6-O-demethylancistroealaine A - Compound Card

6-O-demethylancistroealaine A

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6-O-demethylancistroealaine A

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(O)c(c2c1C(=N[C@H](C2)C)C)c1ccc(c2c1cc(C)cc2OC)OC
InChI InChI=1S/C25H27NO4/c1-13-9-17-16(7-8-20(28-4)25(17)21(10-13)29-5)24-18-11-14(2)26-15(3)23(18)22(30-6)12-19(24)27/h7-10,12,14,27H,11H2,1-6H3/t14-/m0/s1
InChIKey CFBIKBQUHRRMOQ-AWEZNQCLSA-N
Formula C25H27NO4
HBA 5
HBD 1
MW 405.49
Rotatable Bonds 4
TPSA 60.28
LogP 5.3
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 405.19
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus congolensis Ancistrocladaceae Plantae 714097

Showing of synonyms

  • 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: 135550840

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 405.49 g/mol

Structure

SMILES: C1=NCCc(c12)cccc2

Level: 0

Mol. Weight: 405.49 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 405.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.730
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.1

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.590
Plasma Protein Binding
86.62
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.660
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.600
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
6.450
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
-27.770
Rat (Acute)
2.540
Rat (Chronic Oral)
2.390
Fathead Minnow
5.530
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
494.470
Hydration Free Energy
-5.270
Log(D) at pH=7.4
4.110
Log(P)
5.15
Log S
-6.72
Log(Vapor Pressure)
-7.91
Melting Point
166.73
pKa Acid
9.93
pKa Basic
7.62
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 0.9439
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9439
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9140
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9140
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9032
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9032
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9007
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9007
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8729
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8729
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8544
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8544
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8514
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8514
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8185
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8185
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8157
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8157
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8114
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8114
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8018
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8018
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.8015
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.8015
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8006
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8006
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7942
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7942
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7795
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7795
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7789
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7789
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7729
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7729
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7703
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7703
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7700
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7700
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7658
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7658
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7622
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7622
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7569
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7569
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7553
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7553
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7486
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7486
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7470
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7470
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7452
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7452
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7448
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7448
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7432
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7432
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7424
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7424
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7424
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7424
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7386
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7386
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7384
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7384
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7358
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7358
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7298
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7298
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7296
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7296
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7283
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7283
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7258
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7258
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7256
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7256
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7216
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7216
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7209
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7209
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7209
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7209
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7190
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7190
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7138
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7138
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7115
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7115
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7111
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7111
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7101
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7101
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7088
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7088
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 3 0.7082
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 3 0.7082
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7064
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7064
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7059
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7059
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7055
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7055
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7048
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7048
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7045
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7045

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