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Pseudopalmatine
- Family: Plantae - Annonaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Protoberberine Alkaloid
| Canonical Smiles | COc1cc2CC[n+]3c(c2cc1OC)cc1c(c3)cc(c(c1)OC)OC |
|---|---|
| InChI | InChI=1S/C21H22NO4/c1-23-18-8-13-5-6-22-12-15-10-20(25-3)19(24-2)9-14(15)7-17(22)16(13)11-21(18)26-4/h7-12H,5-6H2,1-4H3/q+1 |
| InChIKey | CLFBXKHKECKSQM-UHFFFAOYSA-N |
| Formula | C21H22NO4+ |
| HBA | 4 |
| HBD | 0 |
| MW | 352.41 |
| Rotatable Bonds | 4 |
| TPSA | 40.8 |
| LogP | 3.38 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 26 |
| Formal Charge | 1 |
| Fraction CSP3 | 0.29 |
| Exact Mass | 352.15 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Enantia chlorantha | Annonaceae | Plantae | 306909 |
Showing of synonyms
Pseudopalmatine
19716-66-6
2,3,10,11-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium
DTXSID30349252
2,3,10,11-tetramethoxy-5,6-dihydroisoquinolino(2,1-b)isoquinolin-7-ium
DTXCID90300324
Dibenzo[a,g]quinolizinium, 5,6-dihydro-2,3,10,11-tetramethoxy-
CHEBI:70647
Pseudopalmatine Trifluoroacetate
CHEMBL1270850
CHEMBL376300
5,6-Dihydro-8-demethylcoralyne
SCHEMBL25571345
5,6-Dihydro-2,3,10,11-tetramethoxydibenzo[a,g]quinolizinium
BDBM50328694
AKOS028108703
Q27138980
B0005-172977
- Nyongbela KD, Samje M, et al. (2019). Evaluation of anti-onchocercal activity of pseudopalmatine, a quaternary protoberberine alkaloid of Enantia chlorantha (Syn. Annickia chlorantha). Journal of the Cameroon Academy of Sciences, 2019, 14(3). [View]
Pubchem:
644002
Cas:
19716-66-6
Gnps:
CCMSLIB00009919230
Zinc:
ZINC000014682001
Chebi:
70647
Nmrshiftdb2:
60068889
Metabolights:
MTBLC70647
Chembl:
CHEMBL376300
Comptox:
DTXSID30349252
Bindingdb:
50328694
No compound-protein relationship available.
SMILES: c1cccc(c12)CC[n+]3c2cc4c(c3)cccc4
Level: 0
Mol. Weight: 352.41 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.22
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.460
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.86
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.950
- Plasma Protein Binding
- 50.24
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.630
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.730
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.640
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 10.170
- 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
- Toxic
- T. Pyriformis
- -7.180
- Rat (Acute)
- 2.790
- Rat (Chronic Oral)
- 1.350
- Fathead Minnow
- 5.570
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 441.050
- Hydration Free Energy
- -7.600
- Log(D) at pH=7.4
- 2.720
- Log(P)
- -0.13
- Log S
- -1.24
- Log(Vapor Pressure)
- -8.11
- Melting Point
- 201.4
- pKa Acid
- 11.24
- pKa Basic
- 5.36
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9865 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9761 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.9569 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.9514 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.9414 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.9368 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9325 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 3 | 0.9200 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9145 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.9065 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.9012 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8947 |
| Nodulin-13 | P93330 | NOD13_MEDTR | Medicago truncatula | 3 | 0.8908 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 4 | 0.8794 |
| ATP synthase subunit alpha, mitochondrial | P19483 | ATPA_BOVIN | Bos taurus | 3 | 0.8785 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8756 |
| Phytohormone-binding protein CSBP | A0A1S3THR8 | PHBP_VIGRR | Vigna radiata var. radiata | 3 | 0.8695 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.8646 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 4 | 0.8635 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.8633 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8566 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.8559 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.8488 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 4 | 0.8376 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8353 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.8286 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.8189 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.8188 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8030 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7990 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7932 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.7916 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 3 | 0.7912 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7891 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7880 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7875 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 3 | 0.7863 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7850 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7849 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 3 | 0.7847 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7782 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.7782 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 3 | 0.7759 |
| Farnesyl pyrophosphate synthase | P14324 | FPPS_HUMAN | Homo sapiens | 2 | 0.7753 |
| RNA polymerase sigma factor SigA | Q5SKW1 | Q5SKW1_THET8 | Thermus thermophilus | 3 | 0.7751 |
| Squalene synthase | P37268 | FDFT_HUMAN | Homo sapiens | 3 | 0.7743 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7739 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7700 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7688 |
| Caspase-3 | P42574 | CASP3_HUMAN | Homo sapiens | 2 | 0.7678 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 3 | 0.7672 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7657 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.7656 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7632 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.7628 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 2 | 0.7624 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.7600 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7577 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7527 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7514 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7502 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7494 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7493 |
| Phosphoenolpyruvate carboxykinase [GTP] | P9WIH3 | PCKG_MYCTU | Mycobacterium tuberculosis | 3 | 0.7488 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7484 |
| ATP synthase subunit alpha, mitochondrial | P19483 | ATPA_BOVIN | Bos taurus | 3 | 0.7478 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7475 |
| ATP synthase subunit alpha, mitochondrial | P19483 | ATPA_BOVIN | Bos taurus | 3 | 0.7472 |
| Beta sliding clamp | P0A988 | DPO3B_ECOLI | Escherichia coli | 2 | 0.7471 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7469 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7452 |
| Dihydroflavonol 4-reductase | P51110 | DFRA_VITVI | Vitis vinifera | 3 | 0.7451 |
| FMN-dependent NAD(P)H:quinone oxidoreductase 1 | Q9I5F3 | AZOR1_PSEAE | Pseudomonas aeruginosa | 2 | 0.7421 |
| Bromodomain protein, putative | Q8I240 | Q8I240_PLAF7 | Plasmodium falciparum | 4 | 0.7419 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7419 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7418 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7392 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7389 |
| Phosphoenolpyruvate carboxykinase [GTP] | A5TYT6 | PCKG_MYCTA | Mycobacterium tuberculosis | 3 | 0.7374 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 2 | 0.7366 |
| Dihydroflavonol 4-reductase | P51110 | DFRA_VITVI | Vitis vinifera | 3 | 0.7360 |
| TetR family transcriptional regulator | Q58L87 | Q58L87_MYCSM | Mycolicibacterium smegmatis | 2 | 0.7349 |
| Phosphoenolpyruvate carboxykinase [GTP] | A5TYT6 | PCKG_MYCTA | Mycobacterium tuberculosis | 3 | 0.7343 |
| 17beta-hydroxysteroid dehydrogenase | O93874 | O93874_COCLU | Cochliobolus lunatus | 2 | 0.7343 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 3 | 0.7339 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7333 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7328 |
| Focal adhesion kinase 1 | Q05397 | FAK1_HUMAN | Homo sapiens | 3 | 0.7316 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7307 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7296 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 2 | 0.7274 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7261 |
| Carbonic anhydrase 4 | P22748 | CAH4_HUMAN | Homo sapiens | 3 | 0.7257 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 3 | 0.7256 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 2 | 0.7254 |
| Aminoglycoside 3'-phosphotransferase AphA1-IAB | B0VD92 | B0VD92_ACIBY | Acinetobacter baumannii | 3 | 0.7249 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 2 | 0.7246 |
| Beta-adrenergic receptor kinase 1 | P25098 | ARBK1_HUMAN | Homo sapiens | 3 | 0.7246 |
| HTH-type transcriptional regulator EthR | P9WMC1 | ETHR_MYCTU | Mycobacterium tuberculosis | 3 | 0.7244 |
| 4,4'-diapophytoene synthase | A9JQL9 | CRTM_STAAU | Staphylococcus aureus | 2 | 0.7230 |
| DNA topoisomerase 4 subunit B | H7C794 | PARE_ENTFA | Enterococcus faecalis | 2 | 0.7229 |
| UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase | Q8DNV6 | Q8DNV6_STRR6 | Streptococcus pneumoniae | 2 | 0.7226 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7213 |
| Non-receptor tyrosine-protein kinase TYK2 | P29597 | TYK2_HUMAN | Homo sapiens | 3 | 0.7209 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 4 | 0.7208 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7208 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 2 | 0.7205 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7198 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7177 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.7176 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 2 | 0.7174 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7173 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7171 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.7167 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 2 | 0.7166 |
| Prostaglandin E synthase 2 | Q9N0A4 | PGES2_MACFA | Macaca fascicularis | 3 | 0.7150 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7146 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7129 |
| Anthocyanidin 3-O-glucosyltransferase UFGT | P51094 | UFOG_VITVI | Vitis vinifera | 3 | 0.7127 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7101 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7093 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 2 | 0.7084 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7074 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 2 | 0.7069 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7063 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7030 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 2 | 0.7026 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7024 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7024 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7021 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 2 | 0.7020 |
| FMN-dependent NAD(P)H:quinone oxidoreductase 1 | Q9I5F3 | AZOR1_PSEAE | Pseudomonas aeruginosa | 3 | 0.7013 |
| Beta-secretase 2 | Q9Y5Z0 | BACE2_HUMAN | Homo sapiens | 2 | 0.7011 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7003 |