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Details

Stereochemistry ACHIRAL
Molecular Formula C4H4O4.2C3H6N2
Molecular Weight 256.2584
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of BIS(3-AMINOPROPIONONITRILE) FUMARATE

SMILES

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

InChI

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

HIDE SMILES / InChI

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

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

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
Effect of beta-aminopropionitrile on in vitro bone lipid synthesis.
1975 Feb
Megakaryocyte pathology and bone marrow fibrosis: the lysyl oxidase connection.
2012 Aug 30
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 15:00:13 GMT 2023
Edited
by admin
on Fri Dec 15 15:00:13 GMT 2023
Record UNII
1O0893POYK
Record Status Validated (UNII)
Record Version
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Name Type Language
BIS(3-AMINOPROPIONONITRILE) FUMARATE
Systematic Name English
.BETA.-AMMONIUMPROPIONITRILE HEMIFUMARATE
Common Name English
FUMARIC ACID, SALT WITH 3-AMINOPROPIONITRILE
Systematic Name English
PROPIONITRILE, 3-AMINO-, FUMARATE (2:1)
Systematic Name English
DI-.BETA.-AMINOPROPIONITRILE FUMARATE
Common Name English
PROPANENITRILE, 3-AMINO-, (2E)-2-BUTENEDIOATE (2:1)
Systematic Name English
PROPANENITRILE, 3-AMINO-, (E)-2-BUTENEDIOATE (2:1)
Systematic Name English
.BETA.-AMINOPROPIONITRILE FUMARATE
Systematic Name English
Code System Code Type Description
ECHA (EC/EINECS)
218-208-7
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
EPA CompTox
DTXSID0045751
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
CAS
2079-89-2
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
PUBCHEM
5462653
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
FDA UNII
1O0893POYK
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE