Pretazettine - Compound Card

Pretazettine

Select a section from the left sidebar

Pretazettine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CO[C@@H]1C=C[C@]23[C@H](C1)N(C)C[C@@H]2O[C@H](c1c3cc2OCOc2c1)O
InChI InChI=1S/C18H21NO5/c1-19-8-16-18(4-3-10(21-2)5-15(18)19)12-7-14-13(22-9-23-14)6-11(12)17(20)24-16/h3-4,6-7,10,15-17,20H,5,8-9H2,1-2H3/t10-,15+,16+,17-,18+/m1/s1
InChIKey KLJOYDMUWKSYBP-YNBLHMCPSA-N
Formula C18H21NO5
HBA 6
HBD 1
MW 331.37
Rotatable Bonds 1
TPSA 60.39
LogP 1.33
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 Zephyranthes candida Amaryllidaceae Plantae 82257

Showing of synonyms

  • Shawky E, El Sohafy S.M, et al. (2021). Profiling of acetylcholinesterase inhibitory alkaloids from some Crinum, Habranthus and Zephyranthes species by GC–MS combined with multivariate analyses and in silico studies.. Nat Prod Res, 2021, 35(5), 807-814.. [View] [PubMed]
Pubchem: 73360
Kegg Ligand: C08536
Chebi: 8402
Nmrshiftdb2: 60027216
Metabolights: MTBLC8402
CPRiL: 258932
Structure

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

Level: 0

Mol. Weight: 331.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
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
-1.6

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.490
Plasma Protein Binding
29.57
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
10.060
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.720
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.070
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
9.980
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
-7.480
Rat (Acute)
2.960
Rat (Chronic Oral)
1.450
Fathead Minnow
4.010
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
370.830
Hydration Free Energy
-8.620
Log(D) at pH=7.4
1.510
Log(P)
0.82
Log S
-1.47
Log(Vapor Pressure)
-8.24
Melting Point
166.72
pKa Acid
8.33
pKa Basic
7.03
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.9438
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9227
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8998
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8568
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8540
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8527
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8173
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8140
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8136
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8103
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8042
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7991
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7922
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7779
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 3 0.7690
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7670
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7665
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7426
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7345
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7338
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7331
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7323
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7315
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7308
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7297
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7288
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7271
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic P49235 HGGL1_MAIZE Zea mays 3 0.7267
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7209
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7133
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7109
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7081
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7038
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7024
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7019

Download SDF