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

1beta-hydroxy-8alphaH-eremophil-7(11),9-dien-8beta,12-olide

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1beta-hydroxy-8alphaH-eremophil-7(11),9-dien-8beta,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC1=C2C[C@]3(C)[C@@H](C)CC[C@H](C3=C[C@H]2OC1=O)O
InChI InChI=1S/C15H20O3/c1-8-4-5-12(16)11-6-13-10(7-15(8,11)3)9(2)14(17)18-13/h6,8,12-13,16H,4-5,7H2,1-3H3/t8-,12+,13+,15+/m0/s1
InChIKey YMWUFVDLAIZPKY-VFJFRJDUSA-N
Formula C15H20O3
HBA 3
HBD 1
MW 248.32
Rotatable Bonds 0
TPSA 46.53
LogP 2.36
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 248.14
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: 44575412
Nmrshiftdb2: 70034911

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 248.32 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.35
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.58

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
41.37
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
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
8.8
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.28
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.12
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.12
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
-0.54
Rat (Acute)
2.43
Rat (Chronic Oral)
1.79
Fathead Minnow
3.89
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
324.27
Hydration Free Energy
-5.89
Log(D) at pH=7.4
2.3
Log(P)
2.06
Log S
-2.73
Log(Vapor Pressure)
-4.76
Melting Point
139.54
pKa Acid
8.59
pKa Basic
7.13
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 0.9269
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9269
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8140
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8140
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8106
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8106
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7991
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7991
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7892
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7892
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7593
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7593
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7508
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7508
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7332
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7332
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7299
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7299
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7290
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7290
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7267
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7267
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7057
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7057
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7010
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7010
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7002
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7002

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