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Compound Summary

(-)-Rapamycin

Compound Information

(-)-Rapamycin

Compound Name:	(-)-Rapamycin
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

(-)-Rapamycin

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

(-)-Rapamycin

(-)-Rapamycin	(-)-Rapamycin
(-)-Rapamycin	53123-88-9
AY 22989	AY-22989
I 2190A	I-2190A
I2190A	NSC 226080
RAPA	Rapammune
Rapamune	Rapamycin
SIIA 9268A	Sirolimus
Wy 090217	Rapamycin (Sirolimus)
Antibiotic AY 22989	UNII-W36ZG6FT64
CHEBI:9168	W36ZG6FT64
WY-090217	DE-109
MFCD00867594	NCGC00021305-05
DSSTox_CID_3582	sirolimusum
DSSTox_RID_77091	DSSTox_GSID_23582
SILA 9268A	Supralimus
C51H79NO13	(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
(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	CAS-53123-88-9
Perceiva	Cypher
CCRIS 9024	NSC226080
HSDB 7284	1fkb
1pbk	NSC-226080
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)-9,27-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
BiomolKI2_000084	Rapamycin C-7, analog 4
SCHEMBL3463	Rapamycin,Sirolimus,Rapamune
BIDD:PXR0165	23,27-Epoxy-3H-pyrido2,1-c1,4oxaazacyclohentriacontine
MLS006010168	Sirolimus USAN:INN:BAN
GTPL6031	DTXSID5023582
BDBM36609	L04AA10
MS-R001	SYN1185
SM-88 COMPONENT SIROLIMUS	HMS2089A21
HMS3403F11	HMS3884C03
(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	EX-A1044
Tox21_110870	Tox21_112750
AC-722	BDBM50064359
STL570275	AKOS015850976
AKOS015961618	ZINC169289388
ACN-035837	CCG-100684
CS-0063	DB00877
NSC-2260804	NCGC00021305-06
NCGC00021305-07	Rapamycin from Streptomyces hygroscopicus
AS-11687	HY-10219
SMR004701276	UNM-0000358684
A-275	R0097
Rapamycin, RAPA, Rapamune, Sirolimus, RPM	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
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%	Sirolimus solution, 1.0 mg/mL in acetonitrile, ampule of 1 mL, certified reference material
(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-{(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-epoxypyrido2,1-c1,4oxazacyclohentriacontine-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-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

(-)-Rapamycin

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
Mus musculus	4.000000000000000	mg/kg			0.000000000000000				S	C57BL/6J	MALES	19934433	Active
Mus musculus	2.240000000000000	mg/kg				1094.000000000000000	1245.000000000000000	14.000000000000000	Unclear	ALL SITES	FEMALES	19587680
Saccharomyces cerevisiae	0.550000000000000	nM							Unclear			18513215
Caenorhabditis elegans	1.000000000000000	ug/mL							Unclear	N2		33683565
Mus musculus	2.240000000000000	mg/kg				1078.000000000000000	1179.000000000000000	9.000000000000000	Unclear	ALL SITES	MALES	19587680
Mus musculus	8.000000000000000	mg/kg	925.000000000000000	1054.000000000000000	14.000000000000000				S	C57BL/6JNia	MALES	27549339	Active
Mus musculus	14.000000000000000	ppm			14.000000000000000			16.000000000000000	S	C57BL/6J	FEMALES	24409289	Active
Drosophila melanogaster	200.000000000000000	umol/L	95.000000000000000	100.000000000000000	0.050000000000000				Unclear	yw	FEMALES	20074526
Mus musculus	2.240000000000000	mg/kg			5.000000000000000	1035.000000000000000	1142.000000000000000	10.000000000000000	Unclear	TJL	MALES	19587680
Mus musculus	14.000000000000000	ppm			7.000000000000000			11.000000000000000	S	C57BL/6J	MALES	24409289	Active
Drosophila melanogaster	200.000000000000000	umol/L	92.000000000000000	100.000000000000000	0.090000000000000				Unclear	WDAB	FEMALES	20074526
Mus musculus	8.000000000000000	mg/kg	231.000000000000000	372.000000000000000	61.000000000000000				S	C57BL/6JNia	MALES	27549339	Active
Mus musculus	2.240000000000000	mg/kg			16.000000000000000	1094.000000000000000	1250.000000000000000	14.000000000000000	Unclear	UM	FEMALES	19587680
Mus musculus	2.240000000000000	mg/kg			7.000000000000000	1089.000000000000000	1179.000000000000000	8.000000000000000	Unclear	UT	FEMALES	19587680
Caenorhabditis elegans	10.000000000000000	umol/L	23.140000000000000	27.640000000000000	18.930000000000000				S	N2		26676933	Active
Drosophila melanogaster	200.000000000000000	umol/L	78.000000000000000	81.000000000000000	0.040000000000000				Unclear	WDAB	FEMALES	20074526
Mus musculus	2.240000000000000	mg/kg			15.000000000000000	1100.000000000000000	1282.000000000000000	17.000000000000000	Unclear	TJL	FEMALES	19587680
Mus musculus	8.000000000000000	mg/kg	188.000000000000000	231.000000000000000	22.000000000000000				S	C57BL/6JNia		27549339	Active
Mus musculus	4.700000000000000	mg/kg	896.000000000000000	1043.000000000000000	16.000000000000000	1159.000000000000000	1218.000000000000000	5.000000000000000	S	UM-HET3	FEMALES	24341993	Active
Caenorhabditis elegans	400.000000000000000	umol/L	13.500000000000000	15.000000000000000	0.110000000000000	21.500000000000000	26.000000000000000	0.210000000000000	S	N2		34091442	Active
Caenorhabditis elegans	100.000000000000000	umol/L	21.890000000000000	25.940000000000000	19.000000000000000				S	N2		22560223	Active
Drosophila melanogaster	20.000000000000000	umol/L	52.830000000000000	55.100000000000000	4.290000000000000				NS		FEMALES	33008901	Inactive
Caenorhabditis elegans	100.000000000000000	umol/L	24.050000000000000	32.660000000000000	36.000000000000000				S	N2		22560223	Active
Caenorhabditis elegans	100.000000000000000	umol/L	23.550000000000000	28.890000000000000	23.000000000000000				S	N2		22560223	Active
Mus musculus	8.000000000000000	mg/kg	161.000000000000000	161.000000000000000	0.000000000000000				NS	C57BL/6JNia	FEMALES	27549339	Inactive
Drosophila melanogaster	10.000000000000000	umol/L	62.400000000000000	70.500000000000000	13.000000000000000				S	w1118	FEMALES	28025308	Active
Mus musculus	42.000000000000000	mg/kg	807.000000000000000	992.000000000000000	23.000000000000000	1094.000000000000000	1185.000000000000000	8.000000000000000	S	UM-HET3	MALES	24341993	Active
Caenorhabditis elegans	2.000000000000000	nM	18.920000000000000	20.680000000000000	0.090000000000000				S	N2		34771018	Active
Drosophila melanogaster	0.005000000000000	mM			14.000000000000000			4.700000000000000	S	Canton-S		24096697	Active
Mus musculus	2.000000000000000	mg/kg	859.900000000000000	972.000000000000000	13.000000000000000	897.000000000000000	960.000000000000000	7.000000000000000	S	C57BL/6JNia	FEMALES	27091134	Active
Mus musculus	42.000000000000000	mg/kg	896.000000000000000	1132.000000000000000	26.000000000000000	1159.000000000000000	1282.000000000000000	11.000000000000000	S	UM-HET3	FEMALES	24341993	Active
Mus musculus	14.000000000000000	mg/kg	807.000000000000000	909.000000000000000	13.000000000000000	1094.000000000000000	1180.000000000000000	8.000000000000000	S	UM-HET3	MALES	24341993	Active
Caenorhabditis elegans	100.000000000000000	umol/L	15.470000000000000	18.760000000000000	21.000000000000000				S	N2		29874838	Active
Caenorhabditis elegans	1.000000000000000	nM	21.900000000000000	25.300000000000000	0.160000000000000				Unclear			23698443
Drosophila melanogaster	5.000000000000000	umol/L	62.400000000000000	72.600000000000000	16.400000000000000				S	w1118	FEMALES	28025308	Active
Drosophila melanogaster	200.000000000000000	umol/L	47.160000000000000	38.860000000000000	-17.600000000000000				NS		MALES	33008901	Inactive
Mus musculus	2.240000000000000	mg/kg			8.000000000000000	1141.000000000000000	1188.000000000000000	4.000000000000000	Unclear	UM	MALES	19587680
Mus musculus	1.500000000000000	mg/kg			10.100000000000000			9.300000000000000	S	129/Sv	FEMALES	22107964	Active
Caenorhabditis elegans	10.000000000000000	umol/L			18.930000000000000				S	N2		33683565	Active
Mus musculus	8.000000000000000	mg/kg	847.000000000000000	847.000000000000000	0.000000000000000				NS	C57BL/6JNia	FEMALES	27549339	Inactive
Mus musculus	14.000000000000000	mg/kg	896.000000000000000	1086.000000000000000	21.000000000000000	1159.000000000000000	1285.000000000000000	11.000000000000000	S	UM-HET3	FEMALES	24341993	Active
Caenorhabditis elegans	100.000000000000000	umol/L	23.360000000000000	26.330000000000000	13.000000000000000				S	N2		22560223	Active
Mus musculus	4.700000000000000	mg/kg	807.000000000000000	834.000000000000000	3.000000000000000	1094.000000000000000	1162.000000000000000	6.000000000000000	NS	UM-HET3	MALES	24341993	Inactive
Caenorhabditis elegans	100.000000000000000	umol/L			26.000000000000000	21.000000000000000	31.000000000000000	0.480000000000000	S	N2		24332851	Active
Drosophila melanogaster	0.005000000000000	mM			12.000000000000000			4.800000000000000	S	Canton-S		24096697	Active
Mus musculus	2.240000000000000	mg/kg			15.000000000000000	1020.000000000000000	1179.000000000000000	16.000000000000000	Unclear	UT	MALES	19587680
Drosophila melanogaster	200.000000000000000	umol/L	86.000000000000000	96.000000000000000	0.120000000000000				Unclear	w1118	FEMALES	20074526
Drosophila melanogaster	0.500000000000000	umol/L	34.000000000000000	36.000000000000000	0.060000000000000	48.000000000000000	74.000000000000000	0.540000000000000	S	Canton-S	FEMALES	20017609	Active
Drosophila melanogaster	0.500000000000000	umol/L	37.000000000000000	39.000000000000000	0.050000000000000	71.000000000000000	46.000000000000000	-0.350000000000000	S	Canton-S	MALES	20017609	Active

Experimental Data Visualization

(-)-Rapamycin

Statistics Data

(-)-Rapamycin

Species	Avg/Med Lifespan Change(%)	Max Lifespan Change(%)	Count Reference	Count Data point
Caenorhabditis elegans	36.000000000000000	0.480000000000000	8	12
Drosophila melanogaster	16.400000000000000	4.800000000000000	5	12
Mus musculus	61.000000000000000	17.000000000000000	7	24
Saccharomyces cerevisiae			1	1

Statistics Data Visualization

(-)-Rapamycin

Compound Name:

(-)-Rapamycin

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

Rapamycin (Sirolimus)

Antibiotic AY 22989

UNII-W36ZG6FT64

CHEBI:9168

W36ZG6FT64

WY-090217

DE-109

MFCD00867594

NCGC00021305-05

DSSTox_CID_3582

sirolimusum

DSSTox_RID_77091

DSSTox_GSID_23582

SILA 9268A

Supralimus

C51H79NO13

(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

NSC-226080

NCGC00181146-01

LCP-Siro

RAP

S1039

BiomolKI2_000084

Rapamycin C-7, analog 4

(-)-Rapamycin

53123-88-9

AY 22989

AY-22989

I 2190A

More...

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)