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Citroside A
- Family: Plantae - Apiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpenoid Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@]2(C)C[C@@H](O)CC(C2=C=CC(=O)C)(C)C)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C19H30O8/c1-10(21)5-6-13-18(2,3)7-11(22)8-19(13,4)27-17-16(25)15(24)14(23)12(9-20)26-17/h5,11-12,14-17,20,22-25H,7-9H2,1-4H3/t6?,11-,12+,14+,15-,16+,17-,19+/m0/s1 |
| InChIKey | XTODSGVDHGMKSN-SIEIHWOKSA-N |
| Formula | C19H30O8 |
| HBA | 8 |
| HBD | 5 |
| MW | 386.44 |
| Rotatable Bonds | 4 |
| TPSA | 136.68 |
| LogP | -0.59 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.79 |
| Exact Mass | 386.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Tribulus parvispinus | Zygophyllaceae | Plantae | 2603131 |
| 2 | Eryngium tricuspidatum | Apiaceae | Plantae | 488472 |
Showing of synonyms
Citroside A
Citroside B
120330-44-1
CHEBI:69850
3-Buten-2-one, 4-[(2R,4S)-2-(beta-D-glucopyranosyloxy)-4-hydroxy-2,6,6-trimethylcyclohexylidene]-, (3R)-
CHEMBL1814429
DTXSID701318300
HY-N9046
AKOS040761513
(1R,5S)-5-Hydroxy-1,3,3-trimethyl-2-(3-oxobut-1-en-1-ylidene)cyclohexyl beta-D-glucopyranoside
DA-62353
CS-0149597
Q27138189
3-Buten-2-one, 4-[(2R,4S)-2-(|A-D-glucopyranosyloxy)-4-hydroxy-2,6,6-trimethylcyclohexylidene]-, (3R)-
4-[(4S,6R)-4-hydroxy-2,2,6-trimethyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-cyclohexylidene]but-3-en-2-one
- Benmerache A, Magid A.A, et al. (2016). Chemical composition, antibacterial, antioxidant and tyrosinase inhibitory activities of glycosides from aerial parts of Eryngium tricuspidatum. Phytochemistry Letters, 2016, 18, 23 - 28. [View]
- Perrone A, Plaza A, et al. (2005). Cytotoxic furostanol saponins and a megastigmane glucoside from Tribulus parvispinus. Journal of Natural Products,2005,68(10),1549-1553. [View] [PubMed]
Pubchem:
14312562
Cas:
120330-44-1
Zinc:
ZINC000031155114
Chebi:
69850
Nmrshiftdb2:
60067644
Metabolights:
MTBLC69850
Chembl:
CHEMBL1814429
CPRiL:
106836
SMILES: C1CCCC(C1=C=C)OC2CCCCO2
Level: 1
Mol. Weight: 386.44 g/mol
SMILES: C=C=C1CCCCC1
Level: 0
Mol. Weight: 386.44 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 386.44 g/mol
Antibacterial
Antioxidant
Absorption
- Caco-2 (logPapp)
- -5.15
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.850
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.62
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.600
- Plasma Protein Binding
- 63.96
- 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
- Non-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
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 2.720
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.420
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.930
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 3.990
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -6.540
- Rat (Acute)
- 2.430
- Rat (Chronic Oral)
- 2.990
- Fathead Minnow
- 3.440
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 455.720
- Hydration Free Energy
- -16.750
- Log(D) at pH=7.4
- 0.180
- Log(P)
- -0.82
- Log S
- -1.47
- Log(Vapor Pressure)
- -11.54
- Melting Point
- 145.22
- pKa Acid
- 7.41
- pKa Basic
- 6.05
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7869 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7869 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7744 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7744 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7090 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7090 |