Cadambine

Catalog Number	ACM54422490
CAS Number	54422-49-0
Synonyms	(20α)-16,17-Didehydro-3β,21β-epoxy-19α-(β-D-glucopyranosyloxy)-21a-homo-18-oxayohimban-16-carboxylic acid methyl ester
Molecular Weight	544.5
InChI	InChI=1S/C27H32N2O10/c1-35-24(34)15-11-36-25(38-26-22(33)21(32)20(31)18(10-30)37-26)19-14(15)8-27-23-13(6-7-29(27)9-17(19)39-27)12-4-2-3-5-16(12)28-23/h2-5,11,14,17-22,25-26,28,30-33H,6-10H2,1H3/t14,17,18-,19?,20-,21+,22-,25,26+,27-/m0/s1
InChI Key	OVRROYYXOBYCSR-JPXAJPAESA-N
Melting Point	207-211 °C
Purity	95%+
Complexity	998
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	6
Exact Mass	544.20569522
Heavy Atom Count	39
Hydrogen Bond Acceptor Count	11
Hydrogen Bond Donor Count	5
Isomeric SMILES	COC(=O)C1=COC(C2C1C[C@]34C5=C(CCN3CC2O4)C6=CC=CC=C6N5)O[C@@H]7[C@H]([C@@H]([C@H]([C@@H](O7)CO)O)O)O
Monoisotopic Mass	544.20569522
PhysicalState	Powder
Rotatable Bond Count	5
Topological Polar Surface Area	163 Ų

Case Study

Potent DNA Topoisomerase IB Inhibitory Activity of Cadambine

Kumar, Ashish, et al. Natural Product Communications, 2015, 10(2), 1934578X1501000221.

Four alkaloids have been isolated from the stem bark of Anthocephalus cadamba, including anthocephaline(1), strictosamide(2), vincosamide(3) and cadambine(4). Among them, the plasmid relaxation test results showed that cadambine exhibited effective DNA topoisomerase IB inhibitory activity, and the inhibitory effect of the compound increased in a dose-dependent manner.
Plasmid relaxation assay and results
· The effects of the above four alkaloids on on the unusual bi-subunit type IB topoisomerase of Leishmania donovani (LdTOP1LS) was examined by plasmid relaxation assays. Type I DNA topoisomerase was assayed by decreased mobility of the relaxed isomers of supercoiled pBS (SK+) [pBluescript (SK+)] DNA in 1.2% agarose gel. The relaxation assay was carried out with LdTOP1LS serially diluted in the relaxation buffer and super coiled plasmid pBS (SK+) DNA.
· LdTOP1LS effectively relaxes supercoiled plasmid DNA in the absence of inhibitors after 30 minutes of incubation. When tested at a concentration of 200 μM, cadambine completely inhibits the catalytic activity of LdTOP1LS under the same conditions.
· Further experiments were conducted to determine the inhibitory effects of cadambine. Results showed that cadambine can fully inhibit the enzyme's relaxation activity at a dosage of 25 μM, with over 50% inhibition observed at a concentration as low as 10 μM.

Custom Q&A

What is the product name of the chemical compound described in the reference?

Cadambine

What are the synonyms of Cadambine?

Cadambine, (20α)-16,17-Didehydro-3β,21β-epoxy-19α-(β-D-glucopyranosyloxy)-21a-homo-18-oxayohimban-16-carboxylic acid methyl ester, 8H-5,14b-Epoxypyrano[4'',3'':4',5']azepino[1',2':1,2]pyrido[3,4-b]indole-1-carboxylic acid, 4-(β-D-glucopyranosyloxy)-4,4a,5,6,9,14,15,15a-octahydro-, methyl ester, (4S,4aS,5S,14bS,15aS)-

What is the CAS number of Cadambine?

54422-49-0

What is the molecular formula of Cadambine?

C27H32N2O10

What is the molecular weight of Cadambine?

544.56

What is the melting point of Cadambine?

207-211 0 C

What is the boiling point of Cadambine?

795.7±60.0 °C (Predicted)

What is the density of Cadambine?

1.60±0.1 g/cm3 (Predicted)

In what plant does cadambine naturally occur?

Anthocephalus cadamba

How has cadambine been characterized in terms of specific rotation?

It has a specific rotation of [α]D25 - 71 0

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