Sirolimus

Details

• Internal ID: e23763e4-c272-45f8-8edf-fb8c4bbfc58f
• Taxonomy: Phenylpropanoids and polyketides > Macrolide lactams
• 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
• InChI Key: QFJCIRLUMZQUOT-HPLJOQBZSA-N
• Popularity: 54,397 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₁H₇₉NO₁₃
• Molecular Weight: 914.20 g/mol
• Exact Mass: 913.55514157 g/mol
• Topological Polar Surface Area (TPSA): 195.00 Ų
• XlogP: 6.00
• Atomic LogP (AlogP): 6.18
• H-Bond Acceptor: 13
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• 53123-88-9
• AY 22989
• AY-22989
• I 2190A
• I-2190A
• I2190A
• NSC 226080
• RAPA
• Rapammune
• Rapamune
• Rapamycin
• SIIA 9268A
• Sirolimus
• Wy 090217
• rapalimus
• Supralimus
• WY-090217
• Rapamycin (Sirolimus)
• HYFTOR
• sirolimusum
• Cypher
• Antibiotic AY 22989
• Rapamycin (GMP)
• FYARRO
• CCRIS 9024
• CHEBI:9168
• SILA 9268A
• W36ZG6FT64
• HSDB 7284
• L04AA10
• Npc-12g
• SM-88 COMPONENT SIROLIMUS
• DE-109
• NSC-226080
• UNII-W36ZG6FT64
• DTXSID5023582
• Rapamycin Immunosuppressant Drug
• NAB-RAPAMYCIN COMPONENT RAPAMYCIN
• SIROLIMUS (MART.)
• SIROLIMUS [MART.]
• EC 610-965-5
• SIROLIMUS (USP-RS)
• SIROLIMUS [USP-RS]
• NSC226080
• (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,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
• EVEROLIMUS IMPURITY A (EP IMPURITY)
• EVEROLIMUS IMPURITY A [EP IMPURITY]
• (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
• DTXCID503582
• Perceiva
• 1fkb
• 1pbk
• NCGC00021305-05
• Rapamycin/Sirolimus
• LCP-Siro
• (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,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-((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-{(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
• RAP
• RPM
• MFCD00867594
• S1039
• SIROLIMUS [INN]
• SIROLIMUS [JAN]
• RAPAMYCIN [MI]
• Human Blood - Sirolimus
• SIROLIMUS [HSDB]
• SIROLIMUS [USAN]
• SIROLIMUS [VANDF]
• BiomolKI2_000084
• SCHEMBL3463
• SIROLIMUS [WHO-DD]
• Rapamycin,Sirolimus,Rapamune
• BIDD:PXR0165
• SIROLIMUS [EMA EPAR]
• MLS006010168
• Sirolimus [USAN:INN:BAN]
• GTPL6031
• SIROLIMUS [ORANGE BOOK]
• BDBM36609
• MS-R001
• S01XA23
• QFJCIRLUMZQUOT-HPLJOQBZSA-N
• HMS2089A21
• HMS3403F11
• HMS3884C03
• EX-A1044
• AC-722
• BDBM50064359
• HY-10219G
• AKOS015850976
• AKOS015961618
• CCG-100684
• CS-0063
• DB00877
• NSC-2260804
• NCGC00021305-06
• NCGC00021305-07
• Rapamycin from Streptomyces hygroscopicus
• AS-11687
• HY-10219
• SMR004701276
• Fyarro (sirolimus albumin-bound particles)
• UNM-0000358684
• A-275
• CS-0626126
• R0097
• Rapamycin, VETRANAL(TM), analytical standard
• M02444
• Q32089
• Q-201659
• BRD-K84937637-001-04-0
• BRD-K84937637-001-06-5
• BRD-K89626439-001-01-0
• Z2568665260
• 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-((1R)-2-((1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl)-1-methylethyl)-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-pentaone
• (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
• (3 S ,6 R ,7 E ,9 R ,10 R ,12 R ,14 S ,15 E ,17 E , 19 E ,21 S ,23 S ,26 R ,27 R ,34a S )-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34, 34a-hexadecahydro-9,27-dihydroxy-3-
• (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)-9,27-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-epoxypyrido[2,1-c][1,4]oxazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone
• 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)
• 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-1,5,11,2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6264	62.64%
Caco-2	-	0.8549	85.49%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6324	63.24%
OATP2B1 inhibitior	-	0.5897	58.97%
OATP1B1 inhibitior	+	0.8152	81.52%
OATP1B3 inhibitior	+	0.9231	92.31%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9652	96.52%
P-glycoprotein inhibitior	+	0.7705	77.05%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.7803	78.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8922	89.22%
CYP3A4 inhibition	-	0.9333	93.33%
CYP2C9 inhibition	-	0.9125	91.25%
CYP2C19 inhibition	-	0.9158	91.58%
CYP2D6 inhibition	-	0.9414	94.14%
CYP1A2 inhibition	-	0.9007	90.07%
CYP2C8 inhibition	+	0.7728	77.28%
CYP inhibitory promiscuity	-	0.9742	97.42%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4593	45.93%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9097	90.97%
Skin irritation	-	0.7427	74.27%
Skin corrosion	-	0.9342	93.42%
Ames mutagenesis	-	0.5770	57.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6705	67.05%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.8802	88.02%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.7838	78.38%
Acute Oral Toxicity (c)	III	0.6165	61.65%
Estrogen receptor binding	+	0.8657	86.57%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.7678	76.78%
Glucocorticoid receptor binding	+	0.8052	80.52%
Aromatase binding	+	0.7216	72.16%
PPAR gamma	+	0.8205	82.05%
Honey bee toxicity	-	0.5861	58.61%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.7540	75.40%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1902	P62942	FK506-binding protein 1A	1 nM; 0.6 nM	Ki; Ki	via Super-PRED; via Super-PRED
CHEMBL2430	P68106	FK506-binding protein 1B	0.2 nM	Kd	via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	0.6 nM	Potency	via Super-PRED
CHEMBL2052031	Q13451	Peptidyl-prolyl cis-trans isomerase FKBP5	3 nM	Ki	via Super-PRED
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	0.1 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.50%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.38%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.63%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.88%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.71%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.44%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.27%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.29%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	89.46%	93.04%
CHEMBL3401	O75469	Pregnane X receptor	88.85%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.20%	93.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.78%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.89%	96.95%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.40%	96.90%
CHEMBL204	P00734	Thrombin	84.24%	96.01%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.13%	97.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.55%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.00%	100.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.71%	93.03%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.18%	90.08%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.01%	92.62%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5284616
• LOTUS: LTS0107850
• wikiData: Q32089