19-desoxy-15-chlorojanerin - Compound Card

19-desoxy-15-chlorojanerin

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19-desoxy-15-chlorojanerin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae-Compositae
  • 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(=C)C
InChI InChI=1S/C19H23ClO6/c1-8(2)17(22)25-12-5-9(3)11-6-13(21)19(24,7-20)15(11)16-14(12)10(4)18(23)26-16/h11-16,21,24H,1,3-7H2,2H3/t11-,12-,13-,14+,15-,16-,19+/m0/s1
InChIKey ONMAQPPVCANFPB-URUZQALBSA-N
Formula C19H23ClO6
HBA 6
HBD 2
MW 382.84
Rotatable Bonds 3
TPSA 93.06
LogP 1.5
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.58
Exact Mass 382.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea musimomum Asteraceae-Compositae 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: 182337
CPRiL: 215438
Structure

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

Level: 0

Mol. Weight: 382.84 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.8
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.52
Plasma Protein Binding
52.04
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
9.77
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.63
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.58
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.74
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
-1.4
Rat (Acute)
4.02
Rat (Chronic Oral)
2.11
Fathead Minnow
3.94
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
389.73
Hydration Free Energy
-7.94
Log(D) at pH=7.4
1.6
Log(P)
2.05
Log S
-3.24
Log(Vapor Pressure)
-8.8
Melting Point
152.63
pKa Acid
6.66
pKa Basic
4.05
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8281
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8281
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8123
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8123
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7881
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7881
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7688
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7688
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7394
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7394
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7260
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7260

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