biotinoyl)-Ala-Ala-Phe-D-Thr(PO3H2)-piperidine-2-carboxylic acid-beta-(2-naphthyl)Ala-Gln-NH2
-
-
Ac-Phe-D-Thr(PO3H2)-piperidine-2-carboxylic acid-beta-(2-naphthyl)Ala-Gln-NH2
-
-
Ac-Phe-Thr(PO3H2)-piperidine-2-carboxylic acid-beta-(2-naphthyl)Ala-Gln-NH2
-
-
acetyl-Ala-Ala-D-Ser(PO3H2)-Pro-Leu-NH-4-nitroanilide
-
IC50: 0.001 mM
acetyl-Ala-Ala-D-Ser-Pro-Leu-NH-4-nitroanilide
-
IC50: 0.085 mM
acetyl-Ala-Pro-Phe-4-(trimethylammonium)anilide
-
IC50: 7 mM
acetyl-Ala-Pro-Phe-4-nitroanilide
-
IC50: 0.77 mM
Ala-Pro
benzyl (2S)-1-[[(1S,2R,5R)-1-hydroxy-5-[(1R)-1-methoxy-3-methylbut-2-en-1-yl]-2-methylcyclohexyl](oxo)acetyl]piperidine-2-carboxylate
-
-
benzyl (2S)-1-[[(1S,2R,5R)-1-hydroxy-5-[(1S)-1-methoxy-3-methylbutyl]-2-methylcyclohexyl](oxo)acetyl]piperidine-2-carboxylate
-
-
benzyl (2S)-1-[[(1S,2R,5R)-1-hydroxy-5-[(1S)-1-methoxyethyl]-2-methylcyclohexyl](oxo)acetyl]piperidine-2-carboxylate
-
-
cyclic CRYPEVEIC
-
the cyclic peptide is specific for the active site of the PPIase domain
cyclo(Arg-Arg-Arg-D-pThr-Pip-Nal-Arg-Arg-Gln)
-
-
cyclo(Arg-Arg-Arg-D-Thr-Pip-Nal-Arg-Arg-Gln)
-
-
cyclo(D-Ala-Gln-Glu-Mpa-Mal-Ile-Gln)
-
-
cyclo(D-Ala-Gly-D-pThr-Pip-Nal-Orn-Gln)
-
-
cyclo(D-Ala-Ile-D-pSer-Pro-Nal-Orn-Gln)
-
-
cyclo(D-Ala-Sar-D-pThr-Pip-Nal-Tyr-Gln)
-
-
cyclo(D-Ala-Sar-D-pThr-Pip-Nal-Tyr-Gln)-Lys-SH
-
-
cyclo(D-Arg-D-Arg-D-pThr-Pip-Nal-Arg-D-Arg-D-Arg-D-Arg-Gln)
-
-
cyclo(D-Arg-D-Arg-D-pThr-Pip-Nal-Arg-Gln)
-
-
cyclo(D-Arg-D-Arg-D-Thr-Pip-Nal-Arg-D-Arg-D-Arg-D-Arg-Gln)
-
-
cyclo(D-Arg-D-Arg-D-Thr-Pip-Nal-Arg-Gln)
-
-
cycloheximide
-
-
cyclosporin A
D-Ser(PO3H2)-Pro
-
1 mM, 20% inhibition
diethyl 2,2'-(1,3,6,8-tetraoxo-1,3,6,8-tetrahydrobenzo[lmn][3,8]phenanthroline-2,7-diyl)diacetate
-
-
diethyl 2,2'-(1,3,8,10-tetraoxo-1,3,8,10-tetrahydroisoquinolino[4',5',6':6,5,10]anthra[2,1,9-def]isoquinoline-2,9-diyl)diacetate
-
-
dipentamethylene thiuram monosulfide
-
-
epigallocatechin-3-gallate
-
10 microM, 55% residual activity
ethyl (2S)-1-(4,4-dimethyl-2-oxohexanoyl)piperidine-2-carboxylate
-
-
ethyl (2S)-1-[(2-methoxycyclohexyl)(oxo)acetyl]piperidine-2-carboxylate
-
-
ethyl (2S)-1-[cyclohexyl(oxo)acetyl]piperidine-2-carboxylate
-
-
ethyl 1-(4,4-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
-
-
ethyl 1-(4-methyl-2-oxopentanethioyl)piperidine-2-carboxylate
-
-
ethyl 1-(4-methyl-2-oxopentanoyl)piperidine-2-carboxylate
-
-
ethyl 1-(5-ethoxy-4,4-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
-
-
ethyl 1-[(1-methoxycyclohexyl)(oxo)acetyl]pyrrolidine-2-carboxylate
-
-
ethyl 1-[(3-methoxytetrahydro-2H-pyran-2-yl)(oxo)acetyl]piperidine-2-carboxylate
-
-
FK506
-
-
juglone
linear CRYPEVEIC
-
-
methyl N-([(1R,2E)-2-[(2S)-2-hydroxy-4-methylpentylidene]-1-methylcyclopentyl]carbonyl)-L-tyrosinate
-
-
N,N''-(4,6-dibromo-1,3-phenylene)bis[3-(4-iodophenyl)urea]
-
-
N,N'-1,3-phenylenebis(3,5-dichlorobenzamide)
-
-
Phe-Ser(PO3H2)-PSI[CS-N]-Pro-Phe-NH-4-nitroanilide
-
IC50: 0.004 mM
Phe-Ser-PSI[CS-N]-Pro-Phe-NH-4-nitroanilide
-
IC50: 0.097 mM
QAEGPK
peptide corresponding to peptide QAEGP487KR at the N-terminus of the enzyme's isomerase domain. Peptide binds to the active site, but the enzyme does not catalyze its isomerization
Ser(PO3H2)-Pro
-
; IC50: 2.0 mM
Ser-Pro
-
-
Ser-PSI[CS-N]-Pro
-
-
Suc-Ala-Ala-Pro-Phe-4-nitroanilide
-
transition-state analogue of peptidylprolyl isomerase activity of cyclophilin Cyp-18, Kd value 0.138 mM
Suc-Ala-GlyPSI(PO2Et-N)Pro-Phe-4-nitroanilide
-
transition-state analogue of peptidylprolyl isomerase activity of cyclophilin Cyp-18, Kd value 0.02 mM. Selectively inhibits Cyp-18, but not enzyme isoform FKBP12
succinyl-Ala-Ala-Pro-NH2
-
IC50: 14 mM
succinyl-Ala-Ala-Pro-Phe-4-carboxymethylanilide
-
IC50: 4.4 mM
succinyl-Ala-Ala-Pro-Phe-4-nitroanilide
-
IC50: 0.54 mM
succinyl-Ala-Pro-Phe-4-aminoanilide
-
IC50: 5.8 mM
succinyl-Ala-Pro-Phe-4-carboxmethylanilide
-
IC50: 0.7 mM
succinyl-Ala-Pro-Phe-4-nitroanilide
-
IC50: 0.17 mM
succinyl-Pro-Phe-4-nitroanilide
-
IC50: 1.09 mM
[(1S,2R,3S,6R,7aR)-2-(benzylcarbamoyl)-6-methoxy-3-naphthalen-2-ylhexahydro-1H-pyrrolizin-1-yl]methyl dihydrogen phosphate
-
-
[(1S,2R,3S,6S,7aR)-2-(benzylcarbamoyl)-6-fluoro-3-naphthalen-2-ylhexahydro-1H-pyrrolizin-1-yl]methyl dihydrogen phosphate
-
-
[(1S,2R,3S,7aR)-2-(benzylcarbamoyl)-3-(pentafluorophenyl)hexahydro-1H-pyrrolizin-1-yl]methyl dihydrogen phosphate
-
-
[(1S,2R,3S,7aR)-2-(benzylcarbamoyl)-3-naphthalen-2-ylhexahydro-1H-pyrrolizin-1-yl]methyl dihydrogen phosphate
-
-
[(1S,2R,3S,7aR)-2-(benzylcarbamoyl)-3-phenylhexahydro-1H-pyrrolizin-1-yl]methyl dihydrogen phosphate
-
-
[(1S,2R,3S,7aR)-2-[(1,3-benzodioxol-5-ylmethyl)carbamoyl]-3-naphthalen-2-ylhexahydro-1H-pyrrolizin-1-yl]methyl dihydrogen phosphate
-
-
[3-[(5'-fluoro-2',4-dihydroxy-1,1'-biphenyl-3-yl)carbonyl]-2-methyl-1-benzofuran-5-yl]acetonitrile
-
-
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ATP
-
stimulation
additional information
-
GM-CSF-induced activation of Erk1/2, which phosphorylated Thr167 of the pro-apoptotic Bcl-2-associated X protein, Bax, facilitates de novo interaction of Bax with the prolyl isomerase Pin1
-