8alpha-hydroxy-11beta,13-dihydro-4-epi-sonchucarpolide - Compound Card

8alpha-hydroxy-11beta,13-dihydro-4-epi-sonchucarpolide

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8alpha-hydroxy-11beta,13-dihydro-4-epi-sonchucarpolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C[C@H]1CC[C@H]([C@]2(C1[C@H]1OC(=O)[C@H]([C@@H]1[C@H](C2)O)C)C)O
InChI InChI=1S/C15H22O5/c1-7-11-9(17)5-15(2)10(18)4-3-8(6-16)12(15)13(11)20-14(7)19/h6-13,17-18H,3-5H2,1-2H3/t7-,8+,9-,10+,11+,12?,13-,15-/m0/s1
InChIKey PJGXBSCTZLDUJY-PPAXCSNISA-N
Formula C15H22O5
HBA 5
HBD 2
MW 282.34
Rotatable Bonds 1
TPSA 83.83
LogP 0.52
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.87
Exact Mass 282.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea pullata Asteraceae Plantae 347528

Showing of synonyms

  • Djeddi S, Karioti A, et al. (2008). A novel sesquiterpene lactone from Centaurea pullata: Structure elucidation, antimicrobial activity, and prediction of pharmacokinetic properties. Bioorganic and Medicinal Chemistry,2008,16,3725-3731. [View] [PubMed]
Pubchem: 163006665

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C12)C3C(CC2)CCCC3

Level: 0

Mol. Weight: 282.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.520
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.320
Plasma Protein Binding
34.98
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
7.490
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.350
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.010
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.270
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
-2.440
Rat (Acute)
4.110
Rat (Chronic Oral)
1.230
Fathead Minnow
3.680
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
367.110
Hydration Free Energy
-9.570
Log(D) at pH=7.4
0.430
Log(P)
-0.45
Log S
-1.67
Log(Vapor Pressure)
-7.02
Melting Point
181.31
pKa Acid
6.82
pKa Basic
5.82
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9040
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9040
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7632
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7632
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7088
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7088

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