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Record Information
Version3.6
Creation Date2013-07-09 16:15:01 UTC
Update Date2016-02-11 08:17:37 UTC
HMDB IDHMDB61048
Secondary Accession NumbersNone
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
Thumb
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=1/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?/s2
InChI KeyInChIKey=RGRYVHKBWYXMGM-LWTPZQEWNA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Macrolide
  • Alpha-amino acid ester
  • Cyclohexanol
  • Piperidine
  • Oxane
  • Tertiary carboxylic acid amide
  • Cyclic alcohol
  • Cyclic ketone
  • Tertiary amine
  • Secondary alcohol
  • Lactone
  • Lactam
  • Ketone
  • Hemiacetal
  • Carboxylic acid ester
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0044 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity245.91 m3·mol-1ChemAxon
Polarizability97.71 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00389
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB61048
Metagene LinkHMDB61048
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available