2,10-dihydroxy-3,9-dimethoxy-8-oxo-protoberberine - Compound Card

2,10-dihydroxy-3,9-dimethoxy-8-oxo-protoberberine

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2,10-dihydroxy-3,9-dimethoxy-8-oxo-protoberberine

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Protoberberine Alkaloid
Canonical Smiles COc1cc2CCN3[C@H](c2cc1O)Cc1c(C3=O)c(OC)c(cc1)O
InChI InChI=1S/C19H19NO5/c1-24-16-8-10-5-6-20-13(12(10)9-15(16)22)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 MIPGMQDGLYCHSS-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]

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)
-4.6
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.940
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.850
Plasma Protein Binding
71.09
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.810
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.020
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.120
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.900
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
-0.010
Rat (Acute)
1.860
Rat (Chronic Oral)
2.350
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
455.030
Hydration Free Energy
-9.810
Log(D) at pH=7.4
1.840
Log(P)
1.63
Log S
-3.52
Log(Vapor Pressure)
-8.09
Melting Point
236.29
pKa Acid
8.48
pKa Basic
6.61
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.9550
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9429
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9203
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9180
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9105
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.9009
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8911
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8880
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8832
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8821
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8792
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8734
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8722
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8668
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8657
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8655
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8586
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8553
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.8549
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.8537
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8503
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8477
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8382
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8379
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8307
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8242
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8238
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.8206
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8181
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.8150
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8147
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8139
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8123
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8122
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.8121
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8088
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8086
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8068
Reticuline oxidase P30986 RETO_ESCCA Eschscholzia californica 4 0.7983
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7954
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7943
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7940
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7931
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7914
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 4 0.7913
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7872
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7853
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7843
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7775
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.7749
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7748
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7747
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7746
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7732
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7724
Reticuline oxidase P30986 RETO_ESCCA Eschscholzia californica 5 0.7713
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7696
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7688
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7641
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7635
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7604
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7583
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7580
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7551
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7523
DNA gyrase subunit B Q839Z1 GYRB_ENTFA Enterococcus faecalis 3 0.7497
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7479
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7468
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7458
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7455
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7453
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7452
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7450
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7444
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7427
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7420
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7404
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7403
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7392
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7381
Lanosterol 14-alpha demethylase A6ZSR0 A6ZSR0_YEAS7 Saccharomyces cerevisiae 3 0.7378
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7375
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 4 0.7365
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7360
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7347
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7333
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7322
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7279
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7268
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7264
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7254
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7240
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7240
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7232
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 5 0.7227
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7217
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7199
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7195
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7183
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7169
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7165
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7150
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 4 0.7147
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7146
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7141
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7134
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7128
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7121
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7117
16S rRNA (adenine(1408)-N(1))-methyltransferase A8C927 NPMA_ECOLX Escherichia coli 3 0.7114
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7106
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7099
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7094
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7091
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7089
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7087
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7080
Histone-lysine N-methyltransferase 2C Q8NEZ4 KMT2C_HUMAN Homo sapiens 3 0.7079
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7071
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7066
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7065
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7059
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7045
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7042
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7036
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7032
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7019
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7013
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7008
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 2 0.7007
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7003

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