Ikelacongoline C - Compound Card

Ikelacongoline C

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Ikelacongoline C

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(O)c(c2c1[C@H](C)N(C)[C@@H](C2)C)c1ccc(c2c1cc(C)cc2OC)OC
InChI InChI=1S/C26H31NO4/c1-14-10-18-17(8-9-21(29-5)26(18)22(11-14)30-6)25-19-12-15(2)27(4)16(3)24(19)23(31-7)13-20(25)28/h8-11,13,15-16,28H,12H2,1-7H3/t15-,16+/m1/s1
InChIKey RNLKCMIGQLHEKX-CVEARBPZSA-N
Formula C26H31NO4
HBA 5
HBD 1
MW 421.54
Rotatable Bonds 4
TPSA 51.16
LogP 5.48
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 421.23
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus sp. Ancistrocladaceae Plantae 300538

Showing of synonyms

  • Mufusama JP, Feineis D, et al. (2019). Antiprotozoal dimeric naphthylisoquinolines, mbandakamines B3 and B4 , and related 5,8'-coupled monomeric alkaloids, ikelacongolines A – D, from a Congolese. Ancistrocladus liana.. RSC advances,2019, 9(21), 12034-12046. [View] [PubMed]
Pubchem: 162942967
Nmrshiftdb2: 70059372

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 421.54 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 421.54 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 421.54 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.99
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.830
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.170
Plasma Protein Binding
73.01
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
9.760
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.360
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.120
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
10.500
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
-52.250
Rat (Acute)
2.630
Rat (Chronic Oral)
1.960
Fathead Minnow
5.310
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
459.430
Hydration Free Energy
-4.470
Log(D) at pH=7.4
4.500
Log(P)
4.61
Log S
-4.85
Log(Vapor Pressure)
-9.1
Melting Point
135.39
pKa Acid
9.82
pKa Basic
9.22
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 0.9326
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9326
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9312
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9312
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9124
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9124
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9054
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9054
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9044
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9044
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.9021
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.9021
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8512
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8512
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8351
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8351
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8139
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8139
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8137
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8137
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8085
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8085
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8006
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8006
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7993
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7993
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7960
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7960
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7926
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7926
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7866
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7866
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7848
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7848
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7748
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7748
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7712
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7712
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7682
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7682
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7664
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7664
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7656
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7656
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7652
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7652
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7617
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7617
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7615
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7615
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7606
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7606
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7577
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7577
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7565
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7565
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7564
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7564
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7544
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7544
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7532
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7532
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7522
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7522
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7387
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7387
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7384
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7384
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7372
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7372
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7370
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7370
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7321
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7321
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7299
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7299
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7291
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7291
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7284
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7284
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7282
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7282
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7268
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7268
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7248
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7248
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7241
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7241
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7240
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7240
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7206
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7206
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7192
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7192
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7188
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7188
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7166
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7166
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7158
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7158
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7136
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7136
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7135
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7135
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7113
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7113
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7111
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7111
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7106
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7106
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7079
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7079
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7073
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7073
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7060
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7060
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7047
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7047
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7025
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7025
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7021
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7021
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7013
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7013

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