Sirolimus

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Sirolimus are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Sirolimus?

The molecule Sirolimus presents a molecular formula of C51H79NO13 and its IUPAC name is (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-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.

Sirolimus is a macrolide immunosuppressant drug that was discovered in a soil sample from Easter Island. It is used to prevent the body from rejecting organ transplants. It is also used to treat a rare lung disease called lymphangioleiomyomatosis, and certain types of kidney cancer..

Sirolimus works by binding to a protein called mTOR (mammalian target of rapamycin). mTOR is a protein that participes in cell growth and proliferation. By binding to mTOR, sirolimus inhibits the protein's ability to promote cell growth. This action helps to prevent the body from rejecting transplanted organs, and also helps to slow the growth of certain types of cancer cells..

Sirolimus exists as a tablet, an oral solution, and a suspension. It is usually taken once a day, with or without food. The oral solution and suspension must be taken on an empty stomach..

Common side effects of sirolimus include mouth sores, diarrhea, constipation, stomach pain, headache, dizziness, and fatigue. Sirolimus can also cause serious side effects, such as kidney problems, high blood pressure, and an increased risk of infection..

Sirolimus is a potent immunosuppressant drug that has a wide range of uses. It is important to discuss the risks and benefits of sirolimus with your doctor before starting treatment..

3D structure

Cartesian coordinates

Geometry of Sirolimus in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Sirolimus QFJCIRLUMZQUOT-HPLJOQBZSA-N chemical compound 2D structure molecule svg
Sirolimus

 

Molecule descriptors

 
IUPAC name(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-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
InChI codeInChI=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-/m1/s1
InChI KeyQFJCIRLUMZQUOT-HPLJOQBZSA-N
SMILESCO[C@H]1C[C@@H]2CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N2CCCC[C@H]2C(=O)O[C@H]([C@H](C)C[C@@H]2CC[C@@H](O)[C@H](OC)C2)CC(=O)[C@H](C)/C=C(\C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C/C=C/C=C/1C

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (-)-Rapamycin
  • (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-Dihydroxy-12-{(2S)-1-[(1S,3R,4R)-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
  • (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-{(2S)-1-[(1S,3R,4R)-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
  • (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34 aS)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-Hex adecahydro-9,27-dihydroxy-3-[(1R)-2-[(1S,3R,4R)-4-hydro xy-3-methoxycyclohexyl]-1-methylethyl]-10,21-dimethoxy- 6,8,12,14,20,26-hexamethyl-23,27-ep
  • (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-4,9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-heptadecahydro-9,27-dihydroxy-3-[(1R)-2-[(1S,3,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-223,27-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine-1,5,11,28,29(6H,31H)-pentone
  • (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-Hexadecahydro-9,27-dihydroxy-3-((1R)-2-((1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl)-1-methylethyl)-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-23,27-epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone
  • (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-Hexadecahydro-9,27-dihydroxy-3-[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-23,27-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone
  • (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,27-dihydroxy-3-{(1R)-2-[(1S,3R,4R)-4-hydroxy-3-(methyloxy)cyclohexyl]-1-methylethyl}-6,8,12,14,20,26-hexamethyl-10,21-bis(methyloxy)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro
  • (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,27-dihydroxy-3-{(1R)-2-[(1S,3R,4R)-4-hydroxy-3-(methyloxy)cyclohexyl]-1-methylethyl}-6,8,12,14,20,26-hexamethyl-10,21-bis(methyloxy)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-3H-23,27-epoxypyrido[2,1-c][1,4]oxazacyclohentriacontine-1,5,11,28,29(6H,31H)-pentone
  • (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,27-dihydroxy-3-{(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl}-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-3H-23,27-epoxypyrido[2,1-c][1,4]oxazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone
  • (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,27-dihydroxy-3-{(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-3H-23,27-epoxypyrido[2,1-c][1,4]oxazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone
  • (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,27-dihydroxy-3-{1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-9,10,12,13,14,21,22,23,
  • 1,18-Dihydroxy-12-[2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-ethyl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-aza-tricyclo[30.3.1.0*4,9*]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentaone (Rapamycin)
  • 123R889
  • 1fkb
  • 1pbk
  • 24,25,26,27,32,33,34,34a-hexadecahydro-3H-23,27-epoxypy
  • 53123-88-9
  • A-275
  • AC-722
  • AS-11687
  • AY 22989
  • AY-22989
  • Antibiotic AY 22989
  • BDBM36609
  • BDBM50064359
  • BIDD:PXR0165
  • BiomolKI2_000084
  • CCG-100684
  • CCRIS 9024
  • CS-0063
  • Cypher
  • DB00877
  • DE-109
  • DSSTox_CID_3582
  • DSSTox_GSID_23582
  • DSSTox_RID_77091
  • EC 610-965-5
  • EX-A1044
  • FYARRO
  • Fyarro (sirolimus albumin-bound particles)
  • GTPL6031
  • HMS2089A21
  • HMS3403F11
  • HMS3884C03
  • HSDB 7284
  • HY-10219
  • HYFTOR
  • I 2190A
  • I-2190A
  • I2190A
  • L04AA10
  • LCP-Siro
  • M02444
  • MFCD00867594
  • MLS006010168
  • MS-R001
  • NAB-RAPAMYCIN COMPONENT RAPAMYCIN
  • NCGC00021305-05
  • NCGC00021305-06
  • NCGC00021305-07
  • NCGC00181146-01
  • NSC 226080
  • NSC-226080
  • NSC-2260804
  • NSC226080
  • Npc-12g
  • Perceiva
  • Q-201659
  • Q32089
  • R0097
  • RAP
  • RAPA
  • RAPA, Rapamune, Sirolimus, RPM
  • RPM
  • Rapammune
  • Rapamune
  • Rapamycin
  • Rapamycin (Sirolimus)
  • Rapamycin C-7, analog 4
  • Rapamycin from Streptomyces hygroscopicus
  • Rapamycin,Sirolimus,Rapamune
  • Rapamycin/Sirolimus
  • S1039
  • SIIA 9268A
  • SILA 9268A
  • SM-88 COMPONENT SIROLIMUS
  • SMR004701276
  • STL570275
  • Sirolimus
  • Supralimus
  • UNM-0000358684
  • W36ZG6FT64
  • WY-090217
  • Wy 090217
  • rapalimus
  • sirolimusum

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC169289388
  • CAS-53123-88-9
  • UNII-W36ZG6FT64
  • AKOS015850976
  • AKOS015961618
  • BRD-K84937637-001-04-0
  • BRD-K84937637-001-06-5
  • BRD-K89626439-001-01-0
  • DTXSID5023582
  • CHEBI:9168
  • Tox21_110870
  • Tox21_112750
  • SCHEMBL3463

Physico-Chemical properties

IUPAC name(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-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
Molecular formulaC51H79NO13
Molecular weight914.172
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity253.68
LogP6.1
Topological polar surface area195.4

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.