6alpha-acetoxy-10beta-hydroxyguaia-1,4(15),11(13)-trien-8alpha,12-olide - Compound Card

6alpha-acetoxy-10beta-hydroxyguaia-1,4(15),11(13)-trien-8alpha,12-olide

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6alpha-acetoxy-10beta-hydroxyguaia-1,4(15),11(13)-trien-8alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)O[C@H]1[C@H]2[C@@H](OC(=O)C2=C)C[C@](C2=CCC(=C)[C@@H]12)(C)O
InChI InChI=1S/C17H20O5/c1-8-5-6-11-13(8)15(21-10(3)18)14-9(2)16(19)22-12(14)7-17(11,4)20/h6,12-15,20H,1-2,5,7H2,3-4H3/t12-,13+,14+,15+,17-/m0/s1
InChIKey UZPZTTSOLZSZDW-GHYKFQNRSA-N
Formula C17H20O5
HBA 5
HBD 1
MW 304.34
Rotatable Bonds 1
TPSA 72.83
LogP 1.67
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 304.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Brocchia cinerea Asteraceae Plantae 282208

Showing of synonyms

  • Jakupovic J, Aal MA, et al. (1988). Further glaucolides and other sesquiterpene lactones from Brocchia cinerea.. Phytochemistry,1988,27(7),2219-2224. [View]
Pubchem: 14137546
Nmrshiftdb2: 70018562

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(CC2)C1CC(C2=3)C(=C)CC3

Level: 0

Mol. Weight: 304.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.64
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.6
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.56
Plasma Protein Binding
45.42
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
8.5
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.21
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.15
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.72
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
-0.28
Rat (Acute)
3.44
Rat (Chronic Oral)
1.8
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
342.62
Hydration Free Energy
-7.45
Log(D) at pH=7.4
0.97
Log(P)
0.76
Log S
-2.75
Log(Vapor Pressure)
-6.42
Melting Point
157.46
pKa Acid
6.28
pKa Basic
4.97
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7151
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7151
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7005
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7005

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