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4'-O-demethylknipholone-4'-O-beta-D-glucopyranoside
- Family: Plantae - Asphodelaceae
- Kingdom: Plantae
-
Class: Anthraquinone
- Subclass: Phenylanthraquinone
| Canonical Smiles | OC[C@H]1O[C@@H](Oc2cc(O)c(c(c2C(=O)C)O)c2c(C)cc(c3c2C(=O)c2cccc(c2C3=O)O)O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C29H26O13/c1-9-6-13(33)21-22(23(35)11-4-3-5-12(32)19(11)26(21)38)17(9)20-14(34)7-15(18(10(2)31)25(20)37)41-29-28(40)27(39)24(36)16(8-30)42-29/h3-7,16,24,27-30,32-34,36-37,39-40H,8H2,1-2H3/t16-,24-,27+,28-,29-/m1/s1 |
| InChIKey | AOJYFODHRHWWEN-GQUXZSRASA-N |
| Formula | C29H26O13 |
| HBA | 13 |
| HBD | 8 |
| MW | 582.51 |
| Rotatable Bonds | 5 |
| TPSA | 231.51 |
| LogP | 0.64 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 42 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.28 |
| Exact Mass | 582.14 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Bulbine frutescens | Asphodelaceae | Plantae | 210954 |
Showing of synonyms
4'-O-demethylknipholone-4'-O-beta-D-glucopyranoside
CHEBI:65741
2-acetyl-4-(4,5-dihydroxy-2-methyl-9,10-dioxo-9,10-dihydroanthracen-1-yl)-3,5-dihydroxyphenyl beta-D-glucopyranoside
BULBINELONESIDE D
CHEMBL447622
Q27134223
1-[3-acetyl-2,6-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-4,5-dihydroxy-2-methylanthracene-9,10-dione
- Abegaz BM, Bezabih M, et al. (2002). Gaboroquinones A and B and 4′-O-Demethylknipholone-4′-O-â-D-glucopyranoside, Phenylanthraquinones from the Roots of Bulbine frutescens. Journal of natural products, 2002, 65(8), 1117–1121. [View]
Pubchem:
10008440
Zinc:
ZINC000044305016
Chebi:
65741
Nmrshiftdb2:
60063503
Metabolights:
MTBLC65741
Chembl:
CHEMBL447622
No compound-protein relationship available.
SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3-c4ccc(cc4)OC5CCCCO5
Level: 2
Mol. Weight: 582.51 g/mol
SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3-c4ccccc4
Level: 1
Mol. Weight: 582.51 g/mol
SMILES: c1ccccc1OC2CCCCO2
Level: 1
Mol. Weight: 582.51 g/mol
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 582.51 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 582.51 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 582.51 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.49
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.260
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 5.52
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.750
- Plasma Protein Binding
- 78.03
- 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
- 10.060
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.510
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.940
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.780
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- 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
- -7654.800
- Rat (Acute)
- 2.620
- Rat (Chronic Oral)
- 4.590
- Fathead Minnow
- 17.620
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 530.020
- Hydration Free Energy
- -3.020
- Log(D) at pH=7.4
- 0.760
- Log(P)
- 2.64
- Log S
- -5.98
- Log(Vapor Pressure)
- -10.3
- Melting Point
- 230.99
- pKa Acid
- 4.72
- pKa Basic
- 5.57
| 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 | 0.8870 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 4 | 0.8832 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7835 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 4 | 0.7640 |
| L-malyl-CoA/beta-methylmalyl-CoA lyase | Q3J5L6 | MCAL_RHOS4 | Cereibacter sphaeroides | 4 | 0.7571 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7410 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7362 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7339 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7281 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.7265 |
| 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase | Q3JRA0 | ISPF_BURP1 | Burkholderia pseudomallei | 4 | 0.7227 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7226 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7206 |
| UTP-monosaccharide-1-phosphate uridylyltransferase | D3G6S4 | D3G6S4_LEIMA | Leishmania major | 3 | 0.7186 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7119 |