Cynarascoloside A - Compound Card

Cynarascoloside A

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Cynarascoloside A

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OC[C@H]1O[C@@H](O[C@H]2CC(=C)[C@H]3[C@@H]([C@@H]4[C@@H]2[C@H](C)C(=O)O4)[C@@H]([C@@H](C3)O)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C21H32O9/c1-7-4-12(28-21-18(26)17(25)16(24)13(6-22)29-21)15-9(3)20(27)30-19(15)14-8(2)11(23)5-10(7)14/h8-19,21-26H,1,4-6H2,2-3H3/t8-,9+,10+,11-,12+,13-,14+,15-,16-,17+,18-,19-,21-/m1/s1
InChIKey BOYYQYRAKVYWCI-JSBOQLKZSA-N
Formula C21H32O9
HBA 9
HBD 5
MW 428.48
Rotatable Bonds 3
TPSA 145.91
LogP -1.06
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 428.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cynara cardunculus Asteraceae Plantae 4265

Showing of synonyms

  • Farag MA, El-Ahmady SH, et al. (2013). Metabolomics driven analysis of artichoke leaf and its commercial products via UHPLC–q-TOF-MS and chemometrics. Phytochemistry,2013,95,177-187. [View] [PubMed]
Pubchem: 44144276

No compound-protein relationship available.

Structure

SMILES: C1CCC2C(=C)CC(C(C3C12)CC(=O)O3)OC4CCCCO4

Level: 1

Mol. Weight: 428.48 g/mol

Structure

SMILES: C1CCC2C(=C)CCC(C3C12)CC(=O)O3

Level: 0

Mol. Weight: 428.48 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 428.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.6
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.020
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.19

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.740
Plasma Protein Binding
67.13
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.270
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.350
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.100
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.080
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-34.710
Rat (Acute)
3.920
Rat (Chronic Oral)
3.200
Fathead Minnow
3.710
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
486.110
Hydration Free Energy
-6.800
Log(D) at pH=7.4
0.280
Log(P)
-0.67
Log S
-1.78
Log(Vapor Pressure)
-12.91
Melting Point
176.11
pKa Acid
6.02
pKa Basic
4.56
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8256
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8256
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8028
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8028
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7802
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7802
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7795
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7795
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7663
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7663
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7241
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7241
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7165
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7165
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7055
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7055
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7044
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7044

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