Galantamine

Details

• Internal ID: 3fd1a85e-b0ea-4ee3-a34c-eaf4701419bf
• Taxonomy: Alkaloids and derivatives > Amaryllidaceae alkaloids > Galanthamine-type amaryllidaceae alkaloids
• IUPAC Name: (1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol
• SMILES (Canonical): CN1CCC23C=CC(CC2OC4=C(C=CC(=C34)C1)OC)O
• SMILES (Isomeric): CN1CC[C@@]23C=C[C@@H](C[C@@H]2OC4=C(C=CC(=C34)C1)OC)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
• InChI Key: ASUTZQLVASHGKV-JDFRZJQESA-N
• Popularity: 2,481 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₁NO₃
• Molecular Weight: 287.35 g/mol
• Exact Mass: 287.15214353 g/mol
• Topological Polar Surface Area (TPSA): 41.90 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.85
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• Galantamine
• 357-70-0
• (-)-Galanthamine
• Lycoremin
• Lycoremine
• Galantamin
• Reminyl
• Jilkon
• Galantamina
• (-)-Galantamine
• Galanthaminum
• Nivalin
• Razadyne
• Nivaline
• Galantaminum
• Razadyne ER
• Galantaminum [INN-Latin]
• Galantamina [INN-Spanish]
• (+/-)-Galantamine
• Bodamine
• Galantamine [USAN:INN]
• Reminyl (TN)
• NSC 100058
• BRN 0093736
• (+/-)-Galanthamine
• HSDB 7361
• Galantamine, (+/-)-
• Galantamine (USAN/INN)
• Galanthamine, (+/-)-
• CHEMBL659
• UNII-0D3Q044KCA
• Galantamine [USAN:INN:BAN]
• 0D3Q044KCA
• CHEBI:42944
• 1T835Z585R
• NSC-100058
• (4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol
• 23173-12-8
• Razadyne (TN)
• 4-27-00-02184 (Beilstein Handbook Reference)
• GNT
• (1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6,8,10(17),15-tetraen-14-ol
• (1S,12S,14R)-9-methoxy-4-methyl-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-11-methyl-5,6,9,10,11,12-hexahydro-4aH-benzo[2,3]benzofuro[4,3-cd]azepin-6-ol
• (4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-ol
• 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-
• 6H-Benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, (4aS,6R,8aS)-
• 6H-Benzofuro[3a,3,2-ef][2]benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, (4aS,6R,8aS)-
• SR-05000001783
• 1qti
• Galanthamine, 12
• Nivalin (TN)
• Razadyne ER (TN)
• Spectrum_001271
• 1dx6
• GALANTAMINE [MI]
• Prestwick0_000588
• Prestwick1_000588
• Prestwick2_000588
• Prestwick3_000588
• Spectrum3_001738
• Spectrum4_000839
• Spectrum5_001673
• GALANTAMINE [INN]
• GALANTAMINE [HSDB]
• GALANTAMINE [USAN]
• D0R9VR
• Probes1_000055
• Probes2_000395
• GALANTAMINE [VANDF]
• SCHEMBL2577
• BSPBio_000436
• BSPBio_003416
• GALANTAMINE [WHO-DD]
• KBioGR_001417
• KBioSS_001751
• BIDD:GT0517
• DivK1c_000590
• SPBio_002655
• BPBio1_000480
• GTPL6693
• SCHEMBL3293474
• UNII-1T835Z585R
• ASUTZQLVASHGKV-JDFRZJQESA-
• BDBM10404
• KBio1_000590
• KBio2_001751
• KBio2_004319
• KBio2_006887
• KBio3_002636
• ASUTZQLVASHGKV-JDFRZJQESA-N
• NINDS_000590
• HMS2089H03
• HMS3885C10
• Pharmakon1600-01501202
• MFCD00867189
• NSC759861
• s3866
• AKOS015965330
• AM62710
• CCG-212961
• CS-1217
• CS-O-01567
• DB00674
• NSC-759861
• SDCCGMLS-0066737.P001
• IDI1_000590
• SMP1_000131
• NCGC00017256-05
• NCGC00017256-11
• NCGC00017256-17
• NCGC00024731-02
• (4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofurol[3a,3,2,-ef][2]benzazepin-6-ol
• AC-20240
• AC-34328
• AS-56354
• HY-76299
• LS-71039
• SBI-0051689.P002
• C08526
• D04292
• EN300-708805
• AB00053614-09
• AB00053614_10
• Q412690
• SR-05000001783-4
• BRD-K49481516-004-03-5
• BRD-K49481516-004-04-3
• BRD-K49481516-004-09-2
• (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
• (4aS,6R,8aS)-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-ol
• 1008759-59-8
• 6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL, 4A,5,9,10,11,12-HEXAHYDRO-3-METHOXY-11-METHYL-, (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-, (4aalpha,6beta,8ar*)-
• 6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL, 4A,5,9,10,11,12-HEXAHYDRO-3-METHOXY-11-METHYL-, (4AS,6R,8AS)
• InChI=1/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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9949	99.49%
Caco-2	+	0.8469	84.69%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Lysosomes	0.5635	56.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9392	93.92%
OATP1B3 inhibitior	+	0.9498	94.98%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7042	70.42%
P-glycoprotein inhibitior	-	0.9165	91.65%
P-glycoprotein substrate	+	0.5424	54.24%
CYP3A4 substrate	+	0.7588	75.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.7066	70.66%
CYP3A4 inhibition	-	0.8832	88.32%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.8301	83.01%
CYP2D6 inhibition	-	0.5414	54.14%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.8226	82.26%
CYP inhibitory promiscuity	-	0.9439	94.39%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6110	61.10%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9877	98.77%
Skin irritation	-	0.8137	81.37%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5207	52.07%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.8050	80.50%
Respiratory toxicity	+	0.9667	96.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.7182	71.82%
Acute Oral Toxicity (c)	III	0.4944	49.44%
Estrogen receptor binding	-	0.6248	62.48%
Androgen receptor binding	-	0.8513	85.13%
Thyroid receptor binding	+	0.5953	59.53%
Glucocorticoid receptor binding	-	0.6879	68.79%
Aromatase binding	-	0.8282	82.82%
PPAR gamma	-	0.6077	60.77%
Honey bee toxicity	-	0.8501	85.01%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.7513	75.13%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	550 nM; 2600 nM; 350 nM; 800 nM; 800 nM; 300 nM; 1000 nM; 300 nM; 2090 nM; 2000 nM; 2090 nM; 2010 nM; 2090 nM; 800 nM; 1100 nM; 2670 nM; 700 nM; 2000 nM; 350 nM; 2010 nM; 300 nM; 500 nM; 100 nM; 2600 nM; 1156 nM; 600 nM; 980 nM; 800 nM; 590 nM; 800 nM; 600 nM; 635.33 nM; 1180 nM; 1070 nM; 2010 nM; 350 nM; 500 nM; 530 nM; 2100 nM; 2010 nM; 500 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50	PMID: 24606395; PMID: 21189039; PMID: 21216144; PMID: 21459491; PMID: 21459491; PMID: 22425563; PMID: 22775474; PMID: 23199476; PMID: 23454132; PMID: 23540646; PMID: 23570788; PMID: 23984975; PMID: 24461561; PMID: 12166941; PMID: 24704612; PMID: 24934993; PMID: 25189690; PMID: 25537270; PMID: 26159481; PMID: 26735910; PMID: 26841168; DOI: 10.1007/s00044-011-9804-0; DOI: 10.1016/0960-894X(96)00102-3; DOI: 10.1039/C5MD00274E; via CMAUP; PMID: 20575555; PMID: 10869205; PMID: 15715468; PMID: 16483771; PMID: 16570913; PMID: 16945529; PMID: 16945529; PMID: 16989531; PMID: 17822295; PMID: 17850125; PMID: 18479118; PMID: 18650096; PMID: 20954721; PMID: 20025280; PMID: 18954037; PMID: 18681480
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	15848.9 nM	Potency	via CMAUP
CHEMBL1914	P06276	Butyrylcholinesterase	8400 nM; 10000 nM; 7300 nM; 18000 nM; 18600 nM; 8000 nM; 7300 nM; 7000 nM; 7300 nM; 8500 nM; 15800 nM; 12700 nM; 8394.6 nM; 8000 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50	PMID: 16945529; PMID: 23540646; PMID: 12166941; PMID: 12824041; PMID: 21216144; DOI: 10.1007/s00044-011-9754-6; PMID: 15715468; PMID: 23199476; PMID: 16570913; PMID: 18681480; PMID: 24508831; PMID: 24934993; PMID: 16945529; PMID: 18650096
CHEMBL1293235	P02545	Prelamin-A/C	35481.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.24%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.86%	93.99%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.81%	97.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.22%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.23%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.80%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.70%	86.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.62%	89.62%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	86.38%	90.95%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.74%	91.03%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.98%	85.14%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	82.50%	94.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.99%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.63%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.18%	100.00%

Plants that contains it

• Amaryllidaceae
• Aralia elata var. elata
• Atriplex muricata
• Brunsvigia bosmaniae
• Chromolaena laevigata
• Crinum asiaticum
• Crinum jagus
• Crinum moorei
• Crotalaria crispata
• Cyrtanthus elatus
• Ferula persica
• Galanthus elwesii
• Galanthus nivalis
• Haemanthus coccineus
• Haplopappus deserticola
• Hesperocyparis arizonica
• Hippeastrum papilio
• Hippeastrum puniceum
• Hymenocallis littoralis
• Hymenocallis rotata
• Leucojum aestivum
• Leucojum vernum
• Ligularia przewalskii
• Lycoris aurea
• Lycoris incarnata
• Lycoris radiata
• Lycoris sanguinea
• Lycoris squamigera
• Lycoris traubii
• Narcissus × tortifolius
• Narcissus bulbocodium subsp. bulbocodium
• Narcissus confusus
• Narcissus obesus
• Narcissus tazetta
• Neorautanenia mitis
• Nerine bowdenii
• Pancratium maritimum
• Pancratium trianthum
• Phaedranassa dubia
• Pittosporum eugenioides
• Pteroxygonum giraldii
• Salvia yunnanensis
• Scadoxus multiflorus subsp. multiflorus
• Seriphidium junceum
• Stachys aegyptiaca
• Ungernia sewerzowi
• Ungernia victoris
• Viburnum lantana

Cross-Links

• PubChem: 9651
• NPASS: NPC78359
• ChEMBL: CHEMBL659
• LOTUS: LTS0038419
• wikiData: Q412690