Ancistrotanzanine B - Compound Card

Ancistrotanzanine B

Select a section from the left sidebar

Ancistrotanzanine B

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline Alkaloid
Canonical Smiles COc1cc(OC)c2c(c1c1ccc(c3c1cc(C)cc3OC)OC)C[C@@H](N=C2C)C
InChI InChI=1S/C26H29NO4/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/h8-11,13,15H,12H2,1-7H3/t15-/m0/s1
InChIKey MIMNIDIHOQDTFD-HNNXBMFYSA-N
Formula C26H29NO4
HBA 5
HBD 0
MW 419.52
Rotatable Bonds 5
TPSA 49.28
LogP 5.6
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 419.21
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus tanzaniensis Ancistrocladaceae Plantae 714107
2 Ancistrocladus ealaensis Ancistrocladaceae Plantae 714098
3 Ancistrocladus likoko Ancistrocladaceae Plantae 714102
4 Ancistrocladus likoko Ancistrocladaceae Plantae 714102
5 Ancistrocladus congolensis Ancistrocladaceae Plantae 714097

Showing of synonyms

  • Bringmann G, Hamm A, et al. (2000). Ancistroealaines A and B, two new bioactive naphthylisoquinolines, and related naphthoic acids from Ancistrocladus ealaensis. Journal of natural products,2000, 63(11), 1465-1470. [View] [PubMed]
  • Bringmann G, Saeb W, et al. (2003). Ancistrolikokine D, a 5,8'-coupled naphthylisoquinoline alkaloid, and related natural products from Ancistrocladus likoko. Phytochemistry,2003, 62(4), 631-636. [View] [PubMed]
  • Fayez S, Feineis D, et al. (2017). Ancistrolikokines E-H and related 5,8'-coupled naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus likoko with antiausterity activities against PANC-1 human pancreatic cancer cells.. RSC Adv., 2017,7, 53740-53751. [View]
  • 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]
  • Bringmann G, Spuziak J, et al. (2008). Six naphthylisoquinoline alkaloids and a related benzopyranone from a Congolese Ancistrocladus species related to Ancistrocladus congolensis. Phytochemistry,2008, 69(4), 1065-1075. [View] [PubMed]
Pubchem: 10002166
Chebi: 65407
Nmrshiftdb2: 60049026
Metabolights: MTBLC65407

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2-c3cccc(c34)C=NCC4

Level: 1

Mol. Weight: 419.52 g/mol

Structure

SMILES: C1=NCCc(c12)cccc2

Level: 0

Mol. Weight: 419.52 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 419.52 g/mol

Anti-leishmanial
Antiprotozoal

Absorption

Caco-2 (logPapp)
-5.07
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.750
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.750
Plasma Protein Binding
82.64
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
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.620
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.100
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.050
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.660
Micronucleos
Safe
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
-50.860
Rat (Acute)
2.920
Rat (Chronic Oral)
2.220
Fathead Minnow
5.900
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
509.600
Hydration Free Energy
-3.910
Log(D) at pH=7.4
3.870
Log(P)
5.73
Log S
-6.5
Log(Vapor Pressure)
-7.32
Melting Point
149.81
pKa Acid
12.19
pKa Basic
8.04
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 0.9563
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9563
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9501
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9501
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9136
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9136
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9131
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9131
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8748
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8748
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8713
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8713
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8660
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8660
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8567
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8567
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8558
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8558
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8409
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8409
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8342
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8342
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8339
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8339
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8305
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8305
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8300
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8300
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8137
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8137
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.8092
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.8092
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8045
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8045
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7999
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7999
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7972
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7972
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7940
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7940
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7895
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7895
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7698
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7698
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7641
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7641
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7635
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7635
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7614
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7614
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7611
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7611
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7577
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7577
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7523
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7523
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7516
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7516
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7515
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7515
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7506
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7506
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7492
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7492
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7461
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7461
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7457
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7457
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7433
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7433
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7402
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7402
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7397
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7397
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7382
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7382
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 4 0.7379
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 4 0.7379
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7370
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7370
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7333
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7333
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7329
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7329
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7322
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7322
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7320
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7320
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7309
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7309
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7304
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7304
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7288
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7288
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7278
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7278
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7269
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7269
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7268
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7268
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7260
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7260
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7243
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7243
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7199
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7199
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7191
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7191
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7189
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7189
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7179
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7179
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7166
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7166
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7163
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7163
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7160
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7160
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7141
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7141
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7114
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7114
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7098
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7098
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7064
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7064
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7063
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7063
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7063
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7063
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7024
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7024
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7016
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7016
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7009
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7009

Download SDF