Ancistrobertsonine C - Compound Card

Ancistrobertsonine C

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Ancistrobertsonine C

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)C
InChI InChI=1S/C27H33NO4/c1-15-11-19-18(9-10-21(29-5)27(19)22(12-15)30-6)26-20-13-16(2)28(4)17(3)25(20)23(31-7)14-24(26)32-8/h9-12,14,16-17H,13H2,1-8H3/t16-,17+/m0/s1
InChIKey GFQFSIXPKFVWIW-DLBZAZTESA-N
Formula C27H33NO4
HBA 5
HBD 0
MW 435.56
Rotatable Bonds 5
TPSA 40.16
LogP 5.79
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.41
Exact Mass 435.24
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus robertsoniorum Ancistrocladaceae Plantae 714105
2 Ancistrocladus likoko Ancistrocladaceae Plantae 714102

Showing of synonyms

  • Bringmann G, Teltschika F, et al. (1999). Ancistrobertsonines B, C, and D as well as 1,2-didehydroancistrobertsonine D from Ancistrocladus robertsoniorum. Phytochemistry,1999,52(2),321-332. [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]
Pubchem: 10410728
Nmrshiftdb2: 70059359

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 435.56 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 435.56 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 435.56 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.16
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.780
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.12

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.140
Plasma Protein Binding
69.42
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
9.450
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.870
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.210
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.890
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
-88.130
Rat (Acute)
3.030
Rat (Chronic Oral)
1.840
Fathead Minnow
5.840
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
479.900
Hydration Free Energy
-3.380
Log(D) at pH=7.4
4.070
Log(P)
5.35
Log S
-4.73
Log(Vapor Pressure)
-8.66
Melting Point
132.38
pKa Acid
11.83
pKa Basic
9.85
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 0.9569
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9569
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9416
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9416
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9141
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9141
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9112
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9112
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9029
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9029
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8894
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8894
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8669
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8669
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8492
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8492
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8298
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8298
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8259
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8259
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8229
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8229
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8221
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8221
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8194
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8194
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8061
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8061
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8051
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8051
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8024
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8024
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7997
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7997
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7970
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7970
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7952
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7952
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7881
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7881
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 4 0.7741
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 4 0.7741
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7716
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7716
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7702
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7702
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7699
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7699
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7693
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7693
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7642
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7642
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7627
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7627
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7597
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7597
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7578
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7578
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7577
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7577
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7533
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7533
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7505
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7505
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7496
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7496
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7495
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7495
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7467
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7467
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7428
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7428
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7426
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7426
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7416
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7416
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7416
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7416
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7412
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7412
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7370
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7370
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7328
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7328
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7306
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7306
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7281
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7281
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7279
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7279
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7272
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7272
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7270
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7270
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7269
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7269
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7252
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7252
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7250
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7250
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7227
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7227
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7219
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7219
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7160
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7160
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7155
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7155
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7146
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7146
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7091
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7091
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7084
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7084
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7076
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7076
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7076
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7076
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7067
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7067
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7008
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7008

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