Basic information
- CAS
519-23-3- Standard SMILES
Cc1c2ccncc2c(C)c2c1[nH]c1ccccc12- InChIKey
CTSPAMFJBXKSOY-UHFFFAOYSA-N- Molecular formula
- C17H14N2
- Average molar mass
- 246.31 g/mol
- Monoisotopic mass
- 246.11569845
Overview
Ellipticine is a organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11. It has a role as an antineoplastic agent and a plant metabolite. It is an organonitrogen heterocyclic compound, an organic heterotetracyclic compound, a polycyclic heteroarene and an indole alkaloid.
Names & identifiers
- Preferred name
- Ellipticine
- IUPAC
- 5,11-dimethyl-6H-pyrido[4,3-b]carbazole
- English name
- ELLIPTICINE
- Molecular formula
- C17H14N2
- Molecular weight
- 246.31
Names & synonyms
ellipticine519-23-35,11-Dimethyl-6H-pyrido[4,3-b]carbazoleElliptisineNSC 71795NSC-71795elliptecine5,11-Dimethyl-6H-pyrido(4,3-b)carbazole117VLW7484CHEBI:4776DTXSID30199855RefChem:136522
Show more names
K00071LP00531CS-1794icig770CP-3025CCG36483CCG 36483DB-052047CCG-36483LS-133282
DTXCID90122346208-264-0TCMDC-125546ICIG 770NSC71795MFCD00010524CHEMBL123MLS000028487
Database identifiers
- CAS
519-23-3- PubChem CID
- 3213
- DTXSID
DTXSID30199855- ChEMBL
CHEMBL123- ChEBI
CHEBI:4776- UNII
- 117VLW7484
- EC Number
- 208-264-0
- Nikkaji
Properties
Computed structural properties
- XLogP
- 4.8
- Topological polar surface area
- 28.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 342
Experimental & physicochemical properties
LogP4.8
Physicochemical properties
- Melting point
- 316 · 316-318°C
- Boiling point
- 379.31 °C · 379.31°C (rough estimate)
- Density
- 1.257 · 1.257±0.06 g/cm3 (20 ºC 760 Torr)
- refractive index
- 1.5794 · 1.5794 (estimate)
- storage temp.
- 2 · Keep in dark place,Sealed in dry,2-8°C
- solubility
- DMSO: soluble
- form
- Bright yellow solid
- pka
- 16.59 · 16.59±0.40(Predicted)
- color
- Light yellow to yellow
- Merck
- 13 · 13,3581
- InChI
- 1S/C17H14N2/c1-10-14-9-18-8-7-12(14)11(2)17-16(10)13-5-3-4-6-15(13)19-17/h3-9,19H,1-2H3
- InChIKey
- CTSPAMFJBXKSOY-UHFFFAOYSA-N
- SMILES
- [nH]1c2c(c4c1cccc4)c(c3c(c2C)ccnc3)C
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]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Safety data
- wgk
- 3
- rtecs
- UU8825000
- ridadr
- UN 3462 6.1/PG 3
- Toxicity
- LD50 in mice (mg/kg): 19.5-22.4 i.v.; 178-204 orally (Rakieten)
- risk_code
- 25
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T
- safety_code
- 45
- hazard_class
- 6.1(b)
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301
- Hazard Classifications
- Acute Tox. 3 Oral
- Precautionary statements
- P264-P270-P301+P310-P405-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Chemical agents that uncouple oxidation from phosphorylation in the metabolic cycle so that ATP synthesis does not occur. Included here are those IONOPHORES that disrupt electron transfer by short-circuiting the proton gradient across mitochondrial membranes.
Applications
DescriptionEllipticine is an alkaloid isolated from Apocyanaceae plants that exhibits antitumor activities by intercalating into DNA and/or inhibiting DNA topoisomerase II. It forms covalent adducts in DNA after being enzymatically activated with cytochrome P450 isoforms (e.g., CYP3A4, CYP1A1, or CYP1A2) or by peroxidases in target tissues. Ellipticine has been shown to inhibit the proliferation of human breast adenocarcinoma MCF-7 cells, leukemia HL-60 and CCRF-CEM cells, neuroblastoma IMR-32, UKF-NB-3, and UKF-NB-4 cells, and U87MG glioblastoma cells with IC50 values ranging from 0.27-4.7 μM.
UsesEllipticine is a DNA intercalating agent and exhibits antitumor activities.
General DescriptionA topoisomerase II inhibitor. Acts as an intercalative alkaloid that stimulates topoisomerase II-mediated DNA breakage. Is also capable of uncoupling mitochondrial oxidative phosphorylation.
Suppliers84 total
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
陕西科贝莱药物研发有限公司13119135307 13119135307 · [email protected]
苏州道澜生物医药科技有限公司15952404857 · [email protected]
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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