nopaline profile

Nopaline is a non-protein amino acid derivative of arginine and pyruvate. It is produced by certain strains of Agrobacterium, a genus of bacteria known for their ability to transfer genes into plants. Nopaline is synthesized via the action of the nopaline synthase (nos) gene, which is a key component of the Ti plasmid of Agrobacterium. Nopaline is thought to be a source of nitrogen and carbon for Agrobacterium, and its presence is often used as an indicator of Agrobacterium infection in plants. The biosynthesis of nopaline involves the condensation of arginine and pyruvate, catalyzed by the nos enzyme. Nopaline is a key player in the interaction between Agrobacterium and plants. It is involved in the induction of crown gall disease, a plant disease caused by Agrobacterium. Nopaline has also been studied for its potential use as a biofertilizer, due to its ability to stimulate plant growth. Research into nopaline has contributed to our understanding of plant-bacterial interactions, and its role in the development of crown gall disease. Nopaline is also studied in the context of genetic engineering, as it can be used as a selectable marker for Agrobacterium-mediated transformation.'

nopaline: utilized by virulent strains of Agrobacterium; metabolites of crown-gall tumors; isonopaline refers to (R-isomer) of nopaline; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

D-nopaline : An amino acid opine resulting from the formal reductive condensation of the amino group of L-arginine with the keto group of 2-oxopentanedioic acid. [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]

ID Source	ID
PubMed CID	108012
CHEBI ID	17249
SCHEMBL ID	7823698
MeSH ID	M0052710

Synonym
n(2)-(d-1,3-dicarboxypropyl)-l-arginine
n-[4-[(aminoiminomethyl)amino]-1-carboxybutyl]-d-glutamic acid(ecl)
CHEBI:17249
(s)-n-(4-((aminoiminomethyl)amino)-1-carboxybutyl)-d-glutamic acid
(2r)-2-{[(1s)-4-carbamimidamido-1-carboxybutyl]amino}pentanedioic acid
n2-(d-1,3-dicarboxypropyl)-l-arginine
nopaline
C01682
n-[(1s)-4-carbamimidamido-1-carboxybutyl]-d-glutamic acid
22350-70-5
d-nopaline
d-glutamic acid, n-[(1s)-4-[(aminoiminomethyl)amino]-1-carboxybutyl]-
isonopaline
qj8ep5f7x8 ,
d-glutamic acid, n-(4-((aminoiminomethyl)amino)-1-carboxybutyl)-, (s)-
unii-qj8ep5f7x8
d-glutamic acid,n-[(1s)-4-[(aminoiminomethyl)amino]-1-carboxybutyl]-
SCHEMBL7823698
(2r)-2-[[(1s)-1-carboxy-4-(diaminomethylideneamino)butyl]amino]pentanedioic acid
DTXSID20945005
Q27102284
2w2 ,
(r)-2-(((s)-1-carboxy-4-guanidinobutyl)amino)pentanedioic acid
d-glutamic acid, n-[4-[(aminoiminomethyl)amino]-1-carboxybutyl]-, (s)-
n-[(1s)-4-[(aminoiminomethyl)amino]-1-carboxybutyl]-d-glutamic acid
(2r)-2-{[(1s)-1-carboxy-4-[(diaminomethylidene)amino]butyl]amino}pentanedioic acid

Class	Description
guanidines	Any organonitrogen compound containing a carbamimidamido (guanidino) group. Guanidines have the general structure (R(1)R(2)N)(R(3)R(4)N)C=N-R(5) and are related structurally to amidines and ureas.
tricarboxylic acid	An oxoacid containing three carboxy groups.
secondary amino compound	A compound formally derived from ammonia by replacing two hydrogen atoms by organyl groups.
amino acid opine	Any opine whose structure is based on the condensation of an amino acid with a carbohydrate or a keto-acid.
L-arginine derivative	A proteinogenic amino acid derivative resulting from reaction of L-arginine at the amino group, the carboxy group, or the guanidyl group, or from the replacement of any hydrogen of L-arginine by a heteroatom.
D-glutamic acid derivative	A non-proteinogenic amino acid derivative resulting from the formal reaction of D-glutamic acid at the amino group or either carboxy group, or from the replacement of any hydrogen of D-glutamic acid by a heteroatom.
[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]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	44 (42.72)	18.7374
1990's	35 (33.98)	18.2507
2000's	12 (11.65)	29.6817
2010's	11 (10.68)	24.3611
2020's	1 (0.97)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	2 (1.89%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	104 (98.11%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.	3.46	2	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	1.96	1	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
glutamine Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.	1.98	1	amino acid zwitterion; glutamine family amino acid; glutamine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	1.95	1	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	1.96	1	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
kanamycin a Kanamycin: Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components.. kanamycin : Kanamycin is a naturally occurring antibiotic complex from Streptomyces kanamyceticus that consists of several components: kanamycin A, the major component (also usually designated as kanamycin), and kanamycins B, C, D and X the minor components.	1.95	1	kanamycins	bacterial metabolite
methionine Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.	1.96	1	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
mannitol [no description available]	3.12	5	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
ornithine Ornithine: An amino acid produced in the urea cycle by the splitting off of urea from arginine.. ornithine : An alpha-amino acid that is pentanoic acid bearing two amino substituents at positions 2 and 5.	1.96	1	non-proteinogenic L-alpha-amino acid; ornithine	algal metabolite; hepatoprotective agent; mouse metabolite
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.	7.54	103	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
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	1	amino acid zwitterion; homoserine	algal metabolite; Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite
acetosyringone acetosyringone: plant inducer which induces expression of VirE & VirG in A. tumefaciens. acetosyringone : A member of the class of acetophenones that is 1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.	3.23	6	acetophenones; dimethoxybenzene; phenols	anti-asthmatic drug; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug; plant metabolite
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.02	1	benzenes; phenyl acetates
octopine D-octopine : The (1R)-1-carboxyethyl derivative of L-arginine. It is a metabolite released by plant tumours.	6.86	52	amino acid opine; amino dicarboxylic acid; D-alpha-amino acid zwitterion; D-arginine derivative; guanidines; secondary amino compound	animal metabolite; xenobiotic metabolite
tanshinone tanshinone: from root of Salvia miltiorrhiza Bunge; RN given refers to tanshinone I; cardioprotective agent and neuroprotective agent	1.98	1	abietane diterpenoid	anticoronaviral agent
mannopine mannopine: mannityl opine analog; RN given refers to (S)-isomer. mannopine : A hexitol derivative that is D-mannitol in which the hydroxy group at position 1 is replaced by the alpha-amino group of L-glutamine. It is produced in crown gall tumours induced in a wide range of dicotyledenous plants by Agrobacterium tumefaciens.	3.12	5	amino acid opine; dicarboxylic acid monoamide; hexitol derivative; L-glutamine derivative; non-proteinogenic L-alpha-amino acid; secondary amino compound	plant metabolite
agropine agropine: RN given refers to (S)-isomer; structure given in first source	4	4
mannopinic acid mannopinic acid: mannityl opine analog; RN given refers to (S)-isomer	2	1
n-(3-oxo-octanoyl)-l-homoserine lactone N-(beta-oxooctan-1-oyl)homoserine lactone: involved in conjugation and tra gene regulation in Agrobacterium tumefaciens; structure in first source	2	1
agrocinopine agrocinopine: opine phosphorylated sugar synthesized by crown gall tumors & utilized as nutrient source by bacteria responsible for infection. agrocinopine : A subclass of opines, which are low molecular weight compounds found in plant crown gall tumours or hairy root tumours produced by parasitic bacteria of the genus Agrobacterium. Agrocinopines are set of sugar phosphodiester opines known to induce transfer of another Ti plasmid, pTiBo542.. agrocinopine A : A member of the class of agrocinopines that consists of sucrose and L-arabinose units joined via a phosphodiester linkage between position 4(F) of sucrose and position 2 of arabinose.	3.25	6
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	2.66	3	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
agropinic acid agropinic acid: mannityl opine analog; RN given refers to (S)-isomer	2	1
cucumopine cucumopine: an opine from Agrobacterium vitis; RN given refers to cucumopine (4S-trans)-isomer; mikimopine is (4R-cis)-isomer	2	1	non-proteinogenic alpha-amino acid
zeatin Zeatin: An aminopurine factor in plant extracts that induces cell division. (Grant & Hackh's Chemical Dict, 5th ed)	7.4	2	zeatin	plant metabolite
succinamopine succinamopine: crown gall opine, host plant metabolite incited by Agrobacterium; structure given in first source	7.42	2
ribose ribopyranose : The pyranose form of ribose.	2.02	1	D-ribose; ribopyranose
agrocin 84 agrocin 84: contains glucose, deoxy arabinose & other yet unidentified sugars. agrocin 84 : A nucleotide conjugate that is produced by Agrobacterium radiobacter strain K-84. A 'Trojan horse' antibiotic used to control crown gall.	2.67	3	purines
chrysopine chrysopine: an opine-like molecule from plant galls; d-lactone of N-1-deoxy-D-fructosyl-L-glutamine. chrysopine : A spiroketal and delta-lactone resulting from the formal condensation of the carboxy group of L-glutamine with the anomeric hydroxy group of D-fructose and substitution of the 1-hydroxy group of the fructose by the alpha-amino group of the glutamine. It is found in crown gall tumours induced in chrysanthemums by Agrobacterium tumefaciens.	1.98	1	amino acid opine; carboxamide; delta-lactone; secondary amino compound; spiroketal; triol	plant metabolite
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	1.98	1

Condition	Indicated	Relationship Strength	Studies	Trials
Diathesis [description not available]	0	1.98	1	0
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	0	1.97	1	0

nopaline

Description

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Synonyms (26)

Research Excerpts

Drug Classes (6)

Research

Studies (103)

Market Indicators

Research Demand Index: 32.16

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