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3beta-trans cinnamoyloxylup-20(29)-ene
- 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)C)C)/C=C/c1ccccc1 |
|---|---|
| InChI | InChI=1S/C39H56O2/c1-26(2)28-18-21-36(5)24-25-38(7)29(34(28)36)15-16-31-37(6)22-20-32(35(3,4)30(37)19-23-39(31,38)8)41-33(40)17-14-27-12-10-9-11-13-27/h9-14,17,28-32,34H,1,15-16,18-25H2,2-8H3/b17-14+/t28-,29+,30-,31+,32-,34+,36+,37-,38+,39+/m0/s1 |
| InChIKey | HHCSYPMWJQHCMZ-HWCKACSDSA-N |
| Formula | C39H56O2 |
| HBA | 2 |
| HBD | 0 |
| MW | 556.88 |
| Rotatable Bonds | 4 |
| TPSA | 26.3 |
| LogP | 10.29 |
| Number Rings | 6 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 41 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.72 |
| Exact Mass | 556.43 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Baillonella toxisperma (Pierre) | Sapotaceae | Plantae | 568230 |
Showing of synonyms
3beta-trans cinnamoyloxylup-20(29)-ene
Lupeol trans-cinnamate
66609-69-6
[(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] (E)-3-phenylprop-2-enoate
Lup-20(29)-en-3-ol, (2E)-3-phenyl-2-propenoate, (3beta)-
Lupenyl cinnamate
NSC712806
SCHEMBL6444488
AKOS040752752
NSC-712806
- 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: 556.88 g/mol
SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5
Level: 0
Mol. Weight: 556.88 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 556.88 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.77
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.62
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 1.43
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 2.48
- Plasma Protein Binding
- 105.37
- 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
- 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
- Non-Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 5.58
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.74
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.52
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.79
- 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
- -7014.27
- Rat (Acute)
- 2.2
- Rat (Chronic Oral)
- 2.17
- Fathead Minnow
- 22.2
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 371.4
- Hydration Free Energy
- -2.8
- Log(D) at pH=7.4
- 8.82
- Log(P)
- 10.71
- Log S
- -7.42
- Log(Vapor Pressure)
- -14.11
- Melting Point
- 209.82
- pKa Acid
- 12.79
- pKa Basic
- 7.16
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8622 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7748 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7398 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7358 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7324 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7298 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7287 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7247 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7175 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7070 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7059 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7039 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7014 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7008 |