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Michellamine A3
- Family: Plantae - Ancistrocladaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Quinoline Alkaloid
| Canonical Smiles | COc1cc(C)cc2c1c(O)c(cc2c1c(O)cc(c2c1C[C@H](C)N([C@@H]2C)C)O)c1cc(c2c(O)cc(c3c2C[C@@H](C)N[C@@H]3C)O)c2c(c1O)c(OC)cc(c2)C |
|---|---|
| InChI | InChI=1S/C47H50N2O8/c1-20-10-26-28(42-32-14-22(3)48-24(5)40(32)34(50)18-36(42)52)16-30(46(54)44(26)38(12-20)56-8)31-17-29(27-11-21(2)13-39(57-9)45(27)47(31)55)43-33-15-23(4)49(7)25(6)41(33)35(51)19-37(43)53/h10-13,16-19,22-25,48,50-55H,14-15H2,1-9H3/t22-,23+,24-,25-/m1/s1 |
| InChIKey | BWDHNUUYBZPQFQ-ZFFYZDHPSA-N |
| Formula | C47H50N2O8 |
| HBA | 10 |
| HBD | 7 |
| MW | 770.92 |
| Rotatable Bonds | 5 |
| TPSA | 155.11 |
| LogP | 9.39 |
| Number Rings | 8 |
| Number Aromatic Rings | 6 |
| Heavy Atom Count | 57 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.32 |
| Exact Mass | 770.36 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ancistrocladus likoko | Ancistrocladaceae | Plantae | 714102 |
Showing of synonyms
Michellamine A3
Michellamine E
Michellamine B3
(1R,3S)-5-[3-[4-[(1R,3R)-6,8-dihydroxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-1-hydroxy-8-methoxy-6-methyl-2-naphthyl]-4-hydroxy-5-methoxy-7-methyl-1-naphthyl]-1,2,3-trimethyl-3,4-dihydro-1H-isoquinoline-6,8-diol
CHEMBL454272
- Fayez S, Feineis D, et al. (2018). Ancistrolikokine I and further 5,8′-coupled naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus likoko and their cytotoxic activities against drug-sensitive and multidrug resistant human leukemia cells.. Fitoterapia,2018, 129, 114-125. [View] [PubMed]
No compound-protein relationship available.
SMILES: C1CNCc(c12)cccc2-c3cc(cc(c34)cccc4)-c(cc(c56)cccc6)cc5-c7cccc(c78)CNCC8
Level: 3
Mol. Weight: 770.92 g/mol
SMILES: c1cccc(c12)ccc(c2)-c(cc(c34)cccc4)cc3-c5cccc(c56)CNCC6
Level: 2
Mol. Weight: 770.92 g/mol
SMILES: c1cccc(c12)cccc2-c3cccc(c34)CNCC4
Level: 1
Mol. Weight: 770.92 g/mol
SMILES: c1cccc(c12)ccc(c2)-c(c3)ccc(c34)cccc4
Level: 1
Mol. Weight: 770.92 g/mol
SMILES: C1CNCc(c12)cccc2
Level: 0
Mol. Weight: 770.92 g/mol
SMILES: c1cccc(c12)cccc2
Level: 0
Mol. Weight: 770.92 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.83
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 66.570
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 9520.27
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.210
- Plasma Protein Binding
- 82.35
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 7.400
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -223.270
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.650
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.080
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Safe
- NR-Aromatase
- Toxic
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -17271716.850
- Rat (Acute)
- 2.020
- Rat (Chronic Oral)
- 2.720
- Fathead Minnow
- 21807.390
- 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
- 1936767.520
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 5.170
- Log(P)
- 7.73
- Log S
- -6.89
- Log(Vapor Pressure)
- -63727.77
- Melting Point
- 278.3
- pKa Acid
- -427.47
- pKa Basic
- 10.28
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 3 | 0.9339 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.9140 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.9111 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.8882 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.8485 |
| Diphtheria toxin | P00588 | DTX_CORBE | Corynephage beta | 3 | 0.8302 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 4 | 0.8080 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7812 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7807 |
| Histamine N-methyltransferase | P50135 | HNMT_HUMAN | Homo sapiens | 4 | 0.7805 |
| DNA polymerase theta | O75417 | DPOLQ_HUMAN | Homo sapiens | 4 | 0.7567 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7456 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7455 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7444 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7436 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7428 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7381 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7342 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7339 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.7323 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.7317 |
| Poly [ADP-ribose] polymerase 1 | P09874 | PARP1_HUMAN | Homo sapiens | 3 | 0.7302 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7282 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7204 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.7162 |
| Thiamine-monophosphate kinase | O67883 | THIL_AQUAE | Aquifex aeolicus | 3 | 0.7143 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7133 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | P0AF12 | MTNN_ECOLI | Escherichia coli | 3 | 0.7093 |
| Genome polyprotein | A0EKU1 | A0EKU1_9FLAV | Meaban virus | 3 | 0.7008 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | Q27552 | Q27552_CRYPV | Cryptosporidium parvum | 3 | 0.7000 |