Ancistrobertsonine A - Compound Card

Ancistrobertsonine A

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Ancistrobertsonine A

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(O)c(c2c1[C@H](C)N(C)[C@H](C2)C)c1ccc(c2c1cc(C)cc2OC)OC
InChI InChI=1S/C26H31NO4/c1-14-10-18-17(8-9-21(29-5)26(18)22(11-14)30-6)25-19-12-15(2)27(4)16(3)24(19)23(31-7)13-20(25)28/h8-11,13,15-16,28H,12H2,1-7H3/t15-,16-/m0/s1
InChIKey RNLKCMIGQLHEKX-HOTGVXAUSA-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 robertsoniorum Ancistrocladaceae Plantae 714105
2 Ancistrocladus robertsoniorum Ancistrocladaceae Plantae 714105

Showing of synonyms

  • Bringmann G, Teltschik F, et al. (1998). Ancistrobertsonine A and related naphthylisoquinoline alkaloids from Ancistrocladus robertsoniorum. Phytochemistry,1998,47(1),31-35. [View] [PubMed]
  • 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]
Pubchem: 15840195
Nmrshiftdb2: 70059354

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)
-4.99
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.830
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.170
Plasma Protein Binding
73.02
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
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.720
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.370
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
10.500
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
-52.090
Rat (Acute)
2.640
Rat (Chronic Oral)
1.950
Fathead Minnow
5.340
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
459.090
Hydration Free Energy
-4.460
Log(D) at pH=7.4
4.570
Log(P)
4.62
Log S
-4.84
Log(Vapor Pressure)
-9.1
Melting Point
136.25
pKa Acid
9.81
pKa Basic
9.26
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 0.9421
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9421
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9072
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9072
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8940
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8940
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8737
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8737
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8609
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8609
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8484
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8484
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8318
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8318
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8186
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8186
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8140
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8140
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7910
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7910
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7798
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7798
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7782
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7782
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7587
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7587
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7580
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7580
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7481
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7481
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7466
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7466
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7456
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7456
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7416
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7416
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7391
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7391
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7378
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7378
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7364
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7364
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7336
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7336
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7322
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7322
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7303
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7303
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7290
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7290
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7210
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7210
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7195
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7195
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7182
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7182
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7143
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7143
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7129
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7129
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7099
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7099
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7092
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7092
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7071
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7071
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7070
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7070
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7049
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7049
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7049
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7049
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7022
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7022

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