Artemisinin - Compound Card

Artemisinin

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Artemisinin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles O=C1O[C@@H]2O[C@@]3(C)CC[C@@H]4[C@]2([C@H]([C@H]1C)CC[C@H]4C)OO3
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
Formula C15H22O5
HBA 5
HBD 0
MW 282.34
Rotatable Bonds 0
TPSA 53.99
LogP 2.39
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 282.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia annua Asteraceae Plantae 35608

Showing of synonyms

  • Reale S, Pace L, et al. (2008). A rapid method for the quantification of artemisinin in Artemisia annua L. plants cultivated for the first time in Burundi. Natural Product Research,2008,22(4),360-364. [View] [PubMed]
Pubchem: 68827
Kegg Ligand: C09538
Chebi: 223316
Nmrshiftdb2: 20253147
Metabolights: MTBLC223316
Drugbank: DB13132
Bindingdb: 50088447
Selleck: Artemisinin
CPRiL: 3856
Structure

SMILES: C123C4CC(=O)OC2OC(OO3)CCC1CCC4

Level: 0

Mol. Weight: 282.34 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.66
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.13

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.51
Plasma Protein Binding
37.88
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
15.26
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.17
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.24
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.52
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-0.75
Rat (Acute)
1.95
Rat (Chronic Oral)
1.3
Fathead Minnow
3.64
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
320.13
Hydration Free Energy
-5.19
Log(D) at pH=7.4
2.2
Log(P)
2.91
Log S
-3.62
Log(Vapor Pressure)
-4.86
Melting Point
130.0
pKa Acid
7.71
pKa Basic
3.66
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8326
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8326
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7736
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7736
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7714
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7714
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7420
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7420
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7245
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7245

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