Metabolomics Structure Database

MDLMOL SDF CSV TSV

MW REGNO:	21276
Common Name:	Tacrolimus
Systematic Name:	(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-prop-2-enyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone
RefMet Name:	Tacrolimus
Synonyms:	[PubChem Synonyms]
Exact Mass:	803.4820 (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:	C44H69NO12
InChIKey:	QJJXYPPXXYFBGM-LFZNUXCKSA-N
LIPID MAPS Category:	Polyketides [PK]
LIPID MAPS mainclass:	Macrolides and lactone polyketides [PK04]
SMILES:	C=CC[C@@H]1/C=C(C)/C[C@H](C)C[C@@H]([C@@H]2[C@H](C[C@@H](C)[C@@](C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@H](/C(=C/[C@@H]3CC[C@H]([C@@H](C3)OC)O)/C)[C@H](C)[C@H](CC1=O)O)(O)O2)OC)OC
Studies:	Available studies (via RefMet name)

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All Database Links Calculated Properties Human Pathways

External database links:

PubChem CID:	445643
LIPID MAPS ID:	LMPK04000003
CHEBI ID:	61049
HMDB ID:	HMDB0015002
KEGG ID:	C01375
Chemspider ID:	393220
EPA CompTox DB:	DTXCID00810388
Plant Metabolite Hub(Pmhub):	MS000006946

Calculated physicochemical properties (?):

Heavy Atoms:	57
Rings:	4
Aromatic Rings:	0
Rotatable Bonds:	7
van der Waals Molecular volume:	818.32 Å3 molecule-1
Toplogical Polar Sufrace Area:	182.50 Å2 molecule-1
Hydrogen Bond Donors:	3
Hydrogen Bond Acceptors:	13
logP:	7.50
Molar Refractivity:	217.69
Fraction sp3 Carbons:	0.77
sp3 Carbons:	34

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