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Glucofrangulin A
- Family: Plantae - Rhamnaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Anthraquinone Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](Oc2cc(O[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O)O)cc3c2C(=O)c2c(C3=O)cc(cc2O)C)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C27H30O14/c1-8-3-11-16(13(29)4-8)21(33)17-12(19(11)31)5-10(39-26-24(36)22(34)18(30)9(2)38-26)6-14(17)40-27-25(37)23(35)20(32)15(7-28)41-27/h3-6,9,15,18,20,22-30,32,34-37H,7H2,1-2H3/t9-,15+,18-,20+,22+,23-,24+,25+,26-,27+/m0/s1 |
| InChIKey | GPSQZOFVCVOOIE-QWVHOXPHSA-N |
| Formula | C27H30O14 |
| HBA | 14 |
| HBD | 8 |
| MW | 578.52 |
| Rotatable Bonds | 5 |
| TPSA | 232.9 |
| LogP | -2.14 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 41 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.48 |
| Exact Mass | 578.16 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Rhamnus prinoides | Rhamnaceae | Plantae | 280022 |
Showing of synonyms
Glucofrangulin A
21133-53-9
MB7V137HOF
GLUCOFRAGULIN A
UNII-MB7V137HOF
GLUCOFRANGULIN A [MI]
GLUCOFRANGULIN A [WHO-DD]
EINECS 244-234-3
1-hydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyanthracene-9,10-dione
3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-1-(.BETA.-D-GLUCOPYRANOSYLOXY)-8-HYDROXY-6-METHYLANTHRAQUINONE
9,10-ANTHRACENEDIONE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-1-(.BETA.-D-GLUCOPYRANOSYLOXY)-8-HYDROXY-6-METHYL-
1-hydroxy-3-methyl-8-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-6-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyanthracene-9,10-dione
9,10-ANTHRACENEDIONE, 3-((6-DEOXY-ALPHA-L-MANNOPYRANOSYL)OXY)-1-(BETA-D-GLUCOPYRANOSYLOXY)-8-HYDROXY-6-METHYL-
3-((6-deoxy-alpha-l-mannopyranosyl)oxy)-1-(beta-d-glucopyranosyloxy)-8-hydroxy-6-methylanthraquinone
3-[(6-deoxy-alpha-l-mannopyranosyl)oxy]-1-(beta-d-glucopyranosyloxy)-8-hydroxy-6-methylanthraquinone
SCHEMBL1426728
CHEBI:80739
FS-6813
NS00050959
Q27149793
Pubchem:
20054929
Cas:
21133-53-9
Zinc:
ZINC000095628104
Kegg Ligand:
C16802
Chebi:
80739
Nmrshiftdb2:
70009146
No compound-protein relationship available.
SMILES: c1cccc(C2=O)c1C(=O)c(c23)cc(OC4CCCCO4)cc3OC5CCCCO5
Level: 2
Mol. Weight: 578.52 g/mol
SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3OC4CCCCO4
Level: 1
Mol. Weight: 578.52 g/mol
SMILES: c1cccc(C2=O)c1C(=O)c(c23)ccc(c3)OC4CCCCO4
Level: 1
Mol. Weight: 578.52 g/mol
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 578.52 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 578.52 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.73
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.250
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 2.12
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.750
- Plasma Protein Binding
- 74.44
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.510
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.790
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.680
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.000
- 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
- -5139.450
- Rat (Acute)
- 2.660
- Rat (Chronic Oral)
- 4.570
- Fathead Minnow
- 12.100
- 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
- 548.870
- Hydration Free Energy
- -2.940
- Log(D) at pH=7.4
- -0.150
- Log(P)
- -0.37
- Log S
- -3.27
- Log(Vapor Pressure)
- -11.73
- Melting Point
- 199.67
- pKa Acid
- 3.8
- pKa Basic
- 4.04
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9173 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9173 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.8919 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.8919 |
| E3 ubiquitin-protein ligase Mdm2 | P56273 | MDM2_XENLA | Xenopus laevis | 3 | 0.8701 |
| E3 ubiquitin-protein ligase Mdm2 | P56273 | MDM2_XENLA | Xenopus laevis | 3 | 0.8701 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8661 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8661 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8343 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8343 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.8272 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.8272 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8266 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8266 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.8261 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.8261 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8240 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8240 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8237 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8237 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 3 | 0.8170 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 3 | 0.8170 |
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.7963 |
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.7963 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7945 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7945 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7666 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7666 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 4 | 0.7508 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 4 | 0.7508 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7496 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7496 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7476 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7476 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7372 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7372 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7359 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7359 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7324 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7324 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.7261 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.7261 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7247 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7247 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 3 | 0.7219 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 3 | 0.7219 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7197 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7197 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7189 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7189 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | O67060 | ISPE_AQUAE | Aquifex aeolicus | 3 | 0.7123 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | O67060 | ISPE_AQUAE | Aquifex aeolicus | 3 | 0.7123 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7123 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7123 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7122 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7122 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7114 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7114 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7029 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7029 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7011 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7011 |