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Ricinine
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyridine Alkaloid
| Canonical Smiles | N#Cc1c(OC)ccn(c1=O)C |
|---|---|
| InChI | InChI=1S/C8H8N2O2/c1-10-4-3-7(12-2)6(5-9)8(10)11/h3-4H,1-2H3 |
| InChIKey | PETSAYFQSGAEQY-UHFFFAOYSA-N |
| Formula | C8H8N2O2 |
| HBA | 4 |
| HBD | 0 |
| MW | 164.16 |
| Rotatable Bonds | 1 |
| TPSA | 55.02 |
| LogP | 0.27 |
| Number Rings | 1 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 12 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.25 |
| Exact Mass | 164.06 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Chrozophora oblongifolia | Euphorbiaceae | Plantae | 344429 |
| 2 | Ricinus communis | Euphorbiaceae | Plantae | 3988 |
Showing of synonyms
Ricinine
524-40-3
Ricinin
Ricidine
Ritsinin
Recinine
4-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
1,2-Dihydro-4-methoxy-1-methyl-2-oxonicotinonitrile
NSC 409913
NSC 642604
4-methoxy-1-methyl-2-oxopyridine-3-carbonitrile
3-Pyridinecarbonitrile, 1,2-dihydro-4-methoxy-1-methyl-2-oxo-
EINECS 208-359-7
UNII-130UFS7AE0
BRN 0139222
130UFS7AE0
CHEBI:18043
RICININE [MI]
NSC-409913
NSC-642604
Nicotinonitrile, 1,2-dihydro-4-methoxy-1-methyl-2-oxo-
DTXSID50200412
5-22-07-00318 (Beilstein Handbook Reference)
1,2-dihydro-4-methoxy-1-methyl-2-oxo-3-pyridimecarbonitrile
1,2-Dihydro-4-methoxy-1-methyl-2-oxo-Nicotinonitrile
4-Methoxy-1-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile
DTXCID50122903
3-cyano-4-methoxy-n-methyl-2-pyridone
3-Pyridinecarbonitrile, 1,2-dihydro-4-methoxy-1-methyl-2-oxo-(9CI)
208-359-7
Petsayfqsgaeqy-uhfffaoysa-n
NSC409913
NSC642604
MFCD00171320
Prestwick_1041
Ricinine-(methyl-d3)
1,2-Dihydro-4-methoxy-1-methyl-2-oxo-3-pyridinecarbonitrile
Prestwick0_000678
Prestwick1_000678
Prestwick2_000678
Prestwick3_000678
TimTec1_001989
Oprea1_847597
BSPBio_000775
MLS001048969
SCHEMBL257955
SPBio_002696
4-methoxy-1-methyl-2-oxohydropyridine-3-carbonitrile
BPBio1_000853
MEGxp0_000747
CHEMBL1329957
ACon1_001266
WLN: T6NVJ A1 CCN DO1
GLXC-05239
HMS1539K09
HMS1570G17
HMS2097G17
HMS2268G21
TNP00192
CCG-36061
STL564798
AKOS003673683
Ricinine, >=95% (LC/MS-ELSD)
FR27726
FS-7365
NCGC00016487-01
NCGC00016487-02
NCGC00016487-03
NCGC00016487-04
NCGC00016487-05
NCGC00142397-01
NCGC00169517-01
NCGC00169517-02
CAS-524-40-3
SMR000386989
SY256804
DB-052124
HY-121944
CS-0083725
NS00015447
C01526
E88580
4-methoxy-1-methyl-2-oxo-pyridine-3-carbonitrile
Q907865
BRD-K82561139-001-01-9
BRD-K82561139-001-05-0
Nicotinonitrile,2-dihydro-4-methoxy-1-methyl-2-oxo-
3-Pyridinecarbonitrile,2-dihydro-4-methoxy-1-methyl-2-oxo-
1,2-Dihydro-1-methyl-4-methoxy-2-oxo-3-pyridine carbonitrile
- El-Naggar M.H, Elgaml A, et al. (2019). Antimicrobial and antiquorum-sensing activity of Ricinus communis extracts and ricinine derivatives. Natural product research, 2019, 33(11), 1556-1562. [View] [PubMed]
- Kamel M.R, Nafady A.M, et al. (2021). Ent-trachylobane-3β-hydroperoxide, a new diterpene from the root bark of Chrozophora oblongifolia (Fam.; Euphorbiaceae). Natural product research, 2021, 35(19), 3177-3184. [View] [PubMed]
Pubchem:
10666
Cas:
524-40-3
Gnps:
CCMSLIB00004716125
Zinc:
ZINC000000113473
Kegg Ligand:
C01526
Chebi:
18043
Nmrshiftdb2:
70070105
Metabolights:
MTBLC18043
Chembl:
CHEMBL1329957
Comptox:
DTXSID50200412
CPRiL:
67580
SMILES: O=c1cccc[nH]1
Level: 0
Mol. Weight: 164.16 g/mol
Antimicrobial
Antiquorum-sensing
Absorption
- Caco-2 (logPapp)
- -4.63
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -3.990
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.98
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.310
- Plasma Protein Binding
- 19.46
- 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
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 3.470
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.030
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.380
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.500
- 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
- 2.700
- Rat (Acute)
- 2.000
- Rat (Chronic Oral)
- 1.450
- Fathead Minnow
- 3.680
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 305.350
- Hydration Free Energy
- -9.660
- Log(D) at pH=7.4
- -0.440
- Log(P)
- 0.13
- Log S
- -1.42
- Log(Vapor Pressure)
- -3.73
- Melting Point
- 182.01
- pKa Acid
- 1.74
- pKa Basic
- 0.86
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.9738 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.9618 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9384 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.9359 |
| AGAP003309-PA | A0A1U7F4W2 | A0A1U7F4W2_ANOGA | Anopheles gambiae | 3 | 0.9201 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.9161 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.8956 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8955 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8726 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8697 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 3 | 0.8403 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8039 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.8037 |
| O-GlcNAcase NagJ | Q0TR53 | OGA_CLOP1 | Clostridium perfringens | 3 | 0.7923 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7841 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7773 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7729 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7699 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7675 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7647 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7598 |
| 3',5'-cyclic-AMP phosphodiesterase 4A | P27815 | PDE4A_HUMAN | Homo sapiens | 3 | 0.7573 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 2 | 0.7529 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7506 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 2 | 0.7440 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7426 |
| TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase | Q6T1W8 | FDTA_ANETH | Aneurinibacillus thermoaerophilus | 3 | 0.7421 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7415 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7396 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7371 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7354 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7350 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7349 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7347 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7347 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7340 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7337 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 3 | 0.7322 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7319 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7316 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7286 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7283 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7257 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7255 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7252 |
| RNA-dependent RNA polymerase | Q6A562 | Q6A562_9VIRU | Thosea asigna virus | 2 | 0.7247 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 2 | 0.7227 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7222 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7217 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7207 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 3 | 0.7198 |
| RNA polymerase sigma factor SigA | Q5SKW1 | Q5SKW1_THET8 | Thermus thermophilus | 2 | 0.7116 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7105 |
| Eugenol synthase 1 | Q15GI4 | EGS1_OCIBA | Ocimum basilicum | 3 | 0.7101 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7068 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7063 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7036 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7035 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7034 |
| Eugenol synthase 1 | Q15GI4 | EGS1_OCIBA | Ocimum basilicum | 3 | 0.7013 |
| cysteine-S-conjugate beta-lyase | Q8DST5 | Q8DST5_STRMU | Streptococcus mutans serotype c | 3 | 0.7011 |