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Harpagoside B
- Family: Plantae - Scrophulariaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Acylated Iridoid Glycoside
| Canonical Smiles | CO[C@@H]1C[C@]([C@@H]2[C@@]1(O)C=CO[C@H]2O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)(C)OC(=O)/C=C/c1ccccc1 |
|---|---|
| InChI | InChI=1S/C25H32O11/c1-24(36-17(27)9-8-14-6-4-3-5-7-14)12-16(32-2)25(31)10-11-33-23(21(24)25)35-22-20(30)19(29)18(28)15(13-26)34-22/h3-11,15-16,18-23,26,28-31H,12-13H2,1-2H3/b9-8+/t15-,16-,18-,19+,20-,21-,22+,23+,24+,25-/m1/s1 |
| InChIKey | BEHDYQAAWZWDFR-FJHINEFRSA-N |
| Formula | C25H32O11 |
| HBA | 11 |
| HBD | 5 |
| MW | 508.52 |
| Rotatable Bonds | 7 |
| TPSA | 164.37 |
| LogP | -0.55 |
| Number Rings | 4 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 36 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.56 |
| Exact Mass | 508.19 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Scrophularia saharae | Scrophulariaceae | Plantae | 1357627 |
Showing of synonyms
Harpagoside B
- 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]
No compound-protein relationship available.
SMILES: c1ccccc1C=CC(=O)OC2CCC(C23)C=COC3OC4CCCCO4
Level: 2
Mol. Weight: 508.52 g/mol
SMILES: c1ccccc1C=CC(=O)OC2CCC(C23)C=COC3
Level: 1
Mol. Weight: 508.52 g/mol
SMILES: C1CCC(C12)C(OC=C2)OC3CCCCO3
Level: 1
Mol. Weight: 508.52 g/mol
SMILES: C1CCC(C12)COC=C2
Level: 0
Mol. Weight: 508.52 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 508.52 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 508.52 g/mol
Anti-inflammatory
Absorption
- Caco-2 (logPapp)
- -5.59
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.670
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.06
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.880
- Plasma Protein Binding
- 68.24
- 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
- 3.380
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.210
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.100
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.880
- 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
- -537.780
- Rat (Acute)
- 2.770
- Rat (Chronic Oral)
- 3.480
- Fathead Minnow
- 3.950
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 489.820
- Hydration Free Energy
- -3.100
- Log(D) at pH=7.4
- 1.220
- Log(P)
- 0.66
- Log S
- -2.08
- Log(Vapor Pressure)
- -12.14
- Melting Point
- 142.2
- pKa Acid
- 4.96
- pKa Basic
- 2.4
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9233 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9233 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8070 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8070 |
| Adenosine kinase | Q9TVW2 | ADK_TOXGO | Toxoplasma gondii | 3 | 0.7906 |
| Adenosine kinase | Q9TVW2 | ADK_TOXGO | Toxoplasma gondii | 3 | 0.7906 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7862 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7862 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7706 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7706 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 4 | 0.7615 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 4 | 0.7615 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7598 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7598 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7456 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7456 |
| Pantothenate kinase | P9WPA7 | COAA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7300 |
| Pantothenate kinase | P9WPA7 | COAA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7300 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 4 | 0.7276 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 4 | 0.7276 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7059 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7059 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7054 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7054 |
| Glutaminyl-peptide cyclotransferase | Q16769 | QPCT_HUMAN | Homo sapiens | 3 | 0.7010 |
| Glutaminyl-peptide cyclotransferase | Q16769 | QPCT_HUMAN | Homo sapiens | 3 | 0.7010 |