Tacrolimus（anhydrous）(FK506) - Moligand™, analytical standard, ≥98% , Inhibitor of FKBP prolyl isomerase 1A;Activator of TRPM8, CAS No.104987-11-3, Inhibitor of FKBP prolyl isomerase 1A;Activator of TRPM8

CAS: 104987-11-3 Cat. No.: T101159 Molecular Weight: 804.02 EC Number: 627-021-3

GRADE & PURITY Analytical standard, Moligand™, ≥98%

Synonyms

(7aR)-4,4,7a-trimethyl-6,7-dihydro-5H-benzofuran-2-one;Dihydroactinidiolide | CHEBI:93221 | DB00864 | HMS1792O21 | UNII-WM0HAQ4WNM | FR900506 | FR-900506 | Modigraf | NCGC00163470-05 | NSC758659 | NSC-758659 | HY-100943 | L-679934 | M2258 | AM81227 | L04A

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

(7aR)-4, 4, 7a-trimethyl-6, 7-dihydro-5H-benzofuran-2-one;Dihydroactinidiolide | CHEBI:93221 | DB00864 | HMS1792O21 | UNII-WM0HAQ4WNM | FR900506 | FR-900506 | Modigraf | NCGC00163470-05 | NSC758659 | NSC-758659 | HY-100943 | L-679934 | M2258 | AM81227 | L04A

Specifications & Purity

Moligand™, analytical standard, ≥98%

Biochemical and Physiological Mechanisms

Description:
IC50 Value: 0.47 nM (Inhibition of lymphocyte proliferation) [1]
Tacrolimus is a potent immunosuppressive drug often administered to transplant recipient patients and exhibits a variety of adverse cardiovascular effects.
in vit

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Analytical standard, Moligand™

Action Type

ACTIVATOR, INHIBITOR

Mechanism of action

Inhibitor of FKBP prolyl isomerase 1A;Activator of TRPM8

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Toxic, refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: 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
• 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
• InChIKey: QJJXYPPXXYFBGM-LFZNUXCKSA-N
• 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
• Isomeric SMILES: 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
• WGK Germany: 3
• RTECS: KD4201200
• UN Number: 2811
• Molecular Weight: 804.02
• Reaxy-Rn: 14244277
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=14244277&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Macrolide lactams

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Macrolide lactams
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Macrolide lactams
• Alternative Parents: Alpha amino acid esters Macrolides and analogues Cyclohexanols Piperidines Oxanes Tertiary carboxylic acid amides Carboxylic acid esters Cyclic alcohols and derivatives Cyclic ketones Hemiacetals Lactams Lactones Azacyclic compounds Dialkyl ethers Oxacyclic compounds Monocarboxylic acids and derivatives Hydrocarbon derivatives Organopnictogen compounds Organonitrogen compounds Organic oxides
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Macrolide lactam - Alpha-amino acid ester - Macrolide - Alpha-amino acid or derivatives - Cyclohexanol - Oxane - Piperidine - Cyclic alcohol - Tertiary carboxylic acid amide - Cyclic ketone - Secondary alcohol - Carboxamide group - Carboxylic acid ester - Hemiacetal - Ketone - Lactam - Lactone - Organoheterocyclic compound - Azacycle - Carboxylic acid derivative - Oxacycle - Dialkyl ether - Ether - Monocarboxylic acid or derivatives - Organopnictogen compound - Alcohol - Organic oxygen compound - Carbonyl group - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.
• External Descriptors: Macrolides and lactone polyketides

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CYP3A4 Tclin Cytochrome P450 3A4 (0 Activities)

Discover Target: CYP3A4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CYP3A5 Tclin Cytochrome P450 3A5 (0 Activities)

Discover Target: CYP3A5

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

FKBP1A Tclin Peptidyl-prolyl cis-trans isomerase FKBP1A (1 Activities)

Discover Target: FKBP1A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

FKBP1B Tchem Peptidyl-prolyl cis-trans isomerase FKBP1B (0 Activities)

Discover Target: FKBP1B

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

FKBP5 Tchem Peptidyl-prolyl cis-trans isomerase FKBP5 (0 Activities)

Discover Target: FKBP5

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SF3B3 Tchem Splicing factor 3B subunit 3 (0 Activities)

Discover Target: SF3B3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPM8 Tclin Transient receptor potential cation channel subfamily M member 8 (0 Activities)

Discover Target: TRPM8

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PPP3CA Tchem Serine/threonine-protein phosphatase 2B catalytic subunit alpha isoform (0 Activities)

Discover Target: PPP3CA

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MTOR Tclin Serine/threonine-protein kinase mTOR (0 Activities)

Discover Target: MTOR

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Sensitivity: heat sensitive
• Molecular Weight: 804.000 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 7
• Exact Mass: 803.482 Da
• Monoisotopic Mass: 803.482 Da
• Topological Polar Surface Area: 178.000 Ų
• Heavy Atom Count: 57
• Formal Charge: 0
• Complexity: 1480.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 14
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1

References

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2. Xiaoqian Jiang, Xinxin Xu, Hua Kuang, Liqiang Liu, Liguang Xu, Aihua Qu, Chuanlai Xu.  (2023)  A gold-based immunochromatographic strip for the specific detection of tacrolimus in whole blood.  Journal of Materials Chemistry B,  11  (20): (4464-4474).  [PMID:37159048] [10.1039/D3TB00569K]

3. Fei Gong, Huihui Hu, Ying Ouyang, Zheng-Zheng Liao, Ying Kong, Jin-Fang Hu, Hua He, Ying Zhou.  (2023)  Physiologically-based pharmacokinetic modeling-guided rational combination of tacrolimus and voriconazole in patients with different CYP3A5 and CYP2C19 alleles.  TOXICOLOGY AND APPLIED PHARMACOLOGY,      [PMID:36931438] [10.1016/j.taap.2023.116475]

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6. Gao Ping, Du Xiaoyi, Liu Lili, Xu Hua, Liu Maochang, Guan Xinlei, Zhang Chengliang.  (2021)  Astragaloside IV Alleviates Tacrolimus-Induced Chronic Nephrotoxicity via p62-Keap1-Nrf2 Pathway.  Frontiers in Pharmacology,      [PMID:33536919] [10.3389/fphar.2020.610102]

7. Shoubao Wang, Yao Xiong, Yinmin Wang, Jingting Chen, Jun Yang, Binbin Sun.  (2020)  Evaluation of PLGA microspheres with triple regimen on long-term survival of vascularized composite allograft – an experimental study.  TRANSPLANT INTERNATIONAL,  33  (4): (450-461).  [PMID:31930539] [10.1111/tri.13574]

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10. Hongyan Zhang, Fengjiao Bu, Lei Li, Zheng Jiao, Guo Ma, Weimin Cai, Xiaomei Zhuang, Hai-Shu Lin, Jae-Gook Shin, Xiaoqiang Xiang.  (2017)  Prediction of Drug–Drug Interaction between Tacrolimus and Principal Ingredients of Wuzhi Capsule in Chinese Healthy Volunteers Using Physiologically-Based Pharmacokinetic Modelling.  BASIC & CLINICAL PHARMACOLOGY & TOXICOLOGY,  122  (3): (331-340).  [PMID:28945011] [10.1111/bcpt.12914]

11. Ping Gao, Xinwei Cheng, Maochang Liu, Hui Peng, Guodong Li, Tianze Shang, Jianqiao Wang, Qianyan Gao, Chenglong Zhu, Zhenpeng Qiu, Chengliang Zhang.  (2025)  GADD45α is a direct target of TFEB and contributes to tacrolimus-induced chronic nephrotoxicity.  JCI Insight,      [PMID:39913188] [10.1172/jci.insight.183560]

12. Xin Wang, Feiyang Pu, Xuanye Yang, Xili Feng, Jiayou Zhang, Kai Duan, Xuanxuan Nian, Zhongren Ma, Xiao-Xia Ma, Xiao-Ming Yang.  (2024)  Immunosuppressants exert antiviral effects against influenza A(H1N1)pdm09 virus via inhibition on nucleic acid synthesis, mRNA splicing and protein stability.  Virulence,      [PMID:38170681] [10.1080/21505594.2023.2301242]

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