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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-18 17:48:10 UTC
Update Date2019-07-23 07:14:48 UTC
HMDB IDHMDB0060661
Secondary Accession Numbers
  • HMDB60661
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
Data?1563866088
Synonyms
ValueSource
1,2-PropanedioneChEBI
2-KetopropionaldehydeChEBI
2-OxopropanalChEBI
2-OxopropionaldehydeChEBI
AcetylformaldehydeChEBI
AcetylformylChEBI
alpha-KetopropionaldehydeChEBI
CH3COCHOChEBI
Pyruvic aldehydeChEBI
a-KetopropionaldehydeGenerator
Α-ketopropionaldehydeGenerator
1-KetopropionaldehydeHMDB
2-Keto propionaldehydeHMDB
2-oxo-PropionaldehydeHMDB
KetopropionaldehydeHMDB
MethylglyoxalHMDB
PropanedioneHMDB
PropanoloneHMDB
Pyroracemic aldehydeHMDB
Aldehyde, pyruvicHMDB
OxopropanalHMDB
APC CPDMeSH
7-Ethyl-10-(4-N-(5-aminopentanoic acid)-1-piperidino)carbonyloxycamptothecinMeSH
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
Description Belongs to the class of organic compounds known as alpha ketoaldehydes. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha ketoaldehydes
Alternative Parents
Substituents
  • Alpha-ketoaldehyde
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Process

Naturally occurring process

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 Solubility0.048 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity164.03 m³·mol⁻¹ChemAxon
Polarizability66.5 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+239.65731661259
DarkChem[M-H]-236.11131661259
DeepCCS[M-2H]-284.97330932474
DeepCCS[M+Na]+259.40530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
APCCCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(CC3)NCCCCC(O)=O)C=C125461.0Standard polar33892256
APCCCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(CC3)NCCCCC(O)=O)C=C124652.8Standard non polar33892256
APCCCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(CC3)NCCCCC(O)=O)C=C125625.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
APC,1TMS,isomer #1CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(NCCCCC(=O)O)CC3)C=C125237.2Semi standard non polar33892256
APC,1TMS,isomer #2CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(NCCCCC(=O)O[Si](C)(C)C)CC3)C=C125168.0Semi standard non polar33892256
APC,1TMS,isomer #3CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O)[Si](C)(C)C)CC3)C=C125266.4Semi standard non polar33892256
APC,2TMS,isomer #1CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(NCCCCC(=O)O[Si](C)(C)C)CC3)C=C125074.6Semi standard non polar33892256
APC,2TMS,isomer #2CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O)[Si](C)(C)C)CC3)C=C125179.6Semi standard non polar33892256
APC,2TMS,isomer #3CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O[Si](C)(C)C)[Si](C)(C)C)CC3)C=C125112.4Semi standard non polar33892256
APC,3TMS,isomer #1CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O[Si](C)(C)C)[Si](C)(C)C)CC3)C=C125027.0Semi standard non polar33892256
APC,3TMS,isomer #1CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O[Si](C)(C)C)[Si](C)(C)C)CC3)C=C125009.7Standard non polar33892256
APC,3TMS,isomer #1CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O[Si](C)(C)C)[Si](C)(C)C)CC3)C=C126557.1Standard polar33892256
APC,1TBDMS,isomer #1CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C(C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(NCCCCC(=O)O)CC3)C=C125426.4Semi standard non polar33892256
APC,1TBDMS,isomer #2CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(NCCCCC(=O)O[Si](C)(C)C(C)(C)C)CC3)C=C125387.8Semi standard non polar33892256
APC,1TBDMS,isomer #3CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O)[Si](C)(C)C(C)(C)C)CC3)C=C125465.5Semi standard non polar33892256
APC,2TBDMS,isomer #1CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C(C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(NCCCCC(=O)O[Si](C)(C)C(C)(C)C)CC3)C=C125435.7Semi standard non polar33892256
APC,2TBDMS,isomer #2CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C(C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O)[Si](C)(C)C(C)(C)C)CC3)C=C125538.6Semi standard non polar33892256
APC,2TBDMS,isomer #3CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC3)C=C125497.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - APC GC-MS (1 TMS) - 70eV, Positivesplash10-00ba-3200019000-0f121ba3b50d1e9655872017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - APC GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - APC GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - APC GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - APC GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - APC GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - APC GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - APC GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - APC GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - APC GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - APC GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - APC GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - APC GC-MS ("APC,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-11-02Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - APC 10V, Positive-QTOFsplash10-0udi-0341049000-7513ad575f77fd51def92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - APC 20V, Positive-QTOFsplash10-0ugi-2942031000-d25ec79870cfe710f25a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - APC 40V, Positive-QTOFsplash10-0udi-5940000000-188d67903155f2e16c882017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - APC 10V, Negative-QTOFsplash10-01b9-0141198000-2caccacf3add053c51c42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - APC 20V, Negative-QTOFsplash10-00vm-0454192000-e9d5fd01fd23b2c567422017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - APC 40V, Negative-QTOFsplash10-0037-3894020000-46ebd1df6ec7bd8c5fc42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - APC 10V, Positive-QTOFsplash10-0gb9-0000009000-492e35b52563dcd8aa252021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - APC 20V, Positive-QTOFsplash10-0udi-0000089000-6495393de2962bd71a212021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - APC 40V, Positive-QTOFsplash10-0900-9218411000-cccb21d7ce03f63811372021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - APC 10V, Negative-QTOFsplash10-014i-0002059000-981e8115208bea24955f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - APC 20V, Negative-QTOFsplash10-05tb-0002091000-df410fa1c698619938fb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - APC 40V, Negative-QTOFsplash10-014l-2734297000-26884603c52a800389f22021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDDB03587
Phenol Explorer Compound IDNot Available
FooDB IDFDB031000
KNApSAcK IDC00007562
Chemspider ID857
KEGG Compound IDC00546
BioCyc IDNot Available
BiGG ID35307
Wikipedia LinkMethylglyoxal
METLIN ID6049
PubChem Compound880
PDB IDNot Available
ChEBI ID17158
Food Biomarker OntologyNot Available
VMH IDMTHGXL
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available