8-O-acetylharpagide

Iupac Name：[(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] acetate

CAS No.: 6926-14-3

Molecular Weight：406.384

Modify Date.: 2023-02-11 21:22

Introduction:

8-O-Acetylharpagide is an iridoid isolated from Ajuga reptans with antitumoral, antiviral, antibacterial, and anti-inflammatory activities. 8-O-Acetylharpagide also has a biological activity on isolated smooth muscle preparations from guinea pig[1][2].

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1. Names and Identifiers

1.1 Name: 8-O-acetylharpagide
1.2 Synonyms: (1S,4aS,5R,7S,7aS)-1-(D-Glucopyranosyloxy)-4a,5-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl acetate (1S,4aS,5R,7S,7aS)-1-(hexopyranosyloxy)-4a,5-dihydroxy-7-Methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-ylacetate (1S,4aS,5R,7S,7aS)-1-(Β-D-Glucopyranosyloxy)-4a,5-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl acetate (1S,4aS,5R,7S,7aS)-7-(Acetyloxy)-1,4a,5,6,7,7a-hexahydro-4a,5-dihydroxy-7-methylcyclopenta[c]pyran-1-yl β-D-glucopyranoside (4aS,7S,7aS)-7-Methyl-1-{[(2S,3R,4R,6R)-3,4,5,5,6-pentahydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl acetate 3-Acetylharpagide 6-Thio-8-propylthiotheophylline 8-Acetylharpagide 8-n-Propylthio-6-thiotheophyllin 8-O-acetylharpagide 8-O-acetyl-harpagide 8-O-Acetylharpagide Acetylharpagide Acetylharpagide(8-O-Acetylharpagide) beta-D-Glucopyranoside, (1S,4aS,5R,7S,7aS)-7-(acetyloxy)-1,4a,5,6,7,7a-hexahydro-4a,5-dihydroxy-7-methylcyclopenta[c]pyran-1-yl D-Glucopyranoside, (1S,4aS,5R,7S,7aS)-7-(acetyloxy)-1,4a,5,6,7,7a-hexahydro-4a,5-dihydroxy-7-methylcyclopenta[c]pyran-1-yl Glucopyranoside, 1β,4a,5,6,7,7aα-hexahydro-4aα,5α,7α-trihydroxy-7-methylcyclopenta[c]pyran-1-yl, 7-acetate, β-D- Harpagide 7-acetate Harpagide 7-acetyl Harpagide acetate Harpagide, 8-acetate Uric acid,1,3-dimethyl-8-propylthio-6-thio β-D-Glucopyranoside, (1S,4aS,5R,7S,7aS)-7-(acetyloxy)-1,4a,5,6,7,7a-hexahydro-4a,5-dihydroxy-7-methylcyclopenta[c]pyran-1-yl β-D-Glucopyranoside, 7-(acetyloxy)-1,4a,5,6,7,7a-hexahydro-4a,5-dihydroxy-7-methylcyclopenta(c)pyran-1-yl, (1S-(1α,4aα,5α,7α,7aα))- β-D-Glucopyranoside, 7-(acetyloxy)-1,4a,5,6,7,7a-hexahydro-4a,5-dihydroxy-7-methylcyclopenta[c]pyran-1-yl, [1S-(1α,4aα,5α,7α,7aα)]-

1.3 CAS No.: 6926-14-3

1.4 CID: 9978650

1.5 Molecular Formula: C17H26O11 (isomer)

1.6 Inchi: InChI=1S/C17H26O11/c1-7(19)28-16(2)5-9(20)17(24)3-4-25-15(13(16)17)27-14-12(23)11(22)10(21)8(6-18)26-14/h3-4,8-15,18,20-24H,5-6H2,1-2H3/t8-,9-,10-,11+,12-,13-,14+,15+,16+,17-/m1/s1

1.7 InChkey: CAFTUQNGDROXEZ-XBDCZORHSA-N

1.8 Canonical Smiles: CC(=O)OC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)C

1.9 Isomers Smiles: CC(=O)O[C@]1(C[C@H]([C@]2([C@@H]1[C@@H](OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)C

2. Properties

2.1 Density: 1.58

2.1 Melting point: 227-229 oC

2.1 Boiling point: 607.2°C at 760 mmHg

2.1 Refractive index: 1.623

2.1 Flash Point: 215.9°C

2.1 Precise Quality: 406.14800

2.1 PSA: 175.37000

2.1 logP: -2.89340

2.1 Storage: ?20°C

2.2 Color/Form: Powder

2.3 pKa: 11.88±0.70(Predicted)

3. Safety and Handling

3.1 Safety Statements: 24/25

3.1 RIDADR: NONH for all modes of transport

3.1 WGK Germany: 3

4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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5. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

6. Other Information

6.0 Mesh Entry Terms: 8-O-acetylharpagid

7. Computational chemical data

Molecular Weight: 406.384g/mol
Molecular Formula: C₁₇H₂₆O₁₁
Compound Is Canonicalized: True
XLogP3-AA: -2.7
Exact Mass: 406.14751164
Monoisotopic Mass: 406.14751164
Complexity: 626
Rotatable Bond Count: 5
Hydrogen Bond Donor Count: 6
Hydrogen Bond Acceptor Count: 11
Topological Polar Surface Area: 175
Heavy Atom Count: 28
Defined Atom Stereocenter Count: 10
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4PAAAAAAAAAAAAAAAAAAAAYAAAAAkQAAAAAAAAEAAAAAAGgAACAAADVSwgAMCCAAABgCIACDSCAAACAAgIAAIAAAAAAgRFAIAAAAiQAAFwAAHEAHA4CwOgAAAAAAAAAAAAAAAAAAAAYQADCAAAA==

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9. Realated Product Infomation

97169-44-3 6-Epi-8-O-acetylharpagide

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