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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:15:01 UTC
Update Date2021-09-14 15:19:00 UTC
HMDB IDHMDB0061048
Secondary Accession Numbers
  • HMDB61048
Metabolite Identification
Common Name41-O-demethylrapamycin
Description41-O-demethylrapamycin is a metabolite of sirolimus. Sirolimus, also known as rapamycin, is an immunosuppressant drug used to prevent rejection in organ transplantation; it is especially useful in kidney transplants. It prevents activation of T cells and B-cells by inhibiting their response to interleukin-2 (IL-2). A macrolide, sirolimus was first discovered as a product of the bacterium Streptomyces hygroscopicus in a soil sample from Easter Island — an island also known as Rapa Nui, hence the name. (Wikipedia)
Structure
Data?1563866139
SynonymsNot Available
Chemical FormulaC50H77NO13
Average Molecular Weight900.1453
Monoisotopic Molecular Weight899.539491555
IUPAC Name(9S,12S,15S,16Z,18R,19S,21R,23S,24Z,26Z,28Z,30S,32S,35R)-12-[(2R)-1-[(1R,3S,4S)-3,4-dihydroxycyclohexyl]propan-2-yl]-1,18-dihydroxy-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
Traditional Name(9S,12S,15S,16Z,18R,19S,21R,23S,24Z,26Z,28Z,30S,32S,35R)-12-[(2R)-1-[(1R,3S,4S)-3,4-dihydroxycyclohexyl]propan-2-yl]-1,18-dihydroxy-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
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC[C@@H](C)C(O)(O1)C(=O)C(=O)N1CCCC[C@H]1C(=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=C/C=C\C=C(C)/[C@H](C2)OC)[C@H](C)C[C@H]1CC[C@H](O)[C@@H](O)C1
InChI Identifier
InChI=1S/C50H77NO13/c1-29-15-11-10-12-16-30(2)42(61-8)27-37-20-18-35(7)50(60,64-37)47(57)48(58)51-22-14-13-17-38(51)49(59)63-43(32(4)25-36-19-21-39(52)41(54)26-36)28-40(53)31(3)24-34(6)45(56)46(62-9)44(55)33(5)23-29/h10-12,15-16,24,29,31-33,35-39,41-43,45-46,52,54,56,60H,13-14,17-23,25-28H2,1-9H3/b12-10-,15-11-,30-16-,34-24-/t29-,31+,32-,33-,35-,36-,37+,38+,39+,41+,42+,43+,45-,46-,50?/m1/s1
InChI KeyRGRYVHKBWYXMGM-XMALXIMISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolide lactams
Sub ClassNot Available
Direct ParentMacrolide lactams
Alternative Parents
Substituents
  • Macrolide lactam
  • Alpha-amino acid ester
  • Macrolide
  • Alpha-amino acid or derivatives
  • Cyclohexanol
  • Oxane
  • Piperidine
  • Cyclic alcohol
  • Tertiary carboxylic acid amide
  • Cyclic ketone
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid ester
  • Hemiacetal
  • Ketone
  • Lactam
  • Lactone
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Oxacycle
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0044 g/LALOGPS
logP4.18ALOGPS
logP6.81ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)9.96ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area206.43 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity245.91 m³·mol⁻¹ChemAxon
Polarizability97.71 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-329.8730932474
DeepCCS[M+Na]+303.66630932474
AllCCS[M+H]+297.132859911
AllCCS[M+H-H2O]+296.432859911
AllCCS[M+NH4]+297.832859911
AllCCS[M+Na]+298.032859911
AllCCS[M-H]-270.332859911
AllCCS[M+Na-2H]-278.032859911
AllCCS[M+HCOO]-286.332859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 41-O-demethylrapamycin 10V, Positive-QTOFsplash10-0ue9-0000000095-8b9dc0a2f72068b4a8ad2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 41-O-demethylrapamycin 20V, Positive-QTOFsplash10-03e9-1300000291-e5384dd20e45e019a64f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 41-O-demethylrapamycin 40V, Positive-QTOFsplash10-06s9-8200000290-db56f110a6372033fa3f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 41-O-demethylrapamycin 10V, Negative-QTOFsplash10-0002-0000000090-e1a142d6201df02163e82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 41-O-demethylrapamycin 20V, Negative-QTOFsplash10-001j-0000000090-eca78f9bd5f00b166ca12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 41-O-demethylrapamycin 40V, Negative-QTOFsplash10-0kcr-0000000090-34ef6dd7af3775da36912017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 41-O-demethylrapamycin 10V, Negative-QTOFsplash10-0002-0000000090-f1cf4af297201973d3ee2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 41-O-demethylrapamycin 20V, Negative-QTOFsplash10-0002-0000000290-00dbb432951011dba93e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 41-O-demethylrapamycin 40V, Negative-QTOFsplash10-0k9f-0800000940-2cf8e17056ccb1a1e55e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 41-O-demethylrapamycin 10V, Positive-QTOFsplash10-0udi-0000000091-cbb19f34784f38d1e8f32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 41-O-demethylrapamycin 20V, Positive-QTOFsplash10-0udi-0100000091-fbaffeaaae7c528b96552021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 41-O-demethylrapamycin 40V, Positive-QTOFsplash10-07ml-4000000920-5956e2d7facb50a7af852021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131770013
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available