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Cucurbitacin D 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]3[C@]4(C)C(=O)C[C@]5([C@@]([C@@H]4CC=C3C(C2=O)(C)C)(C)C[C@H](C5[C@](C(=O)/C=C/C(OC(=O)C)(C)C)(O)C)O)C)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C38H56O13/c1-18(40)51-33(2,3)13-12-25(42)38(9,48)30-21(41)15-35(6)24-11-10-19-20(37(24,8)26(43)16-36(30,35)7)14-22(31(47)34(19,4)5)49-32-29(46)28(45)27(44)23(17-39)50-32/h10,12-13,20-24,27-30,32,39,41,44-46,48H,11,14-17H2,1-9H3/b13-12+/t20-,21-,22+,23-,24+,27-,28+,29-,30?,32-,35+,36-,37+,38+/m1/s1 |
| InChIKey | PQOVWWZVVIGRPP-DPXQNDTBSA-N |
| Formula | C38H56O13 |
| HBA | 13 |
| HBD | 6 |
| MW | 720.85 |
| Rotatable Bonds | 8 |
| TPSA | 217.35 |
| LogP | 1.32 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 51 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.79 |
| Exact Mass | 720.37 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Galium brunneum | Rubiaceae | Plantae | 25168 |
Showing of synonyms
Cucurbitacin D 2-O-beta-D-glucoside
NCGC00385062-01
NCGC00385062-01_C38H56O13_(2S,4R,9beta,16alpha,17xi,23E)-2-(beta-D-Glucopyranosyloxy)-16,20-dihydroxy-9,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-5,23-dien-25-yl acetate
- 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]
Pubchem:
45359750
Gnps:
CCMSLIB00000850267
No compound-protein relationship available.
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3CC(C(=O)C4)OC5CCCCO5
Level: 1
Mol. Weight: 720.85 g/mol
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3CCC(=O)C4
Level: 0
Mol. Weight: 720.85 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 720.85 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.93
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.530
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 118.67
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.730
- Plasma Protein Binding
- 107.35
- 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
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 2.940
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.750
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.630
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.520
- 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
- -216783.820
- Rat (Acute)
- 4.770
- Rat (Chronic Oral)
- 3.800
- Fathead Minnow
- 287.630
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 20050.880
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 2.630
- Log(P)
- 1.28
- Log S
- -3.38
- Log(Vapor Pressure)
- -631.71
- Melting Point
- 245.13
- pKa Acid
- 4.42
- pKa Basic
- 3.81
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.8490 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8118 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7770 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7505 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7213 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7188 |