Human Metabolome Database: Showing metabocard for Beta-Aminopropionitrile (HMDB0004101)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

enzymes (4) Show 4 proteins

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2006-08-13 10:54:05 UTC

Update Date

2020-02-26 21:24:58 UTC

HMDB ID

HMDB0004101

Secondary Accession Numbers

HMDB04101

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 , 6422318 , 9394169 , Am J Perinatol. 1997 Oct;14(9):567-71.).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Cyanoethylamine	ChEBI
3-Aminopropionitrile	ChEBI
3-Aminopropiononitrile	ChEBI
Aminopropionitrile	ChEBI
BAPN	ChEBI
beta-Alaninenitrile	ChEBI
beta-Aminoethyl cyanide	ChEBI
beta-Cyanoethylamine	ChEBI
H2NCH2CH2CN	ChEBI
b-Alaninenitrile	Generator
Β-alaninenitrile	Generator
b-Aminoethyl cyanide	Generator
Β-aminoethyl cyanide	Generator
b-Cyanoethylamine	Generator
Β-cyanoethylamine	Generator
b-Aminopropionitrile	Generator
Β-aminopropionitrile	Generator
3-Aminopropanenitrile	HMDB
b-Alaminenitrile	HMDB
beta-Alaminenitrile	HMDB
beta Aminopropionitrile	HMDB
beta-Aminopropionitrile	KEGG

Chemical Formula

C₃H₆N₂

Average Molecular Weight

70.0931

Monoisotopic Molecular Weight

70.053098202

IUPAC Name

3-aminopropanenitrile

Traditional Name

β 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

Description

belongs to the class of organic compounds known as nitriles. Nitriles are compounds having the structure RC#N; thus C-substituted derivatives of hydrocyanic acid, HC#N.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Organic cyanides

Direct Parent

Nitriles

Alternative Parents

Substituents

Nitrile
Carbonitrile
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Primary aliphatic amine
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aminopropionitrile (CHEBI:27413 )

Ontology

Physiological effect

Health effect:

Health condition:

Coma

Respiratory, thoracic and mediastinal disorders:

Apnea

Nervous system disorders:

Seizure

Psychiatric disorders:

Confusion

Ear and labyrinth disorders:

Vertigo

General disorders and administration site conditions:

Pain

Cardiac disorders:

Cardiac arrest

Gastrointestinal disorders:

Vomiting

Ingestion

Source:

Biological:

Plant:

Fabaceae

Biological location:

Cell and elements:

Cell:

Fibroblast

Subcellular:

Cytoplasm

Biofluid and excreta:

Blood

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

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
Water Solubility	37 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-0.85	ChemAxon
logS	-0.28	ALOGPS
pKa (Strongest Basic)	7.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.81 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	19.68 m³·mol⁻¹	ChemAxon
Polarizability	7.53 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-f05f2291dfe77fc789cb	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-3900000000-75972f9c9d6ba1c09de2	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9800000000-a9d53e8af368cf281f3c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-9640000000-2a51789533a4a0d4beed	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f79-2690000000-e7505ee33092ac028fb9	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-7900000000-1aa082aac45073e0b837	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-f05f2291dfe77fc789cb	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-3900000000-75972f9c9d6ba1c09de2	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9800000000-a9d53e8af368cf281f3c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-9640000000-2a51789533a4a0d4beed	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f79-2690000000-e7505ee33092ac028fb9	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-7900000000-1aa082aac45073e0b837	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-3fe507f31005b95d4d19	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-9000000000-6a162c90ff7c10fa232c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-9000000000-d2707111f575b74b6f7d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-f8447d5497483c729855	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-9000000000-bc2e9976335d260923dd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-044e599cd4faa32caadb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-9000000000-7dfadb8fdf3477540781	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-9000000000-ca5db6c876b46ee9a1cf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-39a4d5ba1e275b87d47b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-9000000000-d13e9e176f608de3e76b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9000000000-3b795596647194f89ae6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udl-9000000000-062a72ed70b3ea0ab27c	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-e5c8c009efa6f2441041	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Fibroblasts

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB11483

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012565

KNApSAcK ID

Not Available

Chemspider ID

21241485

KEGG Compound ID

C05670

BioCyc ID

BETA-AMINOPROPIONITRILE

BiGG ID

Not Available

Wikipedia Link

Aminopropionitrile

METLIN ID

7017

PubChem Compound

1647

PDB ID

Not Available

ChEBI ID

27413

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

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

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 ]
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 ]
Peacock EE Jr: Pharmacological control of surgical scar tissue. Am Surg. 1978 Nov;44(11):693-8. [PubMed:367235 ]
Spencer PS, Schaumburg HH: Lathyrism: a neurotoxic disease. Neurobehav Toxicol Teratol. 1983 Nov-Dec;5(6):625-9. [PubMed:6422318 ]
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. [PubMed:9394169 ]

Enzymes

Enzyme Details

1. Gamma-glutamyltranspeptidase 1

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 + Water	details

Enzyme Details

2. Gamma-glutamyltransferase 7

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 + Water	details

Enzyme Details

3. Gamma-glutamyltransferase 6

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 + Water	details

Enzyme Details

4. Gamma-glutamyltransferase 5

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 + Water	details

Showing metabocard for Beta-Aminopropionitrile (HMDB0004101)

Structure for HMDB0004101 (Beta-Aminopropionitrile)

Enzymes

Reactions

Reactions

Reactions

Reactions