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Cycleanine
- Family: Plantae - Menispermaceae
- Kingdom: Plantae
- Class: Alkaloid
| Canonical Smiles | COc1c(OC)cc2c3c1Oc1ccc(cc1)C[C@H]1N(C)CCc4c1c(Oc1ccc(C[C@H]3N(CC2)C)cc1)c(c(c4)OC)OC |
|---|---|
| InChI | InChI=1S/C38H42N2O6/c1-39-17-15-25-21-31(41-3)35(43-5)37-33(25)29(39)19-23-7-11-28(12-8-23)46-38-34-26(22-32(42-4)36(38)44-6)16-18-40(2)30(34)20-24-9-13-27(45-37)14-10-24/h7-14,21-22,29-30H,15-20H2,1-6H3/t29-,30-/m1/s1 |
| InChIKey | ANOXEUSGZWSCQL-LOYHVIPDSA-N |
| Formula | C38H42N2O6 |
| HBA | 8 |
| HBD | 0 |
| MW | 622.76 |
| Rotatable Bonds | 4 |
| TPSA | 61.86 |
| LogP | 7.16 |
| Number Rings | 10 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 46 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.37 |
| Exact Mass | 622.3 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Albertisia delagoensis | Menispermaceae | Plantae | 3021348 |
Showing of synonyms
Cycleanine
518-94-5
O-Methylnorcycleanine
Dimethylisochondodendrine
(-)-Cycleanine
BN8R5T4KQ9
CHEBI:81051
(11R,26R)-4,5,19,20-tetramethoxy-10,25-dimethyl-2,17-dioxa-10,25-diazaheptacyclo[26.2.2.213,16.13,7.118,22.011,36.026,33]hexatriaconta-1(31),3(36),4,6,13,15,18(33),19,21,28(32),29,34-dodecaene
O,O-Dimethylisochondodendrin
O,O-Dimethylisochondrodendrine
Isocycleanine
Cycleanin
Cycleanine (R,R)
UNII-BN8R5T4KQ9
CYCLEANINE [WHO-DD]
Cycleanine + other alkaloids
SCHEMBL21974
CHEMBL443389
BDBM85446
DTXSID40199740
HY-N2005
AKOS037514606
8,11:20,23-Dietheno-1H,12H-(1,10)dioxacyclooctadecino(2,3,4-ij:11,12,13-i'j')diisoquinoline, 2,3,12a,13,14,15,24,24a-octahydro-1,13-dimethyl-5,6,17,18-tetramethoxy-, (12aR-(12aR*,24aR*))-
DA-72460
FC159175
MS-30801
CS-0018325
C17387
AM-331/20713006
Q15410908
Cycleanine (Methylisochondodendrine
7,7'-O,O-Dimethylisochondodendrine)
(12AR,24AR)-2,3,12A,13,14,15,24,24A-OCTAHYDRO-5,6,17,18-TETRAMETHOXY-1,13-DIMETHYL-8,11:20,23-DIETHENO-1H,12H-(1,10)DIOXACYCLOOCTADECINO(2,3,4-IJ:11,12,13-I'J')DIISOQUINOLINE
8,11:20,23-DIETHENO-1H,12H-(1,10)DIOXACYCLOOCTADECINO(2,3,4-IJ:11,12,13-I'J')DIISOQUINOLINE, 2,3,12A,13,14,15,24,24A-OCTAHYDRO-5,6,17,18-TETRAMETHOXY-1,13-DIMETHYL-, (12AR,24AR)-
- De Wet H, Van Heerden FR, et al. (2007). Antiplasmodial activity and cytotoxicity of Albertisia delagoensis. Fitoterapia, 2007, 78(6), 420–422. [View]
Pubchem:
121313
Cas:
518-94-5
Gnps:
CCMSLIB00005720157
Zinc:
ZINC000044281044
Kegg Ligand:
C17387
Chebi:
81051
Metabolights:
MTBLC81051
Chembl:
CHEMBL443389
Comptox:
DTXSID40199740
Bindingdb:
85446
CPRiL:
224279
SMILES: c12c3cccc1Oc4ccc(cc4)CC5c6c(CCN5)cccc6Oc7ccc(cc7)CC2NCC3
Level: 0
Mol. Weight: 622.76 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.33
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -4.300
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 99.17
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.990
- Plasma Protein Binding
- 46.19
- 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
- Non-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
- 8.230
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.830
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.070
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 11.100
- 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
- Safe
- T. Pyriformis
- -183050.580
- Rat (Acute)
- 2.610
- Rat (Chronic Oral)
- 0.490
- Fathead Minnow
- 237.910
- 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
- 15729.280
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 4.670
- Log(P)
- 5.22
- Log S
- -6.21
- Log(Vapor Pressure)
- -543.03
- Melting Point
- 193.06
- pKa Acid
- 9.48
- pKa Basic
- 9.19
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.8928 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.8595 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8452 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8310 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.8283 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7831 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7719 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7155 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7080 |
| RNA-directed RNA polymerase lambda-3 | P0CK31 | RDRP_REOVD | Reovirus type 3 | 3 | 0.7050 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7036 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 2 | 0.7014 |