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3-epi-cucurbitacin B
- Family: Plantae - Cucurbitaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpene
| Canonical Smiles | CC(=O)OC(/C=C/C(=O)[C@@]([C@H]1[C@H](O)C[C@@]2([C@]1(C)CC(=O)[C@@]1([C@H]2CC=C2[C@H]1CC(O)C(=O)C2(C)C)C)C)(O)C)(C)C |
|---|---|
| InChI | InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+/t19-,20?,21-,22+,25+,29+,30-,31+,32+/m1/s1 |
| InChIKey | IXQKXEUSCPEQRD-WURSUFTCSA-N |
| Formula | C32H46O8 |
| HBA | 8 |
| HBD | 3 |
| MW | 558.71 |
| Rotatable Bonds | 5 |
| TPSA | 138.2 |
| LogP | 3.5 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 40 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.75 |
| Exact Mass | 558.32 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Bryonia cretica | Cucurbitaceae | Plantae | 61884 |
Showing of synonyms
3-epi-cucurbitacin B
- Matsuda H, Nakashima S, et al. (2010). Cucurbitane-Type Triterpenes with Anti-proliferative Effects on U937 Cells from an Egyptian Natural Medicine, Bryonia cretica: Structures of New Triterpene Glycosides, Bryoniaosides A and B. Chemical & pharmaceutical bulletin, 2010, 58(5), 747-51. [View] [PubMed]
Pubchem:
53244167
No compound-protein relationship available.
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3CCC(=O)C4
Level: 0
Mol. Weight: 558.71 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.81
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.71
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.4
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.82
- Plasma Protein Binding
- 99.28
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- 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
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.47
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.24
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.05
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.85
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Toxic
- 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
- -1028.28
- Rat (Acute)
- 4.4
- Rat (Chronic Oral)
- 2.15
- Fathead Minnow
- 4.66
- 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
- 478.33
- Hydration Free Energy
- -2.86
- Log(D) at pH=7.4
- 3.32
- Log(P)
- 3.23
- Log S
- -4.81
- Log(Vapor Pressure)
- -9.19
- Melting Point
- 222.79
- pKa Acid
- 6.68
- pKa Basic
- 2.0
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7945 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7862 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7513 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7316 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.7312 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7292 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7134 |
| TamL | D3Y1I2 | D3Y1I2_9ACTN | Streptomyces sp. 307-9 | 2 | 0.7129 |
| Predicted acetyltransferase | Q97ML2 | Q97ML2_CLOAB | Clostridium acetobutylicum | 3 | 0.7003 |