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Teclenatalensine B
- Family: Plantae - Rutaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Furoquinoline Alkaloid
| Canonical Smiles | COc1cc2nc3occc3c(c2cc1OCC=C(C)C)OC |
|---|---|
| InChI | InChI=1S/C18H19NO4/c1-11(2)5-7-22-16-9-13-14(10-15(16)20-3)19-18-12(6-8-23-18)17(13)21-4/h5-6,8-10H,7H2,1-4H3 |
| InChIKey | SGFRKYCYSYEBHF-UHFFFAOYSA-N |
| Formula | C18H19NO4 |
| HBA | 5 |
| HBD | 0 |
| MW | 313.35 |
| Rotatable Bonds | 5 |
| TPSA | 53.72 |
| LogP | 4.34 |
| Number Rings | 3 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.28 |
| Exact Mass | 313.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Teclea natalensis | Rutaceae | Plantae | 1237831 |
Showing of synonyms
Teclenatalensine B
Tecleanatalensine B
4,7-Dimethoxy-6-(3-methylbut-2-enoxy)furo[2,3-b]quinoline
4,7-dimethoxy-6-(3-methylbut-2-enoxy)furo(2,3-b)quinoline
851770-81-5
- Tarus PK, Coombes PH, et al. (2005). Furoquinoline alkaloids from the southern African Rutaceae Teclea natalensis. Phytochemistry, 2005, 66(6), 703–706. [View]
No compound-protein relationship available.
SMILES: c1coc(c12)nc3c(c2)cccc3
Level: 0
Mol. Weight: 313.35 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.58
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.470
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.24
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.190
- Plasma Protein Binding
- 80.67
- 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
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.720
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 2.310
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.190
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.390
- 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
- 2.190
- Rat (Acute)
- 2.610
- Rat (Chronic Oral)
- 2.310
- Fathead Minnow
- 5.310
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 412.100
- Hydration Free Energy
- -8.930
- Log(D) at pH=7.4
- 3.820
- Log(P)
- 4.04
- Log S
- -4.38
- Log(Vapor Pressure)
- -6.5
- Melting Point
- 100.67
- pKa Acid
- 9.14
- pKa Basic
- 6.69
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9518 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9351 |
| Fatty acid-binding protein, intestinal | P12104 | FABPI_HUMAN | Homo sapiens | 3 | 0.9106 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8997 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.8945 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.8883 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8871 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.8783 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8590 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8540 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8480 |
| Prolyl endopeptidase | P23687 | PPCE_PIG | Sus scrofa | 3 | 0.8401 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 4 | 0.8224 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.8155 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.8153 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.8135 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8106 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8032 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 3 | 0.8022 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8010 |
| Beta-2 adrenergic receptor | P07550 | ADRB2_HUMAN | Homo sapiens | 2 | 0.7991 |
| Terminal oxygenase component of carbazole | Q84II6 | Q84II6_JANS3 | Janthinobacterium sp | 3 | 0.7974 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7941 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.7906 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7811 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.7806 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 2 | 0.7787 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7778 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7763 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7756 |
| 4,4'-diapophytoene synthase | A9JQL9 | CRTM_STAAU | Staphylococcus aureus | 2 | 0.7754 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7746 |
| Putative protease I | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron | 2 | 0.7746 |
| Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 3 | 0.7742 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7739 |
| Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 3 | 0.7701 |
| Aclacinomycin 10-hydroxylase RdmB | Q54527 | RDMB_STREF | Streptomyces purpurascens | 3 | 0.7672 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7645 |
| TetR family transcriptional regulator | Q58L87 | Q58L87_MYCSM | Mycolicibacterium smegmatis | 2 | 0.7628 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 3 | 0.7627 |
| Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 3 | 0.7619 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7619 |
| Cell division cycle 7-related protein kinase | O00311 | CDC7_HUMAN | Homo sapiens | 3 | 0.7584 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7564 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7558 |
| Prostaglandin F2a synthase | Q8I6L9 | Q8I6L9_TRYCR | Trypanosoma cruzi | 2 | 0.7558 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7545 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7539 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7530 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7528 |
| Cholinesterase | P06276 | CHLE_HUMAN | Homo sapiens | 2 | 0.7525 |
| Acetyl-CoA carboxylase | Q00955 | ACAC_YEAST | Saccharomyces cerevisiae | 3 | 0.7523 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 2 | 0.7510 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7504 |
| DNA ligase | P43813 | DNLJ_HAEIN | Haemophilus influenzae | 2 | 0.7504 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7497 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7493 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7485 |
| Putative ketoacyl reductase | P16544 | ACT3_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7477 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7459 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7450 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7446 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7436 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 2 | 0.7435 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 2 | 0.7432 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7429 |
| Cytohesin-2 | Q99418 | CYH2_HUMAN | Homo sapiens | 3 | 0.7427 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7427 |
| Putative ketoacyl reductase | P16544 | ACT3_STRCO | Streptomyces coelicolor / M145) | 2 | 0.7417 |
| Protein S100-A13 | Q99584 | S10AD_HUMAN | Homo sapiens | 2 | 0.7414 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7409 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 2 | 0.7407 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 3 | 0.7399 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 2 | 0.7397 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 2 | 0.7387 |
| Catalase-peroxidase 2 | O59651 | KATG2_HALMA | Haloarcula marismortui | 2 | 0.7358 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7358 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 2 | 0.7354 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7349 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7343 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 2 | 0.7343 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 2 | 0.7343 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7336 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 2 | 0.7335 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 3 | 0.7334 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 2 | 0.7315 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7302 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7301 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7297 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 2 | 0.7282 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 2 | 0.7280 |
| Reductase homolog | Q9ZGC1 | Q9ZGC1_STRCY | Streptomyces cyanogenus | 3 | 0.7279 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7254 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7243 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7242 |
| Steroid hormone receptor ERR1 | P11474 | ERR1_HUMAN | Homo sapiens | 3 | 0.7227 |
| Prostaglandin G/H synthase 1 | P05979 | PGH1_SHEEP | Ovis aries | 3 | 0.7225 |
| Cytochrome P450 | S6BVH1 | S6BVH1_RHOER | Rhodococcus erythropolis | 3 | 0.7225 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7223 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7214 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7213 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7205 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7201 |
| ATP synthase subunit alpha, mitochondrial | P19483 | ATPA_BOVIN | Bos taurus | 2 | 0.7185 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7179 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7178 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7175 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7172 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7168 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7166 |
| Prostaglandin G/H synthase 2 | Q05769 | PGH2_MOUSE | Mus musculus | 2 | 0.7158 |
| Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase | Q46381 | BPHB_COMTE | Comamonas testosteroni | 3 | 0.7156 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 2 | 0.7149 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7140 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7126 |
| Tyrosine-protein kinase ITK/TSK | Q08881 | ITK_HUMAN | Homo sapiens | 3 | 0.7123 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7115 |
| Enoyl-ACP reductase | Q9BJJ9 | Q9BJJ9_PLAFA | Plasmodium falciparum | 2 | 0.7113 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 2 | 0.7107 |
| Casein kinase I isoform gamma-3 | Q9Y6M4 | KC1G3_HUMAN | Homo sapiens | 3 | 0.7106 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7099 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 2 | 0.7099 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 2 | 0.7093 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7090 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7087 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 2 | 0.7086 |
| Fatty acid-binding protein, adipocyte | P04117 | FABP4_MOUSE | Mus musculus | 2 | 0.7078 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 2 | 0.7074 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 2 | 0.7069 |
| Cytochrome P450 130 | P9WPN5 | CP130_MYCTU | Mycobacterium tuberculosis | 2 | 0.7069 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7064 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7045 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 2 | 0.7044 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7044 |
| Biphenyl dioxygenase subunit alpha | P37333 | BPHA_PARXL | Paraburkholderia xenovorans | 3 | 0.7027 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7014 |
| Biotin carboxylase | P24182 | ACCC_ECOLI | Escherichia coli | 3 | 0.7014 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7009 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7004 |