Deoxytazettine - Compound Card

Deoxytazettine

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Deoxytazettine

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@@H]2OCc1c3cc2OCOc2c1
InChI InChI=1S/C18H21NO4/c1-19-8-17-18(4-3-12(20-2)6-16(18)19)13-7-15-14(22-10-23-15)5-11(13)9-21-17/h3-5,7,12,16-17H,6,8-10H2,1-2H3/t12-,16+,17+,18+/m1/s1
InChIKey GUOPOINZHOBRSW-IEGACIPQSA-N
Formula C18H21NO4
HBA 5
HBD 0
MW 315.37
Rotatable Bonds 1
TPSA 40.16
LogP 1.84
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.56
Exact Mass 315.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Narcissus tazetta Amaryllidaceae Plantae 54860

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: 23259454
Nmrshiftdb2: 60071266

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 315.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.620
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.470
Plasma Protein Binding
31.28
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.380
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.200
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.220
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
9.910
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
-4.110
Rat (Acute)
3.050
Rat (Chronic Oral)
0.970
Fathead Minnow
3.830
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
364.300
Hydration Free Energy
-7.290
Log(D) at pH=7.4
2.070
Log(P)
1.92
Log S
-1.89
Log(Vapor Pressure)
-7.44
Melting Point
139.58
pKa Acid
9.17
pKa Basic
7.18
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 0.9553
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9553
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9441
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9441
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.9299
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.9299
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9196
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9196
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9032
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9032
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8937
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8937
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8796
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8796
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8768
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8768
Proline iminopeptidase O32449 PIP_SERMA Serratia marcescens 3 0.8691
Proline iminopeptidase O32449 PIP_SERMA Serratia marcescens 3 0.8691
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8610
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8610
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8561
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8561
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8496
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8496
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 3 0.8388
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 3 0.8388
Proline iminopeptidase O32449 PIP_SERMA Serratia marcescens 3 0.8380
Proline iminopeptidase O32449 PIP_SERMA Serratia marcescens 3 0.8380
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8370
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8370
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8239
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8239
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8219
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8219
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8150
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8150
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8129
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8129
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7985
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7985
Cholesterol oxidase P22637 CHOD_BREST Brevibacterium sterolicum 3 0.7900
Cholesterol oxidase P22637 CHOD_BREST Brevibacterium sterolicum 3 0.7900
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7867
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7867
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7758
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7758
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7720
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7720
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7714
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7714
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7698
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7698
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7658
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7658
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7657
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7657
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7648
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7648
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7611
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7611
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7576
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7576
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7576
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7576
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7573
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7573
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7560
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7560
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7539
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7539
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7497
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7497
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7493
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7493
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7428
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7428
Proline iminopeptidase O32449 PIP_SERMA Serratia marcescens 3 0.7384
Proline iminopeptidase O32449 PIP_SERMA Serratia marcescens 3 0.7384
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7358
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7358
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7352
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7352
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7348
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7348
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7346
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7346
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7315
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7315
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7274
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7274
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7243
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7243
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7225
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7225
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7224
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7224
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7217
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7217
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7208
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7208
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7206
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7206
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7178
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7178
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7168
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7168
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7158
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7158
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 4 0.7084
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 4 0.7084
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7074
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7074
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7068
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7068
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7063
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7063
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7054
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7054
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7050
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7050
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7032
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7032
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7030
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7030
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7002
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7002

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