U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C7H14N2O4S2
Molecular Weight 254.327
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DJENKOLIC ACID

SMILES

N[C@@H](CSCSC[C@H](N)C(O)=O)C(O)=O

InChI

InChIKey=JMQMNWIBUCGUDO-WHFBIAKZSA-N
InChI=1S/C7H14N2O4S2/c8-4(6(10)11)1-14-3-15-2-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1

HIDE SMILES / InChI

Molecular Formula C7H14N2O4S2
Molecular Weight 254.327
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24790471 | https://www.ncbi.nlm.nih.gov/pubmed/15262924

Djenkolic acid (or sometimes jengkolic acid) is a sulfur-containing toxin and non-protein amino acid naturally found in Djenkol beans of the South-East Asian legumes jengkol (Archidendron jiringa). Djenkolic acid is toxic to humans, often causing kidney failure. The toxicity of djenkolic acid in humans arises from its poor solubility under acidic conditions after consumption of the Djenkol bean. The amino acid precipitates into crystals which cause mechanical irritation of the renal tubules and urinary tract, resulting in symptoms such as abdominal discomfort, loin pains, severe colic, nausea, vomiting, dysuria, gross hematuria, and oliguria, occurring 2 to 6 hours after the beans were ingested. Treatment for this toxicity requires hydration to increase urine flow and alkalinization of urine by sodium bicarbonate. Furthermore, this poisoning can be prevented when consuming Djenkol beans by boiling them beforehand, since djenkolic acid is removed from the beans.

Originator

Sources: Recueil des Travaux Chimiques des Pays-Bas et de la Belgique (1935), 54, 493-501.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Design and synthesis of dimeric HIV-1 integrase inhibitory peptides.
2003 Oct 6
Zapoteca formosa: sulfur chemistry and phytotoxicity.
2004 Feb
Copper-mediated LDL oxidation by homocysteine and related compounds depends largely on copper ligation.
2004 Jan 20
Arabidopsis mutants in the C-S lyase of glucosinolate biosynthesis establish a critical role for indole-3-acetaldoxime in auxin homeostasis.
2004 Mar
The effects of seed quality and pipecolic and djenkolic acids on bruchid beetle infestation in water deficit-stressed Acacia trees.
2004 Nov
Patents

Patents

Sample Use Guides

10–20 beans contained 0.3-1.3 gm% djenkolic acid
Route of Administration: Oral
B. subtilis was grown in SP medium or in minimal medium (6 mM K2HPO4, 4.4 mM KH2PO4, 0.3 mM trisodium citrate, 4 mM MgCl2, 250 mkM CaCl2, 10 mkM) MnCl2, 0.5% glucose, 50 mg of L-tryptophan liter_1, 11 mg of ferric ammonium citrate liter^-1, 0.1% L-glutamine) supplemented with one of the following sulfur sources: 1 mM K2SO4, 1 mM L-methionine, 1 mM DL-homocysteine, 20 mkM to 1 mM L-cystine, 0.1 to 1 mM DL-cystathionine, 0.1 to 1 mM L-djenkolic acid, or 0.1 to 1 mM S-methylcysteine. In this minimal medium, residual growth in the absence of any added sulfur source was observed. To avoid this problem, an exhausted minimal medium was obtained by growing B. subtilis 168 in a sulfurfree minimal medium and then centrifuging the culture and filtering the supernatant
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:43:09 UTC 2023
Edited
by admin
on Fri Dec 15 19:43:09 UTC 2023
Record UNII
3QHC9R0YFZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DJENKOLIC ACID
MI  
Common Name English
L-CYSTEINE THIOACETAL OF FORMALDEHYDE
Common Name English
NSC-76076
Code English
L-DJENKOLIC ACID
Common Name English
DJENKOLIC ACID [MI]
Common Name English
3,3'-METHYLENEDITHIOBIS(2-AMINOPROPANOIC ACID)
Systematic Name English
S,S'-METHYLENEBIS-L-CYSTEINE
Systematic Name English
Code System Code Type Description
WIKIPEDIA
DJENKOLIC ACID
Created by admin on Fri Dec 15 19:43:09 UTC 2023 , Edited by admin on Fri Dec 15 19:43:09 UTC 2023
PRIMARY
CHEBI
6211
Created by admin on Fri Dec 15 19:43:09 UTC 2023 , Edited by admin on Fri Dec 15 19:43:09 UTC 2023
PRIMARY
CAS
498-59-9
Created by admin on Fri Dec 15 19:43:09 UTC 2023 , Edited by admin on Fri Dec 15 19:43:09 UTC 2023
PRIMARY
PUBCHEM
68134
Created by admin on Fri Dec 15 19:43:09 UTC 2023 , Edited by admin on Fri Dec 15 19:43:09 UTC 2023
PRIMARY
FDA UNII
3QHC9R0YFZ
Created by admin on Fri Dec 15 19:43:09 UTC 2023 , Edited by admin on Fri Dec 15 19:43:09 UTC 2023
PRIMARY
EPA CompTox
DTXSID80198075
Created by admin on Fri Dec 15 19:43:09 UTC 2023 , Edited by admin on Fri Dec 15 19:43:09 UTC 2023
PRIMARY
MESH
C004851
Created by admin on Fri Dec 15 19:43:09 UTC 2023 , Edited by admin on Fri Dec 15 19:43:09 UTC 2023
PRIMARY
MERCK INDEX
m4701
Created by admin on Fri Dec 15 19:43:09 UTC 2023 , Edited by admin on Fri Dec 15 19:43:09 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
207-863-4
Created by admin on Fri Dec 15 19:43:09 UTC 2023 , Edited by admin on Fri Dec 15 19:43:09 UTC 2023
PRIMARY
NSC
76076
Created by admin on Fri Dec 15 19:43:09 UTC 2023 , Edited by admin on Fri Dec 15 19:43:09 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY