Parthenolid-9-one - Compound Card

Parthenolid-9-one

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Parthenolid-9-one

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C/1=C\CC[C@@]2(C)O[C@H]2[C@@H]2[C@@H](CC1=O)C(=C)C(=O)O2
InChI InChI=1S/C15H18O4/c1-8-5-4-6-15(3)13(19-15)12-10(7-11(8)16)9(2)14(17)18-12/h5,10,12-13H,2,4,6-7H2,1,3H3/b8-5+/t10-,12-,13-,15+/m0/s1
InChIKey MZDVWXBIIWIBTB-BPWSPTIZSA-N
Formula C15H18O4
HBA 4
HBD 0
MW 262.3
Rotatable Bonds 0
TPSA 55.9
LogP 1.94
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 Anvillea radiata Asteraceae Plantae 159630
2 Anvillea garcinii Asteraceae Plantae 56519

Showing of synonyms

  • Abdel-Sattar E, McPhail AT (2000). cis-Parthenolid-9-one from Anvillea garcinii.. Journal of Natural Products,2000,63,1587-1589. [View] [PubMed]
  • El Hassany B, El Hanbali F, et al. (2004). Germacranolides from Anvillea radiata.. Fitoterapia,2004,75,573- 576. [View] [PubMed]
Pubchem: 10445414
Nmrshiftdb2: 70046032

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC2C1CC(=O)C=CCCC(O3)C23

Level: 0

Mol. Weight: 262.3 g/mol

Cytotoxic
In vivo antitumor

Absorption

Caco-2 (logPapp)
-5.04
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.52
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.21
Plasma Protein Binding
23.29
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
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
16.3
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.36
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.19
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.73
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
2.06
Rat (Acute)
2.54
Rat (Chronic Oral)
1.83
Fathead Minnow
4.0
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
352.07
Hydration Free Energy
-6.13
Log(D) at pH=7.4
1.27
Log(P)
1.27
Log S
-2.31
Log(Vapor Pressure)
-5.36
Melting Point
85.39
pKa Acid
6.25
pKa Basic
4.57
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7206
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7206
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7154
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7154

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