Chlorojanerin - Compound Card

Chlorojanerin

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Chlorojanerin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OCC(=C)C(=O)O[C@H]1CC(=C)[C@H]2[C@@H]([C@@H]3[C@@H]1C(=C)C(=O)O3)[C@@]([C@H](C2)O)(O)CCl
InChI InChI=1S/C19H23ClO7/c1-8-4-12(26-17(23)9(2)6-21)14-10(3)18(24)27-16(14)15-11(8)5-13(22)19(15,25)7-20/h11-16,21-22,25H,1-7H2/t11-,12-,13-,14+,15-,16-,19+/m0/s1
InChIKey UHEMKMBRGXUBMJ-URUZQALBSA-N
Formula C19H23ClO7
HBA 7
HBD 3
MW 398.84
Rotatable Bonds 4
TPSA 113.29
LogP 0.47
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.58
Exact Mass 398.11
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: 182408
CPRiL: 232307
Structure

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

Level: 0

Mol. Weight: 398.84 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.840
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.510
Plasma Protein Binding
48.82
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
9.180
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.250
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.530
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.970
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
-4.390
Rat (Acute)
4.070
Rat (Chronic Oral)
2.400
Fathead Minnow
3.960
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
422.150
Hydration Free Energy
-8.700
Log(D) at pH=7.4
1.070
Log(P)
0.52
Log S
-2.67
Log(Vapor Pressure)
-9.7
Melting Point
150.3
pKa Acid
5.94
pKa Basic
3.7
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8473
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8473
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8241
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8241
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7888
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7888
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7843
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7843
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7421
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7421
Ascorbate-specific PTS system EIIC component P39301 ULAA_ECOLI Escherichia coli 3 0.7365
Ascorbate-specific PTS system EIIC component P39301 ULAA_ECOLI Escherichia coli 3 0.7365
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7062
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7062

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