Lycoramine

Details

• Internal ID: a992c549-1543-4252-8136-5f5204f9ddac
• Taxonomy: Alkaloids and derivatives > Amaryllidaceae alkaloids > Galanthamine-type amaryllidaceae alkaloids
• IUPAC Name: (1R,12S,14S)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9-trien-14-ol
• SMILES (Canonical): CN1CCC23CCC(CC2OC4=C(C=CC(=C34)C1)OC)O
• SMILES (Isomeric): CN1CC[C@@]23CC[C@@H](C[C@@H]2OC4=C(C=CC(=C34)C1)OC)O
• InChI: InChI=1S/C17H23NO3/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/h3-4,12,14,19H,5-10H2,1-2H3/t12-,14-,17-/m0/s1
• InChI Key: GJRMHIXYLGOZSE-JDFRZJQESA-N
• Popularity: 41 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₃NO₃
• Molecular Weight: 289.40 g/mol
• Exact Mass: 289.16779360 g/mol
• Topological Polar Surface Area (TPSA): 41.90 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.07
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 21133-52-8
• 1,2-Dihydrogalanthamine
• Lycoramine free base
• Dihydrogalanthamine
• UNII-TAG8LU84K2
• TAG8LU84K2
• (+-)-lycoramine
• CHEBI:31789
• CHEMBL469638
• 21133-52-8 (free base)
• 6H-Benzofuro[3a,3,2-ef][2]benzazepin-6-ol, 4a,5,7,8,9,10,11,12-octahydro-3-methoxy-11-methyl-, (4aS,6S,8aR)-
• (-)-lycoramine
• (4aS,6S,8aR)-3-methoxy-11-methyl-4a,5,7,8,9,10,11,12-octahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-ol
• AC1L9F2N
• Lycoramin
• Dihydro Galantamine
• 6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL, 4A,5,7,8,9,10,11,12-OCTAHYDRO-3-METHOXY-11-METHYL-, (4AS,6S,8AR)-
• LYCORAMINE [MI]
• SureCN1395930
• GALANTHAMINE, DIHYDRO-
• SCHEMBL1395930
• HY-N6619A
• DTXSID30175371
• CHEBI:543429
• GALANTHAMINE, 1,2-DIHYDRO-
• BDBM50278097
• AKOS040760538
• MS-24134
• CS-0089534
• W-201863
• Q27114686
• GALANTAMINE HYDROBROMIDE IMPURITY C [EP IMPURITY]
• (1R,12S,14S)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0?,??.0?,??]heptadeca-6(17),7,9-trien-14-ol
• (1R,12S,14S)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9-trien-14-ol
• (4AS,6S,8AR)-3-METHOXY-11-METHYL-5,6,7,8,9,10,11,12-OCTAHYDRO-4AH-(1)BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9957	99.57%
Caco-2	+	0.9362	93.62%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Lysosomes	0.6857	68.57%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.9283	92.83%
OATP1B3 inhibitior	+	0.9465	94.65%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.8376	83.76%
P-glycoprotein inhibitior	-	0.9327	93.27%
P-glycoprotein substrate	+	0.6301	63.01%
CYP3A4 substrate	+	0.7114	71.14%
CYP2C9 substrate	-	0.8139	81.39%
CYP2D6 substrate	+	0.7924	79.24%
CYP3A4 inhibition	-	0.8269	82.69%
CYP2C9 inhibition	-	0.8887	88.87%
CYP2C19 inhibition	-	0.8278	82.78%
CYP2D6 inhibition	-	0.5299	52.99%
CYP1A2 inhibition	-	0.9051	90.51%
CYP2C8 inhibition	-	0.7860	78.60%
CYP inhibitory promiscuity	-	0.9712	97.12%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6350	63.50%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9594	95.94%
Skin irritation	-	0.8107	81.07%
Skin corrosion	-	0.9384	93.84%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5372	53.72%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.6602	66.02%
skin sensitisation	-	0.8281	82.81%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.7624	76.24%
Acute Oral Toxicity (c)	III	0.4757	47.57%
Estrogen receptor binding	-	0.7395	73.95%
Androgen receptor binding	-	0.6709	67.09%
Thyroid receptor binding	+	0.5267	52.67%
Glucocorticoid receptor binding	-	0.7419	74.19%
Aromatase binding	-	0.8598	85.98%
PPAR gamma	-	0.5865	58.65%
Honey bee toxicity	-	0.8433	84.33%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	-	0.4096	40.96%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	610 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.39%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	96.45%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.52%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.37%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.11%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.39%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.31%	97.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.79%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.89%	86.33%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.56%	91.03%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.23%	97.25%
CHEMBL3023	Q9NRA0	Sphingosine kinase 2	83.76%	95.61%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.28%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.83%	100.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	80.94%	90.95%

Plants that contains it

• Brunsvigia gregaria
• Ferula persica
• Hymenocallis littoralis
• Hymenocallis rotata
• Ligularia przewalskii
• Lycoris guangxiensis
• Lycoris incarnata
• Lycoris radiata
• Lycoris sanguinea
• Lycoris traubii
• Narcissus tazetta
• Pancratium maritimum
• Stachys aegyptiaca

Cross-Links

• PubChem: 443723
• NPASS: NPC56540
• LOTUS: LTS0210106
• wikiData: Q27114686