Tazettine - Compound Card

Tazettine

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Tazettine

Structure
Zoomed Structure
  • 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@]3(O)OCc1c2cc2OCOc2c1
InChI InChI=1S/C18H21NO5/c1-19-9-18(20)17(4-3-12(21-2)6-16(17)19)13-7-15-14(22-10-23-15)5-11(13)8-24-18/h3-5,7,12,16,20H,6,8-10H2,1-2H3/t12-,16+,17+,18+/m1/s1
InChIKey YLWAQARRNQVEHD-IEGACIPQSA-N
Formula C18H21NO5
HBA 6
HBD 1
MW 331.37
Rotatable Bonds 1
TPSA 60.39
LogP 1.16
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.56
Exact Mass 331.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Narcissus tazetta Amaryllidaceae Plantae 54860
2 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]
  • Abdallah OM. (1993). Narcisine, an alkaloid from Narcissus tazetta. Phytochemistry,1993,34(5),1447-1448. [View]
Pubchem: 443682
Kegg Ligand: C12179
Nmrshiftdb2: 60027218
CPRiL: 67862
Structure

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

Level: 0

Mol. Weight: 331.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.640
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.58

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.510
Plasma Protein Binding
19.82
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
8.380
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.970
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.310
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.570
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
-4.860
Rat (Acute)
2.880
Rat (Chronic Oral)
1.370
Fathead Minnow
4.040
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
391.000
Hydration Free Energy
-8.030
Log(D) at pH=7.4
1.730
Log(P)
1.39
Log S
-1.22
Log(Vapor Pressure)
-8.14
Melting Point
181.53
pKa Acid
6.94
pKa Basic
7.15
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 0.9111
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9111
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9061
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9061
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8573
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8573
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8302
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8302
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8272
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8272
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8244
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8244
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 3 0.8228
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 3 0.8228
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8151
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8151
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8128
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8128
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8082
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8082
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7850
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7850
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7749
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7749
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7683
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7683
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7674
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7674
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7554
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7554
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7431
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7431
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7421
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7421
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7411
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7411
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7390
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7390
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7374
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7374
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7357
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7357
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7336
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7336
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7285
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7285
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7279
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7279
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7278
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7278
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7252
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7252
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7233
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7233
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7186
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7186
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7170
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7170
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7137
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7137
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7129
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7129
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7096
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7096
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7059
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7059
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7038
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7038
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7029
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7029

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