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Lecomtequinoline B
- Family: Plantae - Rutaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Quinoline Alkaloid
| Canonical Smiles | COc1c2ccc(c(c2nc2c1cco2)OCC=C(C)C)OC[C@@H]1OC1(C)C |
|---|---|
| InChI | InChI=1S/C22H25NO5/c1-13(2)8-10-25-20-16(27-12-17-22(3,4)28-17)7-6-14-18(20)23-21-15(9-11-26-21)19(14)24-5/h6-9,11,17H,10,12H2,1-5H3/t17-/m0/s1 |
| InChIKey | ZDQVEOBNMCAKLI-KRWDZBQOSA-N |
| Formula | C22H25NO5 |
| HBA | 6 |
| HBD | 0 |
| MW | 383.44 |
| Rotatable Bonds | 7 |
| TPSA | 66.25 |
| LogP | 4.89 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.41 |
| Exact Mass | 383.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Vepris lecomteana | Rutaceae | Plantae | 1321803 |
Showing of synonyms
Lecomtequinoline B
No compound-protein relationship available.
SMILES: O1CC1COc(c2)ccc(c3)c2nc(c34)occ4
Level: 1
Mol. Weight: 383.44 g/mol
SMILES: c1coc(c12)nc3c(c2)cccc3
Level: 0
Mol. Weight: 383.44 g/mol
SMILES: C1CO1
Level: 0
Mol. Weight: 383.44 g/mol
Antibacterial
Absorption
- Caco-2 (logPapp)
- -4.74
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.57
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.16
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.11
- Plasma Protein Binding
- 79.18
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-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
- 16.11
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 2.48
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.43
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.74
- 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
- -11.19
- Rat (Acute)
- 2.6
- Rat (Chronic Oral)
- 2.12
- Fathead Minnow
- 5.52
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 453.02
- Hydration Free Energy
- -6.66
- Log(D) at pH=7.4
- 3.8
- Log(P)
- 4.42
- Log S
- -5.91
- Log(Vapor Pressure)
- -7.06
- Melting Point
- 64.75
- pKa Acid
- 7.69
- pKa Basic
- 5.54
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.9351 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.8797 |
| HTH-type transcriptional regulator QacR | P0A0N3 | QACR_STAAM | Staphylococcus aureus | 3 | 0.8752 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8507 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8484 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.8410 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.8297 |
| Squalene synthase | P37268 | FDFT_HUMAN | Homo sapiens | 3 | 0.8224 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.8223 |
| Beta sliding clamp | P0A988 | DPO3B_ECOLI | Escherichia coli | 3 | 0.7984 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7904 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7889 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.7881 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7879 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7821 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7794 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.7784 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7759 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7749 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 2 | 0.7749 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7722 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7721 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7667 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7650 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7646 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 3 | 0.7636 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7632 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7608 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 2 | 0.7606 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7576 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7536 |
| Prostaglandin F2a synthase | Q8I6L9 | Q8I6L9_TRYCR | Trypanosoma cruzi | 2 | 0.7534 |
| Putative protease I | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron | 2 | 0.7515 |
| HTH-type transcriptional regulator QacR | P0A0N3 | QACR_STAAM | Staphylococcus aureus | 3 | 0.7503 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7501 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7469 |
| Cholinesterase | P06276 | CHLE_HUMAN | Homo sapiens | 2 | 0.7449 |
| Terminal oxygenase component of carbazole | Q84II6 | Q84II6_JANS3 | Janthinobacterium sp | 3 | 0.7447 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7444 |
| Prolyl endopeptidase | P23687 | PPCE_PIG | Sus scrofa | 3 | 0.7432 |
| Hexokinase-4 | P35557 | HXK4_HUMAN | Homo sapiens | 3 | 0.7425 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7418 |
| Cytohesin-2 | Q99418 | CYH2_HUMAN | Homo sapiens | 3 | 0.7411 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7406 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7392 |
| Interleukin-2 | P60568 | IL2_HUMAN | Homo sapiens | 2 | 0.7389 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 2 | 0.7382 |
| Peptidyl-prolyl cis-trans isomerase FKBP5 | Q13451 | FKBP5_HUMAN | Homo sapiens | 3 | 0.7380 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 2 | 0.7370 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 2 | 0.7361 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7352 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7336 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7332 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7328 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 2 | 0.7324 |
| Biphenyl dioxygenase subunit alpha | P37333 | BPHA_PARXL | Paraburkholderia xenovorans | 3 | 0.7289 |
| Virginiamycin A acetyltransferase | P26839 | VATA_STAAU | Staphylococcus aureus | 4 | 0.7285 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7274 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7269 |
| TetR family transcriptional regulator | Q58L87 | Q58L87_MYCSM | Mycolicibacterium smegmatis | 2 | 0.7262 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 2 | 0.7253 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 3 | 0.7252 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 2 | 0.7239 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 2 | 0.7226 |
| DNA ligase | P43813 | DNLJ_HAEIN | Haemophilus influenzae | 2 | 0.7221 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7207 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 2 | 0.7204 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7200 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7197 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7183 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.7182 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7181 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7179 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7170 |
| Metallo-beta-lactamase type 2 | P26918 | BLAB_AERHY | Aeromonas hydrophila | 2 | 0.7159 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7157 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7138 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7133 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 2 | 0.7127 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7123 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7123 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7112 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7105 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 2 | 0.7073 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7060 |
| Thymidylate synthase | P0A886 | TYSY_ECO57 | Escherichia coli O157:H7 | 2 | 0.7053 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7053 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 2 | 0.7051 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7051 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.7041 |
| HTH-type transcriptional regulator QacR | P0A0N3 | QACR_STAAM | Staphylococcus aureus | 3 | 0.7038 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7038 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7033 |
| Aclacinomycin 10-hydroxylase RdmB | Q54527 | RDMB_STREF | Streptomyces purpurascens | 3 | 0.7032 |
| Chymotrypsinogen A | P00766 | CTRA_BOVIN | Bos taurus | 3 | 0.7027 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 2 | 0.7025 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 2 | 0.7024 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7023 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7012 |