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Record Information
Version3.6
Creation Date2006-08-13 10:54:05 UTC
Update Date2016-02-11 01:06:34 UTC
HMDB IDHMDB04101
Secondary Accession NumbersNone
Metabolite Identification
Common NameBeta-Aminopropionitrile
Descriptionbeta-Aminopropionitrile is a toxic amino-acid derivative. On an unusual case of the Cantrell-sequence in a premature infant with associated dysmelia, aplasia of the right kidney, cerebellar hypoplasia and circumscribed aplasia of the cutis, maternal history suggested an occupational exposure to aminopropionitriles prior to pregnancy. The characteristic features of the Cantrell-sequence--anterior thoraco-abdominal wall defect with ectopia cordis and diaphragm, sternum, pericardium, and heart defects--have been observed in animals following maternal administration of beta-aminopropionitrile. Some species of lathyrus (chickling pea, Lathyrus sativus- related), notably Lathyrus odoratus, are unable to induce human lathyrism but contain beta-aminopropionitrile, that induces pathological changes in bone ("osteolathyrism") and blood vessels ("angiolathyrism") of experimental animals without damaging the nervous system. The administration of beta-aminopropionitrile has been proposed for pharmacological control of unwanted scar tissue in human beings. beta-Aminopropionitrile is a reagent used as an intermediate in the manufacture of beta-alanine and pantothenic acid. (PMID: 367235 , 6422318 , 9394169 , Am J Perinatol. 1997 Oct;14(9):567-71.).
Structure
Thumb
Synonyms
ValueSource
2-CyanoethylamineChEBI
3-AminopropionitrileChEBI
3-AminopropiononitrileChEBI
AminopropionitrileChEBI
BAPNChEBI
beta-AlaninenitrileChEBI
beta-Aminoethyl cyanideChEBI
beta-CyanoethylamineChEBI
H2NCH2CH2CNChEBI
b-AlaninenitrileGenerator
β-alaninenitrileGenerator
b-Aminoethyl cyanideGenerator
β-aminoethyl cyanideGenerator
b-CyanoethylamineGenerator
β-cyanoethylamineGenerator
b-AlaminenitrileHMDB
b-AminopropionitrileHMDB
beta-AlaminenitrileHMDB
Chemical FormulaC3H6N2
Average Molecular Weight70.0931
Monoisotopic Molecular Weight70.053098202
IUPAC Name3-aminopropanenitrile
Traditional Nameβ aminopropionitrile
CAS Registry Number151-18-8
SMILES
NCCC#N
InChI Identifier
InChI=1S/C3H6N2/c4-2-1-3-5/h1-2,4H2
InChI KeyInChIKey=AGSPXMVUFBBBMO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as nitriles. These are compounds having the structure RC#N; thus C-substituted derivatives of hydrocyanic acid, HC#N.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassNitriles
Sub ClassNot Available
Direct ParentNitriles
Alternative Parents
Substituents
  • Nitrile
  • Carbonitrile
  • Hydrocarbon derivative
  • Primary amine
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility37.0 mg/mLALOGPS
logP-1.1ALOGPS
logP-0.85ChemAxon
logS-0.28ALOGPS
pKa (Strongest Basic)7.85ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.81 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity19.68 m3·mol-1ChemAxon
Polarizability7.53 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-9000000000-7dfadb8fdf3477540781View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9000000000-ca5db6c876b46ee9a1cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-39a4d5ba1e275b87d47bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-d13e9e176f608de3e76bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-3b795596647194f89ae6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udl-9000000000-062a72ed70b3ea0ab27cView in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-e5c8c009efa6f2441041View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Fibroblasts
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
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 IDFDB012565
KNApSAcK IDNot Available
Chemspider ID21241485
KEGG Compound IDC05670
BioCyc IDBETA-AMINOPROPIONITRILE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04101
Metagene LinkHMDB04101
METLIN ID7017
PubChem Compound1647
PDB IDNot Available
ChEBI ID27413
References
Synthesis ReferenceSmolin, Edwin M.; Beegle, L. Clair. Continuous high-pressure synthesis of 3-aminopropionitrile. Journal of Industrial and Engineering Chemistry (Washington, D. C.) (1958), 50 1115-18.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Harrison CA, Gossiel F, Bullock AJ, Sun T, Blumsohn A, Mac Neil S: Investigation of keratinocyte regulation of collagen I synthesis by dermal fibroblasts in a simple in vitro model. Br J Dermatol. 2006 Mar;154(3):401-10. [16445767 ]
  2. Fleisher JH, Peacock EE Jr, Chvapil M: Urinary excretion of beta-aminopropionitrile and cyanoacetic acid. Clin Pharmacol Ther. 1978 May;23(5):520-4. [639425 ]
  3. Peacock EE Jr: Pharmacological control of surgical scar tissue. Am Surg. 1978 Nov;44(11):693-8. [367235 ]
  4. Spencer PS, Schaumburg HH: Lathyrism: a neurotoxic disease. Neurobehav Toxicol Teratol. 1983 Nov-Dec;5(6):625-9. [6422318 ]
  5. Dembinski J, Heyl W, Steidel K, Hermanns B, Hornchen H, Schroder W: The Cantrell-sequence: a result of maternal exposure to aminopropionitriles? Am J Perinatol. 1997 Oct;14(9):567-71. [9394169 ]

Enzymes

General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Initiates extracellular glutathione (GSH) breakdown, provides cells with a local cysteine supply and contributes to maintain intracellular GSH level. It is part of the cell antioxidant defense mechanism. Catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors. Alternatively, glutathione can be hydrolyzed to give Cys-Gly and gamma glutamate. Isoform 3 seems to be inactive.
Gene Name:
GGT1
Uniprot ID:
P19440
Molecular weight:
61409.67
Reactions
Beta-Aminopropionitrile + L-Glutamic acid → gamma-Glutamyl-beta-aminopropiononitrile + Waterdetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT7
Uniprot ID:
Q9UJ14
Molecular weight:
70466.015
Reactions
Beta-Aminopropionitrile + L-Glutamic acid → gamma-Glutamyl-beta-aminopropiononitrile + Waterdetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT6
Uniprot ID:
Q6P531
Molecular weight:
50508.83
Reactions
Beta-Aminopropionitrile + L-Glutamic acid → gamma-Glutamyl-beta-aminopropiononitrile + Waterdetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves the gamma-glutamyl peptide bond of glutathione conjugates, but maybe not glutathione itself. Converts leukotriene C4 (LTC4) to leukotriene D4 (LTD4).
Gene Name:
GGT5
Uniprot ID:
P36269
Molecular weight:
62331.75
Reactions
Beta-Aminopropionitrile + L-Glutamic acid → gamma-Glutamyl-beta-aminopropiononitrile + Waterdetails