2-acetyl-3-methyl-1,8-dimethoxynaphthalene - Compound Card

2-acetyl-3-methyl-1,8-dimethoxynaphthalene

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2-acetyl-3-methyl-1,8-dimethoxynaphthalene

Structure
Zoomed Structure
  • Family: Asphodelaceae
  • Kingdom: Plantae
  • Class: Naphthalene
    • Subclass: Naphthalene Derivative
Canonical Smiles COc1c(C(=O)C)c(C)cc2c1c(OC)ccc2
InChI InChI=1S/C15H16O3/c1-9-8-11-6-5-7-12(17-3)14(11)15(18-4)13(9)10(2)16/h5-8H,1-4H3
InChIKey CVPYOJRRUZFCDK-UHFFFAOYSA-N
Formula C15H16O3
HBA 3
HBD 0
MW 244.29
Rotatable Bonds 3
TPSA 35.53
LogP 3.37
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.27
Exact Mass 244.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Kniphofia reflexa Asphodelaceae Plantae 49723

Showing of synonyms

  • Sema D, Meli Lannang A, et al. (2018). New indane and naphthalene derivatives from the rhizomes of Kniphofia reflexa Hutchinson ex Codd. Phytochemistry Letters, 2018, 26, 78-82. [View] [PubMed]
Pubchem: 10776684
Nmrshiftdb2: 20213308

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 128.17 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.49
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.370
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.120
Plasma Protein Binding
59.38
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
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.660
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.580
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.090
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.200
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
3.510
Rat (Acute)
1.920
Rat (Chronic Oral)
2.080
Fathead Minnow
4.600
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
356.350
Hydration Free Energy
-7.560
Log(D) at pH=7.4
2.620
Log(P)
3.23
Log S
-3.6
Log(Vapor Pressure)
-4.69
Melting Point
71.05
pKa Acid
11.08
pKa Basic
5.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9697
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9527
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9459
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9434
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9427
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9395
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9360
Caspase-7 P55210 CASP7_HUMAN Homo sapiens 3 0.9271
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9144
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9024
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8953
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8877
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8872
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.8681
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8615
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8442
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8346
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8217
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8200
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8165
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8121
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8076
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8072
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8047
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7988
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.7976
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7973
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7946
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7907
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7898
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7856
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.7807
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7795
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.7793
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7788
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7734
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7731
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7717
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7715
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 3 0.7675
Dihydroorotate dehydrogenase (quinone), mitochondrial Q02127 PYRD_HUMAN Homo sapiens 3 0.7660
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7659
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7643
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7627
Orotidine 5'-phosphate decarboxylase Q5L0U0 PYRF_GEOKA Geobacillus kaustophilus 3 0.7621
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7570
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7518
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7514
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7504
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7474
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.7456
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7454
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7443
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7443
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7443
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7434
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7433
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7425
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7400
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7397
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7394
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7389
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7381
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7363
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7363
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7337
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7330
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7324
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7319
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7308
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7308
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7301
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7294
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7273
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7270
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 2 0.7262
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 3 0.7243
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7240
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7238
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7223
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7204
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7198
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.7185
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7182
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7181
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7177
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7156
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7145
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7140
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7138
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7136
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7134
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7125
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7120
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7110
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7105
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 4 0.7095
Reductase homolog Q9ZGC1 Q9ZGC1_STRCY Streptomyces cyanogenus 3 0.7095
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7095
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 3 0.7085
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7080
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7080
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7078
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7077
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7076
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 2 0.7072
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7044
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7035
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7030
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7029
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7021
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7019
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7016
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7011

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