Cephalotaxine
Basic information
- CAS
24316-19-6- Standard SMILES
COC1=C[C@]23CCCN2CCc2cc4c(cc2[C@@H]3[C@@H]1O)OCO4- InChIKey
YMNCVRSYJBNGLD-KURKYZTESA-N- Molecular formula
- C18H21NO4
- Average molar mass
- 315.4 g/mol
Overview
Cephalotaxine is a benzazepine alkaloid isolated from Cephalotaxus harringtonia. It is a secondary alcohol, an organic heteropentacyclic compound, a benzazepine alkaloid, a benzazepine alkaloid fundamental parent, an enol ether, a tertiary amino compound and a cyclic acetal.
Names & identifiers
- Preferred name
- Cephalotaxine
- IUPAC
- (2S,3S,6R)-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,6.06,10.015,19]icosa-1(20),4,13,15(19)-tetraen-3-ol
- English name
- CEPHALOTAXINE
- Molecular formula
- C18H21NO4
- Molecular weight
- 315.36
Names & synonyms
Cephalotaxine24316-19-6(-)-CephalotaxineOmacetaxine84MI6OYN4ZCHEBI:3540NSC-128487NSC-245454(2S,3S,6R)-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,6.06,10.015,19]icosa-1(20),4,13,15(19)-tetraen-3-ol(2S,3S,6R)-4-methoxy-16,18-dioxa-10-azapentacyclo(11.7.0.02,6.06,10.015,19)icosa-1(20),4,13,15(19)-tetraen-3-olRefChem:56711DTXCID4028206
Show more names
(11bS,12S,14aR)-13-methoxy-2,3,5,6,11b,12-hexahydro-1H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-12-olNSC 245454CephalotaxinZINC19795976)CEPHALOTAXINE USP/EP/BPCephalotaxine 24316-19-6Cephalotaxine hydrochloride
636-631-9DTXSID3048231CephalotaxlenMFCD21090383(1S,3aR,14bS)-2-Methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-1-ol(1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-olUNII-84MI6OYN4ZNSC 128487
Properties
Computed structural properties
- XLogP
- 0.2
- Topological polar surface area
- 51.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 1
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 523
Physicochemical properties
- Melting point
- 131 · 131-132 °C(Solv: benzene (71-43-2))
- Boiling point
- 495.2 · 495.2±45.0 °C(Predicted)
- Density
- 1.38 · 1.38±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- 10 mg/mL; · DMF: 10 mg/mL; DMSO: 12 mg/mL; Ethanol: 5 mg/mL
- form
- powder to crystal
- pka
- 13.3 · 13.30±0.40(Predicted)
- color
- White to Orange to Green
- CAS DataBase Reference
- 24316 · 24316-19-6
- FDA UNII
- 84 MI6OYN4Z · 84MI6OYN4Z
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 312 · H312-H302-H332
- Precautionary statements
- 280 · P280-P302+P352-P312-P322-P363-P501-P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P312
- Hazard Codes
- Xn
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
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Hepatotoxicity
In controlled trials, serum aminotransferase elevations occurred in 2% to 6% patients treated with omacetaxine, but most elevations were mild and transient with only rare patients requiring dose modification or discontinuation for liver test abnormalities. Clinically apparent liver injury with jaundice was not reported in the preregistration trials of omacetaxine and is not mentioned in the product label. Since the approval and more wide scale use of omacetaxine, there have been no publications or descriptions of the hepatotoxicity with jaundice associated with its use. Thus, clinically apparent liver injury due to omacetaxine must be rare, if it occurs at all.
Safety data
- wgk
- 3
- ridadr
- UN 1544 6.1/PG 3
- hs_code
- 2939.79.0000
- risk_code
- 20/21/22
- Signal word
- Warning
- Symbol(GHS)
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.
Applications
UsesAntiviral and antitumor agent.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: A benzazepine alkaloid isolated from Cephalotaxus harringtonia.
Related reactions
9 records
Compound notes
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