8alpha-angeloyloxy-5-alpha-hydroxy-2-oxo-11,13-dehydroguaia-1(10),3-dien-6alpha,12-olide - Compound Card

8alpha-angeloyloxy-5-alpha-hydroxy-2-oxo-11,13-dehydroguaia-1(10),3-dien-6alpha,12-olide

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8alpha-angeloyloxy-5-alpha-hydroxy-2-oxo-11,13-dehydroguaia-1(10),3-dien-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]1CC(=C2[C@]([C@@H]3[C@@H]1[C@H](C)C(=O)O3)(O)C(=CC2=O)C)C)/C
InChI InChI=1S/C20H24O6/c1-6-9(2)18(22)25-14-7-10(3)16-13(21)8-11(4)20(16,24)17-15(14)12(5)19(23)26-17/h6,8,12,14-15,17,24H,7H2,1-5H3/b9-6-/t12-,14-,15+,17-,20+/m0/s1
InChIKey LEDWNNAHTKTAEH-YRBQZKPLSA-N
Formula C20H24O6
HBA 6
HBD 1
MW 360.41
Rotatable Bonds 2
TPSA 89.9
LogP 2.02
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.55
Exact Mass 360.16
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: 14021356
Nmrshiftdb2: 60056753

No compound-protein relationship available.

Structure

SMILES: O=C1C=CC(C1=2)C3C(CC(=O)O3)CCC2

Level: 0

Mol. Weight: 360.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.58
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.63
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.46
Plasma Protein Binding
61.89
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.86
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.27
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.58
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.11
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
-5.11
Rat (Acute)
2.87
Rat (Chronic Oral)
2.02
Fathead Minnow
3.94
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
375.0
Hydration Free Energy
-7.28
Log(D) at pH=7.4
1.49
Log(P)
2.5
Log S
-3.35
Log(Vapor Pressure)
-6.98
Melting Point
171.48
pKa Acid
6.9
pKa Basic
3.92
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8578
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8578
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7473
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7473

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