Dioncophylline F - Compound Card

Dioncophylline F

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Dioncophylline F

Structure
Zoomed Structure
  • Family: Plantae - Dioncophyllaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1ccc(c2c1c(OC)cc(c2)C)c1ccc(c2c1C[C@@H](C)N[C@H]2C)O
InChI InChI=1S/C24H27NO3/c1-13-10-18-17(7-9-21(27-4)24(18)22(11-13)28-5)16-6-8-20(26)23-15(3)25-14(2)12-19(16)23/h6-11,14-15,25-26H,12H2,1-5H3/t14-,15+/m1/s1
InChIKey ZJJPBMLFLTUEDN-CABCVRRESA-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

Showing of synonyms

  • 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: 132500908

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2-c3cccc(c34)CNCC4

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

Absorption

Caco-2 (logPapp)
-5.15
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.860
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.59

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.170
Plasma Protein Binding
80.92
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
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
8.150
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.550
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.450
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
8.770
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-13.090
Rat (Acute)
2.540
Rat (Chronic Oral)
1.840
Fathead Minnow
5.110
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
461.530
Hydration Free Energy
-7.110
Log(D) at pH=7.4
3.700
Log(P)
4.77
Log S
-4.26
Log(Vapor Pressure)
-8.47
Melting Point
172.39
pKa Acid
10.51
pKa Basic
9.73
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9552
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9447
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9283
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8895
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8878
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8847
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8845
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8391
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.8366
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8314
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8289
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8280
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8242
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8241
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8152
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7921
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7849
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7830
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7828
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7791
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7763
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7713
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7679
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7621
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7608
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7588
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7588
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7501
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7480
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7442
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7390
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7386
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7383
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7315
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7314
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7311
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7310
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7268
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7262
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7256
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7255
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7250
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7244
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7234
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7189
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7155
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7105
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7091
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7077
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7048
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7048
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7034
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7012
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7011
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7007

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