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Aucubin
- Family: Plantae - Scrophulariaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Iridoid Glycoside
| Canonical Smiles | OCC1=C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O |
|---|---|
| InChI | InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7-,8+,9+,10+,11+,12-,13+,14-,15-/m0/s1 |
| InChIKey | RJWJHRPNHPHBRN-FKVJWERZSA-N |
| Formula | C15H22O9 |
| HBA | 9 |
| HBD | 6 |
| MW | 346.33 |
| Rotatable Bonds | 4 |
| TPSA | 149.07 |
| LogP | -2.8 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.73 |
| Exact Mass | 346.13 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Verbascum dentifolium | Scrophulariaceae | Plantae | 512637 |
Showing of synonyms
Aucubin
479-98-1
Aucuboside
Rhinanthin
UNII-2G52GS8UML
EINECS 207-540-8
2G52GS8UML
NSC 407293
1,4a,5,7a-Tetrahydro-5-hydroxy-7-hydroxymethylcyclopenta(c)pyran-1-yl-beta-D-glucopyranoside
NSC-407293
Aucubuside
AUCUBIN (CONSTITUENT OF CHASTE TREE)
(1S,4AR,5S,7AS)-1,4A,5,7A-TETRAHYDRO-5-HYDROXY-7-(HYDROXYMETHYL)CYCLOPENTA(C)PYRAN-1-YL-beta-D-GLUCOPYRANOSIDE
207-540-8
MFCD00136026
(1S,4aR,5S,7aS)-1,4a,5,7a-Tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl beta-D-glucopyranoside
Aucubine
Rhimantin
CHEBI:69796
(2S,3R,4S,5S,6R)-2-(((1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
(2S,3R,4S,5S,6R)-2-[[(1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Aucubin (Standard)
Aucubin (Rhinanthin)
AUCUBIN [MI]
Aucubin, analytical standard
MLS002473252
SCHEMBL381032
CHEMBL514882
MEGxp0_001729
ACon1_002452
HY-N0664R
DTXSID60963965
RJWJHRPNHPHBRN-FKVJWERZSA-N
HMS3098B08
HY-N0664
S5459
AKOS015896774
CCG-267985
CS-5367
LMPR0102070006
MA08296
NCGC00169833-01
NCGC00169833-02
(1S-(1alpha,4aalpha,5alpha,7aalpha))-1,4a,5,7a-Tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta(c)pyran-1-yl-beta-D-glucopyranoside
(2S,3R,4S,5S,6R)-2-[[(1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
AC-33938
AS-74899
SMR001397339
C09771
AJ-292/21168052
Aucubin, primary pharmaceutical reference standard
Q418014
(1S,4?R,5S,7?S)-1-4?,5,7?-Tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl ?-D-glucopyranoside
(1S,4AR,5S,7AS)-1,4A,5,7A-TETRAHYDRO-5-HYDROXY-7-(HYDROXYMETHYL)CYCLOPENTA(C)PYRAN-1-YL-.BETA.-D-GLUCOPYRANOSIDE
(1S,4aR,5S,7aS)-1,4a,5,7a-Tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl |A-D-glucopyranoside
(2S,3R,4S,5S,6R)-2-((1S,4aR,5R,7aS)-5-Hydroxy-7-hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-1-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
(2S,3R,4S,5S,6R)-2-{[(1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
.beta.-D-Glucopyranoside, (1S,4aR,5S,7aS)-1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl
- Arrif S, Lavaud C, et al. (2008). Iridoids from Verbascum dentifolium. Biochemical Systematics and Ecology,2008,36(8),669-673. [View]
Pubchem:
91458
Cas:
479-98-1
Gnps:
CCMSLIB00006364182
Zinc:
ZINC000004098334
Kegg Ligand:
C09771
Chebi:
69796
Nmrshiftdb2:
60025739
Metabolights:
MTBLC69796
Chembl:
CHEMBL514882
CPRiL:
62197
SMILES: C1=CCC(C12)C=COC2OC3CCCCO3
Level: 1
Mol. Weight: 346.33 g/mol
SMILES: C1=CCC(C12)C=COC2
Level: 0
Mol. Weight: 346.33 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 346.33 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.21
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.84
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.98
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.78
- Plasma Protein Binding
- 42.67
- 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
- 2.96
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.99
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.3
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.05
- 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
- -5.76
- Rat (Acute)
- 2.34
- Rat (Chronic Oral)
- 3.14
- Fathead Minnow
- 2.75
- 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
- 459.91
- Hydration Free Energy
- -18.51
- Log(D) at pH=7.4
- -0.91
- Log(P)
- -2.28
- Log S
- -0.24
- Log(Vapor Pressure)
- -13.09
- Melting Point
- 161.67
- pKa Acid
- 6.03
- pKa Basic
- 4.01
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8709 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8709 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 3 | 0.7936 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 3 | 0.7936 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7326 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7326 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7222 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7222 |