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Isorhamnetin-3-O-robinobioside
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonoid Glycoside
| Canonical Smiles | CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)OC)O)O)O)O)O)O |
|---|---|
| InChI | InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(41-9)40-8-16-19(33)22(36)24(38)28(43-16)44-26-20(34)17-13(31)6-11(29)7-15(17)42-25(26)10-3-4-12(30)14(5-10)39-2/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3 |
| InChIKey | UIDGLYUNOUKLBM-UHFFFAOYSA-N |
| Formula | C28H32O16 |
| HBA | 16 |
| HBD | 9 |
| MW | 624.55 |
| Rotatable Bonds | 7 |
| TPSA | 258.43 |
| LogP | -1.38 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 44 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.46 |
| Exact Mass | 624.17 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Seidlitzia rosmarinus | Amaranthaceae | Plantae | 454547 |
| 2 | Seidlitzia rosmarinus | Leguminosae/Fabaceae | Plantae | 454547 |
Showing of synonyms
Isorhamnetin-3-O-robinobioside
53584-69-3
Isorhamnetin 3-O-robinobioside
Isorhamnetin 3-robinobioside
5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
3-(6-O-alpha-L-Rhamnopyranosyl-beta-D-galactopyranosyloxy)-3'-methoxy-4',5,7-trihydroxyflavone
5,7-DIHYDROXY-2-(4-HYDROXY-3-METHOXYPHENYL)-3-{[(3R,4S,5R,6R)-3,4,5-TRIHYDROXY-6-({[(2R,3R,4R,5R,6S)-3,4,5-TRIHYDROXY-6-METHYLOXAN-2-YL]OXY}METHYL)OXAN-2-YL]OXY}CHROMEN-4-ONE
DTXSID70968360
CHEBI:132898
5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(((3R,4S,5R,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one
HY-N2627
AKOS030567034
DA-74586
OI106504
TS-10143
CS-0023036
3-(6-O-|A-L-Rhamnopyranosyl-|A-D-galactopyranosyloxy)-3'-methoxy-4',5,7-trihydroxyflavone
5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-D-galactopyranoside
5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside
Pubchem:
5491808
Cas:
53584-69-3
Gnps:
CCMSLIB00000221172
Chebi:
132898
Nmrshiftdb2:
70093506
Metabolights:
MTBLC132898
No compound-protein relationship available.
SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5
Level: 3
Mol. Weight: 624.55 g/mol
SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4
Level: 2
Mol. Weight: 624.55 g/mol
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4
Level: 2
Mol. Weight: 624.55 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3
Level: 1
Mol. Weight: 624.55 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 624.55 g/mol
SMILES: O1CCCCC1COC2CCCCO2
Level: 1
Mol. Weight: 624.55 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 624.55 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 624.55 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 624.55 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.63
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.2
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 13.73
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.82
- Plasma Protein Binding
- -9.03
- 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
- 12.26
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.93
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.9
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.66
- 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
- -22485.29
- Rat (Acute)
- 2.26
- Rat (Chronic Oral)
- 4.46
- Fathead Minnow
- 45.67
- 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
- 360.53
- Hydration Free Energy
- -2.93
- Log(D) at pH=7.4
- -0.39
- Log(P)
- -0.23
- Log S
- -4.8
- Log(Vapor Pressure)
- -15.96
- Melting Point
- 208.56
- pKa Acid
- 4.22
- pKa Basic
- 6.03
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.9145 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8855 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8824 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8559 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8425 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8384 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8369 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8286 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.8272 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.8242 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8130 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 4 | 0.8060 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7966 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.7888 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7775 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7732 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7721 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7679 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 6 | 0.7673 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7474 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7457 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7441 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7384 |
| Lethal factor | P15917 | LEF_BACAN | Bacillus anthracis | 4 | 0.7231 |
| ATP synthase subunit alpha, mitochondrial | P19483 | ATPA_BOVIN | Bos taurus | 3 | 0.7228 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7197 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7175 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7172 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7152 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 5 | 0.7106 |
| Periplasmic pH-dependent serine endoprotease DegQ | P39099 | DEGQ_ECOLI | Escherichia coli | 4 | 0.7098 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7096 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7041 |