3-O-beta-D-glucopyranosyl-(1→2)-[beta-D-glucopyranosyl-(1→3)]-beta-D-fucopyranosyl-21-O-beta-D-glucoyranosyl-3beta,16beta,2beta,23-tetrahydroxy-13,28-epoxyolean-11-ene
- Family: Plantae - Umbelliferae
- Kingdom: Plantae
-
Class: Saponin
- Subclass: Triterpene Saponin
| Canonical Smiles | OCC1OC(OC2C(OC(C(C2OC2OC(CO)C(C(C2O)O)O)O)C)O[C@H]2CC[C@]3(C([C@]2(C)CO)CC[C@@]2(C3C=C[C@]34[C@@]2(C)C[C@@H]([C@@]2(C4CC(C)(C)[C@H](C2)OC2OC(CO)C(C(C2O)O)O)CO3)O)C)C)C(C(C1O)O)O |
|---|---|
| InChI | InChI=1S/C54H88O24/c1-22-32(60)42(77-45-40(68)37(65)34(62)24(18-56)73-45)43(78-46-41(69)38(66)35(63)25(19-57)74-46)47(71-22)75-30-10-11-49(4)26(50(30,5)20-58)8-12-51(6)27(49)9-13-54-28-14-48(2,3)31(16-53(28,21-70-54)29(59)15-52(51,54)7)76-44-39(67)36(64)33(61)23(17-55)72-44/h9,13,22-47,55-69H,8,10-12,14-21H2,1-7H3/t22?,23?,24?,25?,26?,27?,28?,29-,30-,31-,32?,33?,34?,35?,36?,37?,38?,39?,40?,41?,42?,43?,44?,45?,46?,47?,49-,50-,51+,52-,53+,54-/m0/s1 |
| InChIKey | HEFLEKPFGWGTJK-DRYNEEKRSA-N |
| Formula | C54H88O24 |
| HBA | 24 |
| HBD | 15 |
| MW | 1121.27 |
| Rotatable Bonds | 12 |
| TPSA | 386.52 |
| LogP | -3.6 |
| Number Rings | 10 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 78 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.96 |
| Exact Mass | 1120.57 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Bupleurum rigidum | Umbelliferae | Plantae | 199748 |
Showing of synonyms
- Chelghoum M, Smati D, et al. (2018). Four new triterpene saponins from Bupleurum rigidum L. Phytochemistry Letters, 2018,27,223–228. [View]
No compound-protein relationship available.
SMILES: O1CCCCC1OC(CC2)CC(C2C345)(CO5)CCC4C6C(C=C3)C7C(CC6)CC(CC7)OC8OCCC(OC9CCCCO9)C8OC1CCCCO1
Level: 4
Mol. Weight: 1121.27 g/mol
SMILES: O1CCCCC1OC(CC2)CC(C2C345)(CO5)CCC4C6C(C=C3)C7C(CC6)CC(CC7)OC(OCCC8)C8OC9CCCCO9
Level: 3
Mol. Weight: 1121.27 g/mol
SMILES: O1CCCCC1OC(CC2)CC(C2C345)(CO5)CCC4C6C(C=C3)C7C(CC6)CC(CC7)OC(OCC8)CC8OC9CCCCO9
Level: 3
Mol. Weight: 1121.27 g/mol
SMILES: C1CCCC(C1C234)(CO4)CCC3C5C(C=C2)C6C(CC5)CC(CC6)OC7OCCC(OC8CCCCO8)C7OC9CCCCO9
Level: 3
Mol. Weight: 1121.27 g/mol
SMILES: O1CCCCC1OC(CC2)CC(C2C345)(CO5)CCC4C6C(C=C3)C7C(CC6)CC(CC7)OC8CCCCO8
Level: 2
Mol. Weight: 1121.27 g/mol
SMILES: C1CCCC(C1C234)(CO4)CCC3C5C(C=C2)C6C(CC5)CC(CC6)OC(OCCC7)C7OC8CCCCO8
Level: 2
Mol. Weight: 1121.27 g/mol
SMILES: C1CCCC(C1C234)(CO4)CCC3C5C(C=C2)C6C(CC5)CC(CC6)OC(OCC7)CC7OC8CCCCO8
Level: 2
Mol. Weight: 1121.27 g/mol
SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3
Level: 2
Mol. Weight: 1121.27 g/mol
SMILES: O1CCCCC1OC(CC2)CC(C2C345)(CO5)CCC4C6C(C=C3)C7C(CC6)CCCC7
Level: 1
Mol. Weight: 1121.27 g/mol
SMILES: C1CCCC(C1C234)(CO4)CCC3C5C(C=C2)C6C(CC5)CC(CC6)OC7CCCCO7
Level: 1
Mol. Weight: 1121.27 g/mol
SMILES: C1OCCCC1OC2CCCCO2
Level: 1
Mol. Weight: 1121.27 g/mol
SMILES: C1COCCC1OC2CCCCO2
Level: 1
Mol. Weight: 1121.27 g/mol
SMILES: C1CCCC(C1C234)(CO4)CCC3C5C(C=C2)C6C(CC5)CCCC6
Level: 0
Mol. Weight: 1121.27 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 1121.27 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.71
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 4322115.42
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 564850915.95
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.68
- Plasma Protein Binding
- 20.08
- 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
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 0.99
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Safe
- Bioconcentration Factor
- -13137145.7
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -5.91
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.05
- 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
- -1025177169143.18
- Rat (Acute)
- 3.93
- Rat (Chronic Oral)
- 2198.65
- Fathead Minnow
- 1294066780.66
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 115304012677.95
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- -64090.8
- Log(P)
- -8.61
- Log S
- -1.83
- Log(Vapor Pressure)
- -3796901971.94
- Melting Point
- 14.66
- pKa Acid
- -27666326.22
- pKa Basic
- -222568.85
No predicted protein targets found for this compound.