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Luteoside B
- Family: Plantae - Bignoniaceae
- Kingdom: Plantae
-
Class: Glycoside
- Subclass: Phenylpropanoid Glycoside
| Canonical Smiles | OC[C@@]1(O)CO[C@H]([C@H]1O)O[C@H]1[C@H](OCCc2ccc(c(c2)O)O)O[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)COC(=O)/C=C/c1ccc(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C34H44O19/c1-15-24(41)26(43)27(44)31(50-15)52-28-25(42)22(12-48-23(40)7-4-16-2-5-18(36)20(38)10-16)51-32(47-9-8-17-3-6-19(37)21(39)11-17)29(28)53-33-30(45)34(46,13-35)14-49-33/h2-7,10-11,15,22,24-33,35-39,41-46H,8-9,12-14H2,1H3/b7-4+/t15-,22+,24-,25+,26+,27+,28-,29+,30+,31-,32+,33-,34+/m0/s1 |
| InChIKey | TXKTYFANELXKLG-WOKZDXPSSA-N |
| Formula | C34H44O19 |
| HBA | 19 |
| HBD | 11 |
| MW | 756.71 |
| Rotatable Bonds | 13 |
| TPSA | 304.21 |
| LogP | -2.55 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 53 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.56 |
| Exact Mass | 756.25 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Tecoma mollis | Bignoniaceae | Plantae | 2822953 |
Showing of synonyms
Luteoside B
[(2R,3R,4S,5R,6R)-5-[(2S,3S,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3-hydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
((2R,3R,4S,5R,6R)-5-(((2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl)oxy)-6-(2-(3,4-dihydroxyphenyl)ethoxy)-3-hydroxy-4-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxy)oxan-2-yl)methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
((2R,3R,4S,5R,6R)-5-((2S,3S,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl)oxy-6-(2-(3,4-dihydroxyphenyl)ethoxy)-3-hydroxy-4-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
[(2R,3R,4S,5R,6R)-5-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3-hydroxy-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
1-O-(3,4--Dihydroxyphenyl)ethyl apiofuranosyl-1-2-rhamnopyranosyl(1-3)-6-O-caffeoylglucopyranoside
188441-29-4
CHEMBL450497
Pubchem:
10818886
Cas:
188441-29-4
Zinc:
ZINC000095615118
Nmrshiftdb2:
60057736
Chembl:
CHEMBL450497
No compound-protein relationship available.
SMILES: c1ccccc1C=CC(=O)OCC2CC(OC3CCCCO3)C(OC4CCCO4)C(O2)OCCc5ccccc5
Level: 4
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1C=CC(=O)OCC2CC(OC3CCCCO3)CC(O2)OCCc4ccccc4
Level: 3
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1C=CC(=O)OCC2CCC(OC3CCCO3)C(O2)OCCc4ccccc4
Level: 3
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1C=CC(=O)OCC2CC(C(CO2)OC3CCCO3)OC4CCCCO4
Level: 3
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1CCOC2OCCC(C2OC3CCCO3)OC4CCCCO4
Level: 3
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OCCc3ccccc3
Level: 2
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1C=CC(=O)OCC2CC(CCO2)OC3CCCCO3
Level: 2
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1C=CC(=O)OCC2CCC(CO2)OC3CCCO3
Level: 2
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1CCOC(OCC2)CC2OC3CCCCO3
Level: 2
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1CCOC(OCCC2)C2OC3CCCO3
Level: 2
Mol. Weight: 756.71 g/mol
SMILES: O1CCCC1OC(COCC2)C2OC3CCCCO3
Level: 2
Mol. Weight: 756.71 g/mol
SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1CCOC2CCCCO2
Level: 1
Mol. Weight: 756.71 g/mol
SMILES: C1COCCC1OC2CCCCO2
Level: 1
Mol. Weight: 756.71 g/mol
SMILES: O1CCCC1OC2CCCOC2
Level: 1
Mol. Weight: 756.71 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 756.71 g/mol
SMILES: C1CCOC1
Level: 0
Mol. Weight: 756.71 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.75
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 1.18
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 934.74
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.7
- Plasma Protein Binding
- 54.91
- 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
- 9.62
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -20.32
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.54
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.75
- 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
- -1696028.03
- Rat (Acute)
- 2.21
- Rat (Chronic Oral)
- 4.69
- Fathead Minnow
- 2148.93
- 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
- 184640.88
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- -0.4
- Log(P)
- -0.83
- Log S
- -4.15
- Log(Vapor Pressure)
- -6044.17
- Melting Point
- 207.62
- pKa Acid
- -11.63
- pKa Basic
- 4.42
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9264 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9264 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8979 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8979 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.8936 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.8936 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8630 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8630 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8314 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8314 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8226 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8226 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 3 | 0.8189 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 3 | 0.8189 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.8181 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.8181 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8165 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8165 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.8001 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.8001 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7900 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7900 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7833 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7833 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7755 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7755 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.7722 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.7722 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7609 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7609 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.7495 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.7495 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7448 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7448 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7448 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7448 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7442 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7442 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 3 | 0.7332 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 3 | 0.7332 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7309 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7309 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7278 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7278 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7149 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7149 |
| Caffeic acid O-methyltransferase | Q9ZTU2 | Q9ZTU2_LOLPR | Lolium perenne | 4 | 0.7143 |
| Caffeic acid O-methyltransferase | Q9ZTU2 | Q9ZTU2_LOLPR | Lolium perenne | 4 | 0.7143 |
| Purine nucleoside phosphorylase DeoD-type | B1JL34 | DEOD_YERPY | Yersinia pseudotuberculosis serotype O:3 | 2 | 0.7123 |
| Purine nucleoside phosphorylase DeoD-type | B1JL34 | DEOD_YERPY | Yersinia pseudotuberculosis serotype O:3 | 2 | 0.7123 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7094 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7094 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7077 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7077 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7071 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7071 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7070 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7070 |
| Tryptophan--tRNA ligase | Q9PIB4 | SYW_CAMJE | Campylobacter jejuni subsp. jejuni serotype O:2 | 4 | 0.7069 |
| Tryptophan--tRNA ligase | Q9PIB4 | SYW_CAMJE | Campylobacter jejuni subsp. jejuni serotype O:2 | 4 | 0.7069 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7067 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7067 |
| DNA (cytosine-5)-methyltransferase 3A | O88508 | DNM3A_MOUSE | Mus musculus | 3 | 0.7046 |
| DNA (cytosine-5)-methyltransferase 3A | O88508 | DNM3A_MOUSE | Mus musculus | 3 | 0.7046 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7041 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7041 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7040 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7040 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | P0AF12 | MTNN_ECOLI | Escherichia coli | 2 | 0.7031 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | P0AF12 | MTNN_ECOLI | Escherichia coli | 2 | 0.7031 |