Ikelacongoline A - Compound Card

Ikelacongoline A

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Ikelacongoline A

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1ccc(c2c1c(OC)cc(c2)C)c1c(O)cc(c2c1C[C@@H](C)N([C@@H]2C)C)O
InChI InChI=1S/C25H29NO4/c1-13-9-17-16(7-8-21(29-5)25(17)22(10-13)30-6)24-18-11-14(2)26(4)15(3)23(18)19(27)12-20(24)28/h7-10,12,14-15,27-28H,11H2,1-6H3/t14-,15-/m1/s1
InChIKey XPNIPHCKKGOJOU-HUUCEWRRSA-N
Formula C25H29NO4
HBA 5
HBD 2
MW 407.51
Rotatable Bonds 3
TPSA 62.16
LogP 5.18
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 407.21
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: 163066508

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 407.51 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 407.51 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 407.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.06
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.880
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.84

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.040
Plasma Protein Binding
78.84
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
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.970
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.070
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.590
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.400
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
-29.870
Rat (Acute)
2.390
Rat (Chronic Oral)
2.150
Fathead Minnow
4.910
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
462.090
Hydration Free Energy
-6.600
Log(D) at pH=7.4
3.880
Log(P)
4.56
Log S
-4.47
Log(Vapor Pressure)
-9.2
Melting Point
158.71
pKa Acid
9.18
pKa Basic
9.39
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 0.9475
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9475
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9340
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9340
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9299
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9299
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9007
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9007
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8939
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8939
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8657
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8657
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8589
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8589
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8519
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8519
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8444
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8444
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8287
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8287
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8012
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8012
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7998
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7998
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7957
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7957
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7912
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7912
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7785
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7785
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7671
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7671
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.7542
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.7542
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7520
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7520
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7510
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7510
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7503
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7503
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7502
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7502
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7495
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7495
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7480
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7480
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7398
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7398
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7320
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7320
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7297
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7297
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7286
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7286
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7284
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7284
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7274
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7274
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7259
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7259
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7247
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7247
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7209
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7209
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7206
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7206
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7187
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7187
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 4 0.7176
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 4 0.7176
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7173
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7173
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7156
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7156
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7124
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7124
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7108
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7108
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7054
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7054
Thiamine-monophosphate kinase O67883 THIL_AQUAE Aquifex aeolicus 3 0.7042
Thiamine-monophosphate kinase O67883 THIL_AQUAE Aquifex aeolicus 3 0.7042
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7036
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7036
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7031
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7031
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7024
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7024
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7009
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7009

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