ChemSpider 2D Image | Doxorubicin | C27H29NO11

Doxorubicin

  • Molecular FormulaC27H29NO11
  • Average mass543.519 Da
  • Monoisotopic mass543.174072 Da
  • ChemSpider ID29400

  • defined stereocentres - 6 of 6 defined stereocentres

More details:

Featured data source
The Merck Index Online

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

Doxorubicin [BAN] [INN] [USAN] [Wiki]
(1S,3S)-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-trideoxy-α-L-lyxo-hexopyranoside
(1S,3S)-3-Glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside [ACD/IUPAC Name]
(1S,3S)-3-Glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl-3-amino-2,3,6-tridesoxy-α-L-lyxo-hexopyranosid [German] [ACD/IUPAC Name]
(1S,3S)-3-Glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside
(8S,10S)-10-[(3-Amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
(8S,10S)-10-{[(2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-8-glycoloyl-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-tetracenedione
(8S-cis)-10-[(3-Amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
23214-92-8 [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

3005 [DBID]
80168379AG [DBID]
25316-40-9 (FREE BASE) [DBID]
AIDS000122 [DBID]
AIDS-000122 [DBID]
BPBio1_000502 [DBID]
BSPBio_000456 [DBID]
BSPBio_001031 [DBID]
C01661 [DBID]
CCRIS 739 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Amine; Ether; Ester; Drug; Antineoplastic Agent; Antibiotic; Antibiotic, Antineoplastic; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D2953

    • Safety:

      L01DB01 Wikidata Q18936

    • Target Organs:

      Topoisomerase inhibitor TargetMol T1456

    • Bio Activity:

      ADCs cytotoxin MedChem Express HY-15142A
      ADCs cytotoxin Topoisomerase MedChem Express HY-15142A
      Antibody-drug conjugates/ADCs Related MedChem Express HY-15142A
      Antibody-drug conjugates/ADCs Related; Cell Cycle/DNA Damage; MedChem Express HY-15142A
      DNA Damage/DNA Repair TargetMol T1456
      Doxorubicin(Adriamycin) is an antibiotic agent that inhibits DNA topoisomerase II and induces DNA damage and apoptosis. MedChem Express
      Doxorubicin(Adriamycin) is an antibiotic agent that inhibits DNA topoisomerase II and induces DNA damage and apoptosis.; IC50 Value:; Target: Topo II; ADCs Toxin; in vitro: Doxorubicin can block the synthesis of DNA by intercalating into the DNA strand, and inhibits DNA topoisomerase II (TOP2). MedChem Express HY-15142A
      Doxorubicin(Adriamycin) is an antibiotic agent that inhibits DNA topoisomerase II and induces DNA damage and apoptosis.;IC50 Value:;Target: Topo II; ADCs Toxin;In vitro: Doxorubicin can block the synthesis of DNA by intercalating into the DNA strand, and inhibits DNA topoisomerase II (TOP2). Doxorubicin is most effective when cells are rapidly proliferating and expressing high levels of TOP2. Additionally, Doxorubicin can trigger apoptosis by producing ceramide (which prompts apoptosis by activating p53 or other downstream pathways such as JNK), the degradation of Akt by serine threonine proteases, the mitochondrial release of cytochrome c, increased FasL (death receptor Fas/CD95 ligand) mRNA production, and a greater production of free radicals. Doxorubicin induced G2/M checkpoint arrest are attributed to elevated cyclin G2 (CycG2) expression and phospho-modification of proteins in the ataxia telangiectasia mutated (ATM) and ATM and Rad3-related (ATR) signaling pathways. Doxorubic MedChem Express HY-15142A
      Topoisomerase TargetMol T1456

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.6±0.1 g/cm3
Boiling Point: 810.3±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.0 mmHg at 25°C
Enthalpy of Vaporization: 123.5±3.0 kJ/mol
Flash Point: 443.8±34.3 °C
Index of Refraction: 1.710
Molar Refractivity: 131.5±0.4 cm3
#H bond acceptors: 12
#H bond donors: 7
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 3
ACD/LogP: 2.82
ACD/LogD (pH 5.5): -1.89
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -0.79
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.48
Polar Surface Area: 206 Å2
Polarizability: 52.1±0.5 10-24cm3
Surface Tension: 96.4±5.0 dyne/cm
Molar Volume: 336.6±5.0 cm3

Click to predict properties on the Chemicalize site


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