Structure Database (LMSD)

Common Name
Sirolimus
Systematic Name
Synonyms
  • (-)-Rapamycin
LM ID
LMPK06000003
Formula
C51H79NO13
Exact Mass
Calculate m/z
913.555144
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Polyenes [PK06]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Streptomyces hygroscopicus (#1912)
Actinomycetes (#1760)
On the chemistry and high field nuclear magnetic resonance spectroscopy of rapamycin,
Can J Chem, 1980

String Representations

InChiKey (Click to copy)
QFJCIRLUMZQUOT-HPLJOQBZSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
N12CCCC[C@@]1([H])C(=O)O[C@@]([H])(CC(=O)[C@H](C)C=C(C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)C=CC=CC=C(C)[C@@H](OC)C[C@@H]1CC[C@@H](C)[C@@](O)(O1)C(=O)C2=O)[C@H](C)C[C@]1([H])CC[C@@H](O)[C@H](OC)C1

Other Databases

Wikipedia
Sirolimus
KEGG ID
C07909
HMDB ID
HMDB0015015
CHEBI ID
9168
PubChem CID
5284616
PDB ID
RAP
GuidePharm ID
6031

Calculated Physicochemical Properties

Heavy Atoms 65
Rings 4
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 942.93
Topological Polar Surface Area 199.57
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 14
logP 9.04
Molar Refractivity 250.24

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Created at
-
Updated at
9th May 2022