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Michellamine B
- Family: Plantae - Ancistrocladaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Naphthylisoquinoline Alkaloid
| Canonical Smiles | COc1cc(C)cc2c1c(O)c(cc2c1c(O)cc(c2c1CC(C)NC2C)O)c1cc(c2c(O)cc(c3c2CC(C)NC3C)O)c2c(c1O)c(OC)cc(c2)C |
|---|---|
| InChI | InChI=1S/C46H48N2O8/c1-19-9-25-27(41-31-13-21(3)47-23(5)39(31)33(49)17-35(41)51)15-29(45(53)43(25)37(11-19)55-7)30-16-28(26-10-20(2)12-38(56-8)44(26)46(30)54)42-32-14-22(4)48-24(6)40(32)34(50)18-36(42)52/h9-12,15-18,21-24,47-54H,13-14H2,1-8H3 |
| InChIKey | GMLBVLXDRNJFGR-UHFFFAOYSA-N |
| Formula | C46H48N2O8 |
| HBA | 10 |
| HBD | 8 |
| MW | 756.9 |
| Rotatable Bonds | 5 |
| TPSA | 163.9 |
| LogP | 9.05 |
| Number Rings | 8 |
| Number Aromatic Rings | 6 |
| Heavy Atom Count | 56 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.3 |
| Exact Mass | 756.34 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ancistrocladus ealaensis | Ancistrocladaceae | Plantae | 714098 |
| 2 | Ancistrocladus ileboensis | Ancistrocladaceae | Plantae | 1367080 |
Showing of synonyms
Michellamine B
Michellamine A
137893-48-2
137793-81-8
5-[3-[4-(6,8-dihydroxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-yl)-1-hydroxy-8-methoxy-6-methylnaphthalen-2-yl]-4-hydroxy-5-methoxy-7-methylnaphthalen-1-yl]-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,8-diol
Michellamine
(-)-Michellamine A
5-[3-[4-(6,8-dihydroxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-yl)-1-hydroxy-8-methoxy-6-methyl
NSC 650898
NSC-661755
6,8-Isoquinolinediol, 5,5'-(1,1'-dihydroxy-8,8'-dimethoxy-6,6'-dimethyl(2,2'-binaphthalene)-4,4'-diyl)bis(1,2,3,4-tetrahydro-1,3-dimethyl-, (1R,1'R,3R,3'R,5R,5'S)-
SCHEMBL6361270
(1R,3R,5P,1'''R,3'''R,5'''P)-Michellamine A
(1R,3R,5S,1'''R,3'''R,5'''S)-Michellamine A
DTXSID50929898
5,5'-(1,1'-Dihydroxy-8,8'-dimethoxy-6,6'-dimethyl[2,2'-binaphthalene]-4,4'-diyl)bis(1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,8-diol)
5-[3-[4-(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]-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,8-diol
5-[3-[4-(6,8-Dihydroxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-yl)-1-hydroxy-8-methoxy-6-methyl-naphthalen-2-yl]-4-hydroxy-5-methoxy-7-methyl-naphthalen-1-yl]-1,3-dimethyl-1,2,3,4-tetrahydroisoqu
6,8-Isoquinolinediol, 5,5'-(1,1'-dihydroxy-8,8'-dimethoxy-6,6'-dimethyl(2,2'-binaphthalene)-4,4'-diyl)bis(1,2,3,4-tetrahydro-1,3-dimethyl-, (1R,1'R,3R,3'R,5S,5'S)-
6,8-Isoquinolinediol, 5,5'-(1,1'-dihydroxy-8,8'-dimethoxy-6,6'-dimethyl(2,2'-binaphthalene)-4,4'-diyl)bis(1,2,3,4-tetrahydro-1,3-dimethyl-, stereoisomer
- Tshitenge DT, Feineis D, et al. (2017). Antiplasmodial ealapasamines A-C,‘mixed’ naphthylisoquinoline dimers from the Central African liana Ancistrocladus ealaensis.. Scientific reports,2017, 7(1), 5767. [View] [PubMed]
- Li J, Seupel R, et al. (2017). Jozilebomines A and B, Naphthylisoquinoline Dimers from the Congolese Liana Ancistrocladus ileboensis, with Antiausterity Activities against the PANC-1 Human Pancreatic Cancer Cell Line.. Journal of natural products,2017, 80(10), 2807-2817. [View] [PubMed]
CPRiL:
209983
SMILES: C1CNCc(c12)cccc2-c3cc(cc(c34)cccc4)-c(cc(c56)cccc6)cc5-c7cccc(c78)CNCC8
Level: 3
Mol. Weight: 756.9 g/mol
SMILES: c1cccc(c12)ccc(c2)-c(cc(c34)cccc4)cc3-c5cccc(c56)CNCC6
Level: 2
Mol. Weight: 756.9 g/mol
SMILES: c1cccc(c12)cccc2-c3cccc(c34)CNCC4
Level: 1
Mol. Weight: 756.9 g/mol
SMILES: c1cccc(c12)ccc(c2)-c(c3)ccc(c34)cccc4
Level: 1
Mol. Weight: 756.9 g/mol
SMILES: C1CNCc(c12)cccc2
Level: 0
Mol. Weight: 756.9 g/mol
SMILES: c1cccc(c12)cccc2
Level: 0
Mol. Weight: 756.9 g/mol
Antimalarial
Absorption
- Caco-2 (logPapp)
- -5.91
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 40.500
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 6115.41
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.210
- Plasma Protein Binding
- 73.92
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-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
- 7.380
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -145.200
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.640
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 8.250
- 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
- -11092650.300
- Rat (Acute)
- 1.960
- Rat (Chronic Oral)
- 2.790
- Fathead Minnow
- 14007.720
- 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
- 1241780.290
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 4.920
- Log(P)
- 7.54
- Log S
- -6.85
- Log(Vapor Pressure)
- -40850.64
- Melting Point
- 305.33
- pKa Acid
- -264.38
- pKa Basic
- 10.79
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.9162 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.9162 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.9117 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.8946 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.8350 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8168 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7737 |
| Diphtheria toxin | P00588 | DTX_CORBE | Corynephage beta | 3 | 0.7606 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7595 |
| Histamine N-methyltransferase | P50135 | HNMT_HUMAN | Homo sapiens | 4 | 0.7476 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7440 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7397 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7389 |
| Thiamine-monophosphate kinase | O67883 | THIL_AQUAE | Aquifex aeolicus | 3 | 0.7220 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7156 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 4 | 0.7139 |
| Poly [ADP-ribose] polymerase 1 | P09874 | PARP1_HUMAN | Homo sapiens | 3 | 0.7114 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | Q27552 | Q27552_CRYPV | Cryptosporidium parvum | 3 | 0.7072 |