Tacrolimus

Details

• Internal ID: 0f0abd10-4871-4763-8852-9353abc1ac1e
• Taxonomy: Phenylpropanoids and polyketides > Macrolide lactams
• 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
• SMILES (Canonical): CC1CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C(CC(=O)C(C=C(C1)C)CC=C)O)C)C(=CC4CCC(C(C4)OC)O)C)O)C)OC)OC
• SMILES (Isomeric): 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
• 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
• InChI Key: QJJXYPPXXYFBGM-LFZNUXCKSA-N
• Popularity: 41,429 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₆₉NO₁₂
• Molecular Weight: 804.00 g/mol
• Exact Mass: 803.48197664 g/mol
• Topological Polar Surface Area (TPSA): 178.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 4.64
• H-Bond Acceptor: 12
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

• Fujimycin
• 104987-11-3
• Prograf
• Tsukubaenolide
• Protopic
• 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)
• Hecoria
• (-)-FK 506
• 8-DEETHYL-8-[BUT-3-ENYL]-ASCOMYCIN
• Tacrolimus (INN)
• UNII-Y5L2157C4J
• PROGRAPH
• TACRO
• CCRIS 7124
• DTXSID5046354
• FR900506
• CHEBI:61049
• HSDB 8195
• Y5L2157C4J
• FK-506 (Tacrolimus)
• Prograf (TN)
• Tacrolimus [USAN]
• NSC-758659
• L 679934
• CHEMBL269732
• DTXCID3026354
• K506
• NCGC00163470-03
• 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
• UNII-WM0HAQ4WNM
• Graceptor
• TACROLIMUS (USP-RS)
• CHEBI:61057
• TACROLIMUS (USP MONOGRAPH)
• 8-DEETHYL-8-(BUT-3-ENYL)-ASCOMYCIN
• NSC 758659
• SR-05000001879
• Tacrolimus [USAN:INN]
• TACROLIMUS MONOHYDRATE (EP MONOGRAPH)
• tacrolimusum
• Talymus
• MFCD00869853
• NSC717865
• ENVARSUS-XR
• TACROLIMUS [MI]
• SCHEMBL3088
• TACROLIMUS [WHO-DD]
• BSPBio_001279
• CHEMBL66247
• L-679934
• GTPL6784
• Tacrolimus in whole human blood
• CHEBI:93221
• HMS503O21
• C44H69NO12.H2O
• D11AH01
• L04AD02
• QJJXYPPXXYFBGM-LFZNUXCKSA-N
• HMS1792O21
• HMS1990O21
• HMS2093M19
• HMS3403O21
• Pharmakon1600-01503968
• 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
• A11860
• 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,
• (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)-5,19-dihydroxy-3-{(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl}-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-(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*))-
• 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)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4842	48.42%
Caco-2	-	0.8548	85.48%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.5721	57.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8236	82.36%
OATP1B3 inhibitior	+	0.9246	92.46%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9433	94.33%
P-glycoprotein inhibitior	+	0.7808	78.08%
P-glycoprotein substrate	+	0.9343	93.43%
CYP3A4 substrate	+	0.7980	79.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8882	88.82%
CYP3A4 inhibition	-	0.8690	86.90%
CYP2C9 inhibition	-	0.9053	90.53%
CYP2C19 inhibition	-	0.8969	89.69%
CYP2D6 inhibition	-	0.9402	94.02%
CYP1A2 inhibition	-	0.8874	88.74%
CYP2C8 inhibition	+	0.6625	66.25%
CYP inhibitory promiscuity	-	0.9807	98.07%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4767	47.67%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9135	91.35%
Skin irritation	-	0.7406	74.06%
Skin corrosion	-	0.9301	93.01%
Ames mutagenesis	-	0.5670	56.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3720	37.20%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	+	0.9772	97.72%
skin sensitisation	-	0.8660	86.60%
Respiratory toxicity	+	0.9667	96.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.7837	78.37%
Acute Oral Toxicity (c)	III	0.6257	62.57%
Estrogen receptor binding	+	0.8571	85.71%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.5281	52.81%
Glucocorticoid receptor binding	+	0.7145	71.45%
Aromatase binding	+	0.6174	61.74%
PPAR gamma	+	0.7740	77.40%
Honey bee toxicity	-	0.6306	63.06%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.8302	83.02%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1902	P62942	FK506-binding protein 1A	0.9 nM	EC50	via Super-PRED
CHEMBL2430	P68106	FK506-binding protein 1B	0.4 nM	Kd	via Super-PRED
CHEMBL2052031	Q13451	Peptidyl-prolyl cis-trans isomerase FKBP5	79 nM	Ki	via Super-PRED
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	0.95 nM	IC50	via Super-PRED
CHEMBL1250378	Q15393	Splicing factor 3B subunit 3	10.9 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.34%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.16%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.90%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	94.39%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	92.69%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.48%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.29%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	89.96%	93.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.87%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.43%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.23%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.97%	93.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.94%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.86%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.89%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.82%	97.25%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.55%	90.08%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.55%	93.04%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.01%	94.00%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	83.64%	98.99%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.19%	91.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.84%	100.00%
CHEMBL1871	P10275	Androgen Receptor	82.36%	96.43%
CHEMBL340	P08684	Cytochrome P450 3A4	81.51%	91.19%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.96%	82.38%
CHEMBL5957	P21589	5'-nucleotidase	80.53%	97.78%

Plants that contains it

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Cross-Links

• PubChem: 445643
• LOTUS: LTS0216864
• wikiData: Q411648