Artemisin - Compound Card

Artemisin

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Artemisin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O[C@H]1C[C@@]2(C)C=CC(=O)C(=C2[C@@H]2[C@@H]1[C@H](C)C(=O)O2)C
InChI InChI=1S/C15H18O4/c1-7-9(16)4-5-15(3)6-10(17)11-8(2)14(18)19-13(11)12(7)15/h4-5,8,10-11,13,17H,6H2,1-3H3/t8-,10-,11+,13-,15+/m0/s1
InChIKey LUHMMHZLDLBAKX-DBIGVJDZSA-N
Formula C15H18O4
HBA 4
HBD 1
MW 262.3
Rotatable Bonds 0
TPSA 63.6
LogP 1.39
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 262.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia ifranensis Asteraceae Plantae 1903206

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones from North African Artemisia species.. Phytochemistry,1994,37(2),477-485. [View]
Pubchem: 65030
Kegg Ligand: C09344
Chebi: 2852
Nmrshiftdb2: 60072408
CPRiL: 135587
Structure

SMILES: C1C(=O)OC(C12)C=3C(CC2)C=CC(=O)C3

Level: 0

Mol. Weight: 262.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.38
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.54
Plasma Protein Binding
48.65
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.98
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.07
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.08
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.56
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-2.14
Rat (Acute)
2.92
Rat (Chronic Oral)
1.78
Fathead Minnow
3.9
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
345.62
Hydration Free Energy
-8.45
Log(D) at pH=7.4
0.85
Log(P)
0.55
Log S
-2.24
Log(Vapor Pressure)
-5.89
Melting Point
200.49
pKa Acid
8.72
pKa Basic
4.98
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8139
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8139
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7888
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7888
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7089
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7089
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7044
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7044

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