Cnicin - Compound Card

Cnicin

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Cnicin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OC/C/1=C\[C@H]2OC(=O)C(=C)[C@@H]2[C@H](C/C(=C/CC1)/C)OC(=O)C(=C)[C@H](CO)O
InChI InChI=1S/C20H26O7/c1-11-5-4-6-14(9-21)8-17-18(13(3)20(25)27-17)16(7-11)26-19(24)12(2)15(23)10-22/h5,8,15-18,21-23H,2-4,6-7,9-10H2,1H3/b11-5+,14-8-/t15-,16-,17+,18+/m0/s1
InChIKey ZTDFZLVUIVPZDU-QGNHJMHWSA-N
Formula C20H26O7
HBA 7
HBD 3
MW 378.42
Rotatable Bonds 5
TPSA 113.29
LogP 0.95
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 378.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea tougourensis Asteraceae Plantae 1486586
2 Centaurea maroccana Asteraceae Plantae 41503
3 Centaurea bombycina Asteraceae Plantae 351311
4 Centaurea granatensis Asteraceae Plantae 444478
5 Centaurea monticola Asteraceae Plantae 351322
6 Centaurea sulphurea Asteraceae Plantae 41539

Showing of synonyms

  • Barrero AF, Oltra JE, et al. (2000). New sources and antifungal activity of sesquiterpene lactones. Fitoterapia,2000,71,60-64. [View] [PubMed]
  • Nacer A, Merza J, et al. (2012). Sesquiterpene lactones from Centaurea tougourensis. Biochemical Systematics and Ecology,2012,43,163-165. [View]
Pubchem: 5281435
Kegg Ligand: C09362
Chebi: 3768
Nmrshiftdb2: 60026315
Bindingdb: 50466111
CPRiL: 177534
Structure

SMILES: C=C1C(=O)OC(C12)C=CCCC=CCC2

Level: 0

Mol. Weight: 378.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.8
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.7
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.82

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.54
Plasma Protein Binding
47.27
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.11
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.63
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.01
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.15
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
-4.1
Rat (Acute)
3.25
Rat (Chronic Oral)
2.61
Fathead Minnow
4.07
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
418.63
Hydration Free Energy
-9.85
Log(D) at pH=7.4
1.15
Log(P)
0.69
Log S
-2.23
Log(Vapor Pressure)
-8.85
Melting Point
135.91
pKa Acid
6.9
pKa Basic
4.68
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8972
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8972
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8817
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8817
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8649
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8649
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.8635
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.8635
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8575
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8575
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7959
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7959
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7844
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7844
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7475
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7475
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7126
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7126

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