Dioncophylline A - Compound Card

Dioncophylline A

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Dioncophylline A

Structure
Zoomed Structure
  • Family: Plantae - Dioncophyllaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cccc2c1c(OC)cc(c2c1ccc2c(c1O)[C@@H](C)N[C@@H](C2)C)C
InChI InChI=1S/C24H27NO3/c1-13-11-20(28-5)23-17(7-6-8-19(23)27-4)21(13)18-10-9-16-12-14(2)25-15(3)22(16)24(18)26/h6-11,14-15,25-26H,12H2,1-5H3/t14-,15-/m1/s1
InChIKey MXIZZLBQRBAZEX-HUUCEWRRSA-N
Formula C24H27NO3
HBA 4
HBD 2
MW 377.48
Rotatable Bonds 3
TPSA 50.72
LogP 5.13
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 377.2
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus ileboensis Ancistrocladaceae Plantae 1367080
2 Ancistrocladus ileboensis Dioncophyllaceae Plantae 1367080
3 Ancistrocladus abbreviatus Ancistrocladaceae Plantae 122295
4 Triphyophyllum peltatum Dioncophyllaceae Plantae 63090

Showing of synonyms

  • François G, Bringmann G, et al. (1995). Activities of extracts and naphthylisoquinoline alkaloids from Triphyophyllum peltatum, Ancistrocladus abbreviatus and Ancistrocladus barteri against Plasmodium berghei (Anka strain) in vitro. Journal of Ethnopharmacology, 1995, 46(2), 115-120. [View]
  • Fayez S, Feineis D, et al. (2018). Ancistrobrevines E-J and related naphthylisoquinoline alkaloids from the West African liana Ancistrocladus abbreviatus with inhibitory activities against Plasmodium falciparum and PANC-1 human pancreatic cancer cells. Fitoterapia, 2018, 131, 245-259. [View]
  • Li J, Seupel R, et al. (2017). Dioncophyllines C2, D2, and F and related naphthylisoquinoline alkaloids from the Congolese Liana Ancistrocladus ileboensis with potent activities against Plasmodium falciparum and against multiple myeloma and leukemia cell lines. Journal of natural products,2017, 80(2), 443-458. [View] [PubMed]
Pubchem: 443773
Kegg Ligand: C12336
Chebi: 66272
Nmrshiftdb2: 60027551
Metabolights: MTBLC31504

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2-c(c3)ccc(c34)CCNC4

Level: 1

Mol. Weight: 377.48 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 377.48 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 377.48 g/mol

Anti-plasmodial
Antimalarial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.19
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.820
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.09

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.200
Plasma Protein Binding
85.6
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.270
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.590
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.610
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.030
Micronucleos
Toxic
NR-AhR
Toxic
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
-13.000
Rat (Acute)
2.720
Rat (Chronic Oral)
2.030
Fathead Minnow
5.100
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
451.860
Hydration Free Energy
-7.410
Log(D) at pH=7.4
3.860
Log(P)
4.33
Log S
-4.15
Log(Vapor Pressure)
-8.71
Melting Point
157.08
pKa Acid
10.16
pKa Basic
9.54
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9496
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9438
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9162
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8965
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8934
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.8701
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8586
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.8576
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8563
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8503
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8478
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8439
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8424
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8313
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8305
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.8296
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8252
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8181
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8118
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8064
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8024
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8015
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7984
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7939
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7931
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7880
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7870
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7814
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7811
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7802
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7687
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7654
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.7648
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7640
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7616
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7602
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7592
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7579
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7540
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7537
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7502
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7497
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7489
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7472
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7469
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7451
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7351
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7272
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7265
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7247
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7210
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7209
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7209
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7202
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7202
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7181
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7165
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 3 0.7122
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7101
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7087
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7077
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7071
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7064
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7059
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 3 0.7025
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7025
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7013

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