Galanthamine - Compound Card

Galanthamine

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Galanthamine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Amaryllidaceae Alkaloid
Canonical Smiles COc1ccc2c3c1O[C@@H]1[C@@]3(CCN(C2)C)C=C[C@@H](C1)O
InChI InChI=1S/C17H21NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,12,14,19H,7-10H2,1-2H3/t12-,14-,17-/m0/s1
InChIKey ASUTZQLVASHGKV-JDFRZJQESA-N
Formula C17H21NO3
HBA 4
HBD 1
MW 287.36
Rotatable Bonds 1
TPSA 41.93
LogP 1.85
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 287.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Lycoris sanguinea Amaryllidaceae Plantae 108053
2 Narcissus tazetta Amaryllidaceae Plantae 54860
3 Haemanthus multiflorus Amaryllidaceae Plantae 82246
4 Narcissus species Amaryllidaceae Plantae 54843

Showing of synonyms

  • Abdallah OM, Ali AA and Itokawa H. (1989). 2-O-acetyl chlidanthine; an alkaloid from Haemanthus multiflorus. Phytochemistry,1989,28(11),3248-3249. [View]
  • Shawky E, Abou-Donia AH, et al. (2015). HPTLC and GC/MS study of Amaryllidaceae alkaloids of two Narcissus species. Chemistry and Biodiversity,2015,12(8),1184-1199. [View] [PubMed]
  • Abdallah OM. (1995). Minor alkaloids from Lycoris sanguinea. Phytochemistry,1995,39(2),477-478. [View]
  • Abdallah OM. (1993). Narcisine, an alkaloid from Narcissus tazetta. Phytochemistry,1993,34(5),1447-1448. [View]
Pubchem: 9651
Kegg Ligand: C08526
Chebi: 42944
Nmrshiftdb2: 20062583
Metabolights: MTBLC42944
Chembl: CHEMBL659
Drugbank: DB00674
Pdb Ligand: GNT
Bindingdb: 10404
CPRiL: 4872
Structure

SMILES: C1=CCCC2Oc(c3C124)cccc3CNCC4

Level: 0

Mol. Weight: 287.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.96
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.660
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.04

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.520
Plasma Protein Binding
34.54
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
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.120
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.330
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
9.140
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
-2.090
Rat (Acute)
3.240
Rat (Chronic Oral)
1.710
Fathead Minnow
4.030
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
347.990
Hydration Free Energy
-9.050
Log(D) at pH=7.4
0.960
Log(P)
1.11
Log S
-0.97
Log(Vapor Pressure)
-6.76
Melting Point
145.25
pKa Acid
9.64
pKa Basic
8.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9792
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9792
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8496
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8496
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 4 0.8413
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 4 0.8413
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.8407
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.8407
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.8364
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.8364
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8324
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8324
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8321
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8321
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8211
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8211
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8211
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8211
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8152
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8152
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8148
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8148
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8095
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8095
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8084
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8084
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7980
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7980
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7929
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7929
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7914
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7914
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7873
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7873
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7861
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7861
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7841
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7841
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7780
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7780
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7744
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7744
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 2 0.7741
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 2 0.7741
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7629
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7629
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7627
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7627
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7616
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7616
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7612
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7612
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7541
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7541
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7536
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7536
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7471
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7471
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7454
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7454
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7446
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7446
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7407
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7407
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7384
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7384
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7359
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7359
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7255
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7255
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7251
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7251
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7245
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7245
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7233
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7233
Sepiapterin reductase Q64105 SPRE_MOUSE Mus musculus 3 0.7221
Sepiapterin reductase Q64105 SPRE_MOUSE Mus musculus 3 0.7221
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7218
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7218
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7197
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7197
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7196
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7196
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7184
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7184
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7175
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7175
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7145
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7145
Mitomycin biosynthesis 6-O-methyltransferase Q9X5T6 MMCR_STRLA Streptomyces lavendulae 3 0.7129
Mitomycin biosynthesis 6-O-methyltransferase Q9X5T6 MMCR_STRLA Streptomyces lavendulae 3 0.7129
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7105
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7105
S-norcoclaurine synthase Q67A25 NCS_THLFG Thalictrum flavum subsp. glaucum 3 0.7102
S-norcoclaurine synthase Q67A25 NCS_THLFG Thalictrum flavum subsp. glaucum 3 0.7102
43.2 kDa salivary protein Q5WPU9 Q5WPU9_LUTLO Lutzomyia longipalpis 3 0.7088
43.2 kDa salivary protein Q5WPU9 Q5WPU9_LUTLO Lutzomyia longipalpis 3 0.7088
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7070
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7070
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7063
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7063
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7059
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7059
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 2 0.7046
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 2 0.7046
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7024
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7024
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7021
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7021
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7013
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7013

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