8-oxodiscretamine - Compound Card

8-oxodiscretamine

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8-oxodiscretamine

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Protoberberine Alkaloid
Canonical Smiles COc1cc2c(cc1O)CCN1[C@H]2Cc2ccc(c(c2C1=O)OC)O
InChI InChI=1S/C19H19NO5/c1-24-16-9-12-10(8-15(16)22)5-6-20-13(12)7-11-3-4-14(21)18(25-2)17(11)19(20)23/h3-4,8-9,13,21-22H,5-7H2,1-2H3/t13-/m0/s1
InChIKey IYRHVIAPCJYOGS-ZDUSSCGKSA-N
Formula C19H19NO5
HBA 5
HBD 2
MW 341.36
Rotatable Bonds 2
TPSA 79.23
LogP 2.41
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 341.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artabotrys thomsonii Annonaceae Plantae 1636230

Showing of synonyms

  • Chimeze VWN, Bankoglu EE, et al. (2022). Cytotoxic and genotoxic properties of artathomsonine, a new oxoberberine alkaloid from Artabotrys thomsonii (annonaceae).. Natural product research,2022, 36(11), 2791-2799. [View] [PubMed]
Pubchem: 132531973

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)CC3c4c(cccc4)CCN3C2=O

Level: 0

Mol. Weight: 341.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.920
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.860
Plasma Protein Binding
68.87
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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.660
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.040
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.150
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.130
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
-0.090
Rat (Acute)
1.950
Rat (Chronic Oral)
2.410
Fathead Minnow
4.330
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
445.430
Hydration Free Energy
-9.760
Log(D) at pH=7.4
2.030
Log(P)
1.51
Log S
-3.55
Log(Vapor Pressure)
-7.99
Melting Point
233.61
pKa Acid
8.38
pKa Basic
6.01
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.9348
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9261
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9131
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.9131
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.9066
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8982
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8931
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8883
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8861
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8858
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8821
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8805
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8791
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8688
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8658
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8509
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8493
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8473
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.8388
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.8384
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8358
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8356
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 4 0.8351
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8313
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8291
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8291
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.8288
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8166
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8148
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8105
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.8096
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8094
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8087
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.8073
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8053
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8012
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7968
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7956
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7952
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7950
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7950
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7929
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7912
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7909
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7901
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.7868
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7835
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7834
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7797
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7793
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.7775
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7751
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7733
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7730
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7692
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7677
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7669
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7628
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7620
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7617
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7605
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7603
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7595
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7585
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7579
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7577
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7572
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7546
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7546
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7537
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7526
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7496
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7496
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7478
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7471
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7461
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7457
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7456
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7454
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7428
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7425
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7394
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7386
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7385
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7380
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7376
Transthyretin P02766 TTHY_HUMAN Homo sapiens 4 0.7366
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7353
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7347
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7337
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7332
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7327
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7314
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7298
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7279
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7266
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7261
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7256
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7248
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7226
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7222
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7210
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7198
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7197
Lanosterol 14-alpha demethylase A6ZSR0 A6ZSR0_YEAS7 Saccharomyces cerevisiae 3 0.7196
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7187
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7185
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7182
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7181
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7169
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7166
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7160
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7154
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 4 0.7152
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 5 0.7152
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7149
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7148
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7140
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7131
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7127
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7123
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7122
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7119
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7117
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7109
Histone-lysine N-methyltransferase 2C Q8NEZ4 KMT2C_HUMAN Homo sapiens 3 0.7108
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 4 0.7103
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7103
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7086
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7086
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7055
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7032
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7011
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7007

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