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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
10–20 beans contained 0.3-1.3 gm% djenkolic acid
Route of Administration: Oral
In Vitro Use Guide
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
Record UNII
3QHC9R0YFZ
Record Status Validated (UNII)
Record Version