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

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

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

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CO[C@@]12OC(=O)C(=C2C[C@]2([C@]3(C1)O[C@@H]3CC[C@@H]2C)C)C
InChI InChI=1S/C16H22O4/c1-9-5-6-12-15(19-12)8-16(18-4)11(7-14(9,15)3)10(2)13(17)20-16/h9,12H,5-8H2,1-4H3/t9-,12+,14+,15+,16+/m0/s1
InChIKey HKAIYTYUJIXIHQ-HMZGLDLJSA-N
Formula C16H22O4
HBA 4
HBD 0
MW 278.35
Rotatable Bonds 1
TPSA 48.06
LogP 2.57
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.81
Exact Mass 278.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio aegyptius Asteraceae-Compositae 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: 11288945
Nmrshiftdb2: 70034913

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 206.24 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.95
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.51
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.12
Plasma Protein Binding
27.07
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.97
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.86
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.42
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.26
Micronucleos
Safe
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
-2.13
Rat (Acute)
1.99
Rat (Chronic Oral)
1.35
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
333.23
Hydration Free Energy
-4.03
Log(D) at pH=7.4
2.9
Log(P)
2.42
Log S
-3.05
Log(Vapor Pressure)
-3.63
Melting Point
95.37
pKa Acid
5.74
pKa Basic
4.47
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 0.9335
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9335
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9145
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9145
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9140
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9140
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9105
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9105
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9077
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9077
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9038
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9038
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.9021
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.9021
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.9003
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.9003
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8925
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8925
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8909
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8909
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8866
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8866
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8861
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8861
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8768
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8768
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8755
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8755
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8729
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8729
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8688
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8688
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8659
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8659
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8520
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8520
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8516
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8516
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8428
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8428
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8412
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8412
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8216
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8216
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8161
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8161
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7950
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7950
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7910
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7910
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7888
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7888
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7867
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7867
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7856
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7856
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7737
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7737
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7734
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7734
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7720
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7720
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7717
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7717
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7717
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7717
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7672
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7672
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7619
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7619
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7599
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7599
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7598
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7598
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7572
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7572
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7569
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7569
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7559
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7559
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7554
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7554
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7547
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7547
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7545
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7545
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7528
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7528
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7523
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7523
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7516
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7516
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7515
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7515
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7513
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7513
Cholesterol oxidase P22637 CHOD_BREST Brevibacterium sterolicum 3 0.7513
Cholesterol oxidase P22637 CHOD_BREST Brevibacterium sterolicum 3 0.7513
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7510
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7510
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7502
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7502
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7493
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7493
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7479
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7479
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7478
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7478
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7472
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7472
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7468
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7468
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7466
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7466
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7458
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7458
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7455
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7455
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7452
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7452
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7439
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7439
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7426
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7426
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7409
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7409
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7406
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7406
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7406
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7406
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7392
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7392
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7383
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7383
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7376
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7376
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7350
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7350
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7334
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7334
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7310
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7310
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7304
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7304
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7298
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7298
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7288
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7288
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7276
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7276
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7246
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7246
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7236
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7236
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7222
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7222
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7219
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7219
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7209
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7209
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7208
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7208
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7179
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7179
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7177
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7177
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7137
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7137
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7133
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7133
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7128
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7128
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7076
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7076
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 2 0.7021
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 2 0.7021
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7008
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7008

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