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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
Canonical Smiles COC(=O)C1=C(CC=C(C)C)C(=O)c2c(C1=O)cccc2
InChI InChI=1S/C17H16O4/c1-10(2)8-9-13-14(17(20)21-3)16(19)12-7-5-4-6-11(12)15(13)18/h4-8H,9H2,1-3H3
InChIKey RGLUQJRFDAZRRZ-UHFFFAOYSA-N
Formula C17H16O4
HBA 4
HBD 0
MW 284.31
Rotatable Bonds 3
TPSA 60.44
LogP 2.89
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 284.1
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]
Pubchem: 617076
Nmrshiftdb2: 70115155

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C(=O)C=CC2=O

Level: 0

Mol. Weight: 284.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.46
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.460
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.97

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.740
Plasma Protein Binding
29.16
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
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
3.560
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.670
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.240
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.020
Micronucleos
Safe
NR-AhR
Toxic
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
4.130
Rat (Acute)
2.460
Rat (Chronic Oral)
2.810
Fathead Minnow
4.790
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
365.300
Hydration Free Energy
-6.980
Log(D) at pH=7.4
2.930
Log(P)
3.71
Log S
-4.75
Log(Vapor Pressure)
-5.31
Melting Point
91.37
pKa Acid
7.58
pKa Basic
4.54
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8291
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8291
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.8168
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.8168
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8019
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8019
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7981
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7981
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7855
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7855
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7815
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7815
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7759
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7759
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7656
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7656
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7573
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7573
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7534
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7534
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7432
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7432
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7389
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7389
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7365
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7365
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7299
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7299
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7269
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7269
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7267
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7267
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7196
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7196
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7184
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7184
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7181
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7181
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7156
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7156
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7151
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7151
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7140
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7140
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 2 0.7139
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 2 0.7139
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7125
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7125
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7105
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7105
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7085
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7085
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7061
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7061
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7056
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7056
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7035
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7035
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7022
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7022
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7021
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7021

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