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1-O-acetyllycorine

Family: Plantae - Amaryllidaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Amaryllidaceae Alkaloid

Canonical Smiles	CC(=O)O[C@@H]1[C@@H](O)C=C2[C@@H]3[C@@H]1c1cc4OCOc4cc1CN3CC2
InChI	InChI=1S/C18H19NO5/c1-9(20)24-18-13(21)4-10-2-3-19-7-11-5-14-15(23-8-22-14)6-12(11)16(18)17(10)19/h4-6,13,16-18,21H,2-3,7-8H2,1H3/t13-,16-,17+,18+/m0/s1
InChIKey	BIGUPJIJZYZJMV-VIBAHUMZSA-N
Formula	C₁₈H₁₉NO₅
HBA	6
HBD	1
MW	329.35
Rotatable Bonds	1
TPSA	68.23
LogP	1.32
Number Rings	5
Number Aromatic Rings	1
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	329.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Narcissus species	Amaryllidaceae	Plantae	54843

Showing of synonyms

Shawky E, Abou-Donia AH, et al. (2015). HPTLC and GC/MS study of Amaryllidaceae alkaloids of two Narcissus species. Chemistry and Biodiversity,2015,12(8),1184-1199. [View] [PubMed]

Pubchem: 443672

Zinc: ZINC000053021570

Kegg Ligand: C12166

Chebi: 31045

Nmrshiftdb2: 60063435

Metabolights: MTBLC31045

Chembl: CHEMBL251077

Bindingdb: 50221063

No compound-protein relationship available.

SMILES: O1COc(c12)cc3c(c2)C4C5C(=CCC4)CCN5C3

Level: 0

Mol. Weight: 329.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.79
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.61
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.44

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.64
Plasma Protein Binding: 38.29
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 13.51
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.53
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.29
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 8.55
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: -4.47
Rat (Acute): 2.75
Rat (Chronic Oral): 1.86
Fathead Minnow: 4.05
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: 393.64
Hydration Free Energy: -9.2
Log(D) at pH=7.4: 1.29
Log(P): 1.23
Log S: -1.8
Log(Vapor Pressure): -8.55
Melting Point: 193.78
pKa Acid: 8.91
pKa Basic: 6.45

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9418
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9418
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8058
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8058
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7965
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7965
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7757
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7757
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7549
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7549
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7457
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7457
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7217
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7217
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7181
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7181
GMP reductase 2	Q9P2T1	GMPR2_HUMAN	Homo sapiens	3	0.7162
GMP reductase 2	Q9P2T1	GMPR2_HUMAN	Homo sapiens	3	0.7162
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7128
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7128
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7126
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7126
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7022
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7022
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7019
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7019
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7017
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7017

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