Basic information
- CAS
108852-90-0- Standard SMILES
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N2CCO[C@H](OC)C2)[C@H](O)[C@H](C)O1- InChIKey
CTMCWCONSULRHO-UHQPFXKFSA-N- Molecular formula
- C32H37NO13
- Average molar mass
- 643.6 g/mol
- Monoisotopic mass
- 643.22649023
Overview
Nemorubicin is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone, a member of morpholines and an anthracycline antibiotic. It is functionally related to a doxorubicin.
Names & identifiers
- Preferred name
- Nemorubicin
- IUPAC
- (7S,9S)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7-[(2R,4S,5S,6S)-5-hydroxy-4-[(2S)-2-methoxymorpholin-4-yl]-6-methyloxan-2-yl]oxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
- English name
- Nemorubicin
- Molecular formula
- C32H37NO13
- Molecular weight
- 643.64
Names & synonyms
Nemorubicin108852-90-0Methoxymorpholino-doxorubicinMethoxymorpholinyl doxorubicinnemorubicinanemorubicineCHEBI:420537618O47BQM(1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2,3,6-trideoxy-3-[(2S)-2-methoxymorpholin-4-yl]-alpha-L-lyxo-hexopyranoside(1S,3S)-3-Glycoloyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl 2,3,6-trideoxy-3-((S)-2-methoxymorpholino)-alpha-L-lyxo-hexopyranosideDTXSID6057619nemorubicinum
Show more names
MMRDXDMM DoxFCE 23762PNU 152243PNU-152243ANeMorubincine-DichlorobenzophenoneNemorubicin (PNU 152243)
(1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2,3,6-trideoxy-3-((2S)-2-methoxymorpholin-4-yl)-alpha-L-lyxo-hexopyranosideRefChem:165053DTXCID301508600Nemorubicin [INN]FCE-23762Nemorubicin (GMP)MFCD008710793'-DESAMINO-3'-(2-METHOXY-4-MORPHOLINYL)-DOXORUBICIN
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 202 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 7
- Heavy atoms
- 46
- Formal charge
- 0
- Complexity
- 1,160
Physicochemical properties
- Boiling point
- 852.2 · 852.2±65.0 °C(Predicted)
- Density
- 1.55 · 1.55±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 60 · DMSO:60.0(Max Conc. mg/mL);101.0(Max Conc. mM)
- pka
- 7.35 · 7.35±0.60(Predicted)
- form
- Powder
- color
- Orange to reddish brown
- InChIKey
- CTMCWCONSULRHO-UZGLGGDGNA-N
- SMILES
- C12C[C@@](C[C@]([H])(O[C@@H]3O[C@H]([C@@H](O)[C@@H](N4CCO[C@H](OC)C4)C3)C)C=1C(O)=C1C(=O)C3=C(OC)C=CC=C3C(=O)C1=C2O)(O)C(=O)CO |&1:2,4,7,9,10,12,17,r|
- FDA UNII
- 7618 O47BQM · 7618O47BQM
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
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
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+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-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-10-2,3,6-trideoxy-3-(2S)-2-methoxy-4-morpholinyl-.alpha.-L-lyxo-hexopyranosyloxy-, (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 CategoriesSkin Irrit. 2 (100%)
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
UsesNemorubicin is a doxorubicin derivative that differs significantly from its parent drug in terms of spectrum of antitumor activity, metabolism and toxicity profile. The drug is active on tumors resistant to alkylating agents, topoisomerase II inhibitors and platinum derivatives. It works primarily through topoisomerase I inhibition. Of note, Nemorubicin is active in cells with upregulation of the nucleotide excision repair (NER) pathway, where current therapies fail. Nemorubicin is biotransformed in the liver into cytotoxic metabolites that may further contribute to render this drug highly active against primary liver tumors or liver metastases.
Suppliers75 total
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
上海哲研生物科技有限公司021-18017610038 18017610038 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
江苏艾康生物医药研发有限公司025-66061636 19370895928 · [email protected]
湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]
Aladdin Scientific[email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
江西瑞威尔生物科技有限公司18502728206 · [email protected]
上海波以尔化工有限公司[email protected]
欧利希（湖北）医药科技有限公司
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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