Chlorogenoquinone - Compound Card

Chlorogenoquinone

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Chlorogenoquinone

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Quinone
Canonical Smiles O=C(O[C@@H]1C[C@](O)(C[C@H]([C@@H]1O)O)C(=O)O)/C=C\C1=CC(=O)C(=O)C=C1
InChI InChI=1S/C16H16O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,19,21,24H,6-7H2,(H,22,23)/b4-2-/t11-,12-,14+,16-/m1/s1
InChIKey ITENTBHADJNDDH-DJTMHQFBSA-N
Formula C16H16O9
HBA 8
HBD 4
MW 352.3
Rotatable Bonds 4
TPSA 158.43
LogP -1.58
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 352.08
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: 163028953
Nmrshiftdb2: 70019518
CPRiL: 407141
Structure

SMILES: C1CCCCC1OC(=O)C=CC2=CC(=O)C(=O)C=C2

Level: 1

Mol. Weight: 352.3 g/mol

Structure

SMILES: O=C1C(=O)C=CC=C1

Level: 0

Mol. Weight: 352.3 g/mol

Structure

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 352.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.08
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.82
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.7
Plasma Protein Binding
46.22
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
2.41
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-3.01
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.13
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.07
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-3.77
Rat (Acute)
2.17
Rat (Chronic Oral)
3.16
Fathead Minnow
3.84
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
434.42
Hydration Free Energy
-11.25
Log(D) at pH=7.4
-1.41
Log(P)
-1.29
Log S
-1.88
Log(Vapor Pressure)
-13.0
Melting Point
184.5
pKa Acid
2.47
pKa Basic
6.38
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8292
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8292
Mevalonate kinase Q4Q6K7 Q4Q6K7_LEIMA Leishmania major 3 0.7413
Mevalonate kinase Q4Q6K7 Q4Q6K7_LEIMA Leishmania major 3 0.7413
Shikimate dehydrogenase (NADP(+)) P56119 AROE_HELPY Helicobacter pylori 3 0.7038
Shikimate dehydrogenase (NADP(+)) P56119 AROE_HELPY Helicobacter pylori 3 0.7038

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