Epi-centaurepensin - Compound Card

Epi-centaurepensin

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Epi-centaurepensin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles ClC[C@@]1(O)[C@H](O)C[C@@H]2[C@H]1[C@@H]1OC(=O)C(=C)[C@@H]1[C@H](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/t10-,11-,12+,13+,14-,15+,18+,19+/m0/s1
InChIKey NUVAJKJDTZTFLK-ZOOYRBDCSA-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

Showing of synonyms

  • Medjroubi K, Benayache F, et al. (2005). Sesquiterpene lactones from Centaurea musimomum. Antiplasmodial and cytotoxic activities. Fitoterapia,2005,76,744-746. [View] [PubMed]
Pubchem: 163046082

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)
-4.95
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.81
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.32

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.63
Plasma Protein Binding
56.38
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.54
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.29
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.28
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.44
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
-7.48
Rat (Acute)
3.78
Rat (Chronic Oral)
2.16
Fathead Minnow
4.02
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
432.65
Hydration Free Energy
-8.1
Log(D) at pH=7.4
1.68
Log(P)
1.1
Log S
-2.82
Log(Vapor Pressure)
-9.24
Melting Point
158.42
pKa Acid
6.52
pKa Basic
4.59
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8232
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8232
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8060
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8060
Glycogen synthase P0A6U8 GLGA_ECOLI Escherichia coli 3 0.8001
Glycogen synthase P0A6U8 GLGA_ECOLI Escherichia coli 3 0.8001
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7936
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7936
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7819
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7819
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7642
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7642
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7235
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7235
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7098
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7098
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7071
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7071
Lactose operon repressor P03023 LACI_ECOLI Escherichia coli 3 0.7061
Lactose operon repressor P03023 LACI_ECOLI Escherichia coli 3 0.7061
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7045
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7045

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