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Daphyllosid
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
- Class: Lignan
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2C(=C[C@@H]3O)COC(=O)C)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C19H26O12/c1-7(21)28-5-8-3-10(22)13-9(17(26)27-2)6-29-18(12(8)13)31-19-16(25)15(24)14(23)11(4-20)30-19/h3,6,10-16,18-20,22-25H,4-5H2,1-2H3/t10-,11+,12+,13-,14+,15-,16+,18-,19-/m0/s1 |
| InChIKey | YSOBQIMODQOGKQ-HOZAMIDDSA-N |
| Formula | C19H26O12 |
| HBA | 12 |
| HBD | 5 |
| MW | 446.41 |
| Rotatable Bonds | 6 |
| TPSA | 181.44 |
| LogP | -2.69 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.68 |
| Exact Mass | 446.14 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Galium brunneum | Rubiaceae | Plantae | 25168 |
Showing of synonyms
Daphyllosid
Daphylloside
14260-99-2
ASPERULOSIDIC ACID METHYL ESTER
(1S)-1alpha-(beta-D-Glucopyranosyloxy)-5beta-hydroxy-7-(acetoxymethyl)-1,4aalpha,5,7aalpha-tetrahydrocyclopenta[c]pyran-4-carboxylic acid methyl ester
Methyl (1S,4aS,5S,7aS)-7-(acetyloxymethyl)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
(1S)-1alpha-(beta-D-Glucopyranosyloxy)-5beta-hydroxy-7-(acetoxymethyl)-1,4aalpha,5,7aalpha-tetrahydrocyclopenta[c]pyra
SCHEMBL9057631
CHEMBL3937733
ASPERULOSIDICACIDMETHYLESTER
CHEBI:182720
(1S)-1|A-(|A-D-Glucopyranosyloxy)-5|A-hydroxy-7-(acetoxymethyl)-1,4a|A,5,7a|A-tetrahydrocyclopenta[c]pyran-4-carboxylic acid methyl ester
HY-N6245
AKOS032962362
NCGC00380265-01
DA-62668
FS-10348
PD100185
CS-0032780
METHYL (1S,4AS,5S,7AS)-7-[(ACETYLOXY)METHYL]-5-HYDROXY-1-{[(2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY}-1H,4AH,5H,7AH-CYCLOPENTA[C]PYRAN-4-CARBOXYLATE
NCGC00380265-01_C19H26O12_Cyclopenta[c]pyran-4-carboxylic acid, 7-[(acetyloxy)methyl]-1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-5-hydroxy-, methyl ester, (1S,4aS,5S,7aS)-
- 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:
21602024
Cas:
14260-99-2
Gnps:
CCMSLIB00006455190
Zinc:
ZINC000031159654
Chebi:
182720
Nmrshiftdb2:
60072147
Chembl:
CHEMBL3937733
No compound-protein relationship available.
SMILES: C1=CCC(C12)C=COC2OC3CCCCO3
Level: 1
Mol. Weight: 446.41 g/mol
SMILES: C1=CCC(C12)C=COC2
Level: 0
Mol. Weight: 446.41 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 446.41 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.75
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -4.940
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.8
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.630
- Plasma Protein Binding
- 50.46
- 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
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.840
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.090
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.010
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.250
- Micronucleos
- Toxic
- 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
- -43.320
- Rat (Acute)
- 2.710
- Rat (Chronic Oral)
- 3.520
- Fathead Minnow
- 4.070
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 482.370
- Hydration Free Energy
- -5.690
- Log(D) at pH=7.4
- -0.320
- Log(P)
- -1.87
- Log S
- -0.96
- Log(Vapor Pressure)
- -12.56
- Melting Point
- 161.42
- pKa Acid
- 4.76
- pKa Basic
- 2.3
| 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 | 0.8013 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7813 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7306 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7213 |