6-methoxytecleanthine - Compound Card

6-methoxytecleanthine

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6-methoxytecleanthine

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles COc1ccc2c(c1OC)n(C)c1c(c2=O)c(OC)c2c(c1)OCO2
InChI InChI=1S/C18H17NO6/c1-19-10-7-12-17(25-8-24-12)18(23-4)13(10)15(20)9-5-6-11(21-2)16(22-3)14(9)19/h5-7H,8H2,1-4H3
InChIKey RATVKISXWJHNNK-UHFFFAOYSA-N
Formula C18H17NO6
HBA 7
HBD 0
MW 343.34
Rotatable Bonds 3
TPSA 68.15
LogP 2.45
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.28
Exact Mass 343.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Teclea trichocarpa Rutaceae Plantae 2695420

Showing of synonyms

  • Muriithi MW, Abraham WR, et al. (2002). Isolation and in vitro antiplasmodial activities of alkaloids from Teclea trichocarpa: in vivo antimalarial activity and X-ray crystal structure of normelicopicine. Journal of Natural Products,2002,65(7),956-959. [View] [PubMed]
Pubchem: 13970980
Nmrshiftdb2: 70014491

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)cc3c(c2)c(=O)c4c([nH]3)cccc4

Level: 0

Mol. Weight: 343.34 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.410
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.96

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.350
Plasma Protein Binding
73.42
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.380
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.350
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.520
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.780
Micronucleos
Toxic
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
0.290
Rat (Acute)
2.450
Rat (Chronic Oral)
1.740
Fathead Minnow
5.270
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
456.430
Hydration Free Energy
-8.320
Log(D) at pH=7.4
1.530
Log(P)
1.91
Log S
-3.31
Log(Vapor Pressure)
-7.33
Melting Point
191.94
pKa Acid
6.7
pKa Basic
2.05
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9744
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9744
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9294
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9294
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9222
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9222
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8900
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8900
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8848
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8848
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.8777
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.8777
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8774
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8774
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8758
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8758
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8641
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8641
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8549
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8549
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8540
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8540
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8517
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8517
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8475
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8475
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8416
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8416
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8343
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8343
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8278
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8278
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8249
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8249
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8203
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8203
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8136
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8136
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8051
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8051
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8034
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8034
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8027
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8027
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8026
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8026
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7991
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7991
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7941
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7941
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7897
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7897
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7886
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7886
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7828
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7828
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7797
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7797
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7752
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7752
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7723
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7723
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7700
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7700
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7688
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7688
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7626
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7626
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7624
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7624
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7614
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7614
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7571
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7571
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7558
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7558
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7478
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7478
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7445
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7445
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7422
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7422
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7404
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7404
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7392
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7392
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7387
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7387
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7383
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7383
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7367
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7367
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7348
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7348
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7344
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7344
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7336
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7336
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7324
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7324
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7318
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7318
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7312
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7312
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7290
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7290
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7287
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7287
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7286
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7286
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7236
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7236
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7230
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7230
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7221
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7221
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7217
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7217
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7215
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7215
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7208
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7208
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7198
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7198
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7192
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7192
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7185
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7185
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7183
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7183
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7165
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7165
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7144
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7144
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7122
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7122
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7096
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7096
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7074
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7074
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7071
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7071
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7071
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7071
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7061
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7061
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7058
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7058
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7034
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7034
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7030
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7030
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7002
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7002

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