N-Desmethylgalantamine

Details

• Internal ID: 28c1c6a3-ecca-4d33-8cd4-7c7976dbbbad
• Taxonomy: Alkaloids and derivatives > Amaryllidaceae alkaloids > Galanthamine-type amaryllidaceae alkaloids
• IUPAC Name: (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
• 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
• InChI Key: AIXQQSTVOSFSMO-RBOXIYTFSA-N
• Popularity: 48 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₉NO₃
• Molecular Weight: 273.33 g/mol
• Exact Mass: 273.13649347 g/mol
• Topological Polar Surface Area (TPSA): 50.70 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.51
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 41303-74-6
• N-Desmethylgalantamine
• 2BPQ4IVQ21
• (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
• (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
• RefChem:927130
• N-Desmethyl Galanthamine
• N-Desmethylgalanthamine
• Norgalantamine
• N-Norgalanthamine
• N-Demethylgalanthamine
• UNII-2BPQ4IVQ21
• CHEMBL1385
• CHEBI:31919
• (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)-; Galanthamine, 10-demethyl-; (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
• F987305
• 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
• (4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-ol;Galanthamine impurity E;N-Norgalanthamine
• 6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL, 4A,5,9,10,11,12-HEXAHYDRO-3-METHOXY-, (4AS,6R,8AS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9974	99.74%
Caco-2	+	0.6829	68.29%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.4555	45.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9247	92.47%
OATP1B3 inhibitior	+	0.9547	95.47%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6223	62.23%
P-glycoprotein inhibitior	-	0.8818	88.18%
P-glycoprotein substrate	-	0.5547	55.47%
CYP3A4 substrate	+	0.6576	65.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.6405	64.05%
CYP3A4 inhibition	-	0.6860	68.60%
CYP2C9 inhibition	-	0.9015	90.15%
CYP2C19 inhibition	-	0.7868	78.68%
CYP2D6 inhibition	-	0.6280	62.80%
CYP1A2 inhibition	-	0.8540	85.40%
CYP2C8 inhibition	-	0.7198	71.98%
CYP inhibitory promiscuity	-	0.7754	77.54%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5184	51.84%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.9477	94.77%
Skin irritation	-	0.7435	74.35%
Skin corrosion	-	0.9184	91.84%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4802	48.02%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.8195	81.95%
skin sensitisation	-	0.7201	72.01%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.8265	82.65%
Acute Oral Toxicity (c)	III	0.4531	45.31%
Estrogen receptor binding	-	0.6799	67.99%
Androgen receptor binding	-	0.7861	78.61%
Thyroid receptor binding	+	0.6537	65.37%
Glucocorticoid receptor binding	-	0.5268	52.68%
Aromatase binding	-	0.7833	78.33%
PPAR gamma	-	0.6262	62.62%
Honey bee toxicity	-	0.7914	79.14%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	-	0.7994	79.94%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	1070 nM	IC50	PMID: 15878275

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.65%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.39%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.52%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.98%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.41%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.97%	94.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.79%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.80%	86.33%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	84.16%	96.39%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.17%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.65%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.15%	97.14%

Plants that contains it

• Ampelocissus leonensis
• Aralia elata var. elata
• Atriplex muricata
• Chromolaena laevigata
• Crinum asiaticum
• Crotalaria crispata
• Ferula persica
• Galanthus elwesii
• Haplopappus deserticola
• Hesperocyparis arizonica
• Hymenocallis rotata
• Leucojum vernum
• Ligularia przewalskii
• Lycoris aurea
• Lycoris guangxiensis
• Lycoris squamigera
• Narcissus bulbocodium subsp. bulbocodium
• Narcissus leonensis
• Narcissus pseudonarcissus
• Pancratium sickenbergeri
• Pittosporum eugenioides
• Pteroxygonum giraldii
• Seriphidium junceum
• Stachys aegyptiaca
• Viburnum lantana

Cross-Links

• PubChem: 9838394
• NPASS: NPC293871
• ChEMBL: CHEMBL1385
• LOTUS: LTS0051706
• wikiData: Q27114718