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N-demethylgalanthamine
- Family: Plantae - Amaryllidaceae
- Kingdom: Plantae
- Class: Alkaloid
| Canonical Smiles | COc1ccc2c3c1O[C@@H]1[C@@]3(CCNC2)C=C[C@@H](C1)O |
|---|---|
| InChI | InChI=1S/C16H19NO3/c1-19-12-3-2-10-9-17-7-6-16-5-4-11(18)8-13(16)20-15(12)14(10)16/h2-5,11,13,17-18H,6-9H2,1H3/t11-,13-,16-/m0/s1 |
| InChIKey | AIXQQSTVOSFSMO-RBOXIYTFSA-N |
| Formula | C16H19NO3 |
| HBA | 4 |
| HBD | 2 |
| MW | 273.33 |
| Rotatable Bonds | 1 |
| TPSA | 50.72 |
| LogP | 1.51 |
| Number Rings | 4 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 273.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Crinum natans | Amaryllidaceae | Plantae | 573721 |
| 2 | Zephyranthes robusta | Amaryllidaceae | Plantae | 1234388 |
| 3 | Zephyranthes rosea | Amaryllidaceae | Plantae | 146470 |
Showing of synonyms
N-demethylgalanthamine
N-Desmethyl Galanthamine
Norgalanthamine
41303-74-6
N-Desmethylgalantamine
N-Desmethylgalanthamine
Norgalantamine
N-Norgalanthamine
UNII-2BPQ4IVQ21
2BPQ4IVQ21
CHEMBL1385
CHEBI:31919
(1S,12S,14R)-9-methoxy-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol
(4aS,6R,8aS)-3-Methoxy-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-ol
N-Desmethyl galantamine
(-)-N-Demethylgalanthamine
Galanthamine, 10-demethyl-
6H-Benzofuro[3a,3,2-ef][2]benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-, (4aS,6R,8aS)-
(4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-ol
6H-Benzofuro[3a,3,2-ef][2]benzazepin-6-
Stephaoxocanidine derivative
SCHEMBL5740733
GALANTAMINE METABOLITE 8
AIXQQSTVOSFSMO-RBOXIYTFSA-N
HY-N7612
BDBM50166809
AKOS030242087
ID21271
Norgalanthamine (N-Demethylgalanthamine)
DA-76054
MS-23881
CS-0134789
NS00094200
F82742
Q27114718
GALANTAMINE HYDROBROMIDE IMPURITY E [EP IMPURITY]
GALANTAMINE HYDROBROMIDE IMPURITY, N-DESMETHYLGALANTAMINE- [USP IMPURITY]
(4AS,6R,8AS)-3-METHOXY-5,6,9,10,11,12-HEXAHYDRO-4AH-(1)BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL
Galanthamine impurity E
6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL, 4A,5,9,10,11,12-HEXAHYDRO-3-METHOXY-, (4AS,6R,8AS)-
Pubchem:
9838394
Cas:
41303-74-6
Zinc:
ZINC000004102384
Kegg Ligand:
C12173
Chebi:
31919
Nmrshiftdb2:
60069616
Chembl:
CHEMBL1385
Bindingdb:
50166809
CPRiL:
125952
SMILES: C1=CCCC2Oc(c3C124)cccc3CNCC4
Level: 0
Mol. Weight: 273.33 g/mol
Ache-inhibitor
Absorption
- Caco-2 (logPapp)
- -5.05
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.740
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.1
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.490
- Plasma Protein Binding
- 36.59
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 3.600
- 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
- -0.170
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 8.910
- 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
- -2.210
- Rat (Acute)
- 3.070
- Rat (Chronic Oral)
- 1.750
- 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
- 350.760
- Hydration Free Energy
- -9.840
- Log(D) at pH=7.4
- 0.720
- Log(P)
- 0.69
- Log S
- -1.04
- Log(Vapor Pressure)
- -6.77
- Melting Point
- 156.49
- pKa Acid
- 10.53
- pKa Basic
- 8.27
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.8480 |
| Sulfotransferase 1A1 | P50225 | ST1A1_HUMAN | Homo sapiens | 3 | 0.8424 |
| 3',5'-cyclic-AMP phosphodiesterase 4A | P27815 | PDE4A_HUMAN | Homo sapiens | 4 | 0.8281 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.8259 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.8216 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8196 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 3 | 0.8045 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.8007 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7997 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | O67060 | ISPE_AQUAE | Aquifex aeolicus | 3 | 0.7851 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7809 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7801 |
| Calmodulin-1 | P0DP29 | CALM1_RAT | Rattus norvegicus | 3 | 0.7637 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7637 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 3 | 0.7623 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7614 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7613 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7570 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 3 | 0.7408 |
| Serine/threonine-protein kinase Nek2 | P51955 | NEK2_HUMAN | Homo sapiens | 3 | 0.7390 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7390 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7361 |
| Eukaryotic translation initiation factor 4E type 3 | Q9DBB5 | IF4E3_MOUSE | Mus musculus | 3 | 0.7205 |
| Mitomycin biosynthesis 6-O-methyltransferase | Q9X5T6 | MMCR_STRLA | Streptomyces lavendulae | 3 | 0.7205 |
| Lactoylglutathione lyase | Q04760 | LGUL_HUMAN | Homo sapiens | 2 | 0.7202 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7194 |
| Class 10 plant pathogenesis-related protein 2B | Q9LLQ2 | P102B_LUPLU | Lupinus luteus | 2 | 0.7194 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7178 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7148 |
| Chloramphenicol 3-O phosphotransferase | Q56148 | CPT_STRVP | Streptomyces venezuelae | 3 | 0.7121 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7088 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 2 | 0.7082 |
| Cytochrome P450 monooxygenase PikC | O87605 | PIKC_STRVZ | Streptomyces venezuelae | 2 | 0.7077 |
| Genome polyprotein | Q2YHF0 | POLG_DEN4T | Dengue virus type 4 | 3 | 0.7020 |
| Pteridine reductase 1 | Q01782 | PTR1_LEIMA | Leishmania major | 2 | 0.7018 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.7013 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7011 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 2 | 0.7010 |
| Biphenyl-2,3-diol 1,2-dioxygenase | P17297 | BPHC_PSES1 | Pseudomonas sp | 3 | 0.7007 |