Compounds > azinomycin b
Page last updated: 2024-11-12

azinomycin b

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Description

azinomycin B: C31H33N3O11; from Streptomyces griseofuscus S42227; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID14476972
CHEBI ID50862
SCHEMBL ID413073
SCHEMBL ID1369422
MeSH IDM0145485

Synonyms (21)

Synonym
nsc 20088
carzinophilin a
azinomycin b
1-naphthalenecarboxylic acid, 3-methoxy-5-methyl-, 2-((1-(3-(acetyloxy)-4-hydroxy-1-azabicyclo(3.1.0)hex-2-ylidene)-2-((1-(hydroxymethylene)-2-oxopropyl)amino)-2-oxoethyl)amino)-1-(2-methyloxiranyl)-2-oxoethyl ester
brn 5696947
carzinophyllin
(1s)-2-{[(1e)-1-[(3r,4r,5s)-3-(acetyloxy)-4-hydroxy-1-azabicyclo[3.1.0]hex-2-ylidene]-2-{[(1z)-1-(hydroxymethylidene)-2-oxopropyl]amino}-2-oxoethyl]amino}-1-[(2s)-2-methyloxiran-2-yl]-2-oxoethyl 3-methoxy-5-methylnaphthalene-1-carboxylate
CHEBI:50862
106486-76-4
unii-051r55x44c
1-naphthalenecarboxylic acid, 3-methoxy-5-methyl-, (1s)-2-(((1e)-1-((3r,4r,5s)-3-(acetyloxy)-4-hydroxy-1-azabicyclo(3.1.0)hex-2-ylidene)-2-(((1z)-1-(hydroxymethylene)-2-oxopropyl)amino)-2-oxoethyl)amino)-1-((2s)-2-methyloxiranyl)-2-oxoethyl ester
051r55x44c ,
1-naphthalenecarboxylic acid, 3-methoxy-5-methyl-, (1s)-2-[[(1e)-1-[(3r,4r,5s)-3-(acetyloxy)-4-hydroxy-1-azabicyclo[3.1.0]hex-2-ylidene]-2-[[(1z)-1-(hydroxymethylene)-2-oxopropyl]amino]-2-oxoethyl]amino]-1-[(2s)-2-methyloxiranyl]-2-oxoethyl ester
carzinophilin a [mi]
SCHEMBL413073
SCHEMBL1369422
DTXSID9040421
Q20164387
Q27236057
[(1s)-2-[[(1e)-1-[(3r,4r,5s)-3-acetyloxy-4-hydroxy-1-azabicyclo[3.1.0]hexan-2-ylidene]-2-[[(z)-1-hydroxy-3-oxobut-1-en-2-yl]amino]-2-oxoethyl]amino]-1-[(2s)-2-methyloxiran-2-yl]-2-oxoethyl] 3-methoxy-5-methylnaphthalene-1-carboxylate
[(1s)-2-[[(1e)-1-[(3r,4r,5s)-3-acetyloxy-4-hydroxy-1-azabicyclo[3.1.0]hexan-2-ylidene]-2-(1,3-dioxobutan-2-ylamino)-2-oxoethyl]amino]-1-[(2s)-2-methyloxiran-2-yl]-2-oxoethyl] 3-methoxy-5-methylnaphthalene-1-carboxylate

Research Excerpts

Overview

Azinomycin B is an environmental DNA crosslinking agent produced by the soil microorganism Streptomyces sahachiroi. It possesses antitumor activity by interacting covalently with duplex DNA and inducing interstrand crosslinks.

ExcerptReferenceRelevance
"Azinomycin B is a hybrid polyketide/nonribosomal peptide natural product and possesses antitumor activity by interacting covalently with duplex DNA and inducing interstrand crosslinks. "( Characterization of a novel DNA glycosylase from S. sahachiroi involved in the reduction and repair of azinomycin B induced DNA damage.
Feng, X; He, J; Lei, L; Li, A; Li, H; Li, S; Liu, K; Wang, S; Xiao, L; Yang, L; Zhang, F, 2016)		2.09
"Azinomycin B is a complex natural product containing densely assembled functionalities with potent antitumor activity. "( Characterization of the azinomycin B biosynthetic gene cluster revealing a different iterative type I polyketide synthase for naphthoate biosynthesis.
Deng, W; Ding, W; Fang, J; He, Q; Kang, Q; Liu, W; Tang, G; Tang, M; Yu, Y; Zhang, Q; Zhao, Q, 2008)		2.1
"Azinomycin B is a potent antitumor antibiotic that features a set of unusual, densely assembled functionalities. "( Biosynthesis of 3-methoxy-5-methyl naphthoic acid and its incorporation into the antitumor antibiotic azinomycin B.
Bi, Y; Deng, W; Ding, W; Liu, W; Tang, G; Tang, M; Zhang, Q, 2010)		2.02
"Azinomycin B is an environmental DNA crosslinking agent produced by the soil microorganism Streptomyces sahachiroi. "( An improved method for culturing Streptomyces sahachiroi: biosynthetic origin of the enol fragment of azinomycin B.
Kelly, GT; Sharma, V; Watanabe, CM, 2008)		2
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (32)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (9.38)18.7374
1990's0 (0.00)18.2507
2000's18 (56.25)29.6817
2010's10 (31.25)24.3611
2020's1 (3.13)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 35.83

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index35.83 (24.57)
Research Supply Index3.53 (2.92)
Research Growth Index5.00 (4.65)
Search Engine Demand Index45.55 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (35.83)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other33 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetone
methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).		2.0510ketone body;
methyl ketone;
propanones;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
human metabolite;
polar aprotic solvent
adenine
[no description available]		2.08106-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
aminoacetone
aminoacetone: RN given refers to parent cpd. aminoacetone : A propanone consisting of acetone having an amino group at the 1-position.		2.0510methyl ketone;
propanones		Escherichia coli metabolite;
mouse metabolite
naphthalene
[no description available]		2.0210naphthalenes;
ortho-fused bicyclic arene		apoptosis inhibitor;
carcinogenic agent;
environmental contaminant;
mouse metabolite;
plant metabolite;
volatile oil component
mechlorethamine
nitrogen mustard : Compounds having two beta-haloalkyl groups bound to a nitrogen atom, as in (X-CH2-CH2)2NR.		2.0210nitrogen mustard;
organochlorine compound		alkylating agent
mitomycin
Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.		1.9710mitomycinalkylating agent;
antineoplastic agent
1-naphthoic acid
naphthoic acid : An aromatic carboxylic acid that consists of a naphthalene skeleton substituted by one or more carboxy groups.		2.4520naphthoic acidbacterial xenobiotic metabolite;
fungal xenobiotic metabolite
daunorubicin
Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.		210aminoglycoside antibiotic;
anthracycline;
p-quinones;
tetracenequinones		antineoplastic agent;
bacterial metabolite
glutamic acid
Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.		2.1510glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
acetyl coenzyme a
Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.		2.1510acyl-CoAacyl donor;
coenzyme;
effector;
fundamental metabolite
azinomycin a
azinomycin A: from Streptomyces griseofuscus S42227; structure given in first source; (but Biochemistry. 2000 Dec 5;39(48):14968-75 says Azinomycin B = carzinophilin A)		4.1150
guanine
[no description available]		2.46202-aminopurines;
oxopurine;
purine nucleobase		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Breast Cancer
[description not available]		02.0110
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.0110
Carcinoma, Ehrlich Tumor
A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.		01.9710
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		01.9710
Cancer of Lung
[description not available]		01.9710
B16 Melanoma
[description not available]		01.9710
Experimental Neoplasms
[description not available]		01.9710
Mast-Cell Sarcoma
A unifocal malignant tumor that consists of atypical pathological MAST CELLS without systemic involvement. It causes local destructive growth in organs other than in skin or bone marrow.		01.9710
Fibrosarcoma
A sarcoma derived from deep fibrous tissue, characterized by bundles of immature proliferating fibroblasts with variable collagen formation, which tends to invade locally and metastasize by the bloodstream. (Stedman, 25th ed)		01.9710
Lung Neoplasms
Tumors or cancer of the LUNG.		01.9710
Leukemia L5178
An experimental lymphocytic leukemia of mice.		01.9610