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Record Information
Version4.0
Creation Date2013-07-04 18:54:01 UTC
Update Date2017-09-23 14:31:19 UTC
HMDB IDHMDB0060706
Secondary Accession Numbers
  • HMDB60706
StatusExpected but not Quantified
Metabolite Identification
Common Name13-Demethyl tacrolimus
Description13-Demethyl tacrolimus is a metabolite of tacrolimus. Tacrolimus (also FK-506 or fujimycin, trade names Prograf, Advagraf, Protopic) is an immunosuppressive drug that is mainly used after allogeneic organ transplant to reduce the activity of the patient's immune system and so lower the risk of organ rejection. It is also used in a topical preparation in the treatment of atopic dermatitis, severe refractory uveitis after bone marrow transplants, exacerbations of minimal change disease, and the skin condition vitiligo. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC43H67NO12
Average Molecular Weight789.9916
Monoisotopic Molecular Weight789.466326613
IUPAC Name(1R,9S,12S,13R,14S,17R,18Z,21S,23S,24S,25S,27R)-1,14,25-trihydroxy-12-[(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23-methoxy-13,19,21,27-tetramethyl-17-(prop-2-en-1-yl)-11,28-dioxa-4-azatricyclo[22.3.1.0⁴,⁹]octacos-18-ene-2,3,10,16-tetrone
Traditional Name(1R,9S,12S,13R,14S,17R,18Z,21S,23S,24S,25S,27R)-1,14,25-trihydroxy-12-[(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23-methoxy-13,19,21,27-tetramethyl-17-(prop-2-en-1-yl)-11,28-dioxa-4-azatricyclo[22.3.1.0⁴,⁹]octacos-18-ene-2,3,10,16-tetrone
CAS Registry NumberNot Available
SMILES
[H][C@]12O[C@](O)([C@H](C)C[C@@H]1O)C(=O)C(=O)N1CCCC[C@H]1C(=O)O[C@@H]([C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)\C=C(C)/C[C@H](C)C[C@@H]2OC)C(\C)=C\[C@@H]1CC[C@@H](O)[C@@H](C1)OC
InChI Identifier
InChI=1S/C43H67NO12/c1-9-12-30-18-24(2)17-25(3)19-37(54-8)39-35(48)21-27(5)43(52,56-39)40(49)41(50)44-16-11-10-13-31(44)42(51)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-32(45)36(22-29)53-7/h9,18,20,25,27-33,35-39,45-46,48,52H,1,10-17,19,21-23H2,2-8H3/b24-18-,26-20+/t25-,27+,28+,29-,30+,31-,32+,33-,35-,36+,37-,38+,39-,43+/m0/s1
InChI KeyOGJRKILIPRVJFS-GOJJZGEOSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassMacrolide lactams
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
  • Polyol
  • Carboxylic acid derivative
  • Azacycle
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
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 Solubility0.0071 mg/mLALOGPS
logP2.49ALOGPS
logP4.95ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)9.96ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area189.36 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity210.87 m3·mol-1ChemAxon
Polarizability86.08 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00670
      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 LinkHMDB0060706
      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