Salonitenolide 8-O-(4'-acetoxy-5'-hydroxyangelate) - Compound Card

Salonitenolide 8-O-(4'-acetoxy-5'-hydroxyangelate)

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Salonitenolide 8-O-(4'-acetoxy-5'-hydroxyangelate)

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C=C(\C(=O)O[C@H]1C/C(=C/CC/C(=C/[C@@H]2[C@@H]1C(=C)C(=O)O2)/CO)/C)/C
InChI InChI=1S/C20H26O5/c1-5-13(3)19(22)24-16-9-12(2)7-6-8-15(11-21)10-17-18(16)14(4)20(23)25-17/h5,7,10,16-18,21H,4,6,8-9,11H2,1-3H3/b12-7+,13-5-,15-10-/t16-,17+,18+/m0/s1
InChIKey ITWYQAIFKHRKRR-XQYCFXPISA-N
Formula C20H26O5
HBA 5
HBD 1
MW 346.42
Rotatable Bonds 3
TPSA 72.83
LogP 3.01
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 346.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea bombycina Asteraceae Plantae 351311

Showing of synonyms

  • Barrero AF, Oltra JE, et al. (2000). New sources and antifungal activity of sesquiterpene lactones. Fitoterapia,2000,71,60-64. [View] [PubMed]
Pubchem: 102119854
Nmrshiftdb2: 60072637

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)C=CCCC=CCC2

Level: 0

Mol. Weight: 346.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.56
Plasma Protein Binding
55.47
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
6.77
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.33
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.21
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.13
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
-2.84
Rat (Acute)
2.48
Rat (Chronic Oral)
2.01
Fathead Minnow
4.51
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
367.18
Hydration Free Energy
-7.16
Log(D) at pH=7.4
2.37
Log(P)
3.11
Log S
-3.99
Log(Vapor Pressure)
-6.67
Melting Point
108.7
pKa Acid
9.04
pKa Basic
4.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8928
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8928
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8496
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8496
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8233
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8233
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7887
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7887
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7741
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7741
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7697
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7697
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7520
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7520
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7443
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7443
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7389
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7389
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7333
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7333
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7299
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7299
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7287
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7287
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7243
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7243
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7134
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7134
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7133
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7133
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7060
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7060
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7041
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7041
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7032
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7032

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