8alpha,9alpha-epoxyparthenolide - Compound Card

8alpha,9alpha-epoxyparthenolide

Select a section from the left sidebar

8alpha,9alpha-epoxyparthenolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C1O[C@H]2C(C1=C)[C@H]1O[C@H]1/C(=C/CC[C@@]1(C2O1)C)/C
InChI InChI=1S/C15H18O4/c1-7-5-4-6-15(3)13(19-15)12-9(11-10(7)17-11)8(2)14(16)18-12/h5,9-13H,2,4,6H2,1,3H3/b7-5+/t9?,10-,11+,12-,13?,15+/m0/s1
InChIKey MJRBWIWRIAWODS-HXVLGYONSA-N
Formula C15H18O4
HBA 4
HBD 0
MW 262.3
Rotatable Bonds 0
TPSA 51.36
LogP 1.75
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 262.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Anvillea radiata Asteraceae Plantae 159630

Showing of synonyms

  • El Hassany B, El Hanbali F, et al. (2004). Germacranolides from Anvillea radiata.. Fitoterapia,2004,75,573- 576. [View] [PubMed]
Pubchem: 163009533

No compound-protein relationship available.

Structure

SMILES: O=C(O1)C(=C)C2C1C(O3)C3CCC=CC(O4)C24

Level: 0

Mol. Weight: 262.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.09
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.53
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.69

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.14
Plasma Protein Binding
6.88
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
16.47
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.7
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.65
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.94
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
0.28
Rat (Acute)
2.6
Rat (Chronic Oral)
1.44
Fathead Minnow
4.24
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
350.09
Hydration Free Energy
-5.29
Log(D) at pH=7.4
1.75
Log(P)
1.93
Log S
-2.5
Log(Vapor Pressure)
-4.52
Melting Point
42.56
pKa Acid
5.49
pKa Basic
3.08
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8668
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8668
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7811
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7811
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7679
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7679
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7628
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7628
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7538
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7538
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7397
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7397
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7261
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7261
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7205
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7205
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7145
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7145

Download SDF