8alpha-O-(4-hydroxy-2-methylenebutanoyloxy)-11beta,13- dihydro-4-epi-sonchucarpolide - Compound Card

8alpha-O-(4-hydroxy-2-methylenebutanoyloxy)-11beta,13- dihydro-4-epi-sonchucarpolide

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8alpha-O-(4-hydroxy-2-methylenebutanoyloxy)-11beta,13- dihydro-4-epi-sonchucarpolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OCCC(=C)C(=O)O[C@H]1C[C@@]2(C)[C@H](O)CC[C@@H](C2[C@@H]2[C@@H]1[C@H](C)C(=O)O2)C=O
InChI InChI=1S/C20H28O7/c1-10(6-7-21)18(24)26-13-8-20(3)14(23)5-4-12(9-22)16(20)17-15(13)11(2)19(25)27-17/h9,11-17,21,23H,1,4-8H2,2-3H3/t11-,12+,13-,14+,15+,16?,17-,20-/m0/s1
InChIKey OWTWBLYOTMJQME-QJPKKHCDSA-N
Formula C20H28O7
HBA 7
HBD 2
MW 380.44
Rotatable Bonds 5
TPSA 110.13
LogP 1.01
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 380.18
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. (2007). Minor sesquiterpene lactones from Centaurea pullata and their antimicrobial activity. Journal of Natural Products,2007,70,1796-1799. [View] [PubMed]
Pubchem: 24178999

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 380.44 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.710
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.18

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.460
Plasma Protein Binding
41.81
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.570
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.080
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
Toxic
Daphnia Maga
5.840
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-7.560
Rat (Acute)
4.570
Rat (Chronic Oral)
1.560
Fathead Minnow
3.920
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
416.210
Hydration Free Energy
-7.550
Log(D) at pH=7.4
1.040
Log(P)
0.19
Log S
-2.78
Log(Vapor Pressure)
-8.47
Melting Point
143.28
pKa Acid
6.96
pKa Basic
4.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7580
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7580
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7454
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7454

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