Metabolomics Structure Database

MDLMOL SDF CSV TSV

MW REGNO:	50022
Common Name:	Sirolimus
Systematic Name:	(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
Synonyms:	(-)-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[30.3.1.0(4,9)]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone; Antibiotic AY 22989; Sirolimus; rapamycin [PubChem Synonyms]
Exact Mass:	913.5551 (neutral)    Calculate m/z: (Choose adduct) [M+H]+ [M+H-H2O]+ [M.]+ [M+2H]2+ [M+3H]3+ [M+4H]4+ [M+K]+ [M+2K]2+ [M-H+2K]+ [M+Na]+ [M+2Na]2+ [M-H+2Na]+ [M+Li]+ [M+2Li]2+ [M+NH4]+ [M-H]- [M-2H]2- [M-3H]3- [M-4H]4- [M+Cl]- [M+OAc]- [M+HCOO]- M(neutral)
Formula:	C51H79NO13
InChIKey:	QFJCIRLUMZQUOT-HPLJOQBZSA-N
ClassyFire superclass:	Phenylpropanoids and polyketides [C0000261]
ClassyFire class:	Macrolide lactams [C0001900]
ClassyFire subclass:	Macrolide lactams [C0001900]
ClassyFire direct parent:	Aliphatic heteropolycyclic compounds
MoNA MS spectra:	View MS spectra
SMILES:	C[C@@H]1/C=C/C=C/C=C(\C)/[C@H](C[C@@H]2CC[C@@H](C)[C@@](C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H](CC(=O)[C@H](C)/C=C(\C)/[C@H]([C@H](C(=O)[C@H](C)C1)OC)O)[C@H](C)C[C@@H]1CC[C@H]([C@@H](C1)OC)O)(O)O2)OC
Studies:	-

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All Database Links Calculated Properties Human Pathways

External database links:

PubChem CID:	5284616
CHEBI ID:	9168
HMDB ID:	HMDB0015015
Natural Products Atlas ID:	NP000414
EPA CompTox DB:	DTXCID00810186
Plant Metabolite Hub(Pmhub):	MS000001878

Calculated physicochemical properties (?):

Heavy Atoms:	65
Rings:	4
Aromatic Rings:	0
Rotatable Bonds:	6
van der Waals Molecular volume:	942.93 Å3 molecule-1
Toplogical Polar Sufrace Area:	199.57 Å2 molecule-1
Hydrogen Bond Donors:	3
Hydrogen Bond Acceptors:	14
logP:	9.04
Molar Refractivity:	250.24
Fraction sp3 Carbons:	0.75
sp3 Carbons:	38

References

LIPID MAPS classification: "Update of the LIPID MAPS comprehensive classification system for lipids", Fahy E, Subramaniam S, Murphy RC, Nishijima M, Raetz CR, Shimizu T, Spener F, van Meer G, Wakelam MJ, and Dennis EA, J. Lipid Res. (2009) 50: S9-S14. DOI: 10.1194/jlr.R800095-JLR200
ClassyFire classification: "ClassyFire: automated chemical classification with a comprehensive, computable taxonomy", Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS, J. Cheminformatics (2016) 8:61. DOI: 10.1186/s13321-016-0174-y