Page last updated: 2024-12-08

i-677

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

Description

4-oxalysine: from Streptomyces reseoviridofuscus; RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

O-(2-aminoethyl)-L-serine : An L-alpha-amino acid that is L-serine in which the hydroxy group at position 3 is converted to the corresponding 2-aminoethyl ether. An antimetabolic antibiotic obtained from Streptomyces reseoviridofuscus. [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 Source	ID
PubMed CID	160555
CHEMBL ID	1234985
CHEBI ID	72341
SCHEMBL ID	479185
MeSH ID	M0088454

Synonyms (33)

Synonym
997-44-4
l-serine, o-(2-aminoethyl)-
(l)-3-(2-aminoethoxy)alanine
o-(2-aminoethyl)-l-serine
alanine, 3-(2-aminoethoxy)-, l-
i 677
chebi:72341 ,
CHEMBL1234985
oxalysine-l
i-677
olz ,
NCGC00014348
l-4-oxalysine
nsc-136035
NCI136035
NCISTRUC1_000654
NCISTRUC2_000650
NCGC00097457-01
(2s)-2-amino-3-(2-aminoethoxy)propanoic acid
15219-97-3
AKOS006237370
l-3-(2-aminoethoxy)alanine
(s)-2-amino-3-(2-aminoethoxy)propionic acid
(s)-2-amino-3-(2-aminoethoxy)propanoic acid
4-oxalysine
serine, o-(2-aminoethyl)-
CCG-37546
NCGC00014348-02
SCHEMBL479185
(s)-(+)-2-amino-3-(2-aminoethoxy)propanoic acid
o-(2-aminoethyl)serine
DTXSID00912533
Q27139916

Research Excerpts

Toxicity

Excerpt	Reference	Relevance
" albicans to some toxic peptides in the presence of L-lysine may be attributed to an increased rate of transport of these peptides."	( Toxicity of oxalysine and oxalysine-containing peptides against Candida albicans: regulation of peptide transport by amino acids. Basrai, MA; Becker, JM; Miller, D; Naider, F; Zhang, HL, 1992)	0.28

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

Role	Description
antimetabolite	A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
antineoplastic agent	A substance that inhibits or prevents the proliferation of neoplasms.
metabolite	Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimicrobial agent	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
[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)

Class	Description
L-serine derivative	A proteinogenic amino acid derivative resulting from reaction of L-serine at the amino group or the carboxy group, or from the replacement of any hydrogen of L-serine by a heteroatom.
non-proteinogenic L-alpha-amino acid	Any 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]

Bioassays (17)

Assay ID	Title	Year	Journal	Article
AID513353	Binding affinity to lysine riboswitch 179 lysc of Bacillus subtilis 168 M1 harboring G163A mutation in P4 motif	2007	Nature chemical biology, Jan, Volume: 3, Issue:1	Antibacterial lysine analogs that target lysine riboswitches.
AID513349	Antibacterial activity against Bacillus subtilis 168 M2 harboring adenosine deletion within 95 to 97 sequence in loop E of P2 motif after 24 hrs by CLSI method	2007	Nature chemical biology, Jan, Volume: 3, Issue:1	Antibacterial lysine analogs that target lysine riboswitches.
AID513350	Inhibition of lysine riboswitch 179 lysc in Bacillus subtilis 168 M1 harboring G163A mutation in P4 motif assessed as reduction of beta-galactosidase activity at 5 mM after 3 hrs by lacZ reporter gene assay	2007	Nature chemical biology, Jan, Volume: 3, Issue:1	Antibacterial lysine analogs that target lysine riboswitches.
AID1204898	Antibacterial activity against Bacillus subtilis in chemical defined medium	2015	Journal of medicinal chemistry, Apr-23, Volume: 58, Issue:8	(Dis)similar Analogues of Riboswitch Metabolites as Antibacterial Lead Compounds.
AID513359	Antibacterial activity against wild type Bacillus subtilis 168 1A1 assessed as inhibition of viable spore formation at 2 mM after 22 to 24 hrs	2007	Nature chemical biology, Jan, Volume: 3, Issue:1	Antibacterial lysine analogs that target lysine riboswitches.
AID513354	Binding affinity to lysine riboswitch 179 lysc of Bacillus subtilis 168 M2 harboring adenosine deletion within 95 to 97 sequence in loop E of P2 motif	2007	Nature chemical biology, Jan, Volume: 3, Issue:1	Antibacterial lysine analogs that target lysine riboswitches.
AID513347	Antibacterial activity against wild type Bacillus subtilis 168 1A1 assessed as inhibition of viable spore formation at 0.2 mM after 22 to 24 hrs	2007	Nature chemical biology, Jan, Volume: 3, Issue:1	Antibacterial lysine analogs that target lysine riboswitches.
AID513346	Inhibition of wild-type Bacillus subtilis 168 1A1 lysine riboswitch 179 lysc assessed as reduction of beta-galactosidase activity at 5 mM after 3 hrs by lacZ reporter gene assay	2007	Nature chemical biology, Jan, Volume: 3, Issue:1	Antibacterial lysine analogs that target lysine riboswitches.
AID513348	Antibacterial activity against Bacillus subtilis 168 M1 harboring G163A mutation in P4 motif after 24 hrs by CLSI method	2007	Nature chemical biology, Jan, Volume: 3, Issue:1	Antibacterial lysine analogs that target lysine riboswitches.
AID1204889	Binding affinity to lysC riboswitch in Bacillus subtilis	2015	Journal of medicinal chemistry, Apr-23, Volume: 58, Issue:8	(Dis)similar Analogues of Riboswitch Metabolites as Antibacterial Lead Compounds.
AID513344	Antibacterial activity against Bacillus subtilis 168 1A1 at 100 uM after 24 hrs by by CLSI method	2007	Nature chemical biology, Jan, Volume: 3, Issue:1	Antibacterial lysine analogs that target lysine riboswitches.
AID513352	Binding affinity to Bacillus subtilis 168 1A1 lysine riboswitch 179 lysc	2007	Nature chemical biology, Jan, Volume: 3, Issue:1	Antibacterial lysine analogs that target lysine riboswitches.
AID513351	Inhibition of lysine riboswitch 179 lysc in Bacillus subtilis 168 M2 harboring adenosine deletion within 95 to 97 sequence in loop E of P2 motif assessed as reduction of beta-galactosidase activity at 5 mM after 3 hrs by lacZ reporter gene assay	2007	Nature chemical biology, Jan, Volume: 3, Issue:1	Antibacterial lysine analogs that target lysine riboswitches.
AID513360	Antibacterial activity against L-4-oxalysine-resistant Bacillus subtilis 168 M2 assessed as inhibition of viable spore formation at 2 mM after 22 to 24 hrs	2007	Nature chemical biology, Jan, Volume: 3, Issue:1	Antibacterial lysine analogs that target lysine riboswitches.
AID513345	Antibacterial activity against Bacillus subtilis 1A40 at 1 mM after 3 hrs by CLSI method	2007	Nature chemical biology, Jan, Volume: 3, Issue:1	Antibacterial lysine analogs that target lysine riboswitches.
AID513357	Antibacterial activity against Bacillus subtilis 168 1A1 after 24 hrs by CLSI method	2007	Nature chemical biology, Jan, Volume: 3, Issue:1	Antibacterial lysine analogs that target lysine riboswitches.
AID513343	Binding affinity to Bacillus subtilis 168 1A1 lysine riboswitch 179 lysc by in-line probing assay	2007	Nature chemical biology, Jan, Volume: 3, Issue:1	Antibacterial lysine analogs that target lysine riboswitches.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (19)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	9 (47.37)	18.7374
1990's	8 (42.11)	18.2507
2000's	1 (5.26)	29.6817
2010's	1 (5.26)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.96

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.

Metric	This Compound (vs All)
Research Demand Index	18.96 (24.57)
Research Supply Index	3.00 (2.92)
Research Growth Index	4.33 (4.65)
Search Engine Demand Index	15.26 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (18.96)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (5.26%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	18 (94.74%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	3.57	9	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; 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.	9.17	5	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
cytarabine [no description available]	2	1	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
homoarginine L-homoarginine : An L-lysine derivative that is the L-enantiomer of homoarginine.	3.57	2	homoarginine; L-lysine derivative; non-proteinogenic L-alpha-amino acid	biomarker; EC 3.1.3.1 (alkaline phosphatase) inhibitor; human metabolite; rat metabolite; xenobiotic metabolite
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	1.96	1	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
fibrinogen Fibrinogen: Plasma glycoprotein clotted by thrombin, composed of a dimer of three non-identical pairs of polypeptide chains (alpha, beta, gamma) held together by disulfide bonds. Fibrinogen clotting is a sol-gel change involving complex molecular arrangements: whereas fibrinogen is cleaved by thrombin to form polypeptides A and B, the proteolytic action of other enzymes yields different fibrinogen degradation products.. D-iditol : The D-enantiomer of iditol.	2.38	2	iditol	fungal metabolite
n-epsilon-acetyllysine N(6)-acetyl-L-lysine : An N(6)-acyl-L-lysine where the N(6)-acyl group is specified as acetyl.	2.03	1	acetyl-L-lysine; amino acid zwitterion; N(6)-acyl-L-lysine	human metabolite
n(alpha)-acetyllysine N(alpha)-acetyllysine: RN given refers to (L)-isomer. acetyl-L-lysine : An N-acetyl-L-amino acid that is the N-acetyl derivative of L-lysine.. N(2)-acetyl-L-lysine : An acetyl-L-lysine where the acetyl group is located at the N(2)-posiiton.	2.03	1	acetyl-L-lysine; amino acid zwitterion	human metabolite
leucylleucine leucylleucine: RN given refers to (DL-Leu-DL-Leu)-isomer	1.98	1	peptide
s-2-aminoethyl cysteine S-2-aminoethyl cysteine: inhibits protein synthesis in mammalian cells; RN given refers to parent cpd; structure. L-thialysine : A cysteine derivative that is the S-(2-aminoethyl) analogue of L-cysteine; reported to have cytotoxic effects.	3.78	3	L-cysteine thioether; non-proteinogenic L-alpha-amino acid	EC 5.4.3.2 (lysine 2,3-aminomutase) inhibitor; metabolite; protein synthesis inhibitor
2-amino-n(6)-hydroxyadenine 2-amino-N(6)-hydroxyadenine: mutagen & bacterial growth inhibitor; structure in first source. 2-amino-6-hydroxyaminopurine : A 2,6-diaminopurine that is the N(6)-hydroxy derivative of 2,6-diamino-3H-purine.	3.21	1	2,6-diaminopurines; hydroxylamines; nucleobase analogue	mutagen; teratogenic agent
ungeremine ungeremine: RN given refers to parent cpd; structure	1.96	1
kynurenine L-kynurenine : A kynurenine that has L configuration.	2.03	1	amino acid zwitterion; kynurenine; non-proteinogenic L-alpha-amino acid	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
homoharringtonine Homoharringtonine: Semisynthetic derivative of harringtonine that acts as a protein synthesis inhibitor and induces APOPTOSIS in tumor cells. It is used in the treatment of MYELOID LEUKEMIA, CHRONIC.. omacetaxine mepesuccinate : A cephalotaxine-derived alkaloid ester obtained from Cephalotaxus harringtonia; used for the treatment of chronic or accelerated phase chronic myeloid leukaemia.	1.96	1	alkaloid ester; enol ether; organic heteropentacyclic compound; tertiary alcohol	anticoronaviral agent; antineoplastic agent; apoptosis inducer; protein synthesis inhibitor
trimethyllysine trimethyllysine: stimulates growth of tumor cells; RN given refers to (S)-isomer	2.03	1	alpha-amino-acid cation	human metabolite; mouse metabolite
n(6)-(1-iminoethyl)lysine N(6)-acetimidoyl-L-lysine : An L-lysine derivative that is L-lysine in which one of the hydrogens attached to N(6) is substituted by an acetimidoyl group	2.03	1	L-lysine derivative; non-proteinogenic L-alpha-amino acid
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	1.94	1	cysteinium	fundamental metabolite
ammonium sulfate Ammonium Sulfate: Sulfuric acid diammonium salt. It is used in CHEMICAL FRACTIONATION of proteins.. ammonium sulfate : An inorganic sulfate salt obtained by reaction of sulfuric acid with two equivalents of ammonia. A high-melting (decomposes above 280degreeC) white solid which is very soluble in water (70.6 g/100 g water at 0degreeC; 103.8 g/100 g water at 100degreeC), it is widely used as a fertilizer for alkaline soils.	1.98	1	ammonium salt; inorganic sulfate salt	fertilizer
nikkomycin [no description available]	1.98	1
dehydrolysine [no description available]	3.57	2
peptones Peptones: Derived proteins or mixtures of cleavage products produced by the partial hydrolysis of a native protein either by an acid or by an enzyme. Peptones are readily soluble in water, and are not precipitable by heat, by alkalis, or by saturation with ammonium sulfate. (Dorland, 28th ed)	1.98	1
caseins Caseins: A mixture of related phosphoproteins occurring in milk and cheese. The group is characterized as one of the most nutritive milk proteins, containing all of the common amino acids and rich in the essential ones.	1.98	1
guanine [no description available]	3.21	1	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
6-hydroxy-2,4,5-triaminopyrimidine 6-hydroxy-2,4,5-triaminopyrimidine: pyrimidine moiety of pterins; RN given refers to parent cpd; structure. 2,5,6-triamino-4-hydroxypyrimidine : A member of the class of aminopyrimidines that is 2,5,6-triaminopyrimidine carrying an additional hydroxy substituent at position 4.	3.21	1	aminopyrimidine; hydroxypyrimidine	antioxidant; chromophore
concanavalin a Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.	1.99	1

Condition	Relationship Strength	Studies
Bacterial Disease [description not available]	3.03	1
Bacterial Infections Infections by bacteria, general or unspecified.	3.03	1
Experimental Neoplasms [description not available]	2.65	3
Sarcoma 180 An experimental sarcoma of mice.	1.96	1
Sarcoma 37 An experimental sarcoma of mice.	1.96	1
Benign Neoplasms, Brain [description not available]	1.95	1
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	1.95	1
Carbon Tetrachloride Poisoning Poisoning that results from ingestion, injection, inhalation, or skin absorption of CARBON TETRACHLORIDE.	1.96	1
Hepatocellular Carcinoma [description not available]	1.99	1
Experimental Hepatoma [description not available]	2.68	3
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	1.99	1
Lipidoses Conditions characterized by abnormal lipid deposition due to disturbance in lipid metabolism, such as hereditary diseases involving lysosomal enzymes required for lipid breakdown. They are classified either by the enzyme defect or by the type of lipid involved.	1.97	1
Cancer of Lung [description not available]	1.96	1
Lung Neoplasms Tumors or cancer of the LUNG.	1.96	1
Delayed Hypersensitivity [description not available]	1.97	1

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