Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for Beta-Aminopropionitrile (HMDB04101)

Record Information
Version 3.5
Creation Date 2006-08-13 04:54:05 -0600
Update Date 2013-02-08 17:13:01 -0700
HMDB ID HMDB04101
Secondary Accession Numbers None
Metabolite Identification
Common Name Beta-Aminopropionitrile
Description beta-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 Link_out, 6422318 Link_out, 9394169 Link_out, Am J Perinatol. 1997 Oct;14(9):567-71.).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Cyanoethylamine
  2. 3-Aminopropanenitrile
  3. 3-Aminopropionitrile
  4. 3-Aminopropiononitrile
  5. Aminopropionitrile
  6. b-Alaminenitrile
  7. b-Alaninenitrile
  8. b-Aminoethyl cyanide
  9. b-Aminopropionitrile
  10. b-Cyanoethylamine
  11. BAPN
  12. beta-Alaminenitrile
  13. beta-Alaninenitrile
  14. beta-Aminoethyl cyanide
  15. beta-Aminopropionitrile
  16. beta-Cyanoethylamine
Chemical Formula C3H6N2
Average Molecular Weight 70.0931
Monoisotopic Molecular Weight 70.053098202
IUPAC Name 3-aminopropanenitrile
Traditional IUPAC Name aminopropionitrile
CAS Registry Number 151-18-8
SMILES NCCC#N
InChI Identifier InChI=1S/C3H6N2/c4-2-1-3-5/h1-2,4H2
InChI Key AGSPXMVUFBBBMO-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Nitriles
Sub Class N/A
Other Descriptors
  • Aliphatic Acyclic Compounds
  • aminopropionitrile(ChEBI)
Substituents
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Nitriles
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point < 25 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP -1.08 ALOGPS
LogP -0.85 ChemAxon
LogS -0.28 ALOGPS
pKa (strongest basic) 7.85 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 49.81 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 19.68 ChemAxon
Polarizability 7.53 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Fibroblasts
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB012565
KNApSAcK ID Not Available
Chemspider ID 21241485 Link_out
KEGG Compound ID C05670 Link_out
BioCyc ID BETA-AMINOPROPIONITRILE Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04101 Link_out
Metagene Link HMDB04101 Link_out
METLIN ID 7017 Link_out
PubChem Compound 1647 Link_out
PDB ID Not Available
ChEBI ID 27413 Link_out
References
Synthesis Reference Smolin, 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. Pubmed: 16445767 Link_out
  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. Pubmed: 639425 Link_out