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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C1O[C@]2(C(=C1C)C[C@]1(C(=C2)[C@H](O)CC[C@@H]1C)C)O
InChI InChI=1S/C15H20O4/c1-8-4-5-12(16)11-7-15(18)10(6-14(8,11)3)9(2)13(17)19-15/h7-8,12,16,18H,4-6H2,1-3H3/t8-,12+,14+,15+/m0/s1
InChIKey ILDMSNFGPQLCNL-AZEZGGBOSA-N
Formula C15H20O4
HBA 4
HBD 2
MW 264.32
Rotatable Bonds 0
TPSA 66.76
LogP 1.68
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 264.14
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: 11357536
Nmrshiftdb2: 70034906

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 264.32 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.43
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.54
Plasma Protein Binding
38.73
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
4.88
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.02
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.1
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.15
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
-1.2
Rat (Acute)
2.8
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
326.66
Hydration Free Energy
-7.41
Log(D) at pH=7.4
1.65
Log(P)
1.78
Log S
-2.4
Log(Vapor Pressure)
-5.82
Melting Point
168.26
pKa Acid
6.49
pKa Basic
6.17
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9262
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9262
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7955
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7955
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7755
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7755
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7439
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7439
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7391
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7391
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7354
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7354
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7280
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7280
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7183
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7183
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7179
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7179

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