1alpha-hydroxyeudesm-4-en-6beta,11betaH-12,6-olide - Compound Card

1alpha-hydroxyeudesm-4-en-6beta,11betaH-12,6-olide

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1alpha-hydroxyeudesm-4-en-6beta,11betaH-12,6-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C1O[C@H]2[C@H]([C@@H]1C)CC[C@@]1(C2=C(C)CC[C@@H]1O)C
InChI InChI=1S/C15H22O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h9-11,13,16H,4-7H2,1-3H3/t9-,10-,11-,13-,15-/m0/s1
InChIKey BWOPOAOBPJWDBF-SFUXALCOSA-N
Formula C15H22O3
HBA 3
HBD 1
MW 250.34
Rotatable Bonds 0
TPSA 46.53
LogP 2.44
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 250.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia ifranensis Asteraceae Plantae 1903206

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones from North African Artemisia species.. Phytochemistry,1994,37(2),477-485. [View]
Pubchem: 101674068
Nmrshiftdb2: 60072402

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C12)C=3C(CC2)CCCC3

Level: 0

Mol. Weight: 250.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.33
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.56
Plasma Protein Binding
41.41
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
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
10.61
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.27
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.26
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.74
Micronucleos
Safe
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
-0.63
Rat (Acute)
1.91
Rat (Chronic Oral)
1.73
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
337.79
Hydration Free Energy
-5.95
Log(D) at pH=7.4
1.57
Log(P)
2.12
Log S
-2.42
Log(Vapor Pressure)
-4.93
Melting Point
143.38
pKa Acid
11.09
pKa Basic
6.96
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 0.8496
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8496
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7819
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7819
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7605
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7605
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7157
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7157

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