Compounds > indospicine
Page last updated: 2024-12-07

indospicine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Indospicine is a non-protein amino acid isolated from the legume Indigofera spicata. It is a potent inhibitor of the enzyme arginase, which is responsible for the conversion of arginine to ornithine. Indospicine has been shown to cause a variety of toxic effects in animals, including liver damage, growth retardation, and infertility. It is studied for its potential as a therapeutic agent for the treatment of certain cancers and other diseases. Indospicine has also been investigated as a potential anti-parasite agent.'

indospicine: RN given refers to (S)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

L-indospicine : An alpha-amino acid that is 2,7-diaminoheptanoic acid substituted by a imino group at position 7 (the 2S stereoisomer). [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID108010
CHEBI ID6253
SCHEMBL ID1512880
MeSH IDM0162686

Synonyms (20)

Synonym
C08288
l-indospicine
16377-00-7
indospicine
l-6-amidinonorleucine
AC1L335Z ,
(2s)-2,7-diamino-7-iminoheptanoic acid
AC1Q5QLR ,
CHEBI:6253
x29q4d9671 ,
6-amidino-2-aminohexanoic acid
heptanoic acid, 2,7-diamino-7-imino-, (s)-
unii-x29q4d9671
indospicine [mi]
l-.alpha.-amino-.epsilon.-amidinocaproic acid
SCHEMBL1512880
(2s)-2,7-diamino-7-imino-heptanoic acid
DTXSID70167659
Q1661793
(2s)-2-amino-6-carbamimidoylhexanoic acid

Research Excerpts

Overview

Indospicine is an arginine analogue and a natural toxin occurring only in Indigofera plant species, including Australian native species. It is a non-proteogenic amino acid that accumulates as the free amino acid in livestock grazing Indig ofera.

ExcerptReferenceRelevance
"Indospicine is an arginine analogue and a natural toxin occurring only in Indigofera plant species, including Australian native species. "( Hepatopathy in Victorian dogs consuming pet meat contaminated with indospicine.
Coghill, A; Dries, LR; Hall, SL; Hawes, MC; Phillips, DE; Salmon, SE; Sarandopoulos, J, 2022)		2.4
"Indospicine is a natural toxin occurring only in Indigofera plant species, including the Australian native species I. "( Assessing the risk of residues of the toxin indospicine in bovine muscle and liver from north-west Australia.
Allen, JG; Fletcher, MT; Masters, AM; Netzel, G; Palmer, DG; Tai, SY, 2019)		2.22
"Indospicine is a hepatotoxic amino acid found in Indigofera plant spp. "( Determination of hepatotoxic indospicine in Australian camel meat by ultra-performance liquid chromatography-tandem mass spectrometry.
Al Jassim, R; D'Arcy, BR; Fletcher, MT; Tan, ET; Yong, KW, 2014)		2.14
"Indospicine is a non-proteogenic amino acid that accumulates as the free amino acid in livestock grazing Indigofera plant species and causes both reproductive losses and hepatotoxic effects. "( Synthesis of l-indospicine, [5,5,6-(2)H3]-l-indospicine and l-norindospicine.
Arthur, DM; Challinor, VL; Chow, S; De Voss, JJ; Fletcher, MT; Lang, CS; Ng, JC; Wong, SH; Yong, KW, 2016)		2.23
"Indospicine is a hepatotoxic amino acid that accumulates in the meat of horses that consume the legume Indigofera linnaei. "( Analysis of the amino acid indospicine in biological samples by high performance liquid chromatography.
Hegarty, MP; Pass, MA; Pollitt, S, 1999)		2.04

Effects

ExcerptReferenceRelevance
"Indospicine has caused both primary and secondary hepatotoxicosis and also reproductive losses, but has only previously been determined in a small number of Indigofera species."( Seasonal and Species Variation of the Hepatotoxin Indospicine in Australian Indigofera Legumes As Measured by UPLC-MS/MS.
Al Jassim, R; D'Arcy, BR; Fletcher, MT; Materne, CM; Silcock, RG; Tan, ET, 2016)		1.41

Toxicity

ExcerptReferenceRelevance
" Indospicine, a toxic amino acid found in the genus Indigofera, was detected in samples of suspect horsemeat."( Hepatotoxicity to dogs of horse meat contaminated with indospicine.
Cameron, R; Hegarty, MP; Kelly, WR; McEwan, D; Williams, OJ, 1988)		1.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
hepatotoxic agentA role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
carboxamidineCompounds having the structure RC(=NR)NR2. The term is used as a suffix in systematic nomenclature to denote the -C(=NH)NH2 group including its carbon atom.
non-proteinogenic L-alpha-amino acidAny L-alpha-amino acid which is not a member of the group of 23 proteinogenic amino acids.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (5.56)18.7374
1990's2 (11.11)18.2507
2000's0 (0.00)29.6817
2010's12 (66.67)24.3611
2020's3 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.34

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index27.34 (24.57)
Research Supply Index2.94 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index27.81 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (27.34)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies1 (5.56%)4.05%
Observational0 (0.00%)0.25%
Other17 (94.44%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
3-nitropropionic acid
3-nitropropionic acid: succinate dehydrogenase inactivator; biosynthesized by FABACEAE plants from ASPARAGINE. 3-nitropropanoic acid : A C-nitro compound that is propanoic acid in which one of the methyl hydrogens has been replaced by a nitro group.		7.4110C-nitro compoundantimycobacterial drug;
EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor;
mycotoxin;
neurotoxin
arginine
Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.		2.7830arginine;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		biomarker;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical
acrylonitrile
[no description available]		2.1310aliphatic nitrile;
volatile organic compound		antifungal agent;
carcinogenic agent;
fungal metabolite;
mutagen;
polar aprotic solvent
homoserine
homoserine : An alpha-amino acid that is glycine substituted at the alpha-position by a 2-hydroxyethyl group.. L-homoserine : The L-enantiomer of homoserine.		2.1310amino acid zwitterion;
homoserine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
Saccharomyces cerevisiae metabolite
norleucine
Norleucine: An unnatural amino acid that is used experimentally to study protein structure and function. It is structurally similar to METHIONINE, however it does not contain SULFUR.. L-norleucine : A non-proteinogenic L-alpha-amino acid comprising hexanoic acid carrying an amino group at C-2. It does not occur naturally.		4.341802-aminohexanoic acid;
L-alpha-amino acid zwitterion;
non-proteinogenic L-alpha-amino acid
tetradecanoylphorbol acetate
Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.		1.9910acetate ester;
diester;
phorbol ester;
tertiary alpha-hydroxy ketone;
tetradecanoate ester		antineoplastic agent;
apoptosis inducer;
carcinogenic agent;
mitogen;
plant metabolite;
protein kinase C agonist;
reactive oxygen species generator
ng-nitroarginine methyl ester
NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.		1.9910alpha-amino acid ester;
L-arginine derivative;
methyl ester;
N-nitro compound		EC 1.14.13.39 (nitric oxide synthase) inhibitor
alpha-aminopimelic acid
alpha-aminopimelic acid: antagonizes glutamate-induced inhibitions of Helix neurones. 2-aminopimelic acid : An amino dicarboxylic acid that is heptanedioic acid in which a hydrogen at position 2 is replaced by an amino group. It is a component of the cell wall peptidoglycan of bacteria.		2.5520amino dicarboxylic acid;
non-proteinogenic alpha-amino acid		bacterial metabolite
omega-n-methylarginine
omega-N-Methylarginine: A competitive inhibitor of nitric oxide synthetase.. N(omega)-methyl-L-arginine : A L-arginine derivative with a N(omega)-methyl substituent.		1.9910amino acid zwitterion;
arginine derivative;
guanidines;
L-arginine derivative;
non-proteinogenic L-alpha-amino acid
canavanine
L-canavanine : A non-proteinogenic L-alpha-amino acid that is L-homoserine substituted at oxygen with a guanidino (carbamimidamido) group. Although structurally related to L-arginine, it is non-proteinogenic.		6.9910amino acid zwitterion;
non-proteinogenic L-alpha-amino acid		phytogenic insecticide;
plant metabolite
sodium bicarbonate
Sodium Bicarbonate: A white, crystalline powder that is commonly used as a pH buffering agent, an electrolyte replenisher, systemic alkalizer and in topical cleansing solutions.		2.1310one-carbon compound;
organic sodium salt		antacid;
food anticaking agent
indigo carmine
Indigo Carmine: Indolesulfonic acid used as a dye in renal function testing for the detection of nitrates and chlorates, and in the testing of milk.. indigo carmine : An organic sodium salt resulting from the formal condensation of indigo carmine (acid form) with two equivalents of sodium hydroxide. It is an indicator at pH 11.5-14, changing from blue to yellow.		2.4110
ConditionIndicatedRelationship StrengthStudiesTrials
Canine Diseases
[description not available]		02.7330
Equine Diseases
[description not available]		02.8930
Liver Dysfunction
[description not available]		02.7330
Liver Diseases
Pathological processes of the LIVER.		02.7330
Benign Neoplasms
[description not available]		02.3110
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.3110
Ataxia
Impairment of the ability to perform smoothly coordinated voluntary movements. This condition may affect the limbs, trunk, eyes, pharynx, larynx, and other structures. Ataxia may result from impaired sensory or motor function. Sensory ataxia may result from posterior column injury or PERIPHERAL NERVE DISEASES. Motor ataxia may be associated with CEREBELLAR DISEASES; CEREBRAL CORTEX diseases; THALAMIC DISEASES; BASAL GANGLIA DISEASES; injury to the RED NUCLEUS; and other conditions.		02.0710
Plant Poisoning
Poisoning by the ingestion of plants or its leaves, berries, roots or stalks. The manifestations in both humans and animals vary in severity from mild to life threatening. In animals, especially domestic animals, it is usually the result of ingesting moldy or fermented forage.		02.0710
Wallerian Degeneration
Degeneration of distal aspects of a nerve axon following injury to the cell body or proximal portion of the axon. The process is characterized by fragmentation of the axon and its MYELIN SHEATH.		02.0710
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		0210
Acute Liver Injury, Drug-Induced
[description not available]		01.9710
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		01.9710