1beta-hydroxy-8alpha-methoxyeremophil-7(11),9-dien-8beta,12-olide - Compound Card

1beta-hydroxy-8alpha-methoxyeremophil-7(11),9-dien-8beta,12-olide

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1beta-hydroxy-8alpha-methoxyeremophil-7(11),9-dien-8beta,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CO[C@@]12OC(=O)C(=C2C[C@]2(C(=C1)[C@H](O)CC[C@@H]2C)C)C
InChI InChI=1S/C16H22O4/c1-9-5-6-13(17)12-8-16(19-4)11(7-15(9,12)3)10(2)14(18)20-16/h8-9,13,17H,5-7H2,1-4H3/t9-,13+,15+,16+/m0/s1
InChIKey KOPBXBMGJCLPOI-CZLJMHDISA-N
Formula C16H22O4
HBA 4
HBD 1
MW 278.35
Rotatable Bonds 1
TPSA 55.76
LogP 2.33
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.69
Exact Mass 278.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio aegyptius Asteraceae Plantae 121537

Showing of synonyms

  • Mohamed AEHH, Ahmed AA (2005). Eremophilane-type sesquiterpene derivatives from Senecio aegyptius var. discoideus. Journal of Natural Products,2005,68,439-442. [View] [PubMed]
Pubchem: 11185028
Nmrshiftdb2: 70034909

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C=12)C=C3C(C2)CCCC3

Level: 0

Mol. Weight: 278.35 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.4
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.62

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.52
Plasma Protein Binding
40.04
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
7.45
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.21
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.34
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.35
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
-1.85
Rat (Acute)
2.61
Rat (Chronic Oral)
1.67
Fathead Minnow
3.92
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
326.86
Hydration Free Energy
-5.33
Log(D) at pH=7.4
2.13
Log(P)
2.12
Log S
-2.84
Log(Vapor Pressure)
-4.94
Melting Point
136.43
pKa Acid
7.5
pKa Basic
6.23
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9104
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9104

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