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Record Information
Version3.6
Creation Date2013-06-18 17:48:10 UTC
Update Date2017-03-02 22:05:18 UTC
HMDB IDHMDB60661
Secondary Accession NumbersNone
Metabolite Identification
Common NameAPC
DescriptionAPC is a metabolite of irinotecan. Irinotecan is a drug used for the treatment of cancer. Irinotecan prevents DNA from unwinding by inhibition of topoisomerase 1. In chemical terms, it is a semisynthetic analogue of the natural alkaloid camptothecin. Its main use is in colon cancer, in particular, in combination with other chemotherapy agents. This includes the regimen FOLFIRI, which consists of infusional 5-fluorouracil, leucovorin, and irinotecan. Irinotecan received accelerated approval by the U.S. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC33H38N4O8
Average Molecular Weight618.6768
Monoisotopic Molecular Weight618.268964212
IUPAC Name5-{[1-({[(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-7-yl]oxy}carbonyl)piperidin-4-yl]amino}pentanoic acid
Traditional Name5-{[1-({[(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-7-yl]oxy}carbonyl)piperidin-4-yl]amino}pentanoic acid
CAS Registry NumberNot Available
SMILES
CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(CC3)NCCCCC(O)=O)C=C12
InChI Identifier
InChI=1S/C33H38N4O8/c1-3-21-22-15-20(45-32(42)36-13-10-19(11-14-36)34-12-6-5-7-28(38)39)8-9-26(22)35-29-23(21)17-37-27(29)16-25-24(30(37)40)18-44-31(41)33(25,43)4-2/h8-9,15-16,19,34,43H,3-7,10-14,17-18H2,1-2H3,(H,38,39)/t33-/m0/s1
InChI KeyBSVVZICJFYZDJJ-XIFFEERXSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).
KingdomChemical entities
Super ClassOrganic compounds
ClassAlkaloids and derivatives
Sub ClassCamptothecins
Direct ParentCamptothecins
Alternative Parents
Substituents
  • Camptothecin
  • Delta amino acid or derivatives
  • Pyranopyridine
  • Quinoline
  • Piperidinecarboxylic acid
  • 4-aminopiperidine
  • Pyridinone
  • Piperidine
  • Dicarboxylic acid or derivatives
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Carbamic acid ester
  • Tertiary alcohol
  • Carbonic acid derivative
  • Lactone
  • Lactam
  • Amino acid
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Secondary aliphatic amine
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locationsNot Available
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 Solubility0.048 mg/mLALOGPS
logP2.32ALOGPS
logP-0.48ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)4.66ChemAxon
pKa (Strongest Basic)10.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area158.6 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity164.03 m3·mol-1ChemAxon
Polarizability66.5 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Irinotecan Metabolism PathwaySMP00600Not Available
Irinotecan PathwaySMP00433Not Available
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 IDNot Available
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC16542
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB60661
      Metagene LinkHMDB60661
      METLIN IDNot Available
      PubChem Compound10077584
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available