8alpha-[2'-hydroxymethyl-2'-butenoyloxy]-sonchucarpolide - Compound Card

8alpha-[2'-hydroxymethyl-2'-butenoyloxy]-sonchucarpolide

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8alpha-[2'-hydroxymethyl-2'-butenoyloxy]-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([C@H]1[C@H]1OC(=O)C(=C)[C@@H]1[C@H](C2)OC(=O)/C(=C\C)/CO)C)O
InChI InChI=1S/C20H26O7/c1-4-11(8-21)19(25)26-13-7-20(3)14(23)6-5-12(9-22)16(20)17-15(13)10(2)18(24)27-17/h4,9,12-17,21,23H,2,5-8H2,1,3H3/b11-4-/t12-,13-,14+,15+,16+,17-,20-/m0/s1
InChIKey JAMSYNVVOFKKIY-FRAXHVOESA-N
Formula C20H26O7
HBA 7
HBD 2
MW 378.42
Rotatable Bonds 4
TPSA 110.13
LogP 0.93
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 378.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea maroccana Asteraceae Plantae 41503

Showing of synonyms

  • Bicha S, Chalard P, et al. (2013). Maroccanin: a new gamma-lactone and other constituents from Centaurea maroccana ball. (Asteraceae). Records of Natural Products,2013,7(2),114-118. [View]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 378.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.720
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.54

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.460
Plasma Protein Binding
49.13
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
7.010
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.460
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.050
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.710
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
Toxic
T. Pyriformis
-6.630
Rat (Acute)
4.670
Rat (Chronic Oral)
1.770
Fathead Minnow
3.960
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
406.730
Hydration Free Energy
-8.190
Log(D) at pH=7.4
1.190
Log(P)
0.25
Log S
-2.89
Log(Vapor Pressure)
-8.39
Melting Point
160.46
pKa Acid
6.27
pKa Basic
4.86

No predicted protein targets found for this compound.

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