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3beta-(trans-p-coumaroyl)oxylup-20(29)-en-28-oïc acid
- Family: Plantae - Sapotaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Pentacyclic Triterpene
| Canonical Smiles | O=C(O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@]1([C@@H]2[C@@H](CC1)C(=C)C)C(=O)O)C)C)/C=C/c1ccccc1 |
|---|---|
| InChI | InChI=1S/C39H54O4/c1-25(2)27-17-22-39(34(41)42)24-23-37(6)28(33(27)39)14-15-30-36(5)20-19-31(35(3,4)29(36)18-21-38(30,37)7)43-32(40)16-13-26-11-9-8-10-12-26/h8-13,16,27-31,33H,1,14-15,17-24H2,2-7H3,(H,41,42)/b16-13+/t27-,28+,29-,30+,31-,33+,36-,37+,38+,39-/m0/s1 |
| InChIKey | LJKUKNYRLPOWIO-KXIJJFQHSA-N |
| Formula | C39H54O4 |
| HBA | 3 |
| HBD | 1 |
| MW | 586.86 |
| Rotatable Bonds | 5 |
| TPSA | 63.6 |
| LogP | 9.35 |
| Number Rings | 6 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 43 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.69 |
| Exact Mass | 586.4 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Baillonella toxisperma (Pierre) | Sapotaceae | Plantae | 568230 |
Showing of synonyms
3beta-(trans-p-coumaroyl)oxylup-20(29)-en-28-oïc acid
- Pierre Yemback, Kenneth O. Eyong, et al. (2023). Lupane derivatives: Design, isolation, synthesis and evaluation of antiplasmodial activity against Plasmodium falciparum 3D7 strain. Phytochemistry Letters, 2023, 57, 26-35. [View]
No compound-protein relationship available.
SMILES: c1ccccc1C=CC(=O)OC(C2)CCC3C2CCC4C3CCC5C4CCC(C56)CCC6
Level: 1
Mol. Weight: 586.86 g/mol
SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5
Level: 0
Mol. Weight: 586.86 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 586.86 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.22
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.79
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 8.08
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 2.69
- Plasma Protein Binding
- 108.91
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-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
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 5.3
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.05
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.27
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.86
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -18015.77
- Rat (Acute)
- 2.53
- Rat (Chronic Oral)
- 2.52
- Fathead Minnow
- 40.83
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 379.66
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 6.39
- Log(P)
- 8.99
- Log S
- -6.98
- Log(Vapor Pressure)
- -11.59
- Melting Point
- 238.37
- pKa Acid
- 7.21
- pKa Basic
- 7.74
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8819 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7969 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7602 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7563 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7521 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.7520 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7363 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7295 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7280 |
| Single-stranded-DNA-specific exonuclease RecJ | D0EM60 | D0EM60_DEIRD | Deinococcus radiodurans | 2 | 0.7206 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7146 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7045 |
| Deacetoxycephalosporin C synthase | P18548 | CEFE_STRCL | Streptomyces clavuligerus | 3 | 0.7000 |