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Dicentrine
- Family: Plantae - Menispermaceae
- Kingdom: Plantae
- Class: Alkaloid
| Canonical Smiles | COc1cc2c(cc1OC)C[C@H]1c3c2c2OCOc2cc3CCN1C |
|---|---|
| InChI | InChI=1S/C20H21NO4/c1-21-5-4-11-7-17-20(25-10-24-17)19-13-9-16(23-3)15(22-2)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3/t14-/m0/s1 |
| InChIKey | YJWBWQWUHVXPNC-AWEZNQCLSA-N |
| Formula | C20H21NO4 |
| HBA | 5 |
| HBD | 0 |
| MW | 339.39 |
| Rotatable Bonds | 2 |
| TPSA | 40.16 |
| LogP | 3.18 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.4 |
| Exact Mass | 339.15 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Albertisia delagoensis | Menispermaceae | Plantae | 3021348 |
Showing of synonyms
Dicentrine
D-Dicentrine
Eximine
O,N-Dimethyllitseferine
(+)-dicentrine
Dicentrine-(+)
CCRIS 3806
UNII-J2ZGT5M0N7
J2ZGT5M0N7
9,10-Dimethoxy-1,2-(methylenedioxy)aporphine
NSC 406035
BRN 0095476
1,2-Methylenedioxy-9,10-dimethoxyaporphine
DICENTRINE [MI]
NSC-406035
DICENTRINE, (+)-
DICENTRINE D-FORM [MI]
DTXSID10199651
4-27-00-06486 (Beilstein Handbook Reference)
6aalpha-Aporphine, 9,10-dimethoxy-1,2-(methylenedioxy)-
9,10-Dimethoxy-1,2-(methylenedioxy)-6a.alpha.-aporphine
6a-alpha-Aporphine, 9,10-dimethoxy-1,2-(methylenedioxy)-
(12S)-16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaene
5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)-
10,11-Dimethoxy-7-methyl-6,7,7a,8-tetrahydro-5H-[1,3]benzodioxolo[6,5,4-de]benzo[g]quinoline-, (S)-
5H-BENZO(G)-1,3-BENZODIOXOLO(6,5,4-DE)QUINOLINE, 6,7,7A,8-TETRAHYDRO-10,11-DIMETHOXY-7-METHYL-, (7AS)-
5H-Benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)-
(S)-Dicentrine
(12S)-16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo(10.7.1.02,6.08,20.014,19)icosa-1(20),2(6),7,14,16,18-hexaene
10,11-Dimethoxy-7-methyl-6,7,7a,8-tetrahydro-5H-(1,3)benzodioxolo(6,5,4-de)benzo(g)quinoline-, (S)-
DICENTRINE D-FORM
Dicentrine, (R)-isomer
DTXCID70122142
9,10-DIMETHOXY-1,2-(METHYLENEDIOXY)-6AALPHA-APORPHINE
6aalpha-Aporphine, 9,10-dimethoxy-1,2-(methylenedioxy)-(8CI)
5H-1,3-Benzodioxolo(6,5,4-de)benzo(g)quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (7aS)-
5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)-(9CI)
Yjwbwqwuhvxpnc-aweznqclsa-n
517-66-8
Dicentrin
CHEMBL464748
CHEBI:81079
NSC406035
5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)- (9CI)
(R)-(-)-Dicentrine
L-Dicentrine
NSC 251699
9,2-(methylenedioxy)aporphine
SCHEMBL6369440
HY-N6969
BDBM50306885
AKOS037514612
DA-72736
MS-25168
CS-0026026
NS00094624
C17426
Q15410930
6a.alpha.-Aporphine,10-dimethoxy-1,2-(methylenedioxy)-
5H-Benzo[g]-1,5,4-de]quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)-
- De Wet H, Van Heerden FR, et al. (2007). Antiplasmodial activity and cytotoxicity of Albertisia delagoensis. Fitoterapia, 2007, 78(6), 420–422. [View]
Pubchem:
101300
Cas:
517-66-8
Gnps:
CCMSLIB00005436041
Zinc:
ZINC000000005319
Kegg Ligand:
C17426
Chebi:
81079
Nmrshiftdb2:
60022991
Metabolights:
MTBLC81079
Chembl:
CHEMBL464748
Comptox:
DTXSID10199651
Bindingdb:
50306885
CPRiL:
107348
SMILES: O1COc(c12)cc3c4c2c5c(cccc5)CC4NCC3
Level: 0
Mol. Weight: 339.39 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.95
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.600
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.48
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.920
- Plasma Protein Binding
- 54.92
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.260
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 2.720
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.120
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 8.560
- 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
- Safe
- T. Pyriformis
- -6.380
- Rat (Acute)
- 2.660
- Rat (Chronic Oral)
- 1.330
- Fathead Minnow
- 4.820
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 406.900
- Hydration Free Energy
- -7.190
- Log(D) at pH=7.4
- 2.820
- Log(P)
- 2.68
- Log S
- -3.43
- Log(Vapor Pressure)
- -7.78
- Melting Point
- 154.4
- pKa Acid
- 11.25
- pKa Basic
- 7.85
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 4 | 0.9737 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.9687 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9604 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9420 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.9299 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 4 | 0.9120 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.8924 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.8914 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8847 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.8704 |
| Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase | Q46381 | BPHB_COMTE | Comamonas testosteroni | 3 | 0.8674 |
| Proliferating cell nuclear antigen | P12004 | PCNA_HUMAN | Homo sapiens | 3 | 0.8534 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8443 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8411 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8372 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.8319 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.8303 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.8288 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8286 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.8270 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.8212 |
| Activin receptor type-1 | Q04771 | ACVR1_HUMAN | Homo sapiens | 3 | 0.8210 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.8204 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8136 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.8112 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8040 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 3 | 0.8038 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8027 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | O02604 | DRTS_PLAVI | Plasmodium vivax | 3 | 0.8001 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7955 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7927 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.7897 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7819 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7772 |
| NAD(P)H dehydrogenase [quinone] 1 | P15559 | NQO1_HUMAN | Homo sapiens | 3 | 0.7761 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7756 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.7742 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 4 | 0.7721 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.7714 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7692 |
| Ephrin type-B receptor 4 | P54760 | EPHB4_HUMAN | Homo sapiens | 3 | 0.7625 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7621 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7608 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7604 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.7567 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7567 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7551 |
| Acetylcholine-binding protein | P58154 | ACHP_LYMST | Lymnaea stagnalis | 3 | 0.7504 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7463 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7458 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 4 | 0.7447 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7443 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.7439 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7432 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | O67060 | ISPE_AQUAE | Aquifex aeolicus | 3 | 0.7432 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 4 | 0.7428 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7403 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7376 |
| Fatty acid-binding protein, intestinal | P12104 | FABPI_HUMAN | Homo sapiens | 3 | 0.7366 |
| Dihydroflavonol 4-reductase | P51110 | DFRA_VITVI | Vitis vinifera | 3 | 0.7354 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7318 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7309 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7305 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7255 |
| Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 3 | 0.7253 |
| L-methionine gamma-lyase | Q84AR1 | Q84AR1_CITFR | Citrobacter freundii | 3 | 0.7247 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7246 |
| Multidrug efflux pump subunit AcrB | P31224 | ACRB_ECOLI | Escherichia coli | 3 | 0.7222 |
| Serine/threonine-protein kinase Nek2 | P51955 | NEK2_HUMAN | Homo sapiens | 3 | 0.7219 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7218 |
| Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 3 | 0.7214 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 2 | 0.7208 |
| Aminoglycoside 3'-phosphotransferase AphA1-IAB | B0VD92 | B0VD92_ACIBY | Acinetobacter baumannii | 3 | 0.7207 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7205 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7204 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7201 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7198 |
| Eukaryotic translation initiation factor 4E type 3 | Q9DBB5 | IF4E3_MOUSE | Mus musculus | 3 | 0.7189 |
| Biphenyl-2,3-diol 1,2-dioxygenase | P17297 | BPHC_PSES1 | Pseudomonas sp | 3 | 0.7152 |
| HTH-type transcriptional regulator EthR | P9WMC1 | ETHR_MYCTU | Mycobacterium tuberculosis | 3 | 0.7141 |
| Peptidyl-prolyl cis-trans isomerase FKBP5 | Q13451 | FKBP5_HUMAN | Homo sapiens | 3 | 0.7108 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7106 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7099 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7089 |
| Dihydroflavonol 4-reductase | P51110 | DFRA_VITVI | Vitis vinifera | 3 | 0.7089 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7078 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7072 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 2 | 0.7066 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 3 | 0.7057 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7051 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7049 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7033 |
| 16S rRNA (guanine(1405)-N(7))-methyltransferase | Q763K9 | Q763K9_ECOLX | Escherichia coli | 3 | 0.7032 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7027 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7023 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7020 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 2 | 0.7014 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7013 |
| Pteridine reductase 1 | Q01782 | PTR1_LEIMA | Leishmania major | 3 | 0.7008 |