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Herbacetin 3-O-alpha-rhamnopyranoside-8-O-beta-glucopyranoside
- Family: Plantae - Ephedraceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonol Di-O-Glycoside
| Canonical Smiles | OC[C@H]1OC(Oc2c(O)cc(c3c2oc(c2ccc(cc2)O)c(c3=O)OC2O[C@H](C)[C@H]([C@@H]([C@@H]2O)O)O)O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C27H30O16/c1-8-15(32)18(35)20(37)26(39-8)43-25-17(34)14-11(30)6-12(31)23(24(14)41-22(25)9-2-4-10(29)5-3-9)42-27-21(38)19(36)16(33)13(7-28)40-27/h2-6,8,13,15-16,18-21,26-33,35-38H,7H2,1H3/t8-,13-,15-,16-,18+,19+,20+,21-,26?,27?/m1/s1 |
| InChIKey | ZBCIMVCVGORQFA-VNYLDBNESA-N |
| Formula | C27H30O16 |
| HBA | 16 |
| HBD | 10 |
| MW | 610.52 |
| Rotatable Bonds | 6 |
| TPSA | 269.43 |
| LogP | -2.04 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 43 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.44 |
| Exact Mass | 610.15 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ephedra aphylla | Ephedraceae | Plantae | 191304 |
Showing of synonyms
Herbacetin 3-O-alpha-rhamnopyranoside-8-O-beta-glucopyranoside
- Hussein SAM, Barakat HH, et al. (1997). Flavonoids from Ephedra aphylla. Phytochemistry,1997,45(7),1529-1532. [View]
Pubchem:
162942334
No compound-protein relationship available.
SMILES: O1CCCCC1Oc(ccc2)c(c23)oc(-c4ccccc4)c(c3=O)OC5CCCCO5
Level: 3
Mol. Weight: 610.52 g/mol
SMILES: O1CCCCC1Oc(ccc2)c(c23)occ(c3=O)OC4CCCCO4
Level: 2
Mol. Weight: 610.52 g/mol
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4
Level: 2
Mol. Weight: 610.52 g/mol
SMILES: O1CCCCC1Oc(ccc2)c(c23)oc(cc3=O)-c4ccccc4
Level: 2
Mol. Weight: 610.52 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3
Level: 1
Mol. Weight: 610.52 g/mol
SMILES: O=c1ccoc(c12)c(ccc2)OC3CCCCO3
Level: 1
Mol. Weight: 610.52 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 610.52 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 610.52 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 610.52 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 610.52 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.6
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.49
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 9.91
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.74
- Plasma Protein Binding
- 59.33
- 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
- 10.0
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.9
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.98
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.62
- 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
- -14296.15
- Rat (Acute)
- 2.26
- Rat (Chronic Oral)
- 4.68
- Fathead Minnow
- 30.97
- 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
- 492.52
- Hydration Free Energy
- -3.11
- Log(D) at pH=7.4
- -1.17
- Log(P)
- -0.63
- Log S
- -4.23
- Log(Vapor Pressure)
- -15.09
- Melting Point
- 214.1
- pKa Acid
- 2.91
- pKa Basic
- 7.25
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.8219 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.8219 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.7853 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.7853 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.7743 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.7743 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7710 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7710 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7505 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7505 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7312 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7312 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7290 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7290 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7285 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7285 |
| Maltose/maltodextrin-binding periplasmic protein | P0AEX9 | MALE_ECOLI | Escherichia coli | 3 | 0.7174 |
| Maltose/maltodextrin-binding periplasmic protein | P0AEX9 | MALE_ECOLI | Escherichia coli | 3 | 0.7174 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7106 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7106 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 3 | 0.7086 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 3 | 0.7086 |