5-epi-4'-O-demethylancistrobertsonine C - Compound Card

5-epi-4'-O-demethylancistrobertsonine C

Select a section from the left sidebar

5-epi-4'-O-demethylancistrobertsonine C

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(OC)c2c(c1c1ccc(c3c1cc(C)cc3O)OC)C[C@@H](N([C@@H]2C)C)C
InChI InChI=1S/C26H31NO4/c1-14-10-18-17(8-9-21(29-5)26(18)20(28)11-14)25-19-12-15(2)27(4)16(3)24(19)22(30-6)13-23(25)31-7/h8-11,13,15-16,28H,12H2,1-7H3/t15-,16+/m0/s1
InChIKey QCRNSFIWXGLJQP-JKSUJKDBSA-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 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: 24814590

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)
-5.0
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.820
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.160
Plasma Protein Binding
74.57
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
9.870
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.630
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.300
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.820
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
-51.660
Rat (Acute)
2.640
Rat (Chronic Oral)
1.890
Fathead Minnow
5.440
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
471.980
Hydration Free Energy
-4.770
Log(D) at pH=7.4
4.350
Log(P)
4.99
Log S
-5.01
Log(Vapor Pressure)
-9.28
Melting Point
143.08
pKa Acid
10.19
pKa Basic
9.69
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9318
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9318
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9190
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9190
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9167
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9167
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9132
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9132
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9113
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9113
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9089
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9089
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9045
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9045
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8993
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8993
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8891
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8891
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8874
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8874
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8670
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8670
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8619
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8619
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8488
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8488
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8487
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8487
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8431
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8431
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8320
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8320
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8219
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8219
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.8210
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.8210
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8149
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8149
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8074
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8074
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7975
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7975
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7965
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7965
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7935
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7935
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7932
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7932
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7890
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7890
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7839
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7839
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7803
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7803
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7796
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7796
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7745
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7745
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7744
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7744
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 4 0.7735
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 4 0.7735
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7713
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7713
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7703
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7703
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7684
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7684
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7630
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7630
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7612
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7612
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7601
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7601
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7595
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7595
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7539
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7539
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7497
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7497
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7472
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7472
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7454
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7454
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7445
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7445
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7397
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7397
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7390
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7390
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 3 0.7368
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 3 0.7368
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7345
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7345
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7317
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7317
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7312
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7312
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7290
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7290
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7286
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7286
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7281
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7281
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7281
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7281
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7251
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7251
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7247
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7247
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7235
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7235
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7229
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7229
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7224
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7224
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7223
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7223
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7211
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7211
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7200
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7200
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7167
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7167
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7164
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7164
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7154
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7154
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7149
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7149
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7124
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7124
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7114
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7114
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7112
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7112
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7110
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7110
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7107
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7107
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7102
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7102
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7062
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7062
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7062
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7062
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7032
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7032
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7015
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7015
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7014
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7014
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7013
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7013

Download SDF