Select a section from the left sidebar
(1R,2R,3R)-2,3-trans-6,7-methylenedioxy-1-(3’,4’-methylenedioxypheny1)-1,2,3,4-tetrahydro-3-hydroxy-methylanaphthalene-2-carboxylic acid lactone
- Family: Plantae - Rutaceae
- Kingdom: Plantae
- Class: Lignan
| Canonical Smiles | O=C1OCC2[C@H]1[C@H](c1ccc3c(c1)OCO3)c1c(C2)cc2c(c1)OC(O2)(C)C |
|---|---|
| InChI | InChI=1S/C22H20O6/c1-22(2)27-17-7-12-5-13-9-24-21(23)20(13)19(14(12)8-18(17)28-22)11-3-4-15-16(6-11)26-10-25-15/h3-4,6-8,13,19-20H,5,9-10H2,1-2H3/t13?,19-,20+/m1/s1 |
| InChIKey | IFPQUMYVNSHRDW-CFNCIARGSA-N |
| Formula | C22H20O6 |
| HBA | 6 |
| HBD | 0 |
| MW | 380.4 |
| Rotatable Bonds | 1 |
| TPSA | 63.22 |
| LogP | 3.4 |
| Number Rings | 6 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.41 |
| Exact Mass | 380.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Haplophyllum tuberculatum | Rutaceae | Plantae | 452784 |
Showing of synonyms
(1R,2R,3R)-2,3-trans-6,7-methylenedioxy-1-(3’,4’-methylenedioxypheny1)-1,2,3,4-tetrahydro-3-hydroxy-methylanaphthalene-2-carboxylic acid lactone
- M. Sheriha G, Abouamer K, et al. (1987). Quinoline alkaloids and cytotoxic lignans from Haplophyllum tuberculatum. Phytochemistry, 1987, 26(12), 3339-3341. [View]
No compound-protein relationship available.
SMILES: O1COc(c12)cc3c(c2)C(C4C(C3)COC4=O)c(c5)ccc(c56)OCO6
Level: 1
Mol. Weight: 380.4 g/mol
SMILES: O1COc(c12)cc3c(c2)CC4C(C3)COC4=O
Level: 0
Mol. Weight: 380.4 g/mol
SMILES: O1COc(c12)cccc2
Level: 0
Mol. Weight: 380.4 g/mol
Antibacterial
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -5.17
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.78
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.19
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.47
- Plasma Protein Binding
- 84.77
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 14.77
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.65
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.45
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.95
- 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
- Safe
- T. Pyriformis
- -25.86
- Rat (Acute)
- 2.34
- Rat (Chronic Oral)
- 1.51
- Fathead Minnow
- 5.17
- 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
- 483.38
- Hydration Free Energy
- -5.07
- Log(D) at pH=7.4
- 2.87
- Log(P)
- 3.56
- Log S
- -4.58
- Log(Vapor Pressure)
- -8.75
- Melting Point
- 184.69
- pKa Acid
- 9.24
- pKa Basic
- 3.63
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Bromodomain testis-specific protein | Q58F21 | BRDT_HUMAN | Homo sapiens | 3 | 0.9456 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8454 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8153 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7926 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.7909 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 3 | 0.7785 |
| Apoptosis regulator Bcl-2 | P10415 | BCL2_HUMAN | Homo sapiens | 3 | 0.7759 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7746 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7577 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7306 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7216 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7152 |
| Phosphodiesterase | Q53I60 | Q53I60_TRYCR | Trypanosoma cruzi | 3 | 0.7099 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7062 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7045 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7045 |
| [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial | Q15119 | PDK2_HUMAN | Homo sapiens | 4 | 0.7021 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7001 |