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Pseudolycorine
- Family: Plantae - Amaryllidaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Amaryllidaceae Alkaloid
| Canonical Smiles | COc1cc2CN3CCC4=C[C@@H]([C@H]([C@@H](c2cc1O)[C@H]34)O)O |
|---|---|
| InChI | InChI=1S/C16H19NO4/c1-21-13-5-9-7-17-3-2-8-4-12(19)16(20)14(15(8)17)10(9)6-11(13)18/h4-6,12,14-16,18-20H,2-3,7H2,1H3/t12-,14-,15+,16+/m0/s1 |
| InChIKey | CKAHWDNDUGDSLE-ARLBYUKCSA-N |
| Formula | C16H19NO4 |
| HBA | 5 |
| HBD | 3 |
| MW | 289.33 |
| Rotatable Bonds | 1 |
| TPSA | 73.16 |
| LogP | 0.73 |
| Number Rings | 4 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 289.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Narcissus tazetta | Amaryllidaceae | Plantae | 54860 |
Showing of synonyms
Pseudolycorine
29429-03-6
Psi-Lycorine
TCMDC-132036
9-Methoxy-3,12-didehydrogalanthan-1,2,10-triol
CHEBI:32074
PSEUDOLYCORINE HYDROCHLORIDE
82372-67-6
NSC 305489
1H-Pyrrolo[3,2,1-de]phenanthridine-1,2,10-triol, 2,4,5,7,11b,11c-hexahydro-9-methoxy-, (1S,2S,11bS,11cS)-
(1S,14S,15S,16S)-5-methoxy-9-azatetracyclo[7.6.1.02,7.012,16]hexadeca-2,4,6,12-tetraene-4,14,15-triol
Pseudo-lycorine
10,11-Secolycoran-1-alpha,2-beta-diol, 3,3a-didehydro-
Pseudolycorine HCl
Galanthan-1,2,10-triol, 3,12-didehydro-9-methoxy-, (1-alpha,2-beta)-
CHEMBL586091
SCHEMBL20455707
DTXSID00231711
GLXC-17414
BDBM50278146
AKOS040735124
FS-9825
DA-77195
HY-117190
CS-0064201
NS00094604
Q27114773
3,12-Didehydro-9-methoxygalanthan-1alpha,2beta,10-triol
(1S,14S,15S,16S)-5-methoxy-9-azatetracyclo[7.6.1.0?,?.0??,??]hexadeca-2,4,6,12-tetraene-4,14,15-triol
- Abdallah OM. (1993). Narcisine, an alkaloid from Narcissus tazetta. Phytochemistry,1993,34(5),1447-1448. [View]
Pubchem:
443689
Cas:
29429-03-6
Gnps:
CCMSLIB00012176151
Kegg Ligand:
C12187
Chebi:
32074
Nmrshiftdb2:
60027217
Chembl:
CHEMBL586091
Comptox:
DTXSID00231711
Bindingdb:
50278146
CPRiL:
62170
SMILES: C1CCC(C2C=13)c4c(cccc4)CN2CC3
Level: 0
Mol. Weight: 289.33 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.13
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.030
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.34
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.520
- Plasma Protein Binding
- 34.03
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.110
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.390
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.100
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 8.700
- Micronucleos
- Toxic
- NR-AhR
- Safe
- 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
- -1.870
- Rat (Acute)
- 3.010
- Rat (Chronic Oral)
- 2.440
- Fathead Minnow
- 4.110
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 403.490
- Hydration Free Energy
- -10.490
- Log(D) at pH=7.4
- 0.450
- Log(P)
- 0.02
- Log S
- -1.11
- Log(Vapor Pressure)
- -7.93
- Melting Point
- 199.42
- pKa Acid
- 7.74
- pKa Basic
- 6.64
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9085 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9085 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8968 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8968 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8593 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8593 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8507 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8507 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8213 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8213 |
| DNA polymerase III subunit epsilon | P03007 | DPO3E_ECOLI | Escherichia coli | 3 | 0.8064 |
| DNA polymerase III subunit epsilon | P03007 | DPO3E_ECOLI | Escherichia coli | 3 | 0.8064 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7910 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7910 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7899 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7899 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7886 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7886 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7868 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7868 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.7749 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.7749 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.7719 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.7719 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7596 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7596 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7508 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7508 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7493 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7493 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7472 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7472 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7411 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7411 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7402 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7402 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7393 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7393 |
| GMP reductase 2 | Q9P2T1 | GMPR2_HUMAN | Homo sapiens | 3 | 0.7367 |
| GMP reductase 2 | Q9P2T1 | GMPR2_HUMAN | Homo sapiens | 3 | 0.7367 |
| Tryptophan--tRNA ligase | Q9PIB4 | SYW_CAMJE | Campylobacter jejuni subsp. jejuni serotype O:2 | 4 | 0.7343 |
| Tryptophan--tRNA ligase | Q9PIB4 | SYW_CAMJE | Campylobacter jejuni subsp. jejuni serotype O:2 | 4 | 0.7343 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7325 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7325 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7284 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7284 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7249 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7249 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7245 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7245 |
| Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 | Q9CCZ4 | Y2640_MYCLE | Mycobacterium leprae | 3 | 0.7215 |
| Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 | Q9CCZ4 | Y2640_MYCLE | Mycobacterium leprae | 3 | 0.7215 |
| Threonine synthase 1, chloroplastic | Q9S7B5 | THRC1_ARATH | Arabidopsis thaliana | 3 | 0.7208 |
| Threonine synthase 1, chloroplastic | Q9S7B5 | THRC1_ARATH | Arabidopsis thaliana | 3 | 0.7208 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7170 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7170 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7106 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7106 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7072 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7072 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7061 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7061 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7050 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7050 |
| Ribosomal RNA small subunit methyltransferase Nep1 | Q57977 | NEP1_METJA | Methanocaldococcus jannaschii | 3 | 0.7021 |
| Ribosomal RNA small subunit methyltransferase Nep1 | Q57977 | NEP1_METJA | Methanocaldococcus jannaschii | 3 | 0.7021 |