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Epigalanthamine
- Family: Plantae - Amaryllidaceae
- Kingdom: Plantae
- Class: Alkaloid
| Canonical Smiles | COc1ccc2c3c1OC1C3(CCN(C2)C)C=CC(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 |
| InChIKey | ASUTZQLVASHGKV-UHFFFAOYSA-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 | Crinum natans | Amaryllidaceae | Plantae | 573721 |
Showing of synonyms
Epigalanthamine
Epigalanthamin
MLS000766281
NSC100058
9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol
Galanthamine #
Galanthamine,(3.alpha.-
Galantamine
HSDB 7361
Oprea1_097473
Oprea1_098077
SCHEMBL220427
CERAPP_13557
CHEMBL1623394
CHEBI:91735
DTXSID70859345
HMS2269H23
HMS3561F13
BCP28966
LSM-1597
BBL028838
STL146336
AKOS000635322
AKOS021856294
NCI60_000004
SMR000528869
NS00066980
BRD-A49148672-001-07-9
BRD-A49148672-004-01-6
Q27163546
(1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12.0^{6,17]heptadeca-6(17),7,9,15-tetraen-14-ol
6H-Benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, (4aS-(4a.alpha.,6.beta.,8aR*))-
6H-Benzofuro[3a,2-ef][2]benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, [4aS-(4a.alpha.,6.beta.,8aR*)]-
6H-Benzofuro[3a,3,2-ef][2]benzazepin-6-ol,4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, (4aR,6S,8aR)-rel-
CPRiL:
435792
SMILES: C1=CCCC2Oc(c3C124)cccc3CNCC4
Level: 0
Mol. Weight: 287.36 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.93
- 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
- -3.05
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.520
- Plasma Protein Binding
- 1.74
- 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
- 5.100
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.440
- 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
- 9.170
- 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
- 0.170
- Rat (Acute)
- 3.220
- Rat (Chronic Oral)
- 1.700
- Fathead Minnow
- 4.120
- 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
- 344.470
- Hydration Free Energy
- -8.900
- Log(D) at pH=7.4
- 1.020
- Log(P)
- 1.23
- Log S
- -0.93
- Log(Vapor Pressure)
- -6.47
- Melting Point
- 134.12
- pKa Acid
- 9.75
- pKa Basic
- 8.25
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.8413 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.8184 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8150 |
| Calmodulin-1 | P0DP29 | CALM1_RAT | Rattus norvegicus | 3 | 0.8122 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8089 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8051 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7880 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7780 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7739 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7737 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7660 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7654 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 3 | 0.7577 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7424 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7334 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7317 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7293 |
| Acetylcholine-binding protein | P58154 | ACHP_LYMST | Lymnaea stagnalis | 3 | 0.7286 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7275 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7243 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7187 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7104 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7067 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7047 |
| Camphor 5-monooxygenase | P00183 | CPXA_PSEPU | Pseudomonas putida | 3 | 0.7039 |
| 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 | O50008 | METE1_ARATH | Arabidopsis thaliana | 2 | 0.7032 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7022 |