Centaurepensin - Compound Card

Centaurepensin

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Centaurepensin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles ClCC1(O)C(O)CC2C1C1OC(=O)C(=C)C1C(CC2=C)OC(=O)C(CCl)(O)C
InChI InChI=1S/C19H24Cl2O7/c1-8-4-11(27-17(24)18(3,25)6-20)13-9(2)16(23)28-15(13)14-10(8)5-12(22)19(14,26)7-21/h10-15,22,25-26H,1-2,4-7H2,3H3
InChIKey NUVAJKJDTZTFLK-UHFFFAOYSA-N
Formula C19H24Cl2O7
HBA 7
HBD 3
MW 435.3
Rotatable Bonds 4
TPSA 113.29
LogP 0.91
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 434.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea musimomum Asteraceae Plantae 41503
2 Centaurea sivasica Asteraceae Plantae 1486579

Showing of synonyms

  • Al-Easa HS, Mann J, et al. (1990). Guaianolides from Centaurea sinaica. Phytochemistry,1990,29(4),1324-1325. [View]
  • Medjroubi K, Benayache F, et al. (2005). Sesquiterpene lactones from Centaurea musimomum. Antiplasmodial and cytotoxic activities. Fitoterapia,2005,76,744-746. [View] [PubMed]
Pubchem: 322747

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)C3C(CCC3)C(=C)CC2

Level: 0

Mol. Weight: 435.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.98
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.81
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.66
Plasma Protein Binding
12.31
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
7.82
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.45
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.34
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.69
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-2.84
Rat (Acute)
3.75
Rat (Chronic Oral)
2.25
Fathead Minnow
4.13
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
413.71
Hydration Free Energy
-8.14
Log(D) at pH=7.4
1.54
Log(P)
1.1
Log S
-2.72
Log(Vapor Pressure)
-8.25
Melting Point
145.53
pKa Acid
6.63
pKa Basic
4.61
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8451
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8451
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8262
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8262
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7865
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7865
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7831
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7831
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7808
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7808
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7380
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7380
Ascorbate-specific PTS system EIIC component P39301 ULAA_ECOLI Escherichia coli 3 0.7304
Ascorbate-specific PTS system EIIC component P39301 ULAA_ECOLI Escherichia coli 3 0.7304
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7171
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7171
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7008
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7008

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