3beta,10alpha-acetoxy-8alpha-angeloyloxy-4alpha-hydroxy-1beta,2beta-epoxy-11,13-dehydroguaia-6alpha,12-olide - Compound Card

3beta,10alpha-acetoxy-8alpha-angeloyloxy-4alpha-hydroxy-1beta,2beta-epoxy-11,13-dehydroguaia-6alpha,12-olide

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3beta,10alpha-acetoxy-8alpha-angeloyloxy-4alpha-hydroxy-1beta,2beta-epoxy-11,13-dehydroguaia-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C=C(\C(=O)O[C@H]1C[C@@](C)(OC(=O)C)[C@@]23[C@@H]([C@@H]4[C@@H]1[C@H](C)C(=O)O4)[C@]([C@H]([C@H]3O2)OC(=O)C)(C)O)/C
InChI InChI=1S/C24H32O10/c1-8-10(2)20(27)31-14-9-22(6,33-13(5)26)24-17(16-15(14)11(3)21(28)32-16)23(7,29)18(19(24)34-24)30-12(4)25/h8,11,14-19,29H,9H2,1-7H3/b10-8-/t11-,14-,15+,16-,17-,18-,19+,22+,23-,24-/m0/s1
InChIKey AEFSKSWVGQICCS-KNBGXYRSSA-N
Formula C24H32O10
HBA 10
HBD 1
MW 480.51
Rotatable Bonds 4
TPSA 137.96
LogP 1.22
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 480.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Otanthus maritimus Asteraceae Plantae 1155244

Showing of synonyms

  • Jakupovic J, Boeker R, et al. (1988). Highly oxygenated guaianolides from Otanthus maritimus. Phytochemistry,1988,27(4),1135-1140. [View]
Pubchem: 14021441
Nmrshiftdb2: 60056734

No compound-protein relationship available.

Structure

SMILES: C123C(O3)CCC1C4C(CC(=O)O4)CCC2

Level: 0

Mol. Weight: 480.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.12
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.64
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.35
Plasma Protein Binding
45.33
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
11.34
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.38
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.69
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.64
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
-136.41
Rat (Acute)
5.53
Rat (Chronic Oral)
2.06
Fathead Minnow
4.02
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
409.39
Hydration Free Energy
-2.72
Log(D) at pH=7.4
0.85
Log(P)
1.58
Log S
-3.4
Log(Vapor Pressure)
-8.39
Melting Point
122.43
pKa Acid
6.6
pKa Basic
0.64
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7066
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7066
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7026
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7026

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