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Isoschaftoside
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonoid Glycoside
| Canonical Smiles | OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)c1c(O)c([C@@H]2OC[C@@H]([C@@H]([C@H]2O)O)O)c(c2c1oc(cc2=O)c1ccc(cc1)O)O |
|---|---|
| InChI | InChI=1S/C26H28O14/c27-6-13-18(32)21(35)23(37)26(40-13)16-20(34)15(25-22(36)17(31)11(30)7-38-25)19(33)14-10(29)5-12(39-24(14)16)8-1-3-9(28)4-2-8/h1-5,11,13,17-18,21-23,25-28,30-37H,6-7H2/t11-,13+,17-,18+,21-,22+,23+,25-,26-/m0/s1 |
| InChIKey | OVMFOVNOXASTPA-VYUBKLCTSA-N |
| Formula | C26H28O14 |
| HBA | 14 |
| HBD | 10 |
| MW | 564.5 |
| Rotatable Bonds | 4 |
| TPSA | 250.97 |
| LogP | -1.75 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 40 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.42 |
| Exact Mass | 564.15 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Artemisia herba-alba | Asteraceae | Plantae | 72329 |
| 2 | Artemisia herba-alba | Asteraceae | Plantae | 72329 |
| 3 | Artemisia judaica | Asteraceae | Plantae | 205369 |
| 4 | Cotula cinerea | Asteraceae | Plantae | — |
Showing of synonyms
Isoschaftoside
Isoshaftoside
UNII-H27X8715V3
H27X8715V3
CHEBI:75589
4H-1-Benzopyran-4-one, 6-alpha-L-arabinopyranosyl-8-beta-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-6-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one
J376.232G
5,7,4'-Trihydroxy-6-C-arabinoside-8-C-glucoside flavone
6-C-alpha-L-arabinopyranosyl-8-C-beta-D-glucosylapigenin
6-C-.ALPHA.-L-ARABINOSYL-8-C-.BETA.-D-GLUCOSYLAPIGENIN
APIGENIN 6-C-.ALPHA.-L-ARABINOSIDE 8-C-.BETA.-D-GLUCOSIDE
APIGENIN 6-C-.ALPHA.-L-ARABINOPYRANOSIDE-8-C-.BETA.-D-GLUCOPYRANOSIDE
2-(4-HYDROXYPHENYL)-5,7-DIHYDROXY-6-(ALPHA-L-ARABINOPYRANOSYL)-8-(BETA-D-GLUCOPYRANOSYL)-4H-1-BENZOPYRAN-4-ONE
5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-8-((2S,3R,4R,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-2-YL)-6-((2S,3R,4S,5S)-3,4,5-TRIHYDROXYTETRAHYDRO-2H-PYRAN-2-YL)-4H-CHROMEN-4-ONE
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-6-[(2S,3R,4S,5S)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]-4H-chromen-4-one
6-(.ALPHA.-L-ARABINOPYRANOSYL)-8-(.BETA.-D-GLUCOPYRANOSYL)-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
6-Arabinosyl-8-galactosylapigenin
Apigenin 6-C-alpha-L-arabinopyranoside-8-C-beta-D-glucopyranoside
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)-6-((2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl)chromen-4-one
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-((2S,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)-6-((2S,4S,5S)-3,4,5-trihydroxyoxan-2-yl)chromen-4-one
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-6-[(2S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one
6-C-alpha-L-Arabinosyl-8-C-beta-D-glucosylapigenin
6-Arabinopyranosyl-8-galactopyranosylapigenin
6-Arabinopyranosyl-8-galactopyranosyl-4',5,7-trihydroxyflavone
6-a-L-Arabinopyranosyl-8-b-D-galactopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9CI
APIGENIN 6-C-ALPHA-L-ARABINOSIDE 8-C-BETA-D-GLUCOSIDE
6-(ALPHA-L-ARABINOPYRANOSYL)-8-(BETA-D-GLUCOPYRANOSYL)-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
826-197-0
52012-29-0
Apigenin 6-C-arabinoside 8-C-glucoside
Isoschaftoside (Standard)
SCHEMBL5082977
CHEMBL2437365
HY-N1458R
DTXSID301317293
HY-N1458
MFCD00210518
MSK158902
AKOS030573652
MI33288
AC-35000
DA-64567
MS-30225
CS-0016904
Q27145412
Isoschaftoside4H-1-Benzopyran-4-one, 6-alpha-L-arabinopyranosyl-8-beta-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-
- Saleh NAM, El-Newumy SI, et al. (1985). Flavonoid glycosides of Artemisia monosperma and A. herba-alba.. Phytochemistry,1985,24(1),201-203. [View]
- Saleh NAM, El-Negoumy SI, et al. (1987). Flavonoids of Artemisia judaica, A. monosperma and A. Herba-alba.. Phytochemistry,1987,26(11),3059-3064. [View]
- Ahmed AA, el-Sayed NH, et al. (1987). Flavonoids of Cotula cinerea. Journal of Natural Products,1987,50(3),519-520. [View]
Pubchem:
3084995
Cas:
52012-29-0
Gnps:
CCMSLIB00006423090
Zinc:
ZINC000059730688
Chebi:
75589
Nmrshiftdb2:
60022858
Metabolights:
MTBLC75589
Chembl:
CHEMBL2437365
CPRiL:
157813
SMILES: c1ccccc1-c(cc2=O)oc(c23)c(C4CCCCO4)cc(c3)C5CCCCO5
Level: 3
Mol. Weight: 564.5 g/mol
SMILES: O=c1ccoc(c12)c(C3CCCCO3)cc(c2)C4CCCCO4
Level: 2
Mol. Weight: 564.5 g/mol
SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCCCO4
Level: 2
Mol. Weight: 564.5 g/mol
SMILES: O1CCCCC1c(ccc2)c(c23)oc(cc3=O)-c4ccccc4
Level: 2
Mol. Weight: 564.5 g/mol
SMILES: O=c1ccoc(c12)ccc(c2)C3CCCCO3
Level: 1
Mol. Weight: 564.5 g/mol
SMILES: O=c1ccoc(c12)c(ccc2)C3CCCCO3
Level: 1
Mol. Weight: 564.5 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 564.5 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 564.5 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 564.5 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 564.5 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.45
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -6.210
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 5.06
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.650
- Plasma Protein Binding
- 68.24
- 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
- 8.410
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -3.850
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.760
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.380
- 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
- -3787.660
- Rat (Acute)
- 2.500
- Rat (Chronic Oral)
- 4.960
- Fathead Minnow
- 7.590
- 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
- 679.520
- Hydration Free Energy
- -3.160
- Log(D) at pH=7.4
- -1.110
- Log(P)
- -0.22
- Log S
- -3.45
- Log(Vapor Pressure)
- -13.83
- Melting Point
- 210.71
- pKa Acid
- 2.12
- pKa Basic
- 10.38
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8326 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8326 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8197 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8197 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.7991 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.7991 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7988 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7988 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7874 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7874 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7740 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7740 |
| F420-dependent NADP reductase | O29370 | FNO_ARCFU | Archaeoglobus fulgidus | 4 | 0.7648 |
| F420-dependent NADP reductase | O29370 | FNO_ARCFU | Archaeoglobus fulgidus | 4 | 0.7648 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7522 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7522 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7296 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7296 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7246 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7246 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7226 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7226 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7089 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7089 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7038 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7038 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7007 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7007 |