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2,11-didehydro-2-dehydroxylycorine

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

Canonical Smiles	OC1C=CC2=CCN3[C@H]2[C@@H]1c1cc2OCOc2cc1C3
InChI	InChI=1S/C16H15NO3/c18-12-2-1-9-3-4-17-7-10-5-13-14(20-8-19-13)6-11(10)15(12)16(9)17/h1-3,5-6,12,15-16,18H,4,7-8H2/t12?,15-,16-/m1/s1
InChIKey	HZRPCZPAUNSTFO-XHAYOOOLSA-N
Formula	C₁₆H₁₅NO₃
HBA	4
HBD	1
MW	269.3
Rotatable Bonds	0
TPSA	41.93
LogP	1.55
Number Rings	5
Number Aromatic Rings	1
Heavy Atom Count	20
Formal Charge	0
Fraction CSP3	0.38
Exact Mass	269.11
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: 162817005

No compound-protein relationship available.

SMILES: O1COc(c12)cc3c(c2)C4C5C(C=CC4)=CCN5C3

Level: 0

Mol. Weight: 269.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.82
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.330
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.99

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.710
Plasma Protein Binding: 45.76
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: Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 13.290
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.770
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.120
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.310
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: 1.550
Rat (Acute): 2.720
Rat (Chronic Oral): 1.410
Fathead Minnow: 4.070
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: 392.470
Hydration Free Energy: -9.560
Log(D) at pH=7.4: 2.060
Log(P): 1.28
Log S: -1.85
Log(Vapor Pressure): -8.38
Melting Point: 187.8
pKa Acid: 9.46
pKa Basic: 7.45

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	0.8895
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8895
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8464
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8464
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8461
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8461
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8435
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8435
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.8065
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.8065
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7996
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7996
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7986
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7986
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7881
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7881
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7777
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7777
Odorant binding protein ASP1	Q8WRW5	Q8WRW5_APIME	Apis mellifera	3	0.7765
Odorant binding protein ASP1	Q8WRW5	Q8WRW5_APIME	Apis mellifera	3	0.7765
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7740
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7740
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7610
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7610
Fatty acid-binding protein, adipocyte	P15090	FABP4_HUMAN	Homo sapiens	2	0.7542
Fatty acid-binding protein, adipocyte	P15090	FABP4_HUMAN	Homo sapiens	2	0.7542
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7489
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7489
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7479
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7479
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7406
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7406
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7341
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7341
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7252
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7252
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7244
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7244
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7234
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7234
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7214
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7214
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7175
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7175
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7144
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7144
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7117
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7117
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7116
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7116
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7077
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7077
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7053
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7053
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7040
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7040
Tryptophan synthase alpha chain	P00929	TRPA_SALTY	Salmonella typhimurium	3	0.7017
Tryptophan synthase alpha chain	P00929	TRPA_SALTY	Salmonella typhimurium	3	0.7017
Jasmonoyl--L-amino acid synthetase JAR1	Q9SKE2	JAR1_ARATH	Arabidopsis thaliana	3	0.7008
Jasmonoyl--L-amino acid synthetase JAR1	Q9SKE2	JAR1_ARATH	Arabidopsis thaliana	3	0.7008
Nucleoside 2-deoxyribosyltransferase	Q8RLY5	Q8RLY5_LACHE	Lactobacillus helveticus	2	0.7001
Nucleoside 2-deoxyribosyltransferase	Q8RLY5	Q8RLY5_LACHE	Lactobacillus helveticus	2	0.7001

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