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Radicinin
- Family: Fungi - Nectriaceae
- Kingdom: Fungi
- Class: Phenolic
| Canonical Smiles | C/C=C/c1cc2O[C@@H](C)[C@@H](C(=O)c2c(=O)o1)O |
|---|---|
| InChI | InChI=1S/C12H12O5/c1-3-4-7-5-8-9(12(15)17-7)11(14)10(13)6(2)16-8/h3-6,10,13H,1-2H3/b4-3+/t6-,10-/m0/s1 |
| InChIKey | SDKXGAICTNHFCN-DCJAWTJCSA-N |
| Formula | C12H12O5 |
| HBA | 5 |
| HBD | 1 |
| MW | 236.22 |
| Rotatable Bonds | 1 |
| TPSA | 76.74 |
| LogP | 1.0 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 17 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.33 |
| Exact Mass | 236.07 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Fusarium sp. | Nectriaceae | Fungi | 29916 |
Showing of synonyms
Radicinin
Stemphylone
10088-95-6
Radicinin (VAN)
NSC 118343
UNII-G01Z2N575M
CCRIS 8483
(2S,3S)-3-hydroxy-2-methyl-7-[(E)-prop-1-enyl]-2,3-dihydropyrano[3,2-c]pyran-4,5-dione
G01Z2N575M
RADICININ [MI]
NSC-118343
2,3-Dihydro-3-alpha-hydroxy-2-beta-methyl-7-propenyl-4H,5H-pyrano(4,3-b)pyran-4,5-dione
4H,5H-Pyrano(4,3-b)pyran-4,5-dione, 2,3-dihydro-3-alpha-hydroxy-2-beta-methyl-7-propenyl-
2H-PYRAN-5-CARBOXYLIC ACID, 3,4-DIHYDRO-3-HYDROXY-6-(2-HYDROXY-1,3-PENTADIENYL)-2-METHYL-4-OXO-, .DELTA.-LACTONE
4H,5H-PYRANO(4,3-B)PYRAN-4,5-DIONE, 2,3-DIHYDRO-3-HYDROXY-2-METHYL-7-((1E)-1-PROPEN-1-YL)-, (2S,3S)-
(2S,3S)-3-Hydroxy-2-Methyl-7-((E)-Prop-1-Enyl)-2,3-Dihydropyrano(3,2-C)Pyran-4,5-Dione
2,3-Dihydro-3-.alpha.-hydroxy-2-.beta.-methyl-7-propenyl-4H,5H-pyrano(4,3-b)pyran-4,5-dione
4H,5H-Pyrano(4,3-b)pyran-4,5-dione, 2,3-dihydro-3-.alpha.-hydroxy-2-.beta.-methyl-7-propenyl-
3,4-Dihydro-3-hydroxy-2-methyl-7-propenyl-2H,5H-pyrano(4,3-b)pyran-4,5-dione
2H-PYRAN-5-CARBOXYLIC ACID, 3,4-DIHYDRO-3-HYDROXY-6-(2-HYDROXY-1,3-PENTADIENYL)-2-METHYL-4-OXO-, DELTA-LACTONE
Sdkxgaictnhfcn-onegzznksa-n
NSC118343
1402-20-6
MLS002706791
3,4-dihydro-3-hydroxy-2-methyl-7-propenyl-2H,5H- pyrano(4,3-b)pyran-4,5-dione
SCHEMBL1531040
SCHEMBL1531042
CHEMBL1994984
DTXSID70871946
CHEBI:183741
AKOS040747350
2,5H-pyrano[4,3-b]pyran-4,5-dione
NCGC00488693-01
4H,5H-Pyrano[4,3-b]pyran-4,5-dione,2,3-dihydro-3-hydroxy-2-methyl-7-[(1E)-1-propen-1-yl]-, (2S,3S)-
DA-70093
HY-113816
CS-0062918
WLN: T66 BVO GO JV&TJ D1U2 H1 IQ
Q27278392
(2S,3S)-3-hydroxy-2-methyl-7-[(E)-prop-1-enyl]-2,3-dihydropyrano[4,3-b]pyran-4,5-dione
4H,3-b]pyran-4,5-dione, 2,3-dihydro-3.alpha.-hydroxy-2.beta.-methyl-7-propenyl-
(2S,3S)-3-hydroxy-2-methyl-7-((E)-prop-1-en-1-yl)-2,3-dihydro-4H,5H-pyrano[4,3-b]pyran-4,5-dione
(2S,3S)-3-Hydroxy-2-methyl-7-[(1E)-prop-1-en-1-yl]-2,3-dihydro-4H,5H-pyrano[4,3-b]pyran-4,5-dione
4H,3-b]pyran-4,5-dione, 2,3-dihydro-3-hydroxy-2-methyl-7-(1-propenyl)-, [2S-[2.alpha.,3.beta.,7(E)]]-
- Kongue Tatong M, Talontsi F, et al. (2014). Banchromene and other secondary metabolites from the endophytic fungus Fusarium sp. obtained from Piper guineense inhibit the motility of phytopathogenic Plasmopara viticola zoospores. Tetrahedron Letters, 2014, 55(30), 4057-4061. [View]
Pubchem:
5381458
Cas:
10088-95-6
Gnps:
CCMSLIB00006126863
Zinc:
ZINC000101123832
Chebi:
183741
Nmrshiftdb2:
70010511
Chembl:
CHEMBL1994984
No compound-protein relationship available.
SMILES: O=c1occc(c12)OCCC2=O
Level: 0
Mol. Weight: 236.22 g/mol
Motility-impairing
Toxin
Absorption
- Caco-2 (logPapp)
- -4.66
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.24
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.29
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.63
- Plasma Protein Binding
- 40.69
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-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
- 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
- Non-Inhibitor
Excretion
- Clearance
- 4.52
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.11
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.2
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.73
- 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
- 2.01
- Rat (Acute)
- 2.42
- Rat (Chronic Oral)
- 1.98
- Fathead Minnow
- 4.02
- 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
- 352.07
- Hydration Free Energy
- -10.87
- Log(D) at pH=7.4
- 0.6
- Log(P)
- 1.25
- Log S
- -2.18
- Log(Vapor Pressure)
- -6.65
- Melting Point
- 189.47
- pKa Acid
- 5.69
- pKa Basic
- 4.0
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Mitogen-activated protein kinase kinase kinase 5 | Q99683 | M3K5_HUMAN | Homo sapiens | 3 | 0.8945 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8528 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.8520 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.8466 |
| Catalase-peroxidase | Q3JNW6 | KATG_BURP1 | Burkholderia pseudomallei | 3 | 0.8387 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | P0AF12 | MTNN_ECOLI | Escherichia coli | 3 | 0.8327 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.8257 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.8217 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8154 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.8090 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.8072 |
| NAD-dependent protein deacetylase | Q9WYW0 | NPD_THEMA | Thermotoga maritima | 3 | 0.7826 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7681 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.7673 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7573 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7443 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 3 | 0.7428 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7405 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7116 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.7115 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7108 |
| Peripheral plasma membrane protein CASK | O14936 | CSKP_HUMAN | Homo sapiens | 3 | 0.7100 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 4 | 0.7023 |