Methyl-2,3-epoxy-3-prenyl-1,4-naphthoquinone-2-carboxylate - Compound Card

Methyl-2,3-epoxy-3-prenyl-1,4-naphthoquinone-2-carboxylate

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Methyl-2,3-epoxy-3-prenyl-1,4-naphthoquinone-2-carboxylate

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
Canonical Smiles CC(=CCC12OC2(C(=O)O)C(=O)c2c(C1=O)c(C)ccc2)C
InChI InChI=1S/C17H16O5/c1-9(2)7-8-16-14(19)12-10(3)5-4-6-11(12)13(18)17(16,22-16)15(20)21/h4-7H,8H2,1-3H3,(H,20,21)
InChIKey GQYVGRMZWVLFHV-UHFFFAOYSA-N
Formula C17H16O5
HBA 4
HBD 1
MW 300.31
Rotatable Bonds 3
TPSA 83.97
LogP 2.32
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 300.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pentas longiflora Rubiaceae Plantae 387060

Showing of synonyms

  • El-Hady S, Bukuru J, et al. (2002). New pyranonaphthoquinone and pyranonaphthohydroquinone from the roots of Pentas longiflora. Journal of Natural Products,2002,65(9),1377-1379. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C12C(O2)C(=O)c3c(C1=O)cccc3

Level: 0

Mol. Weight: 300.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.89
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.81
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.7
Plasma Protein Binding
20.66
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
9.68
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.29
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.27
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.86
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
4.2
Rat (Acute)
2.22
Rat (Chronic Oral)
2.72
Fathead Minnow
4.43
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
358.41
Hydration Free Energy
-7.61
Log(D) at pH=7.4
-0.9
Log(P)
3.15
Log S
-2.9
Log(Vapor Pressure)
-6.88
Melting Point
120.92
pKa Acid
3.32
pKa Basic
4.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8877
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8877
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 3 0.8298
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 3 0.8298
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7989
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7989
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7573
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7573
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7473
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7473
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7446
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7446
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 3 0.7409
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 3 0.7409
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7399
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7399
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7386
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7386
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7304
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7304
Kynurenine 3-monooxygenase P38169 KMO_YEAST Saccharomyces cerevisiae 3 0.7152
Kynurenine 3-monooxygenase P38169 KMO_YEAST Saccharomyces cerevisiae 3 0.7152
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7113
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7113
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7016
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7016

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