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Details

Stereochemistry ACHIRAL
Molecular Formula C4H4O4.C3H6N2
Molecular Weight 186.1653
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of 3-AMINOPROPIONITRILE FUMARATE

SMILES

NCCC#N.OC(=O)\C=C\C(O)=O

InChI

InChIKey=NYPGBHKJFKQTIY-TYYBGVCCSA-N
InChI=1S/C4H4O4.C3H6N2/c5-3(6)1-2-4(7)8;4-2-1-3-5/h1-2H,(H,5,6)(H,7,8);1-2,4H2/b2-1+;

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C3H6N2
Molecular Weight 70.0931
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19440335 | https://www.ncbi.nlm.nih.gov/pubmed/22767499

3-Aminopropionitrile (Beta-amino-propionitrile, BAPN) is a toxic constituent from lathyrus plants. BAPN found in lathyrus odoratus (our more common garden sweet pea plant) is thought to be responsible for osteolathyrism due to irreversible inhibition of lysyl oxidase (LOX), an enzyme necessary for the covalent cross-linking of tropocollagen molecules during the maturation of mature collagen. BAPN demonstrated in antimetastatic and antimyelofibrotic activity in vivo due to inhibition of LOX.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

To generate metastases, 5-6 week old female NIH-III mice were anesthetized by intraperitoneal (i.p.) injection of ketamine (100 mg/kg) and xylazine (6 mg/kg), and then 2×105 MDA-MB-231-Luc2 cells suspended in 100 µl of PBS were injected into the left ventricle of each mouse. Successful intra-cardiac injections were confirmed by immediate whole body bioluminescence imaging. BAPN intraperitoneal injections at a dose of 100 mg/kg in 100 µl PBS, were initiated either 1 day prior, on the same day as, or 7 days after intracardiac tumor cell injection.
Route of Administration: Intraperitoneal
In Vitro Use Guide
Enzyme activlty was measured by a peroxidase-coupled fluorescence assay. Reaction mixtures contained 2.5 mM diaminopentane, 10 ug o horseradish peroxldase, 0.7 mM homovanllllc acid and lysyl oxidase in 50 mM sodium borate buffer. Fluorescence was continuously monitored at excitation wavelength of 315 nm and emission wavelength of 425 nm. Lysyl oxidase was incubated with various amounts (10^-8 - 10^-4 M) of BAPN at 37°C C for 2 h in 16 mH potassium phosphate.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:25:12 GMT 2023
Edited
by admin
on Fri Dec 15 15:25:12 GMT 2023
Record UNII
R5PA45870J
Record Status Validated (UNII)
Record Version
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Name Type Language
3-AMINOPROPIONITRILE FUMARATE
Systematic Name English
NSC-55260
Code English
Code System Code Type Description
CAS
352-96-5
Created by admin on Fri Dec 15 15:25:12 GMT 2023 , Edited by admin on Fri Dec 15 15:25:12 GMT 2023
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FDA UNII
R5PA45870J
Created by admin on Fri Dec 15 15:25:12 GMT 2023 , Edited by admin on Fri Dec 15 15:25:12 GMT 2023
PRIMARY
PUBCHEM
6433176
Created by admin on Fri Dec 15 15:25:12 GMT 2023 , Edited by admin on Fri Dec 15 15:25:12 GMT 2023
PRIMARY
ECHA (EC/EINECS)
206-527-4
Created by admin on Fri Dec 15 15:25:12 GMT 2023 , Edited by admin on Fri Dec 15 15:25:12 GMT 2023
PRIMARY
NSC
55260
Created by admin on Fri Dec 15 15:25:12 GMT 2023 , Edited by admin on Fri Dec 15 15:25:12 GMT 2023
PRIMARY
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