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Hexa-nor-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]3C(=CC[C@@H]4[C@@]3(C)C(=O)C[C@]3([C@@]4(C)C[C@H]([C@@H]3C(=O)C)O)C)C(C2=O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C30H44O10/c1-13(32)21-16(33)10-28(4)19-8-7-14-15(30(19,6)20(34)11-29(21,28)5)9-17(25(38)27(14,2)3)39-26-24(37)23(36)22(35)18(12-31)40-26/h7,15-19,21-24,26,31,33,35-37H,8-12H2,1-6H3/t15-,16-,17+,18-,19+,21+,22-,23+,24-,26-,28+,29-,30+/m1/s1 |
| InChIKey | ZPPOLNNGEVBQFA-CVVUTLENSA-N |
| Formula | C30H44O10 |
| HBA | 10 |
| HBD | 5 |
| MW | 564.67 |
| Rotatable Bonds | 4 |
| TPSA | 170.82 |
| LogP | 0.69 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 40 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.83 |
| Exact Mass | 564.29 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Galium brunneum | Rubiaceae | Plantae | 25168 |
Showing of synonyms
Hexa-nor-cucurbitacin D 2-O-beta-D-glucoside
CHEMBL538690
- 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: 564.67 g/mol
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3CCC(=O)C4
Level: 0
Mol. Weight: 564.67 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 564.67 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.68
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.900
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 0.08
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.840
- Plasma Protein Binding
- 93.32
- 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
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 0.490
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -4.020
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.460
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.680
- 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
- -2144.400
- Rat (Acute)
- 4.200
- Rat (Chronic Oral)
- 3.460
- Fathead Minnow
- 5.160
- 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
- 480.750
- Hydration Free Energy
- -2.840
- Log(D) at pH=7.4
- 2.030
- Log(P)
- 0.39
- Log S
- -3.14
- Log(Vapor Pressure)
- -11.77
- Melting Point
- 235.74
- pKa Acid
- 5.11
- pKa Basic
- 3.01
| 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 | 0.8755 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.8071 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7823 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7805 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7460 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7416 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 3 | 0.7146 |