Cynaropicrin diacetate - Compound Card

Cynaropicrin diacetate

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Cynaropicrin diacetate

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)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)[C@H](C2)OC(=O)C
InChI InChI=1S/C23H26O8/c1-10-7-18(30-22(26)11(2)9-28-14(5)24)20-13(4)23(27)31-21(20)19-12(3)17(8-16(10)19)29-15(6)25/h16-21H,1-4,7-9H2,5-6H3/t16-,17-,18-,19-,20+,21+/m0/s1
InChIKey LGNNWXPKLOJCAU-HQZQWKOLSA-N
Formula C23H26O8
HBA 8
HBD 0
MW 430.45
Rotatable Bonds 5
TPSA 105.2
LogP 2.2
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.48
Exact Mass 430.16
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: 76335787
Nmrshiftdb2: 70061725

No compound-protein relationship available.

Structure

SMILES: O=C(O1)C(=C)C(C1C23)CCC(=C)C3CCC2=C

Level: 0

Mol. Weight: 430.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.6
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.74
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.57

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.55
Plasma Protein Binding
64.89
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.92
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.03
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.47
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.18
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
-29.95
Rat (Acute)
3.16
Rat (Chronic Oral)
2.27
Fathead Minnow
4.14
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
400.1
Hydration Free Energy
-3.53
Log(D) at pH=7.4
2.03
Log(P)
2.37
Log S
-4.21
Log(Vapor Pressure)
-8.59
Melting Point
133.16
pKa Acid
7.8
pKa Basic
3.97
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8508
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8508
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8076
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8076
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7859
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7859
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7792
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7792
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7614
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7614
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7264
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7264

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