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Neoschaftoside
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavone 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-LQYCTPBQSA-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 judaica | Asteraceae | Plantae | 205369 |
Showing of synonyms
Neoschaftoside
61328-41-4
CHEBI:7513
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one
Apigenin 6-C-beta-D-glucopyranosyl-8-C-beta-L-arabinopyranoside
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)-8-((2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl)chromen-4-one
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)-8-((2R,3R,4S,5S)-3,4,5-trihydroxytetrahydropyran-2-yl)chromen-4-one
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]-8-[(2R,3R,4S,5S)-3,4,5-trihydroxytetrahydropyran-2-yl]chromen-4-one
Apigenin 6-C-b-D-glucopyranosyl-8-C-b-L-arabinopyranoside
Apigenin 6-C-I2-D-glucopyranosyl-8-C-I2-L-arabinopyranoside
Neoshaftoside
C10110
DTXSID901317427
AKOS040763561
FS-7480
DA-76094
XN161716
E89000
Q27107518
8-?-L-Arabinopyranosyl-6-?-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
- 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:
442619
Cas:
61328-41-4
Zinc:
ZINC000004098558
Kegg Ligand:
C10110
Chebi:
7513
Nmrshiftdb2:
60027597
Metabolights:
MTBLC7513
No compound-protein relationship available.
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
- 5.17
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.650
- Plasma Protein Binding
- 68.54
- 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
- 8.270
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -3.890
- 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
- -3787.280
- 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
- 682.050
- Hydration Free Energy
- -3.160
- Log(D) at pH=7.4
- -1.120
- Log(P)
- -0.36
- Log S
- -3.43
- Log(Vapor Pressure)
- -13.86
- Melting Point
- 208.38
- pKa Acid
- 2.09
- pKa Basic
- 10.45
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8615 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8615 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8449 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8449 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8362 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8362 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.8328 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.8328 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8231 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8231 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8198 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8198 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7936 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7936 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7888 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7888 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.7791 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.7791 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.7465 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.7465 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7454 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7454 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7290 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7290 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7229 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7229 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 2 | 0.7163 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 2 | 0.7163 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7133 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7133 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7039 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7039 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7026 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7026 |