7-epi-dioncophylline A - Compound Card

7-epi-dioncophylline A

Select a section from the left sidebar

7-epi-dioncophylline A

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(C)c(c2c1c(O)ccc2)c1ccc2c(c1O)[C@@H](C)N[C@@H](C2)C
InChI InChI=1S/C23H25NO3/c1-12-10-19(27-4)22-16(6-5-7-18(22)25)20(12)17-9-8-15-11-13(2)24-14(3)21(15)23(17)26/h5-10,13-14,24-26H,11H2,1-4H3/t13-,14-/m1/s1
InChIKey PBUONONRMDRRLQ-ZIAGYGMSSA-N
Formula C23H25NO3
HBA 4
HBD 3
MW 363.46
Rotatable Bonds 2
TPSA 61.72
LogP 4.83
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 363.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus ileboensis Ancistrocladaceae Plantae 1367080
2 Ancistrocladus ileboensis Ancistrocladaceae 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]
  • Li J, Seupel R, et al. (2017). Jozilebomines A and B, Naphthylisoquinoline Dimers from the Congolese Liana Ancistrocladus ileboensis, with Antiausterity Activities against the PANC-1 Human Pancreatic Cancer Cell Line.. Journal of natural products,2017, 80(10), 2807-2817. [View] [PubMed]
Pubchem: 10384109
Nmrshiftdb2: 70016259

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 363.46 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 363.46 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 363.46 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-5.01
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
Non-Substrate
Skin Permeability
-0.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.050
Plasma Protein Binding
86.27
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
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.030
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.710
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.730
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.590
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
-7.380
Rat (Acute)
2.510
Rat (Chronic Oral)
2.190
Fathead Minnow
4.800
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
450.470
Hydration Free Energy
-8.710
Log(D) at pH=7.4
4.150
Log(P)
4.26
Log S
-4.37
Log(Vapor Pressure)
-8.59
Melting Point
177.72
pKa Acid
9.21
pKa Basic
8.74
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9221
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9122
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8973
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8903
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8790
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8785
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.8713
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8710
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8564
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8548
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8512
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8436
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8419
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8358
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.8305
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8226
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8187
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.8088
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7956
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7949
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7948
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7936
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.7925
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7915
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7912
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7889
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7875
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7849
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7843
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7841
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7772
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7715
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7702
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.7650
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7645
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7572
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7533
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7530
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7523
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7518
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7511
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7497
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7490
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7444
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7390
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7387
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7378
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7362
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7361
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7337
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7334
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7324
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7310
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7297
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7277
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7257
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7224
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7208
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7173
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.7166
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7159
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7140
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7136
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7131
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7113
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7099
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7093
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7088
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7085
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7065
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7054
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7019
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7008
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 3 0.7007

Download SDF