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Antirrhinoside
- Family: Plantae - Plantaginaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Iridoid Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@]3([C@H]2[C@@]2(C)O[C@H]2[C@H]3O)O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C15H22O10/c1-14-9-13(22-3-2-15(9,21)10(20)11(14)25-14)24-12-8(19)7(18)6(17)5(4-16)23-12/h2-3,5-13,16-21H,4H2,1H3/t5-,6-,7+,8-,9-,10-,11+,12+,13+,14-,15+/m1/s1 |
| InChIKey | UBAIOTDKPLIEDD-RNCITLLOSA-N |
| Formula | C15H22O10 |
| HBA | 10 |
| HBD | 6 |
| MW | 362.33 |
| Rotatable Bonds | 3 |
| TPSA | 161.6 |
| LogP | -3.45 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.87 |
| Exact Mass | 362.12 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Linaria aegyptiaca subsp. fruticosa | Scrophulariaceae | Plantae | 2792408 |
| 2 | Anarrhinum pedatum | Plantaginaceae | Plantae | 2500742 |
Showing of synonyms
Antirrhinoside
20770-65-4
DTXSID40331825
(2S,3R,4S,5S,6R)-2-[[(1S,2R,4S,5R,6S,10S)-5,6-dihydroxy-2-methyl-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
(2S,3R,4S,5S,6R)-2-[[(1aR,1bS,2S,5aS,6R,6aS)-5a,6-dihydroxy-1a-methyl-1b,2,6,6a-tetrahydrooxireno[1,2]cyclopenta[4,5-b]pyran-2-yl]oxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
(2S,3R,4S,5S,6R)-2-(((1aR,1bS,2S,5aS,6R,6aS)-5a,6-dihydroxy-1a-methyl-1b,2,6,6a-tetrahydrooxireno(1,2)cyclopenta(4,5-b)pyran-2-yl)oxy)-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
(2S,3R,4S,5S,6R)-2-(((1S,2R,4S,5R,6S,10S)-5,6-dihydroxy-2-methyl-3,9-dioxatricyclo(4.4.0.02,4)dec-7-en-10-yl)oxy)-6-(hydroxymethyl)oxane-3,4,5-triol
DTXCID90282919
CHEBI:2765
CHEMBL364464
C09768
AC1L9CS5
Q27105811
- Beladjila K.A, Berrehal D, et al. (2019). Antiangiogenic Activity of Compounds Isolated from Anarrhinum pedatum. Journal of natural products, 2019, 82(3), 510-519. [View] [PubMed]
- Ferhat M, Harkat H, et al. (2010). Iridoids and flavonoid from Linaria aegyptiaca (L.) Dum. subsp. fruticosa. Biochemical Systematics and Ecology,2010,38(4),833-835. [View]
Pubchem:
442418
Cas:
20770-65-4
Zinc:
ZINC000008234297
Kegg Ligand:
C09768
Chebi:
2765
Nmrshiftdb2:
70129002
Chembl:
CHEMBL364464
Comptox:
DTXSID40331825
No compound-protein relationship available.
SMILES: C12C(O2)CC3C1C(OC=C3)OC4CCCCO4
Level: 1
Mol. Weight: 362.33 g/mol
SMILES: C12C(O2)CC3C1COC=C3
Level: 0
Mol. Weight: 362.33 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 362.33 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.44
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.130
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.71
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.680
- Plasma Protein Binding
- 32.42
- 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
- 6.240
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.340
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.140
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.210
- 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
- -6.860
- Rat (Acute)
- 2.560
- Rat (Chronic Oral)
- 3.340
- Fathead Minnow
- 2.500
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 430.460
- Hydration Free Energy
- -16.170
- Log(D) at pH=7.4
- -2.110
- Log(P)
- -2.28
- Log S
- -0.85
- Log(Vapor Pressure)
- -14.21
- Melting Point
- 120.39
- pKa Acid
- 6.22
- pKa Basic
- 2.92
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7911 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7911 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7149 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7149 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7115 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7115 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7105 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7105 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7026 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7026 |