Vernolide - Compound Card

Vernolide

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Vernolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=C)C(=O)O[C@H]1C[C@]23O[C@@H]3CC/C(=C/[C@@H]3[C@@H]1C(=C)C(=O)O3)/CO[C@H]2O
InChI InChI=1S/C19H22O7/c1-9(2)16(20)25-13-7-19-14(26-19)5-4-11(8-23-18(19)22)6-12-15(13)10(3)17(21)24-12/h6,12-15,18,22H,1,3-5,7-8H2,2H3/b11-6-/t12-,13+,14-,15+,18-,19-/m1/s1
InChIKey ZGXVZQZFVYSUDU-ULYHCOEVSA-N
Formula C19H22O7
HBA 7
HBD 1
MW 362.38
Rotatable Bonds 2
TPSA 94.59
LogP 1.17
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.58
Exact Mass 362.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Vernonia amygdalina Asteraceae Plantae 82755

Showing of synonyms

  • Abay SM, Lucantoni L, et al. (2015). Plasmodium transmission blocking activities of Vernonia amygdalina extracts and isolated compounds. Malaria Journal,2015,14,288. [View] [PubMed]
Pubchem: 5281508
Kegg Ligand: C09583
Chebi: 9965
CPRiL: 107714
Structure

SMILES: O=C(O1)C(=C)C(CC2)C1C=C(CCC(C234)O4)COC3

Level: 0

Mol. Weight: 362.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.21
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.68
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.36
Plasma Protein Binding
22.55
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
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
15.12
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.03
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.63
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.01
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-4.39
Rat (Acute)
4.17
Rat (Chronic Oral)
2.06
Fathead Minnow
3.96
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
394.5
Hydration Free Energy
-6.46
Log(D) at pH=7.4
0.81
Log(P)
0.81
Log S
-2.71
Log(Vapor Pressure)
-8.03
Melting Point
146.76
pKa Acid
5.4
pKa Basic
3.12
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7862
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7862

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