Payload Information

General Information of This Payload
Payload ID
PAY0VYKOO
Name
Tacrolimus
Synonyms
Tacrolimus; Fujimycin; 104987-11-3; Prograf; Protopic; Tsukubaenolide; Tacrolimus anhydrous; FK506; Advagraf; Modigraf; Anhydrous Tacrolimus; Prograft; Fk-506; Protopy; LCP-Tacro; FK 506; Avagraf; Envarsus; FR-900506; tacrolimus (fk506); Astagraf XL; Envarsus XR; Tacrolimus, anhydrous; Tacrolimus (anhydrous); Graceptor; Hecoria; (-)-FK 506; 8-DEETHYL-8-[BUT-3-ENYL]-ASCOMYCIN; Tacrolimus (INN); Prograf (TN); UNII-Y5L2157C4J; PROGRAPH; TACRO; CCRIS 7124; DTXSID5046354; FR900506; K506; CHEBI:61049; HSDB 8195; FR 900506; Tacrolimus hydrate; Y5L2157C4J; Tacrolimus [USAN:INN]; FK-506 (Tacrolimus); Tacrolimus [USAN]; NSC-758659; L 679934; Tacarolimus; CHEMBL269732; DTXCID3026354; NCGC00163470-03; Protopic (TN); TACROLIMUS [INN]; TACROLIMUS (MART.); TACROLIMUS [MART.]; (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-Hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propen-1-yl)-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)tetrone; L-679934; TACROLIMUS (USP-RS); FK5; CHEBI:61057; C44H69NO12.H2O; TACROLIMUS (USP MONOGRAPH); 8-DEETHYL-8-(BUT-3-ENYL)-ASCOMYCIN; NSC 758659; SR-05000001879; TACROLIMUS MONOHYDRATE (EP MONOGRAPH); tacrolimusum; Talymus; TacroBell; MFCD00869853; NSC717865; Advagraf (TN); Tacrolimus (Prograf); ENVARSUS-XR; TACROLIMUS [MI]; D06OMK; SCHEMBL3088; TACROLIMUS [WHO-DD]; BSPBio_001279; CHEMBL66247; Tacrolimus [USAN:BAN:INN]; GTPL6784; CHEBI:93221; HMS503O21; D11AH01; L04AD02; QJJXYPPXXYFBGM-LFZNUXCKSA-N; HMS1792O21; HMS1990O21; HMS2093M19; HMS3403O21; Pharmakon1600-01503968; 15,19-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-(2-(4-hydroxy-3-methoxycyclohexyl)-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propenyl)-, (3S-(3R*(E(1S*,3S*,4S*)),4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,26aR*))-; EX-A1677; Tox21_112056; BDBM50030448; BDBM50079777; HB0289; LMPK04000003; NSC758659; s5003; AKOS005145901; AC-1182; AM81227; CCG-270494; CS-1507; DB00864; IDI1_001040; NCGC00163470-01; NCGC00163470-02; NCGC00163470-04; NCGC00163470-05; NCGC00163470-06; NCGC00163470-07; NCGC00163470-27; HY-13756; SBI-0052894.P002; CAS-104987-11-3; M2258; C01375; D08556; EN300-221601; AB01209746-01; AB01209746_03; Q411648; Q-201775; SR-05000001879-1; SR-05000001879-2; SR-05000001879-5; BRD-K35452788-001-02-1; BRD-K69608737-001-03-7; BRD-K69608737-001-10-2; Z2242006187; [(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-; 15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(23H)-tetrone; 15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(23H)-tetrone,; (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-prop-2-enyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone; (1R,9S,12S,13R,14S,17R,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-{1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-23,25-dimethoxy-13,19,21,27-tetramethyl-17-(prop-2-en-1-yl)-11,28-dioxa-4-azatricyclo[22.3.1.0,4,9]octacos-18-ene-2,3,10,16-tetrone; (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-5,19-dihydroxy-3-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(prop-2-en-1-yl)-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3H-15,19-epoxypyrido[2,1-c][1,4]oxazacyclotricosine-1,7,20,21(4H,23H)-tetrone; (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26AS)-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26A-HEXADECAHYDRO-5,19-DIHYDROXY-3-[(1E)-2-[(1R,3R,4R)-4-HYDROXY-3-METHOXYCYCLOHEXYL]-1-METHYLETHENYL]-14,16-DIMETHOXY-4,10,12,18-TETRAMETHYL-8-(2-PROPEN-1-YL)-15,19; (E)-(1R,9S,12S,13R,14R,21S,23S,24R,25S,27R)-17-Allyl-1,14-dihydroxy-12-[(E)-2-((3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0*4,9*]octacos-18-ene-2,3,10,16-tetraone; 15 19-Epoxy-3H-pyrido[2 1-c][1 4]oxaazacyclotricosine-1 7 20 21(4H 23H)-tetrone 5 6 8 11 12 13 14 15 16 17 18 19 24 25 26 26a-hexadecahydro-5 19-dihydroxy-3-[(1E)-2-[(1R 3R 4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14 16-dimethoxy-4 10 12 18-tet; 15 19-Epoxy-3H-pyrido[2 1-c][1 4]oxaazacyclotricosine-1 7 20 21(4H 23H)-tetrone 5 6 8 11 12 13 14 15 16 17 18 19 24 25 26 26a-hexadecahydro-5 19-dihydroxy-3-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl]-14 16-dimethoxy-4 10 12 18-tetramethyl-8-(2-pr; 15,19-epoxi-3h-pirido[2,1-c][1,4]oxaazaciclotricosina-1,7,20,21(4h,23h)-tetrona, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahidro-5,19-dihidroxi-3-[(1e)-2-[(1r,3r,4r)-4-hidroxi-3-metoxiciclohexil]-1-metiletenil]-14,16-dimetoxi-4,10,12,18-tetram; 15,19-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyc; 15,19-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propen-1-yl)-, (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-; 15,19-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycycl ohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propen-1-yl)-, (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-; 4,5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-heptadecahydro-5,19-dihydroxy-3-; dimethoxy-4,10,12,18-tetramethyl-8-(2-propenyl)-,(3S,4R,5S,8R,12S,14S,15R,16S,18R,19R,26aS)-; lohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propen-1-yl)-, (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-
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Target(s) Peptidyl-prolyl cis-trans isomerase FKBP1A (FKBP1A)
 Target Info 
Structure
Formula
C44H69NO12
Isosmiles
C[C@@H]1C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H]([C@@H]([C@H](CC(=O)[C@@H](/C=C(/C1)\C)CC=C)O)C)/C(=C/[C@@H]4CC[C@H]([C@@H](C4)OC)O)/C)O)C)OC)OC
PubChem CID
445643
InChI
InChI=1S/C44H69NO12/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7/h10,19,21,26,28-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3/b25-19+,27-21+/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+/m0/s1
InChIKey
QJJXYPPXXYFBGM-LFZNUXCKSA-N
IUPAC Name
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-prop-2-enyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone
Pharmaceutical Properties
Molecule Weight
804
Polar area
178
Complexity
1480
xlogp Value
2.7
Heavy Count
57
Rot Bonds
7
Hbond acc
12
Hbond Donor
3
The activity data of This Payload
Standard Type Value Units Cell line Disease Model Cell line ID Reference
Half Maximal Inhibitory Concentration (IC50) 0.000015 ug/mL
T-cells
Normal
Undisclosed [1]
Half Maximal Inhibitory Concentration (IC50) 0.000015 ug/mL
T-cells
Normal
Undisclosed [2]
Half Maximal Inhibitory Concentration (IC50) 0.0016 ug/mL
B-cells
Normal
Undisclosed [1]
Half Maximal Inhibitory Concentration (IC50) 0.034 nM
CD4+ve Th cells
Normal
Undisclosed [3]
Half Maximal Inhibitory Concentration (IC50) 0.18 nM
T-cells
Normal
Undisclosed
Half Maximal Inhibitory Concentration (IC50) 0.19 nM
Jurkat cells
T acute lymphoblastic leukemia
CVCL_0065 
[4]
Half Maximal Inhibitory Concentration (IC50) 0.25 nM
RBL-2H3 cells
Rat leukemia
CVCL_0591 
[5]
Half Maximal Inhibitory Concentration (IC50) 0.25 nM
RBL-2H3 cells
Rat leukemia
CVCL_0591 
[6]
Half Maximal Inhibitory Concentration (IC50) 0.25 nM
RBL-2H3 cells
Rat leukemia
CVCL_0591 
[7]
Half Maximal Inhibitory Concentration (IC50) 0.29 nM
T-cells
Normal
Undisclosed
Half Maximal Inhibitory Concentration (IC50) 0.29 nM
T-cells
Normal
Undisclosed
Half Maximal Inhibitory Concentration (IC50) 0.29 nM
Peripheral blood mononuclear cells
Normal
Undisclosed [4]
Half Maximal Inhibitory Concentration (IC50) 0.5 nM
T-cells
Normal
Undisclosed [8]
Half Maximal Inhibitory Concentration (IC50) 0.9 nM
T-cells
Normal
Undisclosed [8]
Half Maximal Inhibitory Concentration (IC50) 10.9 nM
WiDr cells
Colon adenocarcinoma
CVCL_2760 
[9]
Half Maximal Inhibitory Concentration (IC50) >100000 nM
Hep-G2 cells
Hepatoblastoma
CVCL_0027 
[10]
Half Maximal Inhibitory Concentration (IC50) >100000 nM
Vero 76 cells
Normal
CVCL_0603 
[10]
Half Maximal Inhibitory Concentration (IC50) 10495.93 nM
D283 Med cells
Medulloblastoma
CVCL_1155 
Half Maximal Inhibitory Concentration (IC50) 13.8 nM
U-251MG cells
Astrocytoma
CVCL_0021 
[9]
Half Maximal Inhibitory Concentration (IC50) 2 nM
Jurkat cells
T acute lymphoblastic leukemia
CVCL_0065 
[11]
Half Maximal Inhibitory Concentration (IC50) 3300 nM
HEK293 cells
Normal
CVCL_0045 
[12]
Half Maximal Inhibitory Concentration (IC50) 360 nM
Jurkat cells
T acute lymphoblastic leukemia
CVCL_0065 
[10]
Half Maximal Inhibitory Concentration (IC50) 3700 nM
HEK293 cells
Normal
CVCL_0045 
[13]
Half Maximal Inhibitory Concentration (IC50) 38290 nM
HEK293 cells
Normal
CVCL_0045 
[14]
Half Maximal Inhibitory Concentration (IC50) 5800 nM
Jurkat cells
T acute lymphoblastic leukemia
CVCL_0065 
[15]
Each Antibody-drug Conjugate Related to This Payload
References
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Ref 3 Biosynthesis of Nonimmunosuppressive ProlylFK506 Analogues with Neurite Outgrowth and Synaptogenic Activity. J Nat Prod. 2021 Feb 26;84(2):195-203. doi: 10.1021/acs.jnatprod.0c00767. Epub 2021 Feb 3.
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Ref 5 Vialinin B, a novel potent inhibitor of TNF-alpha production, isolated from an edible mushroom, Thelephora vialis. Bioorg Med Chem Lett. 2006 Oct 15;16(20):5424-6. doi: 10.1016/j.bmcl.2006.07.068. Epub 2006 Aug 9.
Ref 6 Design and synthesis of a vialinin A analog with a potent inhibitory activity of TNF- production and its transformation into a couple of bioprobes. Bioorg Med Chem Lett. 2012 Apr 1;22(7):2385-7. doi: 10.1016/j.bmcl.2012.02.034. Epub 2012 Feb 23.
Ref 7 Vialinin A is a ubiquitin-specific peptidase inhibitor. Bioorg Med Chem Lett. 2013 Aug 1;23(15):4328-31. doi: 10.1016/j.bmcl.2013.05.093. Epub 2013 Jun 6.
Ref 8 The C-32 triacetyl-L-rhamnose derivative of ascomycin: a potent, orally active macrolactone immunosuppressant. J Med Chem. 1995 Apr 14;38(8):1255-8. doi: 10.1021/jm00008a001.
Ref 9 Splicing factor SF3b as a target of the antitumor natural product pladienolide. Nat Chem Biol. 2007 Sep;3(9):570-5. doi: 10.1038/nchembio.2007.16. Epub 2007 Jul 22.
Ref 10 A calcineurin antifungal strategy with analogs of FK506. Bioorg Med Chem Lett. 2017 Jun 1;27(11):2465-2471. doi: 10.1016/j.bmcl.2017.04.004. Epub 2017 Apr 3.
Ref 11 Antifungal polybrominated proxyphylline derivative induces Candida albicans calcineurin stress response in Galleria mellonella. Bioorg Med Chem Lett. 2020 Dec 1;30(23):127545. doi: 10.1016/j.bmcl.2020.127545. Epub 2020 Sep 12.
Ref 12 Targeting breast cancer resistance protein (BCRP/ABCG2): Functional inhibitors and expression modulators. Eur J Med Chem. 2022 Jul 5;237:114346. doi: 10.1016/j.ejmech.2022.114346. Epub 2022 Apr 6.
Ref 13 Characterization of the transport of the bicyclic peptide phalloidin by human hepatic transport proteins. Naunyn Schmiedebergs Arch Pharmacol. 2003 Nov;368(5):415-20. doi: 10.1007/s00210-003-0814-4. Epub 2003 Oct 3.
Ref 14 Discovery of a novel family of FKBP12 "reshapers" and their use as calcium modulators in skeletal muscle under nitro-oxidative stress. Eur J Med Chem. 2021 Mar 5;213:113160. doi: 10.1016/j.ejmech.2021.113160. Epub 2021 Jan 14.
Ref 15 Amino Acid Conjugated Anthraquinones from the Marine-Derived Fungus Penicillium sp. SCSIO sof101. J Nat Prod. 2017 May 26;80(5):1668-1673. doi: 10.1021/acs.jnatprod.7b00269. Epub 2017 May 16.

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