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Shanzhiside methyl ester
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Iridoid
- Subclass: Iridoid Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@@](C)(O)C[C@H]3O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C17H26O11/c1-17(24)3-7(19)9-6(14(23)25-2)5-26-15(10(9)17)28-16-13(22)12(21)11(20)8(4-18)27-16/h5,7-13,15-16,18-22,24H,3-4H2,1-2H3/t7-,8-,9+,10-,11-,12+,13-,15+,16+,17+/m1/s1 |
| InChIKey | KKSYAZCUYVRKML-IRDZEPHTSA-N |
| Formula | C17H26O11 |
| HBA | 11 |
| HBD | 6 |
| MW | 406.38 |
| Rotatable Bonds | 4 |
| TPSA | 175.37 |
| LogP | -3.04 |
| 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 | Barteria fistulosa | Passifloraceae | Plantae | 343952 |
| 2 | Canthium subcordatum | Rubiaceae | Plantae | 2708958 |
Showing of synonyms
Shanzhiside methyl ester
64421-28-9
SHANZHISIDE METHYLESTER
HANZHISIDE METHYL ESTER
Methyl (1S,4aS,5R,7S,7aS)-5,7-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
Methyl (1S,4aS,5R,7S,7aS)-5,7-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-4-carboxylate
Shanzhisidmethylester
MFCD00017416
MEGxp0_000430
CHEMBL1081414
ACon0_000910
ACon1_000460
HY-N0630R
CHEBI:193584
HY-N0630
Shanzhiside methyl ester (Standard)
S9307
AKOS030573532
CCG-268713
FS65452
NCGC00169057-01
NCGC00169057-02
AC-34703
MS-26955
CS-0009621
NS00097692
F17713
BRD-K61757038-001-01-0
Z3247556297
METHYL (1S,4AS,5R,7S,7AS)-5,7-DIHYDROXY-7-METHYL-1-{[(2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY}-1H,4AH,5H,6H,7AH-CYCLOPENTA[C]PYRAN-4-CARBOXYLATE
- Ndjateu F, Tsafack R, et al. (2014). Antimicrobial and antioxidant activities of extracts and ten compounds from three Cameroonian medicinal plants: Dissotis perkinsiae (Melastomaceae), Adenocarpus mannii (Fabaceae) and Barteria fistulosa (Passifloraceae). South African Journal of Botany, 2014, 91, 37-42. [View]
- Joubouhi C, Mabou F, et al. (2015). Five new iridoïd dimers from the fruits of Canthium subcordatum DC (syn. Psydrax subcordata DC). Phytochemistry Letters, 2015, 13, 348-354. [View]
Pubchem:
13892722
Cas:
64421-28-9
Gnps:
CCMSLIB00004720284
Zinc:
ZINC000031156436
Chebi:
193584
Chembl:
CHEMBL1081414
No compound-protein relationship available.
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)
- -5.69
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.170
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.33
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.550
- Plasma Protein Binding
- 55.94
- 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
- 3.040
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.390
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.890
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.670
- 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
- -11.230
- Rat (Acute)
- 2.500
- Rat (Chronic Oral)
- 3.190
- Fathead Minnow
- 2.920
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 468.760
- Hydration Free Energy
- -14.060
- Log(D) at pH=7.4
- -0.620
- Log(P)
- -1.85
- Log S
- -0.83
- Log(Vapor Pressure)
- -13.08
- Melting Point
- 153.04
- pKa Acid
- 5.03
- pKa Basic
- 4.32