Adriamycin aglycone
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Basic information
- CAS
24385-10-2- Standard SMILES
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O- InChIKey
IBZGBXXTIGCACK-CWKPULSASA-N- Molecular formula
- C21H18O9
- Average molar mass
- 414.4 g/mol
- Monoisotopic mass
- 414.09508215
Names & identifiers
- Preferred name
- Adriamycin aglycone
- IUPAC
- (7S,9S)-6,7,9,11-tetrahydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
- English name
- Doxorubicinone
- Molecular formula
- C21H18O9
- Molecular weight
- 414.36
Names & synonyms
DoxorubicinoneAdriamycinone24385-10-2Adriamycin aglyconeDoxorubicin aglyconeX023T6C35L5,12-Naphthacenedione, 7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-DTXSID70875303(7S,9S)-9-glycoloyl-6,7,9,11-tetrahydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-quinoneRefChem:109840DTXCID701772330(7S,9S)-6,7,9,11-tetrahydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
Show more names
D2-N-Nitroso desmethyldoxycyclineadriamycinaglyconeEpirubicin aglyconEpirubicin aglyconeDoxorubicinone-13C-D3Epirubicin Hydrochloride Impurity A
(8S,10S)-6,8,10,11-tetrahydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione(8S,10S)-6,8,10,11-tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dioneCCRIS 7633AdriamycinonUNII-X023T6C35L(8S,10S)-6,8,10,11-Tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydronaphthacene-5,12-dione (Doxorubicin Aglycone, Doxorubicinone)C21H18O9Doxorubicinone; (8S,10S)-6,8,10,11-Tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione; Doxorubicin Hydrochloride Impurity D; Epirubicin Hydrochloride Impurity A; Doxorubicin Impurity D; Epirubicin Impurity A
Database identifiers
- CAS
24385-10-2- PubChem CID
- 72401
- DTXSID
DTXSID70875303- ChEMBL
CHEMBL3544660- ChEBI
CHEBI:165223- UNII
- X023T6C35L
- EC Number
- 685-488-9
- Nikkaji
- J16.717G
Properties
Computed structural propertiesFilling in
- XLogP
- 1.6
- Topological polar surface area
- 162 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 3
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 738
Physicochemical properties
- Melting point
- 223 · 223-225°C
- Boiling point
- 741.2 · 741.2±60.0 °C(Predicted)
- Density
- 1.671 · 1.671±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Amber Vial, -20°C Freezer
- solubility
- Dioxane (Slightly), DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 7.45 · 7.45±0.60(Predicted)
- color
- Red to Very Dark Red
- Stability
- Light Sensitive
- Major Application
- pharmaceutical (small molecule)
- InChI
- InChI=1S/C21H18O9/c1-30-11-4-2-3-8-14(11)20(28)16-15(17(8)25)18(26)9-5-21(29,12(24)7-22)6-10(23)13(9)19(16)27/h2-4,10,22-23,26-27,29H,5-7H2,1H3/t10-,21-/m0/s1
- InChIKey
- IBZGBXXTIGCACK-CWKPULSASA-N
- SMILES
- C1(OC)=C2C(C(=O)C3=C(C2=O)C(O)=C2C(C[C@@](O)(C(CO)=O)C[C@@H]2O)=C3O)=CC=C1
- CAS DataBase Reference
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]；H311 (100%): Toxic in contact with skin [Danger Acute toxicity, dermal]；H331 (100%): Toxic if inhaled [Danger Acute toxicity, inhalation]；H340 (100%): May cause genetic defects [Danger Germ cell mutagenicity]；H350 (100%): May cause cancer [Danger Carcinogenicity]；H360 (100%): May damage fertility or the unborn child [Danger Reproductive toxicity]
P203, P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P318, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Regulatory Information
5,12-Naphthacenedione, 7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 3 (100%)；Acute Tox. 3 (100%)；Acute Tox. 3 (100%)；Muta. 1B (100%)；Carc. 1B (100%)；Repr. 1B (100%)
Regulatory information
Regulatory Information
5,12-Naphthacenedione, 7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Safety data
Chemistry & industry
Applications
DescriptionDoxorubicinone is a metabolite of the anthracycline antitumor antibiotic doxorubicin . Doxorubicinone inhibits mitochondrial succinoxidase from bovine heart and reduces the mitochondrial inner membrane potential in rat heart and liver mitochondria in a concentration-dependent manner. Doxorubicinone (40 μM) increases pentose phosphate pathway flux by 45% and reduces activity of glutathione peroxidase (GPx) and superoxide dismutase (SOD) by 17 and 60%, respectively, in human erythrocytes. It also induces cytotoxicity in patient-derived ovarian cancer colonies in a concentration-dependent manner.
UsesA metabolite of Doxorubicin (Dx).
General DescriptionDoxorubicinone (adriamycinone) is an aglycone. It is a metabolite of adriamycin converted in the body, and another metabolite is amycinol [1]. Adriamycin nephropathy (AN) is a rodent model of chronic kidney disease. AN is characterized by podocyte injury followed by glomerulosclerosis, tubulointerstitial inflammation and fibrosis.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: Adriamycinone is a member of tetracenes and a quinone.
Related reactions
2 records
Compound notes
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