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Ungeremine

HCID 159646
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Basic information

CAS
2121-12-2
Standard SMILES
Oc1cc2c3c(c1)c1cc4c(cc1c[n+]3CC2)OCO4
InChIKey
DFQOXFIPAAMFAU-UHFFFAOYSA-O
Molecular formula
C16H12NO3+
Average molar mass
266.276 g/mol
Monoisotopic mass
266.08116966

Names & identifiers

Preferred name
Ungeremine
IUPAC
2-Hydroxy-4,5-dihydro-10H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-6-ium
English name
ungeremine
Molecular formula
C16H12NO3
Molecular weight
266.275

Names & synonyms

C12189ungeremineUngerimineLycobetaine(Ungeremine)[1,3]Dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridinium, 4,5-dihydro-2-hydroxy-

Database identifiers

CAS
2121-12-2
PubChem CID
159646
DTXSID
DTXSID50175439
ChEMBL
CHEMBL253553、CHEMBL479291
UNII
9EVC5B2RPS

Properties

Physicochemical properties

Melting point
270 · 270-272℃ (dec.)
Boiling point
409.48 °C · 409.48°C (rough estimate)
Density
1.1727 · 1.1727 (rough estimate)
refractive index
1.53 · 1.5300 (estimate)
storage temp.
-20 °C · -20°C
solubility
10 mg/ml · Methanol: 10 mg/ml
form
A solid
FDA UNII
9 EVC5B2RPS · 9EVC5B2RPS

Chemistry & industry

Applications · 1 item

DescriptionUngeremine is a betaine-type alkaloid that has been found in C. zeylanicum and has diverse biological activities.1,2,3,4 It is an inhibitor of acetylcholinesterase (AChE; IC50 = 0.35 µM).2 Ungeremine acts as a topoisomerase poison, inducing double-strand breaks in DNA by stabilizing the linkage between topoisomerase IIβ and DNA.3 It inhibits the relaxation of supercoiled DNA by human topoisomerase I and -IIα and E. coli topoisomerase I and -IV (IC50s = 6.1, 25.8, 15, and 7.3 µM, respectively).4 Ungeremine inhibits the growth of HL-60, MOLT-4, K562, U937, and LXFL 529L cells (IC50s = 1.3, 0.7, 0.8, 2.5, and 1.2 µM, respectively). It is cytotoxic to a variety of drug-sensitive and -resistant cancer cells (IC50s = 4.89-6.45 and 3.67-75.24 µM, respectively) and induces ferroptosis, necroptosis, apoptosis, and autophagy in CCRF-CEM leukemia cells. Ungeremine (60 mg/kg twice per week) also reduces tumor growth in a GXF251L mouse xenograft model.3WARNING This product is not for human or veterinary use.

Suppliers9 total

成都普睿法药物研发有限公司82633860 18982077548 · [email protected]
上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
成都普瑞法科技开发有限公司+86-28-82633860; +86-18080483897 · [email protected]
四川恒诚致远生物科技有限公司18113192475 18113192475 · [email protected]

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
青岛浩海安杰医药科技有限公司
156-6622-8711 18639325623 · [email protected]
BOC Sciences+1-631-485-4226 · [email protected]

Additional notes

DefinitionChEBI: A natural product found particularly in Pancratium maritimum and Nerine bowdenii.