(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(1E)-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[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone

• ChemBase ID: 130465
• Molecular Formular: C44H69NO12
• Molecular Mass: 804.01816
• Monoisotopic Mass: 803.48197665
• SMILES: O=C1C(=O)N2CCCC[C@H]2C(=O)O[C@@H](/C(=C/[C@@H]2CC[C@@H](O)[C@H](OC)C2)/C)[C@H](C)[C@@H](O)CC(=O)[C@@H](/C=C(/C[C@@H](C[C@@H](OC)[C@H]2O[C@]1(O)[C@H](C)C[C@@H]2OC)C)\C)CC=C
• Canonical SMILES: C=CC[C@@H]1/C=C(\C)/C[C@H](C)C[C@@H](OC)[C@H]2O[C@](O)([C@@H](C[C@@H]2OC)C)C(=O)C(=O)N2[C@H](C(=O)O[C@H]([C@@H]([C@H](CC1=O)O)C)/C(=C/[C@@H]1CC[C@H]([C@@H](C1)OC)O)/C)CCCC2
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(1E)-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
• IUPAC Traditional name: tacrolimus
• Synonyms: Tacrolimus

Database IDs

• CAS Number: 104987-11-3
• PubChem SID: 162224744
• PubChem CID: 445643; 6473866
• ATC CODE: L04AD02; D11AH01
• CHEMBL: 1200738
• Chemspider ID: 4976056
• DrugBank ID: DB00864
• Unique Ingredient Identifier: Y5L2157C4J
• Wikipedia Title: Tacrolimus

CALCULATED PROPERTIES

• Acid pKa: 9.955601
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): 5.594105
• LogD (pH = 7.4): 5.5929146
• Log P: 5.59412
• Molar Refractivity: 215.6203 cm^3
• Polarizability: 84.94902 Å^3
• Polar Surface Area: 178.36 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Admin Routes: Topical, oral, iv
• Bioavailability: 20%, less after eating food rich in fat
• Excretion: Mostly faecal
• Half Life: 11.3 h (range 3.5-40.6 h)
• Metabolism: Hepatic CYP3A4
• Protein Bound: 75-99%
• Legal Status: Rx-only
• Pregnancy Category: C