Dioncophylline C2 - Compound Card

Dioncophylline C2

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Dioncophylline C2

Structure
Zoomed Structure
  • Family: Plantae - Dioncophyllaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1ccc(c2c1[C@H](C)N[C@@H](C2)C)c1c(C)cc(c2c1cccc2OC)OC
InChI InChI=1S/C25H29NO3/c1-14-12-22(29-6)25-18(8-7-9-20(25)27-4)23(14)17-10-11-21(28-5)24-16(3)26-15(2)13-19(17)24/h7-12,15-16,26H,13H2,1-6H3/t15-,16+/m1/s1
InChIKey OSUADVGZBWBMHL-CVEARBPZSA-N
Formula C25H29NO3
HBA 4
HBD 1
MW 391.51
Rotatable Bonds 4
TPSA 39.72
LogP 5.44
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 391.21
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: 132500912

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 391.51 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 391.51 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 391.51 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-5.15
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.890
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.350
Plasma Protein Binding
76.16
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.910
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.200
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.090
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.060
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
Toxic
T. Pyriformis
-23.670
Rat (Acute)
2.970
Rat (Chronic Oral)
1.740
Fathead Minnow
5.620
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
458.910
Hydration Free Energy
-6.320
Log(D) at pH=7.4
4.110
Log(P)
5.24
Log S
-4.22
Log(Vapor Pressure)
-8.12
Melting Point
133.81
pKa Acid
12.23
pKa Basic
9.79
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 0.9713
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9479
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9427
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9193
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9071
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.9062
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.9061
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8655
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8569
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8483
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.8458
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8453
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8386
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8326
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8160
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.8156
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.8138
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.8082
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8020
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7931
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7858
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7835
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7773
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7757
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7741
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7721
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7704
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7689
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7657
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7640
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7602
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7468
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7430
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7428
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7416
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7409
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7385
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7381
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7373
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7348
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 3 0.7348
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7338
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7302
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7290
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7258
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7238
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7234
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7218
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7208
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7184
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7148
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7081
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7079
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7055
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7054
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7047
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7044
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7041
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7012

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