HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Compound

Npc37889

HCID 452191
New noteNew reactionRequest quotes
Print preview
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
63968-64-9
Standard SMILES
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3OC4(C)CC[C@@H]1[C@]32OO4
InChIKey
BLUAFEHZUWYNDE-DCJAHCNHSA-N
Molecular formula
C15H22O5
Average molar mass
282.33 g/mol

Overview

(+)-Arteannuin is a terpene lactone.

Names & identifiers

Preferred name
Npc37889
IUPAC
(4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one
English name
Artemisinin
Molecular formula
C15H22O5
Molecular weight
282.33

Names & synonyms

RefChem:1093177Npc37889(+)-ArteannuinArtemisniniNSC369397Prestwick_818Artemisinin, 98%UPCMLD-DP074SPECTRUM1503042Artemisinin, analytical standardSCHEMBL13428542UPCMLD-DP074:001
Show more names
ARTEMETHERARTEANNUINARTEMISIA ANNUAQINGHAOSU3,12-epoxy-12h-pyranol(4,3-j)-1,2-benzodioxepin-10(3h)-one,octahydro-3,6,9-triQHSARTEMISINEAstemisininArtimisininARTEMISININE
HMS502A18CHEBI:182769HMS1569D17HMS1923O03(3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-trimethyloctahydro-3H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(12H)-one(4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-oneCCG-38886AKOS004119830

Database identifiers

CAS
63968-64-9
PubChem CID
452191
ChEBI
CHEBI:182769

Properties

Computed structural properties

XLogP
2.8
Topological polar surface area
54 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
5
Rotatable bonds
0
Heavy atoms
20
Formal charge
0
Complexity
452

Physicochemical properties

Melting point
156 · 156-157 °C (lit.)
alpha
76 · 76 º (c=0.5,MeOH)
Boiling point
344.94 °C · 344.94°C (rough estimate)
Density
1.0984 · 1.0984 (rough estimate)
refractive index
75 ° · 75 ° (C=0.5, MeOH)
storage temp.
-20 °C · -20°C
solubility
100 mM · Soluble to 100mM in DMSO and to 75mM in ethanol
form
White to off-white crystalline solid.
color
Needles
optical activity
20 · [α]20/D +76°, c = 0.5 in methanol
Merck
14 · 14,817
Stability
Stable. Combustible. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides. May absorb, and react with, carbon dioxide from the air.
Major Application
food and beverages
Cosmetics Ingredients Functions
SKIN CONDITIONINGANTIMICROBIAL

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
2
rtecs
KD4170000
hs_code
29322985
Toxicity
LD50 in mice (mg/kg): 5105 orally; 2800 i.m.; 1558 i.p. (Koch); LD50 in mice, rats (mg/kg): 4228, 5576 orally; 3840, 2571 i.m. (China Cooperative Research Group on Qinghaosu)
Signal word
Warning
Symbol(GHS)
GHS02,GHS09
safety_code
22-24/25
Storage Class
11 - Combustible Solids
Hazard statements
H242-H400-H410
REACH Registrations
Active
Precautionary statements
P210-P220-P234-P280-P280-P273-P391-P420-P410

Chemistry & industry

Applications · 8 items

UsesArtemisia annua is used as antimalarial drugs. Clinical application has shown that artemisinin and its derivatives have special effects on treating the malaria and falciparum malaria, especially artemisinin which has stronger killing effect on Plasmodium falciparum intracellular phorozoon than other artemisinin drugs, characterized by high efficiency, rapid efficacy, low toxicity and no cross-resistance with chloroquine, etc. It can be not only used for treatment, but also for emergency treatment. It is applicable to a variety of malaria such as falciparum malaria, vivax malaria, anti-chloroquine malaria and cerebral malaria, including dangerous type. The most notable drug is dihydroartemisinin and its tablets. This drug has its antimalarial effect be 10 times as strong as artemisinin with the recurrence rate of only 1.95%, thus having been rated as China's top ten scientific and technological achievements in 1992. Artemisinin and its derivatives not only are excellent antimalarial drugs, but also have potentially attractive prospect in the treatment of other diseases. Animal experiments have found that artemisinin treatment of Clonorchis sinensis can achieve a rate of pest control being up to 100%; treatment of animal schistosomiasis can achieve a pest control rate of 33.8-99.3%. Application of artemisinin treatment of discoid lupus erythematosus can achieve a total effective rate of 90%. Its efficacy in the treatment of dengue fever is significantly better than morphine biguanide and other western medicines. Immunologists have also found that artemisinin can significantly improve the lymphocyte transformation rate and enhance the immune function of antibodies. People haven’t found toxic effect of this product on the heart, liver and kidney. People haven’t observed any significant side effects in clinical practice.

DescriptionArtemisinin is an antimalarial agent with anticancer activity. It is an iron(II) oxide-reactive endoperoxide that generates reactive oxygen species (ROS) upon cleavage of its endoperoxide bridge. It reduces the growth of various P. falciparum strains in vitro (IC50s = 3.98-20.36 nM) and reduces parasitemia in mice infected with P. falciparum with a curative dose (CD50) value of 140 mg/kg. It also reduces P. berghei infection in mice (ED50 = 5.6 mg/kg per day). Artemisinin (100-400 μM) induces cell cycle arrest in the G0/G1 phase and apoptosis and inhibits growth of SK-N-AS, BE(2)-C, SK-N-DZ, and SHEP1 neuroblastoma cells in a time- and concentration-dependent manner. It also suppresses BE(2)-C cell colony formation in a soft agar assay and reduces tumor growth in a BE(2)-C mouse xenograft model. Formulations containing artemisinin have been used in combination therapies for the treatment of malaria.

Related reactions

0 records
New reaction record

No reaction records under the current filter.

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
New noteNew reactionRequest quotes
InChI
InChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1
InChIKey
BLUAFEHZUWYNDE-NNWCWBAJSA-N
SMILES
O1[C@]23[C@@]4([H])O[C@@](C)(CC[C@@]2([H])[C@H](C)CC[C@@]3([H])[C@@H](C)C(=O)O4)O1
LogP
2.9 · 2.900
FDA UNII
9 RMU91N5K2 · 9RMU91N5K2
ATC code
1 BE01 · P01BE01
UNSPSC Code
41116107 · 41116107
NACRES
79 · NA.79
Symbol(GHS)
2 · GHS02,GHS09
Signal word
Warning
Hazard statements
242 · H242-H400-H410
Precautionary statements
210 · P210-P220-P234-P280-P280-P273-P391-P420-P410
Safety Statements
22 · 22-24/25
WGK Germany
2 · 2
RTECS
4170000 · KD4170000
HS Code
29322985 · 29322985
Storage Class
11 · 11 - Combustible Solids
Toxicity
50 in · LD50 in mice (mg/kg): 5105 orally; 2800 i.m.; 1558 i.p. (Koch); LD50 in mice, rats (mg/kg): 4228, 5576 orally; 3840, 2571 i.m. (China Cooperative Research Group on Qinghaosu)
REACH Registrations
Active

DescriptionArtemisinin, a sesquiterpene isolated from a traditional Chinese remedy (quinghao), is useful in the treatment of Fafciparum malaria, including infections caused by chloroquine resistant strains. It is reported to clear parasitemia quicker than i.v. quinine, and is effective in cerebral malaria.

HistoryThe discovery of artemisinin dramatically changes the landscape to combat malaria and leads to a paradigm shift in antimalarial drug development.However, the discovery of artemisinin is the first stage; the development of artemisinin derivatives and their compound preparations is another important stage. Based on artemisinin, scientists obtained artemisinin ether derivatives by semisynthetic method. After screening of antimalarial activity, artemether was found. To further improve the solubility of artemisinin derivatives, artesunate was also found. The discovery of artesunate makes artemisinin and its derivatives much easier to promote, and more convenient dosage forms to treat malaria enriched the clinic application of artemisinin and its derivatives .

UsesActive antimalarial constituent of the tradional Chinese medicinal herb Artemisia annua L., Compositae, which has been known for almost 2000 years as Qinghao. Antimalarial

UsesAn antimalarial agent that inhibits VEGF expression and NOS2.

UsesArtemisinin inhibits angiogenesis by down-regulating HIF-1α and VEGF expression in mouse embryonic stem cells. Artemisinin crosses the blood-brain barrier and is an inhibitor of human NOS2 (iNOS).

General DescriptionThe artemisinin series are the newest of the antimalarialdrugs and are structurally unique when comparedwith the compounds previously and currently used. Theparent compound, artemisinin, is a natural product extractedfrom the dry leaves of Artemisia Annua (sweetwormwood). The plant has to be grown each year fromseed because mature plants may lack the active drug. The growing conditions are critical to maximize artemisininyield. Thus far, the best yields have been obtained fromplants grown in North Vietnam, Chongqing province inChina, and Tanzania.

Upstream & downstream products

Upstream raw materials

ArtesunateArtemetherArtemisia annua L.Deoxy Artemisinin

Downstream products

DHQHS 2(3R,12aR)-3,6α,9β-Trimethyl-3β,12α-epoxy-3,4,5,5aα,6,7,8,8aα,9,10-decahydro-10α-ethoxypyrano[4,3-j]-1,2-benzodioxepinArteetheralpha-DihydroartemisininDeoxy Arteether

Additional notes

DefinitionChEBI: A sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.