8alpha-O-(3',4'-dihydroxy-2-methylenebutanoyloxy)-15-oxo-5,7RH,6alphaH-eleman-1,3,11(13)-trien-6,12-olide - Compound Card

8alpha-O-(3',4'-dihydroxy-2-methylenebutanoyloxy)-15-oxo-5,7RH,6alphaH-eleman-1,3,11(13)-trien-6,12-olide

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8alpha-O-(3',4'-dihydroxy-2-methylenebutanoyloxy)-15-oxo-5,7RH,6alphaH-eleman-1,3,11(13)-trien-6,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OCC(C(=C)C(=O)O[C@H]1C[C@@](C)(C=C)C([C@@H]2[C@@H]1C(=C)C(=O)O2)C(=C)C=O)O
InChI InChI=1S/C20H24O7/c1-6-20(5)7-14(26-18(24)11(3)13(23)9-22)15-12(4)19(25)27-17(15)16(20)10(2)8-21/h6,8,13-17,22-23H,1-4,7,9H2,5H3/t13?,14-,15+,16?,17-,20+/m0/s1
InChIKey UKOKIVWGORCEQR-LWGFLWSRSA-N
Formula C20H24O7
HBA 7
HBD 2
MW 376.41
Rotatable Bonds 7
TPSA 110.13
LogP 0.87
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.45
Exact Mass 376.15
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)CCCC2

Level: 0

Mol. Weight: 376.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.670
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.1

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.580
Plasma Protein Binding
51.43
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
8.130
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.120
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.620
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.490
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-2.780
Rat (Acute)
5.130
Rat (Chronic Oral)
2.120
Fathead Minnow
4.040
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
385.360
Hydration Free Energy
-8.380
Log(D) at pH=7.4
1.560
Log(P)
1.25
Log S
-2.76
Log(Vapor Pressure)
-8.74
Melting Point
111.97
pKa Acid
5.47
pKa Basic
3.76
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.9590
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8757
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8216
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7729
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7251
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7195
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7173
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7173
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7119

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