4'-acetyl-8alpha-O-(3', 4'-dihydroxy-methylenebutanoyloxy)-4-epi-sonchoucarpolide - Compound Card

4'-acetyl-8alpha-O-(3', 4'-dihydroxy-methylenebutanoyloxy)-4-epi-sonchoucarpolide

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4'-acetyl-8alpha-O-(3', 4'-dihydroxy-methylenebutanoyloxy)-4-epi-sonchoucarpolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles O=C[C@H]1CC[C@H]([C@]2(C1[C@H]1OC(=O)C(=C)C1[C@H](C2)OC(=O)C(=C)C(COC(=O)C)O)C)O
InChI InChI=1S/C22H28O9/c1-10(14(25)9-29-12(3)24)20(27)30-15-7-22(4)16(26)6-5-13(8-23)18(22)19-17(15)11(2)21(28)31-19/h8,13-19,25-26H,1-2,5-7,9H2,3-4H3/t13-,14?,15+,16-,17?,18?,19+,22+/m1/s1
InChIKey OTNZRRSVYLOHOL-ODOBMWSISA-N
Formula C22H28O9
HBA 9
HBD 2
MW 436.46
Rotatable Bonds 6
TPSA 136.43
LogP 0.47
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.64
Exact Mass 436.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea papposa Asteraceae Plantae 1006337

Showing of synonyms

  • Grafakou M.E, Barda C, et al. (2022). In vitro cytotoxic and anti-inflammatory activities of sesquiterpene lactones from Centaurea papposa (Coss.) Greuter. Natural product research, 2022, 36(12), 3211-3215. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 436.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.93
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.750
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.480
Plasma Protein Binding
40.1
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
7.960
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.150
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.590
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.680
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
-32.060
Rat (Acute)
5.060
Rat (Chronic Oral)
1.810
Fathead Minnow
3.970
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
411.160
Hydration Free Energy
-4.550
Log(D) at pH=7.4
0.900
Log(P)
-0.31
Log S
-2.95
Log(Vapor Pressure)
-9.05
Melting Point
154.38
pKa Acid
6.11
pKa Basic
3.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7610
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7286
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7075

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