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Deacetoxycucurbitacin B 2-O-beta-D-glucoside
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Glycosyl Triterpenoid
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@H]2C[C@@H]3C(=CCC4[C@@]3(C)C(=O)C[C@]3([C@@]4(C)C[C@H](C3[C@](C(=O)CC=C(C)C)(O)C)O)C)C(C2=O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C36H54O11/c1-17(2)9-12-24(39)36(8,45)29-20(38)14-33(5)23-11-10-18-19(35(23,7)25(40)15-34(29,33)6)13-21(30(44)32(18,3)4)46-31-28(43)27(42)26(41)22(16-37)47-31/h9-10,19-23,26-29,31,37-38,41-43,45H,11-16H2,1-8H3/t19-,20-,21+,22-,23?,26-,27+,28-,29?,31-,33+,34-,35+,36+/m1/s1 |
| InChIKey | LILYJQDMJMECMD-WENSWKDPSA-N |
| Formula | C36H54O11 |
| HBA | 11 |
| HBD | 6 |
| MW | 662.82 |
| Rotatable Bonds | 7 |
| TPSA | 191.05 |
| LogP | 1.78 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 47 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.81 |
| Exact Mass | 662.37 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Galium brunneum | Rubiaceae | Plantae | 25168 |
Showing of synonyms
Deacetoxycucurbitacin B 2-O-beta-D-glucoside
- Smadi A, Bitam F, et al. (2020). Chemical constituents of the aerial parts of Algerian Galium brunneum:Isolation of new hydroperoxy sterol glucosyl derivatives. Phytochemistry Letters, 2020, 38, 39-45. [View]
No compound-protein relationship available.
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3CC(C(=O)C4)OC5CCCCO5
Level: 1
Mol. Weight: 662.82 g/mol
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3CCC(=O)C4
Level: 0
Mol. Weight: 662.82 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 662.82 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.75
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.990
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 23.57
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.830
- Plasma Protein Binding
- 107.51
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-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
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 1.920
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.520
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.490
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.940
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Toxic
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -44359.280
- Rat (Acute)
- 4.460
- Rat (Chronic Oral)
- 3.610
- Fathead Minnow
- 73.400
- 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
- 1698.780
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 2.970
- Log(P)
- 2.26
- Log S
- -3.51
- Log(Vapor Pressure)
- -39.06
- Melting Point
- 238.77
- pKa Acid
- 4.48
- pKa Basic
- 3.55
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8965 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.8962 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7991 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7911 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7910 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7817 |
| Sodium-dependent dopamine transporter | Q7K4Y6 | DAT_DROME | Drosophila melanogaster | 2 | 0.7350 |