10beta-ethoxy-1alpha-hydroxyguaia-3-en-6alpha,12-olide - Compound Card

10beta-ethoxy-1alpha-hydroxyguaia-3-en-6alpha,12-olide

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10beta-ethoxy-1alpha-hydroxyguaia-3-en-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CCO[C@@]1(C)CC[C@@H]2[C@@H]([C@@H]3[C@@]1(O)CC=C3C)OC(=O)[C@H]2C
InChI InChI=1S/C17H26O4/c1-5-20-16(4)8-7-12-11(3)15(18)21-14(12)13-10(2)6-9-17(13,16)19/h6,11-14,19H,5,7-9H2,1-4H3/t11-,12-,13+,14-,16-,17-/m0/s1
InChIKey XQRDLQSREIYMDZ-JJMGDHPNSA-N
Formula C17H26O4
HBA 4
HBD 1
MW 294.39
Rotatable Bonds 2
TPSA 55.76
LogP 2.45
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.82
Exact Mass 294.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia argentea Asteraceae Plantae 669119

Showing of synonyms

  • El-Emary NA, Makboul MA, et al. (1987). Sesquiterpene lactones from Artemisia argentea.. Phytochemistry,1987,26(1),314-315. [View]
Pubchem: 162978596
Nmrshiftdb2: 70003737

No compound-protein relationship available.

Structure

SMILES: O=C(O1)CC(C1C23)CCCC3CC=C2

Level: 0

Mol. Weight: 294.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.5
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.29

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.44
Plasma Protein Binding
46.25
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
10.98
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.14
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.67
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.02
Micronucleos
Safe
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
-1.31
Rat (Acute)
2.52
Rat (Chronic Oral)
1.5
Fathead Minnow
3.82
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
339.59
Hydration Free Energy
-5.96
Log(D) at pH=7.4
1.59
Log(P)
2.86
Log S
-2.61
Log(Vapor Pressure)
-5.47
Melting Point
139.94
pKa Acid
9.65
pKa Basic
6.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7556
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7556
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7359
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7359
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7004
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7004

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