sodium (2S)-1-{2-[(2R,3R,6S)-2-hydroxy-6-[(2R,3E,5E,7E,9S,11R,13R,14R,15E,17R,19E,21R)-14-hydroxy-21-{[(1S,3S,4R)-4-[2-hydroxy(2H4)ethoxy]-3-methoxycyclohexyl]methyl}-2,13-dimethoxy-3,9,11,15,17-pentamethyl-12,18-dioxodocosa-3,5,7,15,19-pentaen-1-yl]-3-methyloxan-2-yl]-2-oxoacetyl}piperidine-2-carboxylate

• ChemBase ID: 170200
• Molecular Formular: C53H82NNaO14
• Molecular Mass: 980.20625
• Monoisotopic Mass: 979.56330059
• SMILES: N1(CCCC[C@H]1C(=O)[O-])C(=O)C(=O)[C@@]1(O[C@@H](CC[C@H]1C)C[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/[C@@H](C[C@H]1C[C@@H]([C@@H](CC1)OCCO)OC)C)C)/C)O)OC)C)C)/C)OC)O.[Na+]
• Canonical SMILES: OCCO[C@@H]1CC[C@H](C[C@@H]1OC)C[C@H](/C=C/C(=O)[C@@H](/C=C(/[C@H]([C@H](C(=O)[C@@H](C[C@@H](/C=C/C=C/C=C(/[C@@H](C[C@@H]1CC[C@H]([C@](O1)(O)C(=O)C(=O)N1CCCC[C@H]1C(=O)[O-])C)OC)\C)C)C)OC)O)\C)C)C.[Na+]
• InChI: InChI=1S/C53H83NO14.Na/c1-33(16-12-11-13-17-35(3)45(64-8)32-41-22-20-39(7)53(63,68-41)50(59)51(60)54-25-15-14-18-42(54)52(61)62)28-37(5)47(57)49(66-10)48(58)38(6)30-36(4)43(56)23-19-34(2)29-40-21-24-44(67-27-26-55)46(31-40)65-9;/h11-13,16-17,19,23,30,33-34,36-37,39-42,44-46,48-49,55,58,63H,14-15,18,20-22,24-29,31-32H2,1-10H3,(H,61,62);/q;+1/p-1/b13-11+,16-12+,23-19+,35-17+,38-30+;/t33-,34+,36-,37-,39-,40+,41+,42+,44-,45-,46+,48-,49+,53-;/m1./s1
• InChIKey: JZTVNCOLMGNTNU-JBSHEKRESA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S)-1-{2-[(2R,3R,6S)-2-hydroxy-6-[(2R,3E,5E,7E,9S,11R,13R,14R,15E,17R,19E,21R)-14-hydroxy-21-{[(1S,3S,4R)-4-[2-hydroxy(^2H₄)ethoxy]-3-methoxycyclohexyl]methyl}-2,13-dimethoxy-3,9,11,15,17-pentamethyl-12,18-dioxodocosa-3,5,7,15,19-pentaen-1-yl]-3-methyloxan-2-yl]-2-oxoacetyl}piperidine-2-carboxylate
• IUPAC Traditional name: sodium (2S)-1-{2-[(2R,3R,6S)-2-hydroxy-6-[(2R,3E,5E,7E,9S,11R,13R,14R,15E,17R,19E,21R)-14-hydroxy-21-{[(1S,3S,4R)-4-[2-hydroxy(^2H₄)ethoxy]-3-methoxycyclohexyl]methyl}-2,13-dimethoxy-3,9,11,15,17-pentamethyl-12,18-dioxodocosa-3,5,7,15,19-pentaen-1-yl]-3-methyloxan-2-yl]-2-oxoacetyl}piperidine-2-carboxylate
• Synonyms: ########; (19E/Z)-seco-[4-O-[2-Hydroxy(ethyl)-d4]] Rapamycin Sodium Salt

Database IDs

• PubChem SID: 164226110
• PubChem CID: 71748856

CALCULATED PROPERTIES

• Acid pKa: 3.7221262
• H Acceptors: 14
• H Donor: 3
• LogD (pH = 5.5): 6.11263
• LogD (pH = 7.4): 4.5924697
• Log P: 7.8900743
• Molar Refractivity: 275.6908 cm^3
• Polarizability: 102.15736 Å^3
• Polar Surface Area: 218.49 Å^2
• Rotatable Bonds: 27
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H825292

A labelled metabolite of the immunosuppressant macrolide SDZ RAD (also known as Everolimus E945400) which is an analog of the parent drug Rapamycin (R124000).

REFERENCES

• Vidal, C. et al.: J. Am. Soc. Mass Spec., 9, 1267 (1998); Kovarik, J. M., et al.: Clin. Pharmacol. Ther., 69, 48 (2001);