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N13-methyl-3-methoxyrutaecarpine
- Family: Plantae - Rutaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical Smiles | COc1ccc2c(c1)C(=O)N1N(C2)c2c(CC1)c1c(n2C)cccc1 |
|---|---|
| InChI | InChI=1S/C20H19N3O2/c1-21-18-6-4-3-5-15(18)16-9-10-22-20(24)17-11-14(25-2)8-7-13(17)12-23(22)19(16)21/h3-8,11H,9-10,12H2,1-2H3 |
| InChIKey | ZVMGGPJAEXWYLW-UHFFFAOYSA-N |
| Formula | C20H19N3O2 |
| HBA | 4 |
| HBD | 0 |
| MW | 333.39 |
| Rotatable Bonds | 1 |
| TPSA | 37.71 |
| LogP | 3.12 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.25 |
| Exact Mass | 333.15 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Araliopsis soyauxii | Rutaceae | Plantae | 1317904 |
Showing of synonyms
N13-methyl-3-methoxyrutaecarpine
No compound-protein relationship available.
SMILES: c1cccc2[nH]c(c3c12)N4N(CC3)C(=O)c5c(C4)cccc5
Level: 0
Mol. Weight: 333.39 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.91
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.560
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.57
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.130
- Plasma Protein Binding
- 62.87
- 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
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 9.380
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.710
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.300
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.750
- 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
- -1.110
- Rat (Acute)
- 2.260
- Rat (Chronic Oral)
- 1.250
- Fathead Minnow
- 5.000
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 477.190
- Hydration Free Energy
- -6.100
- Log(D) at pH=7.4
- 3.270
- Log(P)
- 3.52
- Log S
- -4.98
- Log(Vapor Pressure)
- -9.13
- Melting Point
- 207.08
- pKa Acid
- 11.43
- pKa Basic
- 5.15
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 3 | 0.9154 |
| Cytochrome P450 1A1 | P04798 | CP1A1_HUMAN | Homo sapiens | 3 | 0.8935 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8849 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.8815 |
| Methionine aminopeptidase 2 | P50579 | MAP2_HUMAN | Homo sapiens | 3 | 0.8774 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.8662 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 3 | 0.8605 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8554 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.8543 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8431 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 4 | 0.8418 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.8414 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 3 | 0.8413 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.8374 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.8345 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 4 | 0.8308 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.8290 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8283 |
| Multidrug-efflux transporter 1 regulator | P39075 | BMRR_BACSU | Bacillus subtilis | 3 | 0.8274 |
| UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase | Q8DNV6 | Q8DNV6_STRR6 | Streptococcus pneumoniae | 3 | 0.8244 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7981 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7888 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7863 |
| Protease | O38896 | O38896_9HIV1 | Human immunodeficiency virus 1 | 2 | 0.7863 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7832 |
| Serine/threonine-protein kinase 10 | O94804 | STK10_HUMAN | Homo sapiens | 3 | 0.7812 |
| AGAP001556-PA | Q7PXT9 | Q7PXT9_ANOGA | Anopheles gambiae | 3 | 0.7781 |
| Chalcone--flavanone isomerase 1 | P28012 | CFI1_MEDSA | Medicago sativa | 3 | 0.7769 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.7758 |
| Chalcone--flavanone isomerase 1 | P28012 | CFI1_MEDSA | Medicago sativa | 3 | 0.7757 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7728 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7698 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7629 |
| Enoyl-acyl carrier reductase | C6KSZ2 | C6KSZ2_PLAF7 | Plasmodium falciparum | 4 | 0.7618 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 2 | 0.7589 |
| Lanosterol synthase | P48449 | ERG7_HUMAN | Homo sapiens | 3 | 0.7581 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7580 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7569 |
| Lanosterol 14-alpha demethylase | A6ZSR0 | A6ZSR0_YEAS7 | Saccharomyces cerevisiae | 3 | 0.7552 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7550 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7545 |
| Sterol 14-alpha demethylase | Q7Z1V1 | CP51_TRYCC | Trypanosoma cruzi | 4 | 0.7526 |
| Nitroreductase domain-containing protein | Q8DW21 | Q8DW21_STRMU | Streptococcus mutans serotype c | 3 | 0.7509 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7486 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | Q5NGQ3 | Q5NGQ3_FRATT | Francisella tularensis subsp. tularensis | 3 | 0.7483 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7476 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7428 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7426 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7423 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 4 | 0.7403 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 3 | 0.7402 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7400 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7397 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7384 |
| Amine oxidase [flavin-containing] B | P27338 | AOFB_HUMAN | Homo sapiens | 3 | 0.7383 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.7361 |
| Sterol 14-alpha demethylase | Q7Z1V1 | CP51_TRYCC | Trypanosoma cruzi | 4 | 0.7360 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 4 | 0.7353 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7327 |
| Cytochrome P450 2C19 | P33261 | CP2CJ_HUMAN | Homo sapiens | 3 | 0.7318 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7311 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7272 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7263 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 4 | 0.7259 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7249 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7221 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7217 |
| Beta-2 adrenergic receptor | P07550 | ADRB2_HUMAN | Homo sapiens | 3 | 0.7205 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7195 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7191 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7187 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 4 | 0.7170 |
| Prostaglandin F2a synthase | Q8I6L9 | Q8I6L9_TRYCR | Trypanosoma cruzi | 2 | 0.7168 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.7167 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7152 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7147 |
| Anthocyanidin 3-O-glucosyltransferase UFGT | P51094 | UFOG_VITVI | Vitis vinifera | 3 | 0.7147 |
| RNA-dependent RNA polymerase | Q6A562 | Q6A562_9VIRU | Thosea asigna virus | 2 | 0.7129 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 2 | 0.7122 |
| Glycylpeptide N-tetradecanoyltransferase | A5K1A2 | A5K1A2_PLAVS | Plasmodium vivax | 3 | 0.7116 |
| Tryptase alpha/beta-1 | Q15661 | TRYB1_HUMAN | Homo sapiens | 3 | 0.7112 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 3 | 0.7103 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 2 | 0.7077 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7052 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 4 | 0.7045 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 3 | 0.7039 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 3 | 0.7037 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7036 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7011 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 3 | 0.7011 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 2 | 0.7008 |
| Uncharacterized protein | Q3F0V8 | Q3F0V8_BACTI | Bacillus thuringiensis serovar israelensis ATCC 35646 | 3 | 0.7007 |