4-hydroxy-3-O-methyl-8-oxodiscretamine - Compound Card

4-hydroxy-3-O-methyl-8-oxodiscretamine

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4-hydroxy-3-O-methyl-8-oxodiscretamine

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Protoberberine Alkaloid
Canonical Smiles COc1cc2[C@@H]3Cc4ccc(c(c4C(=O)N3CCc2c(c1OC)O)O)OC
InChI InChI=1S/C20H21NO6/c1-25-14-5-4-10-8-13-12-9-15(26-2)19(27-3)17(22)11(12)6-7-21(13)20(24)16(10)18(14)23/h4-5,9,13,22-23H,6-8H2,1-3H3/t13-/m0/s1
InChIKey ZUBYPBGSBDELCP-ZDUSSCGKSA-N
Formula C20H21NO6
HBA 6
HBD 2
MW 371.39
Rotatable Bonds 3
TPSA 88.46
LogP 2.42
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 371.14
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]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 371.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.020
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.22

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.960
Plasma Protein Binding
72.96
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.470
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.990
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.100
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.150
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
-5.540
Rat (Acute)
2.050
Rat (Chronic Oral)
2.640
Fathead Minnow
4.410
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
456.790
Hydration Free Energy
-8.640
Log(D) at pH=7.4
1.770
Log(P)
1.92
Log S
-3.54
Log(Vapor Pressure)
-7.89
Melting Point
214.21
pKa Acid
7.94
pKa Basic
6.25
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9724
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9452
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9352
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.9178
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9174
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9148
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9093
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9072
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.9030
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9017
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8955
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8943
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8873
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8849
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8842
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8806
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8762
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8757
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8595
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8519
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8457
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8446
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8427
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 4 0.8410
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8391
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8380
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8351
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8348
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8244
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8240
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8212
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8201
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8198
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8194
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8176
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8155
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8111
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8080
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.8072
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8066
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8060
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8038
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8003
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7940
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7935
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7921
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 3 0.7918
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7916
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7909
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7892
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7827
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7802
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7784
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7774
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7767
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7758
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7755
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7752
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7743
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7720
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7676
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7658
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7656
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7654
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7632
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7626
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7622
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7605
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7591
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7579
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7564
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7543
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7541
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 4 0.7526
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7515
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7506
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7503
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7500
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7500
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7484
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7483
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7454
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7436
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7435
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7434
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7428
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7423
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7416
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7415
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7408
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7397
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7393
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7385
Purine nucleoside phosphorylase 2 P45563 XAPA_ECOLI Escherichia coli 3 0.7378
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7368
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7359
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7353
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7347
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7341
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7340
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7334
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7321
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7298
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7296
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7288
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7282
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7276
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7273
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7264
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.7253
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7241
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7232
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7219
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7198
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7194
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7194
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7191
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7191
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7186
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7173
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7158
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7157
Reticuline oxidase P30986 RETO_ESCCA Eschscholzia californica 4 0.7152
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7151
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7150
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7145
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.7139
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7118
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7103
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7100
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7093
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7084
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7080
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7075
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7067
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial Q6NVY1 HIBCH_HUMAN Homo sapiens 3 0.7065
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7064
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7063
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7059
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7055
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7054
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7052
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7049
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7047
Lanosterol 14-alpha demethylase A6ZSR0 A6ZSR0_YEAS7 Saccharomyces cerevisiae 3 0.7041
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7023
Protein RecA Q59560 RECA_MYCS2 Mycolicibacterium smegmatis155) 3 0.7004

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