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6-O-alpha-L-rhamnopyranosyl catalpol
- Family: Plantae - Scrophulariaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Iridoid Glycoside
| Canonical Smiles | OC[C@H]1OC(O[C@@H]2OC=C[C@@H]3[C@H]2[C@@]2(CO)O[C@H]2[C@H]3OC2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C21H32O14/c1-6-10(24)12(26)14(28)19(31-6)33-16-7-2-3-30-18(9(7)21(5-23)17(16)35-21)34-20-15(29)13(27)11(25)8(4-22)32-20/h2-3,6-20,22-29H,4-5H2,1H3/t6-,7+,8+,9+,10-,11+,12+,13-,14+,15+,16-,17-,18-,19?,20?,21+/m0/s1 |
| InChIKey | GRLJTTHDCMSLHP-VBUSABLASA-N |
| Formula | C21H32O14 |
| HBA | 14 |
| HBD | 8 |
| MW | 508.47 |
| Rotatable Bonds | 6 |
| TPSA | 220.52 |
| LogP | -4.74 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 35 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.9 |
| Exact Mass | 508.18 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Verbascum dentifolium | Scrophulariaceae | Plantae | 512637 |
Showing of synonyms
6-O-alpha-L-rhamnopyranosyl catalpol
- Arrif S, Lavaud C, et al. (2008). Iridoids from Verbascum dentifolium. Biochemical Systematics and Ecology,2008,36(8),669-673. [View]
No compound-protein relationship available.
SMILES: O1CCCCC1OC(C(O2)C23)C4C3C(OC=C4)OC5CCCCO5
Level: 2
Mol. Weight: 508.47 g/mol
SMILES: C1=COCC2C1C(C(O3)C23)OC4CCCCO4
Level: 1
Mol. Weight: 508.47 g/mol
SMILES: C12C(O2)CC3C1C(OC=C3)OC4CCCCO4
Level: 1
Mol. Weight: 508.47 g/mol
SMILES: C12C(O2)CC3C1COC=C3
Level: 0
Mol. Weight: 508.47 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 508.47 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.82
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.25
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.03
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.65
- Plasma Protein Binding
- 40.3
- 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
- 6.58
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.98
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.97
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.69
- 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
- -574.89
- Rat (Acute)
- 2.68
- Rat (Chronic Oral)
- 3.74
- Fathead Minnow
- 2.93
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 494.73
- Hydration Free Energy
- -3.1
- Log(D) at pH=7.4
- -2.7
- Log(P)
- -3.44
- Log S
- -0.99
- Log(Vapor Pressure)
- -17.88
- Melting Point
- 146.58
- pKa Acid
- 5.5
- pKa Basic
- 2.65
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 3 | 0.8084 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 3 | 0.8084 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7782 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7782 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7627 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7627 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 4 | 0.7482 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 4 | 0.7482 |