(1R,2R,4S)-4-[(2R)-2-[(1R,9S,12S,15R,18R,19R,21R,23S,30S,32S,35R)-1,18-dihydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-2,3,10,14,20-pentaoxo-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraen-12-yl]propyl]-2-methoxycyclohexyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate

• ChemBase ID: 154888
• Molecular Formular: C56H87NO16
• Molecular Mass: 1030.28708
• Monoisotopic Mass: 1029.60248571
• SMILES: C[C@@H]1CC[C@H]2C[C@H](/C(=C\C=C\C=C[C@H](C[C@H](C(=O)[C@H]([C@@H](/C(=C/[C@H](C(=O)C[C@@H](OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@@]1(O2)O)[C@H](C)C[C@@H]1CC[C@H]([C@@H](C1)OC)OC(=O)C(C)(CO)CO)C)/C)O)OC)C)C)/C)OC
• Canonical SMILES: CO[C@@H]1C[C@@H](CC[C@H]1OC(=O)C(CO)(CO)C)C[C@H]([C@@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H](CC[C@H]2C)C[C@@H](OC)/C(=C\C=C\C=C[C@H](C[C@H](C(=O)[C@H]([C@@H](/C(=C/[C@H](C(=O)C1)C)/C)O)OC)C)C)/C)C
• InChI: InChI=1S/C56H87NO16/c1-33-17-13-12-14-18-34(2)45(68-9)29-41-22-20-39(7)56(67,73-41)51(63)52(64)57-24-16-15-19-42(57)53(65)71-46(30-43(60)35(3)26-38(6)49(62)50(70-11)48(61)37(5)25-33)36(4)27-40-21-23-44(47(28-40)69-10)72-54(66)55(8,31-58)32-59/h12-14,17-18,26,33,35-37,39-42,44-47,49-50,58-59,62,67H,15-16,19-25,27-32H2,1-11H3/t33-,35-,36-,37-,39-,40+,41+,42+,44-,45+,46+,47-,49-,50+,56-/m1/s1
• InChIKey: CBPNZQVSJQDFBE-AQHKCTBXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,4S)-4-[(2R)-2-[(1R,9S,12S,15R,18R,19R,21R,23S,30S,32S,35R)-1,18-dihydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-2,3,10,14,20-pentaoxo-11,36-dioxa-4-azatricyclo[30.3.1.0^4,^9]hexatriaconta-16,24,26,28-tetraen-12-yl]propyl]-2-methoxycyclohexyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate
• IUPAC Traditional name: (1R,2R,4S)-4-[(2R)-2-[(1R,9S,12S,15R,18R,19R,21R,23S,30S,32S,35R)-1,18-dihydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-2,3,10,14,20-pentaoxo-11,36-dioxa-4-azatricyclo[30.3.1.0^4,^9]hexatriaconta-16,24,26,28-tetraen-12-yl]propyl]-2-methoxycyclohexyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate
• Synonyms: 42-[3-Hydroxy-2-methylpropanoate; CCI-779; Rapamycin; Temsirolimus

Database IDs

• CAS Number: 162635-04-3
• MDL Number: MFCD00934421
• PubChem SID: 162249026
• PubChem CID: 71312019

CALCULATED PROPERTIES

• Acid pKa: 9.96374
• H Acceptors: 14
• H Donor: 4
• LogD (pH = 5.5): 7.1299443
• LogD (pH = 7.4): 7.128776
• Log P: 7.1299596
• Molar Refractivity: 277.0665 cm^3
• Polarizability: 108.30001 Å^3
• Polar Surface Area: 241.96 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: white to off-white powder

Safety Information

• German water hazard class: 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C56H87NO16

DETAILS

Sigma Aldrich - PZ0020

Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
Temsirolimus is a specific inhibitor of mammalian target of rapamycin (mTOR) mTOR Complex 1 (mTORC1). Temsirolimus is an antiproliferative and antiangiogenic, the first-in-class mTOR inhibitor approved for the treatment of patients with advanced poor prognosis renal cell carcinoma.