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Seguinoside L
- Family: Plantae - Bignoniaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Phenolic Glycoside
| Canonical Smiles | OCC1O[C@@H](Oc2ccc(c(c2)O)O)C([C@H]([C@@H]1O)O)O[C@@H]1OCC([C@@H]1O)(O)COC(=O)c1ccc(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C24H28O15/c25-7-16-17(30)18(31)19(22(38-16)37-11-2-4-13(27)15(29)6-11)39-23-20(32)24(34,9-36-23)8-35-21(33)10-1-3-12(26)14(28)5-10/h1-6,16-20,22-23,25-32,34H,7-9H2/t16?,17-,18+,19?,20-,22-,23+,24?/m1/s1 |
| InChIKey | CPLPOIPKVDPNOQ-DFIATEIVSA-N |
| Formula | C24H28O15 |
| HBA | 15 |
| HBD | 9 |
| MW | 556.47 |
| Rotatable Bonds | 8 |
| TPSA | 245.29 |
| LogP | -1.98 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 39 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.46 |
| Exact Mass | 556.14 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Tecoma mollis | Bignoniaceae | Plantae | 2822953 |
Showing of synonyms
Seguinoside L
- Abdel-Mageed W, Al-Wahaibi L, et al. (2017). New phenolic glycosides with cyclooxygenase inhibition from the roots of Tecoma mollis. Phytochemistry Letters, 2017, 21, 98-103. [View]
No compound-protein relationship available.
SMILES: c1ccccc1C(=O)OCC2CC(OC2)OC3C(OCCC3)Oc4ccccc4
Level: 3
Mol. Weight: 556.47 g/mol
SMILES: c1ccccc1C(=O)OCC2CC(OC2)OC3CCCOC3
Level: 2
Mol. Weight: 556.47 g/mol
SMILES: O1CCCC1OC2C(OCCC2)Oc3ccccc3
Level: 2
Mol. Weight: 556.47 g/mol
SMILES: c1ccccc1C(=O)OCC2CCOC2
Level: 1
Mol. Weight: 556.47 g/mol
SMILES: c1ccccc1OC2CCCCO2
Level: 1
Mol. Weight: 556.47 g/mol
SMILES: O1CCCC1OC2CCCOC2
Level: 1
Mol. Weight: 556.47 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 556.47 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 556.47 g/mol
SMILES: C1CCOC1
Level: 0
Mol. Weight: 556.47 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.76
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.64
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 0.99
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.64
- Plasma Protein Binding
- 44.58
- 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
- 13.66
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.52
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.72
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 6.14
- 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
- -2005.76
- Rat (Acute)
- 2.09
- Rat (Chronic Oral)
- 3.88
- Fathead Minnow
- 4.99
- 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
- 607.13
- Hydration Free Energy
- -3.09
- Log(D) at pH=7.4
- -0.16
- Log(P)
- -0.7
- Log S
- -3.95
- Log(Vapor Pressure)
- -11.68
- Melting Point
- 202.72
- pKa Acid
- 4.67
- pKa Basic
- 5.95
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.9401 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.9375 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9100 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9067 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8666 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8548 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8545 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 4 | 0.8489 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.8472 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.8455 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.8445 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.8435 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8318 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8315 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8311 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8285 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8267 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8257 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8147 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 4 | 0.8061 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 4 | 0.8038 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8015 |
| Phenolphthiocerol/phthiocerol polyketide synthase subunit C | P96202 | PPSC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8008 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.7932 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7894 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7747 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7742 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7724 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7686 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7652 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7650 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7629 |
| Basic phospholipase A2 homolog piratoxin-1 | P58399 | PA2H1_BOTPI | Bothrops pirajai | 4 | 0.7627 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7580 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7526 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7492 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7482 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7476 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 4 | 0.7455 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7452 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7443 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7426 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7389 |
| Uncharacterized protein | Q3F0V8 | Q3F0V8_BACTI | Bacillus thuringiensis serovar israelensis ATCC 35646 | 3 | 0.7365 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7345 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7327 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 3 | 0.7301 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 3 | 0.7300 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7278 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7275 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7271 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7252 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7250 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 4 | 0.7229 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7222 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7221 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7211 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7203 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 4 | 0.7195 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7186 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7183 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7166 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.7146 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7137 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7135 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7128 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7122 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7121 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7113 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 2 | 0.7110 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7108 |
| Serine/threonine-protein kinase RAD53 | P22216 | RAD53_YEAST | Saccharomyces cerevisiae | 4 | 0.7103 |
| ATP-dependent protease subunit HslV | P0A7B8 | HSLV_ECOLI | Escherichia coli | 3 | 0.7103 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7102 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7100 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7098 |
| Tubulin--tyrosine ligase | F6Z895 | A9ULH4_XENTR | Xenopus tropicalis | 4 | 0.7097 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7084 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7071 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7051 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.7038 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 2 | 0.7038 |
| Acyl-CoA:acyl-CoA alkyltransferase | Q8PDX2 | OLEA_XANCP | Xanthomonas campestris pv. campestris | 3 | 0.7018 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7017 |
| DNA ligase | P43813 | DNLJ_HAEIN | Haemophilus influenzae | 3 | 0.7013 |
| Small heat shock protein StHsp14.0 | Q970D9 | Q970D9_SULTO | Sulfurisphaera tokodaii | 3 | 0.7011 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7011 |