(+)-cnicin 4'-acetate - Compound Card

(+)-cnicin 4'-acetate

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(+)-cnicin 4'-acetate

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](COC(=O)C)O
InChI InChI=1S/C22H28O8/c1-12-6-5-7-16(10-23)9-19-20(14(3)22(27)30-19)18(8-12)29-21(26)13(2)17(25)11-28-15(4)24/h6,9,17-20,23,25H,2-3,5,7-8,10-11H2,1,4H3/b12-6+,16-9-/t17-,18+,19+,20+/m0/s1
InChIKey CWWRPXCOCWBKLA-XJAMKKJNSA-N
Formula C22H28O8
HBA 8
HBD 2
MW 420.46
Rotatable Bonds 6
TPSA 119.36
LogP 1.53
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 420.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea maroccana Asteraceae Plantae 41503
2 Centaurea monticola Asteraceae Plantae 351322

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]
Pubchem: 162949051
Nmrshiftdb2: 70022537

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 420.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.72
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.93

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.46
Plasma Protein Binding
50.29
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
9.16
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.98
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.74
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.67
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
-16.66
Rat (Acute)
3.29
Rat (Chronic Oral)
2.39
Fathead Minnow
4.24
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
413.57
Hydration Free Energy
-5.83
Log(D) at pH=7.4
1.38
Log(P)
1.41
Log S
-3.09
Log(Vapor Pressure)
-8.75
Melting Point
130.55
pKa Acid
7.51
pKa Basic
4.05
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 0.8448
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8448
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8305
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8305
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8189
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8189
Glycogen synthase P0A6U8 GLGA_ECOLI Escherichia coli 3 0.7706
Glycogen synthase P0A6U8 GLGA_ECOLI Escherichia coli 3 0.7706
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7534
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7534
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7423
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7423
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7292
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7292
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7182
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7182
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.7096
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.7096
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7095
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7095
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7071
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7071
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7045
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7045

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