8alpha-angeloyloxy-10alpha-hydroxy-1alpha,4alpha-peroxy-11,13-dehydroguaia-6alpha,12-olide - Compound Card

8alpha-angeloyloxy-10alpha-hydroxy-1alpha,4alpha-peroxy-11,13-dehydroguaia-6alpha,12-olide

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8alpha-angeloyloxy-10alpha-hydroxy-1alpha,4alpha-peroxy-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)(O)[C@]23[C@@H]([C@@H]4[C@@H]1[C@H](C)C(=O)O4)[C@](OO2)(C=C3)C)/C
InChI InChI=1S/C20H26O7/c1-6-10(2)16(21)24-12-9-19(5,23)20-8-7-18(4,26-27-20)15(20)14-13(12)11(3)17(22)25-14/h6-8,11-15,23H,9H2,1-5H3/b10-6-/t11-,12-,13+,14-,15-,18+,19+,20-/m0/s1
InChIKey KDARIUDGXONUBS-MQZLVKNTSA-N
Formula C20H26O7
HBA 7
HBD 1
MW 378.42
Rotatable Bonds 2
TPSA 91.29
LogP 1.84
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 378.17
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: 14021418
Nmrshiftdb2: 60056743

No compound-protein relationship available.

Structure

SMILES: C1CCC(CC(=O)O2)C2C(C134)C(OO4)C=C3

Level: 0

Mol. Weight: 378.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.59
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.64
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.57

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.47
Plasma Protein Binding
53.94
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.25
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.18
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.19
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.42
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
-11.12
Rat (Acute)
3.91
Rat (Chronic Oral)
1.79
Fathead Minnow
3.92
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
362.91
Hydration Free Energy
-6.55
Log(D) at pH=7.4
1.66
Log(P)
2.14
Log S
-3.78
Log(Vapor Pressure)
-7.2
Melting Point
154.39
pKa Acid
7.4
pKa Basic
2.98
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7416
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7416
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7167
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7167

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