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Compound Summary

sirolimus

Compound Information

sirolimus

Compound Name:	sirolimus
Compound CID:	5284616
Synonyms:	(-)-Rapamycin 53123-88-9 AY 22989 AY-22989 I 2190A More...
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:	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-/m1/s1
InChIKey:	QFJCIRLUMZQUOT-HPLJOQBZSA-N
Canonical Smiles:	CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)C(C(C(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=O)C(=O)C1(O2)O)C(C)CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC
Isomeric 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]4CC[C@H]([C@@H](C4)OC)O)C)/C)O)OC)C)C)/C)OC
Molecular Weight:	914.2
Molecular Formula:	C51H79NO13

Compound Structure

2D Structure:

3D Structure:

Computed Properties

sirolimus

Molecular Weight:	914.2
Molecular Formula:	C51H79NO13
Hydrogen Bond Donor Count:	3
Hydrogen Bond Acceptor Count:	13
Rotatable Bond Count:	6
Heavy Atom Count:	65
Complexity:	1760

Synonyms

sirolimus

sirolimus	sirolimus
(-)-Rapamycin	53123-88-9
AY 22989	AY-22989
I 2190A	I-2190A
I2190A	NSC 226080
RAPA	Rapammune
Rapamune	Rapamycin
SIIA 9268A	Sirolimus
Wy 090217	rapalimus
Rapamycin (Sirolimus)	WY-090217
Rapamycin (GMP)	FYARRO
HYFTOR	L04AA10
Npc-12g	Antibiotic AY 22989
CHEBI:9168	W36ZG6FT64
SM-88 COMPONENT SIROLIMUS	DE-109
MFCD00867594	NSC-226080
NCGC00021305-05	sirolimusum
(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-methoxycyclohexylpropan-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-epoxypyrido2,1-c1,4oxazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone	SILA 9268A
Supralimus	Rapamycin/Sirolimus
(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-methoxycyclohexylpropan-2-yl}-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo30.3.1.0(4,9)hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone	CAS-53123-88-9
Perceiva	Cypher
CCRIS 9024	NSC226080
HSDB 7284	1fkb
1pbk	NCGC00181146-01
LCP-Siro	(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-pyrido2,1-c1,4oxaazacyclohentriacontine-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-3H-23,27-epoxypyrido2,1-c1,4oxazacyclohentriacontine-1,5,11,28,29(6H,31H)-pentone
RAP	S1039
SIROLIMUS INN	SIROLIMUS JAN
RAPAMYCIN MI	SIROLIMUS HSDB
SIROLIMUS USAN	SIROLIMUS VANDF
BiomolKI2_000084	SIROLIMUS MART.
SCHEMBL3463	SIROLIMUS USP-RS
SIROLIMUS WHO-DD	Rapamycin,Sirolimus,Rapamune
UNII-W36ZG6FT64	BIDD:PXR0165
SIROLIMUS EMA EPAR	MLS006010168
Sirolimus USAN:INN:BAN	GTPL6031
SIROLIMUS ORANGE BOOK	DTXSID5023582
BDBM36609	MS-R001
RAPA, Rapamune, Sirolimus, RPM	HMS2089A21
HMS3403F11	HMS3884C03
EX-A1044	RPM
Tox21_110870	Tox21_112750
AC-722	BDBM50064359
HY-10219G	STL570275
AKOS015850976	AKOS015961618
ZINC169289388	CCG-100684
CS-0063	DB00877
NAB-RAPAMYCIN COMPONENT RAPAMYCIN	NSC-2260804
NCGC00021305-06	NCGC00021305-07
Rapamycin from Streptomyces hygroscopicus	AS-11687
HY-10219	SMR004701276
Fyarro (sirolimus albumin-bound particles)	EVEROLIMUS IMPURITY A EP IMPURITY
UNM-0000358684	A-275
CS-0626126	R0097
Rapamycin, VETRANAL(TM), analytical standard	EC 610-965-5
M02444	Q32089
123R889	Q-201659
BRD-K84937637-001-04-0	BRD-K84937637-001-06-5
BRD-K89626439-001-01-0	Z2568665260
24,25,26,27,32,33,34,34a-hexadecahydro-3H-23,27-epoxypy	Rapamycin from Streptomyces hygroscopicus, >=95% (HPLC), powder
Rapamycin from Streptomyces hygroscopicus, Vetec(TM) reagent grade, >=95%	(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-methoxycyclohexylpropan-2-yl}-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo30.3.1.04,9hexatriaconta-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-pyrido2,1-c1,4oxaazacyclohentriacontine-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-(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-{1-(1S,3R,4R)-4-hydroxy-3-methoxycyclohexylpropan-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-tricyclo30.3.1.04,9hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentaone (Rapamycin)

Experimental Data

sirolimus

Species	Dose	Unit	Control(Avg days)	Treatment(Avg days)	Avg/Med Lifespan Change(%)	Control(Max days)	Treatment(Max days)	Max Lifespan Change(%)	Significant	Strain	Gender	PubMed	Avg/Med Lifespan Change tab
Caenorhabditis elegans	50.000000000000000	umol/L			12.150000000000000				S	N2		30970250	Active
Caenorhabditis elegans	50.000000000000000	umol/L			16.140000000000000				S	N2		30970250	Active

Experimental Data Visualization

sirolimus

Statistics Data

sirolimus

Species	Avg/Med Lifespan Change(%)	Max Lifespan Change(%)	Count Reference	Count Data point
Caenorhabditis elegans	16.140000000000000		1	2

Statistics Data Visualization

sirolimus

Compound Name:

sirolimus

Compound CID:

5284616

Synonyms:

(-)-Rapamycin 53123-88-9 AY 22989 AY-22989 I 2190A More...

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:

InChIKey:

QFJCIRLUMZQUOT-HPLJOQBZSA-N

Canonical Smiles:

CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)C(C(C(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=O)C(=O)C1(O2)O)C(C)CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC

Isomeric 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]4CC[C@H]([C@@H](C4)OC)O)C)/C)O)OC)C)C)/C)OC

Molecular Weight:

914.2

Molecular Formula:

C51H79NO13

Molecular Weight:

914.2

Molecular Formula:

C51H79NO13

Hydrogen Bond Donor Count:

3

Hydrogen Bond Acceptor Count:

13

Rotatable Bond Count:

6

Heavy Atom Count:

65

Complexity:

1760

(-)-Rapamycin

53123-88-9

AY 22989

AY-22989

I 2190A

I-2190A

I2190A

NSC 226080

RAPA

Rapammune

Rapamune

Rapamycin

SIIA 9268A

Sirolimus

Wy 090217

rapalimus

Rapamycin (Sirolimus)

WY-090217

Rapamycin (GMP)

FYARRO

HYFTOR

L04AA10

Npc-12g

Antibiotic AY 22989

CHEBI:9168

W36ZG6FT64

SM-88 COMPONENT SIROLIMUS

DE-109

MFCD00867594

NSC-226080

NCGC00021305-05

sirolimusum

SILA 9268A

Supralimus

Rapamycin/Sirolimus

(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-methoxycyclohexylpropan-2-yl}-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo30.3.1.0(4,9)hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone

CAS-53123-88-9

Perceiva

Cypher

CCRIS 9024

NSC226080

HSDB 7284

1fkb

1pbk

NCGC00181146-01

LCP-Siro

RAP

(-)-Rapamycin

53123-88-9

AY 22989

AY-22989

I 2190A

More...