Select a section from the left sidebar
Clausarin
- Family: Plantae - Rutaceae
- Kingdom: Plantae
- Class: Coumarin
| Canonical Smiles | C=CC(c1c2OC(C)(C)C=Cc2c(c2c1oc(=O)c(c2)C(C=C)(C)C)O)(C)C |
|---|---|
| InChI | InChI=1S/C24H28O4/c1-9-22(3,4)16-13-15-18(25)14-11-12-24(7,8)28-20(14)17(23(5,6)10-2)19(15)27-21(16)26/h9-13,25H,1-2H2,3-8H3 |
| InChIKey | LMEKIDFKWUPZGE-UHFFFAOYSA-N |
| Formula | C24H28O4 |
| HBA | 4 |
| HBD | 1 |
| MW | 380.48 |
| Rotatable Bonds | 4 |
| TPSA | 59.67 |
| LogP | 5.61 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.38 |
| Exact Mass | 380.2 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Citrus aurantium | Rutaceae | Plantae | 43166 |
Showing of synonyms
Clausarin
62770-67-6
5-hydroxy-2,2-dimethyl-7,10-bis(2-methylbut-3-en-2-yl)pyrano[3,2-g]chromen-8-one
DTXSID50211841
2H,8H-Benzo(1,2-b:5,4-b')dipyran-2-one, 3,10-bis(1,1-dimethyl-2-propenyl)-5-hydroxy-8,8-dimethyl-
5-hydroxy-2,2-dimethyl-7,10-bis(2-methylbut-3-en-2-yl)pyrano(3,2-g)chromen-8-one
DTXCID80134332
CHEMBL158198
SCHEMBL3366447
AKOS040734627
NCGC00381299-01!5-hydroxy-2,2-dimethyl-7,10-bis(2-methylbut-3-en-2-yl)pyrano[3,2-g]chromen-8-one
- Bissim S, Kenmogne S, et al. (2019). Bioactive acridone alkaloids and their derivatives from Citrus aurantium (Rutaceae). Phytochemistry Letters, 2019, 29, 148-153. [View]
Pubchem:
5315945
Cas:
62770-67-6
Gnps:
CCMSLIB00000848891
Zinc:
ZINC000014927453
Nmrshiftdb2:
60025338
Chembl:
CHEMBL158198
Comptox:
DTXSID50211841
No compound-protein relationship available.
SMILES: c1cc(=O)oc(c12)cc3c(c2)C=CCO3
Level: 0
Mol. Weight: 380.48 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.76
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.45
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.71
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.94
- Plasma Protein Binding
- 54.25
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.41
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 2.17
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.03
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.9
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- 0.18
- Rat (Acute)
- 2.59
- Rat (Chronic Oral)
- 1.31
- Fathead Minnow
- 4.96
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 426.45
- Hydration Free Energy
- -6.34
- Log(D) at pH=7.4
- 4.27
- Log(P)
- 5.97
- Log S
- -6.31
- Log(Vapor Pressure)
- -7.28
- Melting Point
- 140.89
- pKa Acid
- 8.78
- pKa Basic
- 4.95
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8468 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8035 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7710 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7487 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7487 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7455 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7412 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7404 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7387 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7178 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7135 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7100 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7088 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7088 |
| TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase | Q6T1W8 | FDTA_ANETH | Aneurinibacillus thermoaerophilus | 3 | 0.7040 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 2 | 0.7036 |