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Atractyloside
- Family: Plantae - Asteraceae
- Kingdom: Plantae
- Class: Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@@H]2C[C@@H](C(=O)O)[C@@H]3[C@](C2)(C)[C@@H]2CC[C@@H]4C[C@@]2(CC3)[C@@H](O)C4=C)[C@@H]([C@H]([C@@H]1OS(=O)(=O)O)OS(=O)(=O)O)OC(=O)CC(C)C |
|---|---|
| InChI | InChI=1S/C30H46O16S2/c1-14(2)9-22(32)44-25-24(46-48(39,40)41)23(45-47(36,37)38)20(13-31)43-28(25)42-17-10-18(27(34)35)19-7-8-30-11-16(15(3)26(30)33)5-6-21(30)29(19,4)12-17/h14,16-21,23-26,28,31,33H,3,5-13H2,1-2,4H3,(H,34,35)(H,36,37,38)(H,39,40,41)/t16-,17-,18-,19-,20-,21+,23-,24+,25-,26+,28-,29-,30-/m1/s1 |
| InChIKey | FYQXODZRNSCOTR-QLKRWLHJSA-N |
| Formula | C30H46O16S2 |
| HBA | 13 |
| HBD | 5 |
| MW | 726.82 |
| Rotatable Bonds | 11 |
| TPSA | 249.72 |
| LogP | 1.67 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 48 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.87 |
| Exact Mass | 726.22 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Callilepis laureola | Asteraceae | Plantae | 112345 |
Showing of synonyms
Atractyloside
Potassium atractylate
Attrattiloside
Acid, Atractylic
Atractylate de potassium
Attrattiloside [Italian]
Atractylin, potassium salt
UNII-H6WC6L09RM
H6WC6L09RM
Atractylin (C30 glucoside)
Atractylate de potassium [French]
EINECS 241-744-8
ATRACTYLOSIDE [MI]
ATRACTYLIC ACID, DIPOTASSIUM SALT
15-Hydroxy-2-((2-O-(3-methyl-1-oxobutyl)-3,4-di-O-sulfo-beta-D-glucopyranosyl)oxy)-19-norkaur-16-en-18-oic acid dipotassium salt, (2beta,4alpha,15alpha)-
19-Norkaur-16-en-18-oic acid, 15-hydroxy-2-((2-O-(3-methyl-1-oxobutyl)-3,4-di-O-sulfo-beta-D-glucopyranosyl)oxy)-, (2beta,4alpha,15alpha)-
Atractylate
19-Norkaur-16-en-18-oic acid, 15-hydroxy-2-((2-O-(3-methyl-1-oxobutyl)-3,4-di-O-sulfo-beta-D-glucopyranosyl)oxy)-, dipotassium salt, (2beta,4alpha,15alpha)-
Dipotassium hydrogen 15alpha-hydroxy-2beta-((2-O-isovaleryl-3,4alpha-di-O-sulphonato-beta-D-glucopyranosyl)oxy)-19-norkaur-16-en-18-oate
Dipotassium hydrogen 15alpha-hydroxy-2beta-[[2-O-isovaleryl-3,4alpha-di-O-sulphonato-beta-D-glucopyranosyl]oxy]-19-norkaur-16-en-18-oate
19-NORKAUR-16-EN-18-OIC ACID, 15-HYDROXY-2-((2-O-(3-METHYL-1-OXOBUTYL)-3,4-DI-O-SULFO-BETA-D-GLUCOPYRANOSYL)OXY)-, POTASSIUM SALT (1:2), (2BETA,4ALPHA,15ALPHA)-
19-Norkaur-16-en-18-oic acid, 15-hydroxy-2-[[2-O-(3-methyl-1-oxobutyl)-3,4-di-O-sulfo-beta-D-glucopyranosyl]oxy]-, dipotassium salt, (2beta,4alpha,15alpha)-
19-Norkaur-16-en-18-oic acid, 15-hydroxy-2-[[2-O-(3-methyl-1-oxobutyl)-3,4-di-O-sulfo-beta-D-glucopyranosyl]oxy]-, potassium salt (1:2), (2beta,4alpha,15alpha)-
15-HYDROXY-2-((2-O-(3-METHYL-1-OXOBUTYL)-3,4-DI-O-SULFO-.BETA.-D-GLUCOPYRANOSYL)OXY)-19-NORKAUR-16-EN-18-OIC ACID DIPOTASSIUM SALT, (2.BETA.,4.ALPHA.,15.ALPHA.)-
19-NORKAUR-16-EN-18-OIC ACID, 15-HYDROXY-2-((2-O-(3-METHYL-1-OXOBUTYL)-3,4-DI-O-SULFO-.BETA.-D-GLUCOPYRANOSYL)OXY)-, DIPOTASSIUM SALT, (2.BETA.,4.ALPHA.,15.ALPHA.)-
19-NORKAUR-16-EN-18-OIC ACID, 15-HYDROXY-2-((2-O-(3-METHYL-1-OXOBUTYL)-3,4-DI-O-SULFO-.BETA.-D-GLUCOPYRANOSYL)OXY)-, POTASSIUM SALT (1:2), (2.BETA.,4.ALPHA.,15.ALPHA.)-
DIPOTASSIUM HYDROGEN 15.ALPHA.-HYDROXY-2.BETA.-((2-O-ISOVALERYL-3,4.ALPHA.-DI-O-SULPHONATO-.BETA.-D-GLUCOPYRANOSYL)OXY)-19-NORKAUR-16-EN-18-OATE
((2s,3r)-3,5-dimethyl-3-vinyl-2,4-dihydropyrrol-2-yl)-(1h-indol-3-yl)methanone
(2s)-2-(((2s)-2-(((2r)-2-(((2s)-2-amino-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene)amino)-1-hydroxy-3-selanylpropylidene)amino)-1-hydroxy-4-methylpentylidene)amino)-4-methylpentanoate
(2s)-2-{[(2s)-2-{[(2r)-2-{[(2s)-2-amino-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-selanylpropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-4-methylpentanoate
[(2s,3r)-3,5-dimethyl-3-vinyl-2,4-dihydropyrrol-2-yl]-(1h-indol-3-yl)methanone
17754-44-8
Dipotassium
[(2R,3R,4R,5R,6R)-2-[[(1R,4R,5R,7R,9R,10S,13R,15S)-5-carboxy-15-hydroxy-9-methyl-14-methylidene-7-tetracyclo[11.2.1.01,10.04,9]hexadecanyl]oxy]-6-(hydroxymethyl)-3-(3-methylbutanoyloxy)-5-sulfonatooxyoxan-4-yl] sulfate
(1R,4R,5R,7R,9R,10S,13R,15S)-15-Hydroxy-7-[(2R,3R,4R,5R,6R)-6-(hydroxymethyl)-3-(3-methylbutanoyloxy)-4,5-disulfooxyoxan-2-yl]oxy-9-methyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
C09064
Atractyloside, potassium salt
CHEBI:2913
DTXSID201339886
Q27105880
(2beta,4alpha,15alpha)-15-Hydroxy-2-[[2-O-(3-methyl-1-oxobutyl)-3,4-di-O-sulfo-beta-D-glucopyranosyl]oxy]-19-norkaur-16-en-18-oic acid potassium salt (1:2)
- Paul A. Steenkamp, Nial M. Harding, et al. (2004). Determination of atractyloside in Callilepis laureola using solid-phase extraction and liquid chromatography–atmospheric pressure ionisation mass spectrometry. Journal of Chromatography A, 2004, 1058 :153–162. [View]
CPRiL:
28462
SMILES: C=C(C1)C(C2)CCC(C123)C4C(CC3)CCC(C4)OC5CCCCO5
Level: 1
Mol. Weight: 726.82 g/mol
SMILES: C=C(C1)C(C2)CCC(C123)C4C(CC3)CCCC4
Level: 0
Mol. Weight: 726.82 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 726.82 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.16
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.800
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 31.24
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- -0.010
- Plasma Protein Binding
- 82.18
- 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
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- -2.150
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -1.250
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.510
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.080
- 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
- -68619.380
- Rat (Acute)
- 1.900
- Rat (Chronic Oral)
- 3.310
- Fathead Minnow
- 101.120
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 2309.540
- Hydration Free Energy
- -2.950
- Log(D) at pH=7.4
- 1.130
- Log(P)
- -1.85
- Log S
- -1.13
- Log(Vapor Pressure)
- -131.31
- Melting Point
- 311.62
- pKa Acid
- 5.81
- pKa Basic
- 0.54
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.8373 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.8268 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7901 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7861 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7481 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7298 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7140 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7082 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7037 |