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Lespedin
- Family: Plantae - Chenopodiaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonoid Glycoside
| Canonical Smiles | Oc1ccc(cc1)c1oc2cc(O[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O)O)cc(c2c(=O)c1O[C@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O |
|---|---|
| InChI | InChI=1S/C27H30O14/c1-9-17(30)20(33)22(35)26(37-9)39-13-7-14(29)16-15(8-13)40-24(11-3-5-12(28)6-4-11)25(19(16)32)41-27-23(36)21(34)18(31)10(2)38-27/h3-10,17-18,20-23,26-31,33-36H,1-2H3/t9-,10-,17-,18-,20+,21+,22+,23+,26-,27+/m0/s1 |
| InChIKey | PUPKKEQDLNREIM-DGHCMIAQSA-N |
| Formula | C27H30O14 |
| HBA | 14 |
| HBD | 8 |
| MW | 578.52 |
| Rotatable Bonds | 5 |
| TPSA | 228.97 |
| LogP | -0.72 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 41 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.44 |
| Exact Mass | 578.16 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Chenopodium murale | Chenopodiaceae | Plantae | 46091 |
Showing of synonyms
Lespedin
- Gohar AA, Elmazar MMA (1997). Isolation of hypotensive flavonoids from Chenopodium species growing in Egypt. Phytotherapy Research,1997,11(8),564-567. [View]
CPRiL:
106674
SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(-c4ccccc4)c(c3=O)OC5CCCCO5
Level: 3
Mol. Weight: 578.52 g/mol
SMILES: O1CCCCC1Oc(cc2)cc(c23)occ(c3=O)OC4CCCCO4
Level: 2
Mol. Weight: 578.52 g/mol
SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4
Level: 2
Mol. Weight: 578.52 g/mol
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4
Level: 2
Mol. Weight: 578.52 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3
Level: 1
Mol. Weight: 578.52 g/mol
SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3
Level: 1
Mol. Weight: 578.52 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 578.52 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 578.52 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 578.52 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 578.52 g/mol
Bradycardia
Hypotensive
Absorption
- Caco-2 (logPapp)
- -6.6
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.270
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 3.81
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.920
- Plasma Protein Binding
- 83.29
- 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
- 8.560
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -3.200
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.990
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.450
- 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
- -5588.740
- Rat (Acute)
- 2.320
- Rat (Chronic Oral)
- 4.230
- Fathead Minnow
- 13.800
- 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
- 523.840
- Hydration Free Energy
- -3.090
- Log(D) at pH=7.4
- 0.240
- Log(P)
- 0.4
- Log S
- -4.63
- Log(Vapor Pressure)
- -11.82
- Melting Point
- 228.63
- pKa Acid
- 4.45
- pKa Basic
- 4.84
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9460 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9460 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8276 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8276 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7916 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7916 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7859 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7859 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.7838 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.7838 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7774 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7774 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7765 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7765 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7666 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7666 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7596 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7596 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7466 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7466 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | O67060 | ISPE_AQUAE | Aquifex aeolicus | 3 | 0.7374 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | O67060 | ISPE_AQUAE | Aquifex aeolicus | 3 | 0.7374 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7276 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7276 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7215 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7215 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7200 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7200 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7161 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7161 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7149 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7149 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7115 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7115 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7098 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7098 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7066 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7066 |