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Pretazettine

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

Canonical Smiles	CO[C@@H]1C=C[C@]23[C@H](C1)N(C)C[C@@H]2O[C@H](c1c3cc2OCOc2c1)C
InChI	InChI=1S/C19H23NO4/c1-11-13-7-15-16(23-10-22-15)8-14(13)19-5-4-12(21-3)6-17(19)20(2)9-18(19)24-11/h4-5,7-8,11-12,17-18H,6,9-10H2,1-3H3/t11-,12+,17-,18-,19-/m0/s1
InChIKey	BEUAXUHESIYYCT-KDZDZWQKSA-N
Formula	C₁₉H₂₃NO₄
HBA	5
HBD	0
MW	329.4
Rotatable Bonds	1
TPSA	40.16
LogP	2.4
Number Rings	5
Number Aromatic Rings	1
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.58
Exact Mass	329.16
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Narcissus tazetta	Amaryllidaceae	Plantae	54860

Showing of synonyms

Abdallah OM. (1993). Narcisine, an alkaloid from Narcissus tazetta. Phytochemistry,1993,34(5),1447-1448. [View]

Pubchem: 73360

Cas: 17322-84-8

Gnps: CCMSLIB00012176763

Zinc: ZINC000053271495

Kegg Ligand: C08536

Chebi: 8402

Nmrshiftdb2: 60027216

Metabolights: MTBLC8402

Chembl: CHEMBL518912

CPRiL: 258932

SMILES: O1COc(c2)c1cc3c2COC(C345)CNC4CCC=C5

Level: 0

Mol. Weight: 329.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.81
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.680
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -2.17

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.510
Plasma Protein Binding: 36.27
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: 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: 10.950
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.300
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.400
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 9.430
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: -6.730
Rat (Acute): 3.150
Rat (Chronic Oral): 0.980
Fathead Minnow: 3.790
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: 367.460
Hydration Free Energy: -7.270
Log(D) at pH=7.4: 2.300
Log(P): 2.26
Log S: -2.03
Log(Vapor Pressure): -7.39
Melting Point: 133.29
pKa Acid: 9.23
pKa Basic: 7.33

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9271
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9271
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8871
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8871
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8550
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8550
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8517
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8517
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8399
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8399
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8242
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8242
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8239
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8239
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8210
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8210
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7969
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7969
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7932
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7932
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7851
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7851
Beta-2 adrenergic receptor	P07550	ADRB2_HUMAN	Homo sapiens	3	0.7819
Beta-2 adrenergic receptor	P07550	ADRB2_HUMAN	Homo sapiens	3	0.7819
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7756
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7756
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7669
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7669
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7591
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7591
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	3	0.7588
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	3	0.7588
Albumin	P02769	ALBU_BOVIN	Bos taurus	3	0.7522
Albumin	P02769	ALBU_BOVIN	Bos taurus	3	0.7522
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7490
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7490
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7399
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7399
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7395
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7395
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7344
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7344
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7319
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7319
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7308
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7308
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7173
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7173
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7152
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7152
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7102
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7102
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7073
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7073
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7037
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7037
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7022
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7022

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