Haemanthamine is a crinine-type alkaloid isolated from the Amaryllidaceae plants with potent anticancer activity. Haemanthamine targets ribosomal that inhibits protein biosynthesis during the elongation stage of translation. Haemanthamine has pro- apoptotic , antioxidant, antiviral, antimalarial and anticonvulsant activities.

In Vitro

Haemanthamine (1-100 µM; 24-48 hours; A2780 cells) treatment shows a time- and dose-dependent decrease in cell viability. Haemanthamine (10 µM; 24-72 hours; A2780 cells) treatment leads to a significant inhibition of A2780 cell proliferation. Haemanthamine binds at the A-site cleft of the peptidyl transferase center on the large ribosomal subunit, creating unique molecular interactions with the 25S rRNA. Haemanthamine has a highly specific inhibitory effect on pre-rRNA processing, leading to the activation of a p53-dependent antitumoral surveillance pathway known as nucleolar stress. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Viability AssayCell Line: A2780 ovarian cancer cells Concentration: 1 µM, 10 µM, 50 µM, 100 µM Incubation Time: 24 hours, 48 hours Result: Showed a time- and dose-dependent decrease in cell viability. Cell Proliferation AssayCell Line: A2780 ovarian cancer cells Concentration: 10 µM Incubation Time: 24 hours, 48 hours, 72 hours Result: Led to a significant inhibition of A2780 cell proliferation.

In Vivo

A pharmacokinetic study of Haemanthamine in rats shows a rapid distribution phase of 30 min, a half-life of 70.4 min, and a major clearance through renal elimination. The high distribution volume of 13.7 L/kg suggests a high intracellular penetration, and its plasmatic concentration remains higher than 1 μM for at least 1 hr after a single 10-mg/kg administration . MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

Specifications

Synonyms

Specifications & Purity

≥96%

Biochemical and Physiological Mechanisms

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Purity

≥96%

Names and Identifiers

Canonical Smiles	COC1CC2C3(C=C1)C(CN2CC4=CC5=C(C=C34)OCO5)O
IUPAC Name	(1S,13S,15S,18R)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraen-18-ol
InChIKey	YGPRSGKVLATIHT-HSHDSVGOSA-N
INCHI	1S/C17H19NO4/c1-20-11-2-3-17-12-6-14-13(21-9-22-14)4-10(12)7-18(8-16(17)19)15(17)5-11/h2-4,6,11,15-16,19H,5,7-9H2,1H3/t11-,15+,16+,17+/m1/s1
Isomeric SMILES	CO[C@H]1C[C@H]2[C@@]3(C=C1)[C@H](CN2CC4=CC5=C(C=C34)OCO5)O
Alternate CAS	466-75-1
PubChem CID	441593
NSC Number	403140
MeSH Entry Terms	haemanthamine;hemanthamine
Molecular Weight	301.34

Documentation

📋 Safety Data Sheet (SDS)

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Advanced Data

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Alkaloids and derivatives
  - Class Amaryllidaceae alkaloids
    - Subclass Crinine- and Haemanthamine-type amaryllidaceae alkaloids

Kingdom	Organic compounds
Superclass	Alkaloids and derivatives
Class	Amaryllidaceae alkaloids
Subclass	Crinine- and Haemanthamine-type amaryllidaceae alkaloids
Intermediate Tree Nodes	Not available
Direct Parent	Crinine- and Haemanthamine-type amaryllidaceae alkaloids
Alternative Parents	Phenanthridines and derivatives Benzazepines Tetrahydroisoquinolines Indoles and derivatives Benzodioxoles Aralkylamines Azepines N-alkylpyrrolidines Benzenoids Trialkylamines Secondary alcohols 1,2-aminoalcohols Oxacyclic compounds Acetals Dialkyl ethers Azacyclic compounds Hydrocarbon derivatives Organopnictogen compounds
Molecular Framework	Aromatic heteropolycyclic compounds
Substituents	Hemanthamine/crinine alkaloid skeleton - Benzoquinoline - Phenanthridine - Benzazepine - Quinoline - Tetrahydroisoquinoline - Indole or derivatives - Benzodioxole - Aralkylamine - Azepine - Benzenoid - N-alkylpyrrolidine - Pyrrolidine - Tertiary amine - Secondary alcohol - 1,2-aminoalcohol - Tertiary aliphatic amine - Acetal - Azacycle - Dialkyl ether - Organoheterocyclic compound - Oxacycle - Ether - Hydrocarbon derivative - Organic oxygen compound - Organonitrogen compound - Organic nitrogen compound - Organooxygen compound - Amine - Alcohol - Organopnictogen compound - Aromatic heteropolycyclic compound
Description	This compound belongs to the class of organic compounds known as crinine- and haemanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds with a structure based on the crinine or haemanthamine backbone. Both backbones have a common 5,10b-ethano bridge moiety in their frameworks, which is a very significant taxonomic feature, and the configurations of the 5,10b-ethano bridge are opposite to each other.
External Descriptors	Isoquinoline alkaloids
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61. DOI: 10.1186/s13321-016-0174-y

3D Structure

Associated Targets(Human)

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BCHE Tclin Butyrylcholinesterase (7174 Activities)

Discover Target: BCHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHN (49357 Activities)

Solubility	DMSO : 100 mg/mL (331.85 mM; Need ultrasonic)
Molecular Weight	301.340 g/mol
XLogP3	1.300
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	1
Exact Mass	301.131 Da
Monoisotopic Mass	301.131 Da
Topological Polar Surface Area	51.200 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	497.000
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
The total count of all stereochemical bonds	0
Covalently-Bonded Unit Count	1

Haemanthamine - ≥96% , CAS No.466-75-1

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Literature proof

Overview

Specifications

Documentation

📋 Safety Data Sheet (SDS)

✅ Certificate of Analysis (COA)

📊 Datasheet

🔬 Specification Sheet

Advanced Data

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