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Schaftoside
- Family: Plantae - Poaceae
- 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)c2c(c1O)c(=O)cc(o2)c1ccc(cc1)O |
|---|---|
| InChI | InChI=1S/C26H28O14/c27-6-13-18(32)21(35)23(37)26(40-13)15-19(33)14-10(29)5-12(8-1-3-9(28)4-2-8)39-24(14)16(20(15)34)25-22(36)17(31)11(30)7-38-25/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 | MMDUKUSNQNWVET-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 | Atractylis flava | Asteraceae | Plantae | 41483 |
| 4 | Artemisia judaica | Asteraceae | Plantae | 205369 |
| 5 | Hyparrhenia hirta | Poaceae | Plantae | 42079 |
Showing of synonyms
Schaftoside
51938-32-0
6-C-beta-glucopyranosyl-8-C-alpha-arabinopyranosylapigenin
CHEBI:9047
DTXSID201318298
Apigenin 6-C-beta-D-glucopyranosyl-8-C-alpha-L-arabinopyranoside
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one
8alpha-L-arabinopyranosyl-6beta-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-Benzopyran-4-one
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)-8-((2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl)chromen-4-one
DTXCID001748110
4H-1-Benzopyran-4-one, 8alpha-L-arabinopyranosyl-6beta-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-
Apigenin 6-C-glucoside-8-C-arabinoside
Apigenin-6-glucoside-8-arabinoside
Schaftoside (Standard)
SCHEMBL1425661
HY-N0703R
HY-N0703
MSK158039
AKOS030573646
FS73932
Apigenin-6-c-glucoside-8-c-arabinoside
AC-34871
AS-82969
CS-0009719
Q27108250
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]-4H-chromen-4-one
Schaftoside6-C-beta-glucopyranosyl-8-C-alpha-arabinopyranosylapigenin
Shaftoside
- Chabani S, Haba H, et al. (2013). Flavonoid glycosides and triterpenoids from Atractylis flava.. Phytochemistry Letters,2013,6,9-13. [View]
- Saleh NAM, El-Newumy SI, et al. (1985). Flavonoid glycosides of Artemisia monosperma and A. herba-alba.. Phytochemistry,1985,24(1),201-203. [View]
- Bouaziz M, Simmonds MS, et al. (2001). Flavonoids from Hyparrhenia hirta Stapf (Poaceae) growing in Tunisia. Biochemical Systematics and Ecology,2001,29(8),849-851. [View] [PubMed]
- 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]
Pubchem:
442658
Cas:
51938-32-0
Gnps:
CCMSLIB00006477844
Zinc:
ZINC000004098602
Kegg Ligand:
C10181
Chebi:
9047
Nmrshiftdb2:
60022857
CPRiL:
55004
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
- -6.200
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 5.18
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.650
- Plasma Protein Binding
- 68.36
- 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
- 8.280
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -3.820
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.740
- 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
- -3787.130
- Rat (Acute)
- 2.490
- Rat (Chronic Oral)
- 4.890
- Fathead Minnow
- 7.540
- 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
- 681.840
- Hydration Free Energy
- -3.160
- Log(D) at pH=7.4
- -1.110
- Log(P)
- -0.36
- Log S
- -3.44
- Log(Vapor Pressure)
- -13.87
- Melting Point
- 210.97
- pKa Acid
- 2.1
- pKa Basic
- 10.44
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.9363 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.9363 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8664 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8664 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 4 | 0.8452 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 4 | 0.8452 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8442 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8442 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.8263 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.8263 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8052 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8052 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.8019 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.8019 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7906 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7906 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7643 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7643 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7617 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7617 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7560 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7560 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7528 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7528 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7451 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7451 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7247 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7247 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7172 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7172 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7151 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7151 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7093 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7093 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7035 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7035 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 4 | 0.7030 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 4 | 0.7030 |