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Ancistrocladine
- Family: Plantae - Dioncophyllaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Isoquinoline Alkaloid
| Canonical Smiles | COc1cc(O)c(c2c1[C@H](C)N[C@H](C2)C)c1c(C)cc(c2c1cccc2OC)OC |
|---|---|
| InChI | InChI=1S/C25H29NO4/c1-13-10-20(29-5)25-16(8-7-9-19(25)28-4)22(13)24-17-11-14(2)26-15(3)23(17)21(30-6)12-18(24)27/h7-10,12,14-15,26-27H,11H2,1-6H3/t14-,15-/m0/s1 |
| InChIKey | XUFOYASAFNKRRE-GJZGRUSLSA-N |
| Formula | C25H29NO4 |
| HBA | 5 |
| HBD | 2 |
| MW | 407.51 |
| Rotatable Bonds | 4 |
| TPSA | 59.95 |
| LogP | 5.14 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.36 |
| Exact Mass | 407.21 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ancistrocladus robertsoniorum | Ancistrocladaceae | Plantae | 714105 |
| 2 | Ancistrocladus robertsoniorum | Ancistrocladaceae | Plantae | 714105 |
| 3 | Ancistrocladus ileboensis | Dioncophyllaceae | Plantae | 1367080 |
Showing of synonyms
Ancistrocladine
Ancistrocladin
32221-59-3
Hamatine
5-(4,5-Dimethoxy-2-methyl-1-naphthalenyl)-1,2,3,4-tetrahydro-8-methoxy-1,3-dimethyl-6-isoquinolinol
(+)-Hamatine
(-)-Ancistrocladine
( )-Hamatine
(1s,3s)-5-(4,5-dimethoxy-2-methyl-1-naphthyl)-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-ol
CHEBI:2707
SCHEMBL3132504
DTXSID60930490
(1S,3S)-5-(4,5-dimethoxy-2-methylnaphthalen-1-yl)-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-ol
C09335
Q27105775
1395-04-6
5-(4,5-dimethoxy-2-methylnaphthalen-1-yl)-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-ol
6-Isoquinolinol, 5-(4,5-dimethoxy-2-methyl-1-naphthalenyl)-1,2,3,4- tetrahydro-8-methoxy-1,3-dimethyl-, (1S,3S,5R)-
6-Isoquinolinol, 5-(4,5-dimethoxy-2-methyl-1-naphthalenyl)-1,2,3,4-tetrahydro-8-methoxy-1,3-dimethyl-, stereoisomer
- 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]
- Li J, Seupel R, et al. (2017). Dioncophyllines C2, D2, and F and related naphthylisoquinoline alkaloids from the Congolese Liana Ancistrocladus ileboensis with potent activities against Plasmodium falciparum and against multiple myeloma and leukemia cell lines. Journal of natural products,2017, 80(2), 443-458. [View] [PubMed]
Pubchem:
161741
Cas:
32221-59-3
Gnps:
CCMSLIB00008851199
Zinc:
ZINC000004098020
Kegg Ligand:
C09335
Chebi:
2707
Nmrshiftdb2:
70016114
No compound-protein relationship available.
SMILES: c1cccc(c12)cccc2-c3cccc(c34)CNCC4
Level: 1
Mol. Weight: 407.51 g/mol
SMILES: C1CNCc(c12)cccc2
Level: 0
Mol. Weight: 407.51 g/mol
SMILES: c1cccc(c12)cccc2
Level: 0
Mol. Weight: 407.51 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.99
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.840
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.95
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.260
- Plasma Protein Binding
- 75.82
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-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
- 9.060
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.490
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.110
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 9.990
- 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
- -34.650
- Rat (Acute)
- 2.490
- Rat (Chronic Oral)
- 2.030
- Fathead Minnow
- 5.350
- 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
- 457.360
- Hydration Free Energy
- -5.510
- Log(D) at pH=7.4
- 4.480
- Log(P)
- 4.2
- Log S
- -4.85
- Log(Vapor Pressure)
- -8.8
- Melting Point
- 150.46
- pKa Acid
- 10.08
- pKa Basic
- 9.56
| 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 | 0.9619 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9619 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9168 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9168 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.9008 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.9008 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8943 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8943 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8466 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8466 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8442 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8442 |
| Renin | P00797 | RENI_HUMAN | Homo sapiens | 3 | 0.8193 |
| Renin | P00797 | RENI_HUMAN | Homo sapiens | 3 | 0.8193 |
| Endolysin | P00720 | ENLYS_BPT4 | Enterobacteria phage T4 | 3 | 0.8122 |
| Endolysin | P00720 | ENLYS_BPT4 | Enterobacteria phage T4 | 3 | 0.8122 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.8075 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.8075 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8074 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8074 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8060 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8060 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8058 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8058 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7875 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7875 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7828 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7828 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7737 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7737 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.7721 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.7721 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 4 | 0.7628 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 4 | 0.7628 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7564 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7564 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7551 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7551 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7531 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7531 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7510 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7510 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7491 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7491 |
| Thyroxine-binding globulin | P05543 | THBG_HUMAN | Homo sapiens | 3 | 0.7488 |
| Thyroxine-binding globulin | P05543 | THBG_HUMAN | Homo sapiens | 3 | 0.7488 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7393 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7393 |
| Thymidylate synthase ThyA | P9WFR9 | TYSY_MYCTU | Mycobacterium tuberculosis | 3 | 0.7352 |
| Thymidylate synthase ThyA | P9WFR9 | TYSY_MYCTU | Mycobacterium tuberculosis | 3 | 0.7352 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7344 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7344 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.7340 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.7340 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7320 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7320 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.7302 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.7302 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7180 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7180 |
| Endoplasmin | P14625 | ENPL_HUMAN | Homo sapiens | 3 | 0.7163 |
| Endoplasmin | P14625 | ENPL_HUMAN | Homo sapiens | 3 | 0.7163 |
| Beta-lactamase | P00811 | AMPC_ECOLI | Escherichia coli | 3 | 0.7142 |
| Beta-lactamase | P00811 | AMPC_ECOLI | Escherichia coli | 3 | 0.7142 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7132 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7132 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7115 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7115 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 4 | 0.7053 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 4 | 0.7053 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 4 | 0.7046 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 4 | 0.7046 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7020 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7020 |