doxorubicin (Q18936)

3,5,12-Trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxyhexopyranoside

doxorubicin (English)

17 November 2016

1 reference

1 reference

inferred from InChI

chemical formula

C₂₇H₂₉NO₁₁

1 reference

doxorubicin (English)

17 November 2016

canonical SMILES

CC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O

1 reference

doxorubicin (English)

17 November 2016

isomeric SMILES

C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O

1 reference

World Health Organisation international non-proprietary name

doxorubicin (English)

17 November 2016

1 reference

14 February 2018

doxorubicin (English)

1 reference

doxorubicin (English)

19 October 2016

found in taxon

Streptomyces peucetius

34 references

Characterization of the Streptomyces peucetius ATCC 29050 genes encoding doxorubicin polyketide synthase

Expression of doxorubicin-daunorubicin resistance genes in different anthracycline-producing mutants of Streptomyces peucetius

Identification and characterization of the afsR homologue regulatory gene from Streptomyces peucetius ATCC 27952.

A bacterial analog of the mdr gene of mammalian tumor cells is present in Streptomyces peucetius, the producer of daunorubicin and doxorubicin

Exploration of geosmin synthase from Streptomyces peucetius ATCC 27952 by deletion of doxorubicin biosynthetic gene cluster

Enhancement of doxorubicin production by expression of structural sugar biosynthesis and glycosyltransferase genes in Streptomyces peucetius.

Self-resistance mechanism in Streptomyces peucetius: overexpression of drrA, drrB and drrC for doxorubicin enhancement

Isolation and genetic manipulation of the antibiotic down-regulatory gene, wblA ortholog for doxorubicin-producing Streptomyces strain improvement

Superoxide dismutase (SOD) genes in Streptomyces peucetius: effects of SODs on secondary metabolites production.

Enhancing macrolide production in Streptomyces by coexpressing three heterologous genes.

Exploration of two epimerase homologs in Streptomyces peucetius ATCC 27952.

The DrrAB efflux system of Streptomyces peucetius is a multidrug transporter of broad substrate specificity

Switching antibiotics production on and off in actinomycetes by an IclR family transcriptional regulator from Streptomyces peucetius ATCC 27952.

One-Pot Combinatorial Biosynthesis of Glycosylated Anthracyclines by Cocultivation of Streptomyces Strains Producing Aglycones and Nucleotide Deoxysugars

Complete genome sequence of Streptomyces peucetius ATCC 27952, the producer of anticancer anthracyclines and diverse secondary metabolites

Implication of orphan histidine kinase (OhkAsp) in biosynthesis of doxorubicin and daunorubicin in Streptomyces peucetius ATCC 27952

Isolation and characterization of a gene from Streptomyces sp. strain C5 that confers the ability to convert daunomycin to doxorubicin on Streptomyces lividans TK24

Expression and characterization of DrrA and DrrB proteins of Streptomyces peucetius in Escherichia coli: DrrA is an ATP binding protein

Minimal Streptomyces sp. strain C5 daunorubicin polyketide biosynthesis genes required for aklanonic acid biosynthesis

Production of the antitumor drug epirubicin (4'-epidoxorubicin) and its precursor by a genetically engineered strain of Streptomyces peucetius

The Streptomyces peucetius dpsY anddnrX Genes Govern Early and Late Steps of Daunorubicin and Doxorubicin Biosynthesis

Purification, properties, and characterization of recombinant Streptomyces sp. strain C5 DoxA, a cytochrome P-450 catalyzing multiple steps in doxorubicin biosynthesis

Doxorubicin overproduction in Streptomyces peucetius: cloning and characterization of the dnrU ketoreductase and dnrV genes and the doxA cytochrome P-450 hydroxylase gene

Glucose kinases from Streptomyces peucetius var. caesius.

NdgR, an IclR-like regulator involved in amino-acid-dependent growth, quorum sensing, and antibiotic production in Streptomyces coelicolor

Precursor for biosynthesis of sugar moiety of doxorubicin depends on rhamnose biosynthetic pathway in Streptomyces peucetius ATCC 27952.

Identification of the duplicated genes for S-adenosyl-l-methionine synthetase (metK1-sp and metK2-sp) in Streptomyces peucetius var. caesius ATCC 27952.

Improvement in doxorubicin productivity by overexpression of regulatory genes in Streptomyces peucetius

Enhanced doxorubicin production by Streptomyces peucetius using a combination of classical strain mutation and medium optimization

The Streptomyces peucetius drrC gene encodes a UvrA-like protein involved in daunorubicin resistance and production

Interspecies DNA microarray analysis identifies WblA as a pleiotropic down-regulator of antibiotic biosynthesis in Streptomyces

Genome analyses of Streptomyces peucetius ATCC 27952 for the identification and comparison of cytochrome P450 complement with other Streptomyces

Limitations in doxorubicin production from Streptomyces peucetius

Isolation and characterization of stable mutants of Streptomyces peucetius defective in daunorubicin biosynthesis

Actinoallomurus

1 reference

Halogenated Spirotetronates from Actinoallomurus

Escherichia coli

1 reference

A comprehensive genome-scale reconstruction of Escherichia coli metabolism--2011.

Ixora coccinea

1 reference

Ixorapeptide I and ixorapeptide II, bioactive peptides isolated from Ixora coccinea

Dracocephalum kotschyi

1 reference

Xanthomicrol is the main cytotoxic component of Dracocephalum kotschyii and a potential anti-cancer agent

Xylopia laevigata

1 reference

Cytotoxic Alkaloids from the Stem of Xylopia laevigata.

Beta vulgaris

1 reference

Antioxidant and cell growth activities of beet root pomace extracts

Streptomyces venezuelae

1 reference

Development of a Streptomyces venezuelae-based combinatorial biosynthetic system for the production of glycosylated derivatives of doxorubicin and its biosynthetic intermediates

Penicillium variabile

2 references

Varitatin A, a Highly Modified Fatty Acid Amide from Penicillium variabile Cultured with a DNA Methyltransferase Inhibitor

Inducing Secondary Metabolite Production by Combined Culture of Talaromyces aculeatus and Penicillium variabile.

Annona muricata

3 references

Additional bioactive acetogenins, annomutacin and (2,4-trans and cis)-10R-annonacin-A-ones, from the leaves of Annona muricata

New cytotoxic monotetrahydrofuran annonaceous acetogenins from Annona muricata

Two New Cytotoxic Monotetrahydrofuran Annonaceous Acetogenins, Annomuricins A and B, from the Leaves of Annona muricata

Xylopia aromatica

1 reference

Bioactive annonaceous acetogenins from the bark of Xylopia aromatica

Peniophora incarnata

1 reference

Cytotoxic Xanthone Derivatives from the Mangrove-Derived Endophytic Fungus Peniophora incarnata Z4

Ophioparma ventosa

1 reference

Minor Pyranonaphthoquinones from the Apothecia of the Lichen Ophioparma ventosa

Moorea producens

1 reference

Cytotoxic Microcolin Lipopeptides from the Marine Cyanobacterium Moorea producens

Streptomyces atratus

1 reference

Antitubercular Ilamycins from Marine-Derived Streptomyces atratus SCSIO ZH16 ΔilaR

Annona senegalensis

1 reference

Bioactive ent-kaurene diterpenoids from Annona senegalensis

Pestalotiopsis palmarum

1 reference

Sinopestalotiollides A-D, cytotoxic diphenyl ether derivatives from plant endophytic fungus Pestalotiopsis palmarum

Viola abyssinica

1 reference

Cyclotides from an extreme habitat: characterization of cyclic peptides from Viola abyssinica of the Ethiopian highlands

Eurycoma longifolia

2 references

Quassinoids from Eurycoma longifolia

Quassinoids from Eurycoma longifolia

Ochrolechia parella

1 reference

Metabolites from the LichenOchrolechia parellaGrowing under Two Different Heliotropic Conditions⊥

Trichodesmium thiebautii

1 reference

Isolation of Isotrichophycin C and Trichophycins G-I from a Collection of Trichodesmium thiebautii

Oscillatoria thiebautii

1 reference

Isolation of Isotrichophycin C and Trichophycins G-I from a Collection of Trichodesmium thiebautii

Zinnia grandiflora

1 reference

Zinagrandinolides A-C, cytotoxic delta-elemanolide-type sesquiterpene lactones from Zinnia grandiflora

Macrohyporia cocos

1 reference

Cytotoxic Lanostanoids from Poria cocos

Wolfiporia cocos

1 reference

Cytotoxic Lanostanoids from Poria cocos

Ipomoea nil

1 reference

Diterpene glycosides from the seeds of Pharbitis nil.

Aspergillus sclerotiorum

1 reference

Lovastatin Analogues from the Soil-Derived Fungus Aspergillus sclerotiorum PSU-RSPG178.

Laurencia tristicha

1 reference

Halogenated Sesquiterpenoids from the Red Alga Laurencia tristicha Collected in Taiwan.

Annona cherimolia

1 reference

Annomolin and annocherimolin, new cytotoxic annonaceous acetogenins from Annona cherimolia seeds

Annona cherimola

1 reference

Annomolin and annocherimolin, new cytotoxic annonaceous acetogenins from Annona cherimolia seeds

Penicillium brocae

1 reference

Brocazines A-F, Cytotoxic Bisthiodiketopiperazine Derivatives from Penicillium brocae MA-231, an Endophytic Fungus Derived from the Marine Mangrove Plant Avicennia marina

Quambalaria cyanescens

1 reference

Quambalarine B, a Secondary Metabolite from Quambalaria cyanescens with Potential Anticancer Properties.

Schisandra chinensis

1 reference

Identification of key structural characteristics of Schisandra chinensis lignans involved in P-glycoprotein inhibition.

Cordyceps farinosa

1 reference

Paecilosetin Derivatives as Potent Antimicrobial Agents from Isaria farinosa

Hamigera fusca

1 reference

Non-geminal Aliphatic Dihalogenation Pattern in Dichlorinated Diaporthins from Hamigera fusca NRRL 35721

Fusarium oxysporum

1 reference

Search for cell motility and angiogenesis inhibitors with potential anticancer activity: beauvericin and other constituents of two endophytic strains of Fusarium oxysporum

Trichoderma cornu-damae

1 reference

Macrocyclic Trichothecene Mycotoxins from a Deadly Poisonous Mushroom, Podostroma cornu-damae

Talaromyces aculeatus

1 reference

Inducing Secondary Metabolite Production by Combined Culture of Talaromyces aculeatus and Penicillium variabile.

Annona mucosa

1 reference

A novel constituent from Rollinia mucosa, rollicosin, and a new approach to develop annonaceous acetogenins as potential antitumor agents

Fusarium solani

1 reference

Cytotoxic Naphthoquinone and Azaanthraquinone Derivatives from an Endophytic Fusarium solani

Alstonia macrophylla

1 reference

Alstoniaphyllines A-C, unusual nitrogenous derivatives from the bark of Alstonia macrophylla

Streptomyces violascens

1 reference

Violapyrones A-G, α-pyrone derivatives from Streptomyces violascens isolated from Hylobates hoolock feces

Streptomyces

6 references

Meliponamycins: Antimicrobials from Stingless Bee-Associated Streptomyces sp

Cytotoxic Dibohemamines D-F from a Streptomyces Species.

Polyketides and Anthranilic Acid Possessing 6-Deoxy-α-l-talopyranose from a Streptomyces Species.

Komodoquinone A, a Novel Neuritogenic Anthracycline, from Marine Streptomyces sp. KS3

Cytotoxic Bagremycins from Mangrove-Derived Streptomyces sp. Q22.

Bioactive Streptoglutarimides A-J from the Marine-Derived Streptomyces sp. ZZ741

Teratosphaeria

1 reference

Cytotoxic and Noncytotoxic Metabolites from Teratosphaeria sp. FL2137, a Fungus Associated with Pinus clausa.

Penicillium

1 reference

Condensation of Macrocyclic Polyketides Produced by Penicillium sp. DRF2 with Mercaptopyruvate Represents a New Fungal Detoxification Pathway

Dothiora

1 reference

Hormonemate Derivatives from Dothiora sp., an Endophytic Fungus.

Actinoalloteichus

1 reference

Bioactive Alkaloids from the Actinomycete Actinoalloteichus sp. ZZ1866

Alternaria

1 reference

Chlorinated Dehydrocurvularins and Alterperylenepoxide A from Alternaria sp. AST0039, a Fungal Endophyte of Astragalus lentiginosus

Verrucosispora

1 reference

Cytotoxic Kendomycins Containing the Carbacylic Ansa Scaffold from the Marine-Derived Verrucosispora sp. SCSIO 07399

Myrothecium

1 reference

Cytotoxic and Antibacterial Quinone Sesquiterpenes from a Myrothecium Fungus

Nocardiopsis

1 reference

Cytotoxic p-Terphenyls from a Marine-Derived Nocardiopsis Species

Dendrodochium

1 reference

Polyhydroxy Cyclohexanols from a Dendrodochium sp. Fungus Associated with the Sea Cucumber Holothuria nobilis Selenka

Chrysosporium

1 reference

Chrysosporazines F-M: P-Glycoprotein Inhibitory Phenylpropanoid Piperazines from an Australian Marine Fish Derived Fungus, Chrysosporium sp. CMB-F294

Oscillatoria

1 reference

Ikoamide, an Antimalarial Lipopeptide from an Okeania sp. Marine Cyanobacterium

Okeania

1 reference

Ikoamide, an Antimalarial Lipopeptide from an Okeania sp. Marine Cyanobacterium

medical condition treated

1 reference

13 December 2016

1 reference

13 December 2016

1 reference

neuroblastoma, susceptibility to

13 December 2016

1 reference

2 October 2018

hepatoblastoma

1 reference

transitional cell carcinoma

2 October 2018

1 reference

2 October 2018

plasmablastic lymphoma

1 reference

mature T-cell and NK-cell lymphoma

2 October 2018

1 reference

2 October 2018

mantle cell lymphoma

1 reference

2 October 2018

T-cell lymphoma

1 reference

precursor T-cell lymphoblastic leukemia

2 October 2018

1 reference

chronic lymphocytic leukemia

2 October 2018

1 reference

2 October 2018

acute myeloid leukemia

1 reference

invasive ductal carcinoma

2 October 2018

1 reference

precursor T-cell acute lymphoblastic leukemia

2 October 2018

1 reference

2 October 2018

non-Hodgkin lymphoma

1 reference

primary mediastinal B-cell lymphoma

2 October 2018

1 reference

2 October 2018

bone sarcoma

1 reference

post-transplant lymphoproliferative disorder

2 October 2018

1 reference

2 October 2018

lymphoma

1 reference

2 October 2018

hematologic cancer

1 reference

2 October 2018

B-cell lymphoma

1 reference

diffuse large B-cell lymphoma

2 October 2018

1 reference

low-grade serous carcinoma

2 October 2018

0 references

physically interacts with

DNA topoisomerase II alpha

subject has role

enzyme inhibitor

1 reference

IUPHAR/BPS Guide to PHARMACOLOGY

Guide to Pharmacology Ligand ID

7069

DNA topoisomerase II alpha

17 August 2016

subject has role

reaction inhibitor

1 reference

Open Targets Platform

https://platform.opentargets.org/drug/CHEMBL53463

14 August 2023

reference URL

pregnancy category

Australian pregnancy category D

1 reference

imported from Wikimedia project

English Wikipedia

US pregnancy category D

1 reference

imported from Wikimedia project

English Wikipedia

subject has role

DNA polymerase inhibitors

1 reference

5 March 2018

topoisomerase inhibitor

1 reference

5 March 2018

antineoplastic antibiotics

1 reference

Medical Subject Headings

MeSH descriptor ID

D004317

topoisomerase II inhibitor

15 March 2018

1 reference

Food and Drug Administration

Medical Subject Headings

15 March 2018

0 references

anthracycline antibiotic

1 reference

27 February 2018

DOXOrubicin

subject named as

Doxorubicin

1 reference

reference URL

https://www.fda.gov/drugs/medication-errors-related-cder-regulated-drug-products/fda-name-differentiation-project

imported from Wikimedia project

2 September 2022

Commons category

Doxorubicin

0 references

Identifiers

GND ID

4150505-0

1 reference

1 reference

National Library of Israel Names and Subjects Authority File

Library of Congress authority ID

sh85001015

subject named as

Doxorubicin

1 reference

Integrated Authority File

InChI

InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1

1 reference

doxorubicin (English)

17 November 2016

2 references

doxorubicin (English)

17 November 2016

ChEBI release 2020-09-01

CAS Registry Number

23214-92-8

2 references

doxorubicin (English)

17 November 2016

https://commonchemistry.cas.org/detail?cas_rn=23214-92-8

8 April 2021

1 reference

Doxorubicin (English)

17 November 2016

2 references

doxorubicin (English)

17 November 2016

ChEBI ID

28748

mapping relation type

3 references

DOXORUBICIN (English)

17 November 2016

ChEBI release 2019-10-02

International Chemical Identifier

InChI

InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1

1 reference

DOXORUBICIN (English)

17 November 2016

2 references

inferred from InChIKey

Hazardous Substances Data Bank

1 reference

1 reference

28 October 2019

DOXORUBICIN (English)

10 May 2021

2 references

Mapping file of InChIStrings, InChIKeys and DTXSIDs for the EPA CompTox Dashboard

DSSTOX compound identifier

0 references

0 references

1 reference

doxorubicin (English)

ECHA Substance Infocard ID

17 November 2016

100.041.344

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

100.041.344

27 December 2018

Doxorubicin (English)

quotation

CAS no.: 23214-92-8 (English)

1 reference

Guide to Pharmacology Ligand ID

Doxorubicin (English)

publication date

17 November 2015

7069

1 reference

IUPHAR/BPS Guide to PHARMACOLOGY

Guide to Pharmacology Ligand ID

7069

D02.455.426.559.847.562.050.200.175

doxorubicin (English)

17 November 2016

Doxorubicin

0 references

MeSH concept ID

M0006784

0 references

MeSH tree code

0 references

D04.615.562.050.200.175

0 references

D09.408.051.059.200.175

0 references

RxNorm ID

3639

1 reference

doxorubicin (English)

17 November 2016

DrugBank ID

DB00997

1 reference

Human Metabolome Database ID

HMDB0015132

2 references

inferred from InChIKey

KNApSAcK ID

C00053046

2 references

inferred from InChIKey

2 references

doxorubicin (English)

17 November 2016

MedlinePlus drug identifier

0 references

1 reference

doxorubicin (English)

17 November 2016

0 references

1 reference

1 reference

electronic Essential Medicines List medicine ID

doxorubicin (English)

19 October 2016

0 references

0 references

0 references

87

0 references

Encyclopædia Britannica Online ID

science/doxorubicin

subject named as

doxorubicin

0 references

1 reference

28 October 2013

1 reference

9 July 2020

Microsoft Academic ID

0 references

0 references

0 references

1 reference

26 January 2022

https://docs.openalex.org/download-snapshot/snapshot-data-format

1 reference

26 January 2022

https://docs.openalex.org/download-snapshot/snapshot-data-format

1 reference

1D12 (English)

19 October 2016

1 reference

1I1E (English)

19 October 2016

1 reference

4DX7 (English)

19 October 2016

1 reference

1P20 (English)

19 October 2016

1 reference

2DR6 (English)

19 October 2016

1 reference

4ZVM (English)

19 October 2016

1 reference

151D (English)

19 October 2016

1 reference

1DA9 (English)

19 October 2016

0 references

1 reference

doxorubicin (English)

17 November 2016

C0699076

1 reference

inferred by common MeSH mappings on source and on Wikidata

25 May 2023

0 references

WordNet 3.1 Synset ID

03234852-n

1 reference