Tacrolimus

C₄₄H₆₉NO₁₂ — CID 71668407

About Tacrolimus

Tacrolimus (PubChem CID 71668407) has the molecular formula C₄₄H₆₉NO₁₂ and a molecular weight of 804.03 g/mol. Its IUPAC name is (1R,9S,12S,13S,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.

Molecular Properties

• Compound Name: Tacrolimus
• PubChem CID: 71668407
• Molecular Formula: C₄₄H₆₉NO₁₂
• Molecular Weight: 804.03 g/mol
• Exact Mass: 803.48
• IUPAC Name: (1R,9S,12S,13S,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: C=CC[C@@H]1/C=C(\C)C[C@H](C)C[C@H](OC)[C@H]2O[C@@](O)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@H](/C(C)=C/[C@@H]3CC[C@@H](O)[C@H](OC)C3)[C@@H](C)[C@@H](O)CC1=O)[C@H](C)C[C@@H]2OC
• 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-ZIUDIOLZSA-N
• XLogP: 4.64
• TPSA: 178.36 Ų
• H-Bond Donors: 3
• H-Bond Acceptors: 12
• Rotatable Bonds: 7
• Heavy Atoms: 57
• Complexity: —

Lipinski Rule of Five

2 violations

Rule	Value
MW ≤ 500	804.03
LogP ≤ 5	4.64
H-Bond Donors ≤ 5	3
H-Bond Acceptors ≤ 10	12

Computed Properties (RDKit)

• Structural Alerts: {'alert_name': 'diketo_group', 'substructure': 'N/A'}, {'alert_name': 'isolated_alkene', 'substructure': 'N/A'}

Frequently Asked Questions

What is the IUPAC name of Tacrolimus?

The IUPAC name of Tacrolimus (CID 71668407) is (1R,9S,12S,13S,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.

What is the SMILES notation for Tacrolimus?

The canonical SMILES for Tacrolimus is C=CC[C@@H]1/C=C(\C)C[C@H](C)C[C@H](OC)[C@H]2O[C@@](O)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@H](/C(C)=C/[C@@H]3CC[C@@H](O)[C@H](OC)C3)[C@@H](C)[C@@H](O)CC1=O)[C@H](C)C[C@@H]2OC.

What is the InChIKey of Tacrolimus?

The InChIKey is QJJXYPPXXYFBGM-ZIUDIOLZSA-N. The full InChI is 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.

What are the key properties of Tacrolimus?

Tacrolimus has a molecular weight of 804.03 g/mol, XLogP of 4.64, 7 rotatable bonds, 3 hydrogen bond donors, and 12 hydrogen bond acceptors.

Where does this data come from?

All data for Tacrolimus is sourced from PubChem (CID 71668407), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).

Sources

• PubChem CID 71668407 — identifiers, structure, computed properties (public domain)
• DrugCentral drug card 2552 — approved-drug record (CC BY-SA 4.0)

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