Ancistrotectoriline A - Compound Card

Ancistrotectoriline A

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Ancistrotectoriline A

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(OC)c2c(c1c1ccc(c3c1cc(C)cc3OC)OC)C[C@@H](N[C@H]2C)C
InChI InChI=1S/C26H31NO4/c1-14-10-18-17(8-9-20(28-4)26(18)21(11-14)29-5)25-19-12-15(2)27-16(3)24(19)22(30-6)13-23(25)31-7/h8-11,13,15-16,27H,12H2,1-7H3/t15-,16-/m0/s1
InChIKey DVVAMMKTYAWPGW-HOTGVXAUSA-N
Formula C26H31NO4
HBA 5
HBD 1
MW 421.54
Rotatable Bonds 5
TPSA 48.95
LogP 5.44
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 tanzaniensis Ancistrocladaceae Plantae 714107

Showing of synonyms

  • Bringmann G, Dreyer M, et al. (2003). Ancistrotanzanine A, the first 5,3'-coupled naphthylisoquinoline alkaloid, and two further, 5,8'-linked related compounds from the newly described species Ancistrocladus tanzaniensis. Journal of Natural Products,2003,66(9),1159-1165. [View] [PubMed]
Pubchem: 10093654
Nmrshiftdb2: 80000280

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

Antiprotozoal

Absorption

Caco-2 (logPapp)
-5.19
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.810
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.42

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.230
Plasma Protein Binding
72.47
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
8.950
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.030
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.010
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.550
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
Toxic
T. Pyriformis
-57.000
Rat (Acute)
2.890
Rat (Chronic Oral)
1.910
Fathead Minnow
5.780
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
477.400
Hydration Free Energy
-4.530
Log(D) at pH=7.4
4.000
Log(P)
5.02
Log S
-4.46
Log(Vapor Pressure)
-8.39
Melting Point
149.37
pKa Acid
12.41
pKa Basic
10.26
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 0.9512
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9512
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9085
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9085
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9082
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9082
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8767
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8767
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8717
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8717
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8678
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8678
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8225
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8225
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8223
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8223
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8209
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8209
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8177
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8177
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8176
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8176
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8112
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8112
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8094
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8094
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8001
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8001
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8001
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8001
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7962
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7962
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7932
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7932
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7923
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7923
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7658
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7658
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7629
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7629
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7614
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7614
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7570
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7570
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7529
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7529
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7510
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7510
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7461
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7461
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7458
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7458
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7448
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7448
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7417
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7417
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7407
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7407
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7396
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7396
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7395
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7395
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7371
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7371
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7358
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7358
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7292
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7292
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 4 0.7288
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 4 0.7288
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7263
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7263
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7255
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7255
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7254
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7254
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7207
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7207
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7185
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7185
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7136
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7136
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7119
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7119
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7087
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7087
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7060
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7060
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7021
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7021

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