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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-20 22:13:31 UTC
Update Date2021-09-14 15:00:03 UTC
HMDB IDHMDB0001833
Secondary Accession Numbers
  • HMDB01833
Metabolite Identification
Common NameAminopterin
DescriptionAminopterin Syndrome Sine Aminopterin (ASSA, OMIM 600325 ) is an embryopathy caused by maternal treatment with the olic acid antagonist aminopterin has been recognized since 1952 when aminopterin was used as an abortifacient. The characteristic phenotype of the children who survived infancy after having been exposed to aminopterin or its methyl derivative, methotrexate, in early pregnancy included a very unusual facies, skull anomalies, and skeletal defects.(OMIM). Aminopterin is an antimetabolite drug used in treatment of cancer and autoimmune diseases. It acts by inhibiting the metabolism of folic acid. - Wikipedia . The effects of the drug on intracellular metabolic processes, due to the inhibitory action on the enzyme dihydrofolate reductase, show that the result of this inhibition is more complex and is not limited to blockade of the reduction of folic acid alone. Although rescue methods are important in prevention of lethal effects of methotrexate, some metabolic pathways are insufficiently rescued, resulting in toxic reactions following methotrexate administration.(PMID 6398629 ).
Structure
Data?1582752211
Synonyms
ValueSource
4-Amino-4-deoxypteroylglutamateHMDB
4-Amino-pgaHMDB
4-AminofolateHMDB
4-Aminofolic acidHMDB
4-AminopteroylglutamateHMDB
4-Aminopteroylglutamic acidHMDB
AminopterineHMDB
APGAHMDB
L-N-[p-[[(2,4-Diamino-6-pteridinyl)methyl]amino]benzoyl]-glutamic acidHMDB
PteraminaHMDB
Aminopterin, disodium saltHMDB
Disodium salt aminopterinHMDB
Sodium, aminopterinHMDB
Aminopterin sodiumHMDB
2-[(4-{[(4-amino-2-imino-2,3-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioateHMDB
AminopterinMeSH
Chemical FormulaC19H20N8O5
Average Molecular Weight440.4127
Monoisotopic Molecular Weight440.15566579
IUPAC Name2-[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
Traditional Nameaminopterin
CAS Registry Number54-62-6
SMILES
NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)C=N2)C(N)=N1
InChI Identifier
InChI=1S/C19H20N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27)
InChI KeyTVZGACDUOSZQKY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as folic acids. These are heterocyclic compounds based on the 4-[(pteridin-6-ylmethyl)amino]benzoic acid skeleton conjugated with one or more L-glutamate units.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentFolic acids
Alternative Parents
Substituents
  • Folic acid
  • Glutamic acid or derivatives
  • Hippuric acid or derivatives
  • Hippuric acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Benzamide
  • Benzoic acid or derivatives
  • Benzoyl
  • Phenylalkylamine
  • Aniline or substituted anilines
  • Aminopyrimidine
  • Aralkylamine
  • Secondary aliphatic/aromatic amine
  • Pyrimidine
  • Pyrazine
  • Monocyclic benzene moiety
  • Benzenoid
  • Imidolactam
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary amine
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Hydrocarbon derivative
  • Amine
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Primary amine
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Role

Industrial application:

Environmental role:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP-0.25ALOGPS
logP-0.95ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.38ChemAxon
pKa (Strongest Basic)2.25ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area219.33 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity114.98 m³·mol⁻¹ChemAxon
Polarizability44.13 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M+H]+ExperimentalNot Available204.433http://allccs.zhulab.cn/database/detail?ID=AllCCS00001071
DarkChem[M+H]+PredictedNot Available205.51631661259
DarkChem[M-H]-PredictedNot Available203.41231661259
AllCCS[M+H]+PredictedNot Available197.66832859911
AllCCS[M-H]-PredictedNot Available195.32332859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Aminopterin,1TMS,#14807.994https://arxiv.org/abs/1905.12712
Aminopterin,1TMS,#24772.383https://arxiv.org/abs/1905.12712
Aminopterin,1TMS,#34925.221https://arxiv.org/abs/1905.12712
Aminopterin,1TMS,#44938.393https://arxiv.org/abs/1905.12712
Aminopterin,1TMS,#54815.0044https://arxiv.org/abs/1905.12712
Aminopterin,1TMS,#64771.257https://arxiv.org/abs/1905.12712
Aminopterin,2TMS,#14614.6226https://arxiv.org/abs/1905.12712
Aminopterin,2TMS,#24741.273https://arxiv.org/abs/1905.12712
Aminopterin,2TMS,#34757.2104https://arxiv.org/abs/1905.12712
Aminopterin,2TMS,#44590.9727https://arxiv.org/abs/1905.12712
Aminopterin,2TMS,#54648.8447https://arxiv.org/abs/1905.12712
Aminopterin,2TMS,#64713.3374https://arxiv.org/abs/1905.12712
Aminopterin,2TMS,#74733.3135https://arxiv.org/abs/1905.12712
Aminopterin,2TMS,#84600.509https://arxiv.org/abs/1905.12712
Aminopterin,2TMS,#94609.007https://arxiv.org/abs/1905.12712
Aminopterin,2TMS,#104916.683https://arxiv.org/abs/1905.12712
Aminopterin,2TMS,#114724.931https://arxiv.org/abs/1905.12712
Aminopterin,2TMS,#124793.154https://arxiv.org/abs/1905.12712
Aminopterin,2TMS,#134735.565https://arxiv.org/abs/1905.12712
Aminopterin,2TMS,#144757.8804https://arxiv.org/abs/1905.12712
Aminopterin,2TMS,#154805.334https://arxiv.org/abs/1905.12712
Aminopterin,2TMS,#164755.2007https://arxiv.org/abs/1905.12712
Aminopterin,2TMS,#174601.2544https://arxiv.org/abs/1905.12712
Aminopterin,1TBDMS,#15076.271https://arxiv.org/abs/1905.12712
Aminopterin,1TBDMS,#25053.893https://arxiv.org/abs/1905.12712
Aminopterin,1TBDMS,#35135.114https://arxiv.org/abs/1905.12712
Aminopterin,1TBDMS,#45156.749https://arxiv.org/abs/1905.12712
Aminopterin,1TBDMS,#55054.509https://arxiv.org/abs/1905.12712
Aminopterin,1TBDMS,#65062.7944https://arxiv.org/abs/1905.12712
Aminopterin,2TBDMS,#15130.8027https://arxiv.org/abs/1905.12712
Aminopterin,2TBDMS,#25163.9717https://arxiv.org/abs/1905.12712
Aminopterin,2TBDMS,#35199.147https://arxiv.org/abs/1905.12712
Aminopterin,2TBDMS,#45124.3994https://arxiv.org/abs/1905.12712
Aminopterin,2TBDMS,#55155.268https://arxiv.org/abs/1905.12712
Aminopterin,2TBDMS,#65152.6377https://arxiv.org/abs/1905.12712
Aminopterin,2TBDMS,#75180.7227https://arxiv.org/abs/1905.12712
Aminopterin,2TBDMS,#85129.6997https://arxiv.org/abs/1905.12712
Aminopterin,2TBDMS,#95133.246https://arxiv.org/abs/1905.12712
Aminopterin,2TBDMS,#105312.676https://arxiv.org/abs/1905.12712
Aminopterin,2TBDMS,#115143.562https://arxiv.org/abs/1905.12712
Aminopterin,2TBDMS,#125206.225https://arxiv.org/abs/1905.12712
Aminopterin,2TBDMS,#135159.736https://arxiv.org/abs/1905.12712
Aminopterin,2TBDMS,#145198.9316https://arxiv.org/abs/1905.12712
Aminopterin,2TBDMS,#155215.912https://arxiv.org/abs/1905.12712
Aminopterin,2TBDMS,#165174.245https://arxiv.org/abs/1905.12712
Aminopterin,2TBDMS,#175088.96https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-2149100000-61d406d05355a4fc3d262017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-014i-3060950000-0b4e0db1ce895d3cb34e2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0030900000-3c3d8f183a438cffe34c2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-006x-0970000000-ddbb8b8c2d06b8da5f922012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00fr-0900000000-dd78e5bb1683a2c0e5312012-07-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fu-0322900000-764b96892d5bbce421b12017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0953200000-ea1dce8ceb8c57ed00912017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1930000000-5593e0d8e055aa5cdebc2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0003900000-8e0519246e877792792b2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00r2-0349500000-5275f7af7a7d4fc7d5422017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-8971000000-0fe59aca81e98939920d2017-09-01View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, 100%_DMSO, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Adipose Tissue
  • Spleen
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022702
KNApSAcK IDNot Available
Chemspider ID2069
KEGG Compound IDD02527
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAminopterin
METLIN ID6341
PubChem Compound2154
PDB IDNot Available
ChEBI ID108080
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Le Blanc PE, Roncari DA, Hoar DI, Adachi AM: Exaggerated triglyceride accretion in human preadipocyte-murine renal line hybrids composed of cells from massively obese subjects. J Clin Invest. 1988 May;81(5):1639-45. [PubMed:3366910 ]
  2. Malone MA, Costa Garcia A, Tunon Blanco P, Smyth MR: Phase-selective AC adsorptive stripping voltammetric assay for aminopterin and 10-Edam in human serum. J Pharm Biomed Anal. 1993 Oct;11(10):939-46. [PubMed:8305599 ]
  3. Raache R, Rapaille A, Sondag-Thull D, Abbadi MC: [Production of monoclonal antibodies specific for the ABO blood group and rhesus D antigens]. Arch Inst Pasteur Alger. 1998;62:118-37. [PubMed:11256302 ]
  4. Lippens RJ: Methotrexate. I. Pharmacology and pharmacokinetics. Am J Pediatr Hematol Oncol. 1984 Winter;6(4):379-95. [PubMed:6398629 ]