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8-O-acetylharpagide
- Family: Plantae - Lamiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Iridoid Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@]3([C@H]2[C@@](C)(OC(=O)C)C[C@H]3O)O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| 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 |
| InChIKey | CAFTUQNGDROXEZ-XBDCZORHSA-N |
| Formula | C17H26O11 |
| HBA | 11 |
| HBD | 6 |
| MW | 406.38 |
| Rotatable Bonds | 4 |
| TPSA | 175.37 |
| LogP | -2.89 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.82 |
| Exact Mass | 406.15 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Scrophularia saharae | Scrophulariaceae | Plantae | 1357627 |
| 2 | Ajuga remota | Lamiaceae | Plantae | 38595 |
Showing of synonyms
8-O-acetylharpagide
6926-14-3
8-Acetylharpagide
Acetylharpagide
8-?O-?Acetylharpagide
CHEMBL523290
(1S,4aS,5R,7S,7aS)-4a,5-Dihydroxy-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl acetate
[(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
8-OAc-harpagide
8--cetylharpagide
MLS002473158
MEGxp0_000602
ACon1_000486
HY-N0757R
CHEBI:228846
DTXSID101346466
HMS2198M04
8-?O-?Acetylharpagide (Standard)
HY-N0757
BDBM50250347
S9474
AKOS030530356
FA73988
NCGC00169032-01
NCGC00169032-03
AC-34969
BS-17945
DA-70385
SMR001397250
8-Acetylharpagide, >=85% (LC/MS-ELSD)
CS-0009785
(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}-1H,5H,6H,7AH-CYCLOPENTA[C]PYRAN-7-YL ACETATE
NCGC00169032-03_C17H26O11_(1S,4aS,5R,7S,7aS)-1-(beta-D-Glucopyranosyloxy)-4a,5-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl acetate
- Chebaki R, Haba H, et al. (2011). Acylated iridoid glycosides from Scrophularia saharae Batt. & Trab.. Biochemical Systematics and Ecology,2011,39(4-6),902-905. [View]
- Kuria KA, Chepkwony H, et al. (2002). The antiplasmodial activity of isolates from Ajuga remota.. Journal of Natural Products,2002,65(5),789-793. [View] [PubMed]
Pubchem:
9978650
Cas:
6926-14-3
Gnps:
CCMSLIB00006455843
Zinc:
ZINC000008952339
Nmrshiftdb2:
70020631
Chembl:
CHEMBL523290
Bindingdb:
50250347
CPRiL:
424333
SMILES: C1CCC(C12)C(OC=C2)OC3CCCCO3
Level: 1
Mol. Weight: 406.38 g/mol
SMILES: C1CCC(C12)COC=C2
Level: 0
Mol. Weight: 406.38 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 406.38 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.57
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.080
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.18
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.670
- Plasma Protein Binding
- 51.12
- 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
- 3.400
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.540
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.420
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.600
- Micronucleos
- Safe
- 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
- -10.920
- Rat (Acute)
- 2.290
- Rat (Chronic Oral)
- 3.210
- Fathead Minnow
- 3.070
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 468.060
- Hydration Free Energy
- -14.490
- Log(D) at pH=7.4
- -0.630
- Log(P)
- -2.03
- Log S
- -0.66
- Log(Vapor Pressure)
- -13.57
- Melting Point
- 119.5
- pKa Acid
- 5.33
- pKa Basic
- 4.36
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7609 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7609 |
| Raucaffricine-O-beta-D-glucosidase | Q9SPP9 | RG1_RAUSE | Rauvolfia serpentina | 4 | 0.7316 |
| Raucaffricine-O-beta-D-glucosidase | Q9SPP9 | RG1_RAUSE | Rauvolfia serpentina | 4 | 0.7316 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7017 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7017 |