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

• ChemBase ID: 179897
• Molecular Formular: C51H79NO13
• Molecular Mass: 914.17186
• Monoisotopic Mass: 913.55514159
• SMILES: C1(=O)[C@@]2(O[C@H](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@@H](OC(=O)[C@H]3N(C1=O)CCCC3)[C@@H](C[C@@H]1C[C@@H]([C@H](CC1)O)OC)C)C)/C)O)OC)C)C)/C)OC)CC[C@H]2C)O
• Canonical SMILES: CO[C@H]1C[C@H](CC[C@@H]1O)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/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32+,33+,34+,36+,37+,38?,39-,40-,42-,43+,44-,46-,47+,51+/m0/s1
• InChIKey: QFJCIRLUMZQUOT-NTHOLEHTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S,12R,15R,16E,18S,19S,21R,23R,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1R,3S,4S)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.0^4,^9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone
• IUPAC Traditional name: (1R,9S,12R,15R,16E,18S,19S,21R,23R,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1R,3S,4S)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.0^4,^9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone
• Synonyms: Rapamycin; Sirolimus

Database IDs

• CAS Number: 53123-88-9
• PubChem SID: 164235807
• PubChem CID: 49652385

CALCULATED PROPERTIES

• Acid pKa: 9.963728
• H Acceptors: 12
• H Donor: 3
• LogD (pH = 5.5): 7.4508247
• LogD (pH = 7.4): 7.4496565
• Log P: 7.45084
• Molar Refractivity: 250.6632 cm^3
• Polarizability: 97.655174 Å^3
• Polar Surface Area: 195.43 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Inhibits the response to interleukin-2 (IL-2) and thereby blocks activation of T- and B-cells

Product Information

• Description: Rotamers (8:2)
• Biological Source: Prod. by Streptomyces hygroscopicus
• Application(s): Antifungal agent; Polyene-type antibiotic; Possesses antineoplastic and immunosuppressant props.

REFERENCES

• Baker, H. et al., J. Antibiot., 1978, 31, 539; 1979, 32, 630
• Morris, R.E. et al., Transpl. Rev., 1992, 16, 39-87