1beta,10beta-epoxy-8alpha-hydroxyeremophil-7(11)-en-8beta,12-olide - Compound Card

1beta,10beta-epoxy-8alpha-hydroxyeremophil-7(11)-en-8beta,12-olide

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1beta,10beta-epoxy-8alpha-hydroxyeremophil-7(11)-en-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@]3(C2)O[C@@H]3CC[C@@H]1C)C)O
InChI InChI=1S/C15H20O4/c1-8-4-5-11-14(18-11)7-15(17)10(6-13(8,14)3)9(2)12(16)19-15/h8,11,17H,4-7H2,1-3H3/t8-,11+,13+,14+,15+/m0/s1
InChIKey NSNPFQLBEDNILE-ZZVMUTNWSA-N
Formula C15H20O4
HBA 4
HBD 1
MW 264.32
Rotatable Bonds 0
TPSA 59.06
LogP 1.92
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.8
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: 11184636
Nmrshiftdb2: 70034910

No compound-protein relationship available.

Structure

SMILES: C123C(O3)CCCC1CC=4C(C2)OC(=O)C4

Level: 0

Mol. Weight: 264.32 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-5.06
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.52
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.12
Plasma Protein Binding
24.4
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
13.82
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.51
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.27
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.04
Micronucleos
Toxic
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
-1.35
Rat (Acute)
2.22
Rat (Chronic Oral)
1.28
Fathead Minnow
3.79
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
331.61
Hydration Free Energy
-5.85
Log(D) at pH=7.4
2.0
Log(P)
2.18
Log S
-2.42
Log(Vapor Pressure)
-4.89
Melting Point
128.23
pKa Acid
5.11
pKa Basic
4.88
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8872
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8872
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8790
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8790
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8635
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8635
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8494
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8494
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8439
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8439
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8238
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8238
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8236
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8236
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8171
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8171
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7948
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7948
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7696
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7696
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7652
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7652
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7569
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7569
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7521
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7521
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7514
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7514
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7407
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7407
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7371
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7371
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7283
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7283
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7267
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7267
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7054
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7054

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