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7-O-(E-caffeoyl)-sylvestroside I
- Family: Caprifoliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Bisiridoid
| Canonical Smiles | C=C[C@H]1[C@@H](OC=C(C1CCOC(=O)/C=C/c1ccc(c(c1)O)O)C(=O)O[C@H]1CC2C([C@H]1C)[C@@H](OC=C2C(=O)OC)O[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O)O[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O |
|---|---|
| InChI | InChI=1S/C42H54O22/c1-4-19-20(9-10-57-29(47)8-6-18-5-7-24(45)25(46)11-18)22(15-58-39(19)63-41-35(52)33(50)31(48)27(13-43)61-41)38(55)60-26-12-21-23(37(54)56-3)16-59-40(30(21)17(26)2)64-42-36(53)34(51)32(49)28(14-44)62-42/h4-8,11,15-17,19-21,26-28,30-36,39-46,48-53H,1,9-10,12-14H2,2-3H3/b8-6+/t17-,19+,20?,21?,26-,27?,28?,30?,31+,32+,33-,34-,35?,36?,39-,40-,41-,42-/m0/s1 |
| InChIKey | GBJKWGZKAQIMJY-BMVVEPAVSA-N |
| Formula | C42H54O22 |
| HBA | 22 |
| HBD | 10 |
| MW | 910.87 |
| Rotatable Bonds | 15 |
| TPSA | 336.58 |
| LogP | -2.07 |
| Number Rings | 6 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 64 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.6 |
| Exact Mass | 910.31 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Scabiosa stellata | Caprifoliaceae | Plantae | 596806 |
Showing of synonyms
7-O-(E-caffeoyl)-sylvestroside I
No compound-protein relationship available.
SMILES: c1ccccc1C=CC(=O)OCCC2CC(OC3CCCCO3)OC=C2C(=O)OC(C4)CC(C45)C(OC=C5)OC6CCCCO6
Level: 4
Mol. Weight: 624.73 g/mol
SMILES: c1ccccc1C=CC(=O)OCCC2CCOC=C2C(=O)OC(C3)CC(C34)C(OC=C4)OC5CCCCO5
Level: 3
Mol. Weight: 524.61 g/mol
SMILES: c1ccccc1C=CC(=O)OCCC2CC(OC3CCCCO3)OC=C2C(=O)OC(C4)CC(C45)COC=C5
Level: 3
Mol. Weight: 524.61 g/mol
SMILES: O1CCCCC1OC(CC2)OC=C2C(=O)OC(C3)CC(C34)C(OC=C4)OC5CCCCO5
Level: 3
Mol. Weight: 450.53 g/mol
SMILES: c1ccccc1C=CC(=O)OCCC2CCOC=C2C(=O)OC(C3)CC(C34)COC=C4
Level: 2
Mol. Weight: 424.49 g/mol
SMILES: c1ccccc1C=CC(=O)OCCC2C=COC(C2)OC3CCCCO3
Level: 2
Mol. Weight: 358.43 g/mol
SMILES: C1CCOC=C1C(=O)OC(C2)CC(C23)C(OC=C3)OC4CCCCO4
Level: 2
Mol. Weight: 350.41 g/mol
SMILES: C1=COCC(C12)CC(C2)OC(=O)C3=COC(CC3)OC4CCCCO4
Level: 2
Mol. Weight: 350.41 g/mol
SMILES: c1ccccc1C=CC(=O)OCCC2C=COCC2
Level: 1
Mol. Weight: 258.32 g/mol
SMILES: C1CCOC=C1C(=O)OC(C2)CC(C23)COC=C3
Level: 1
Mol. Weight: 250.29 g/mol
SMILES: C1CCC(C12)C(OC=C2)OC3CCCCO3
Level: 1
Mol. Weight: 224.3 g/mol
SMILES: O1C=CCCC1OC2CCCCO2
Level: 1
Mol. Weight: 184.23 g/mol
SMILES: C1CCC(C12)COC=C2
Level: 0
Mol. Weight: 124.18 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 86.13 g/mol
SMILES: C1=COCCC1
Level: 0
Mol. Weight: 84.12 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 78.11 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.53
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 1748.97
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 229371.06
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.67
- Plasma Protein Binding
- 49.45
- 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
- 5.56
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Safe
- Bioconcentration Factor
- -5331.88
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.52
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.06
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -416298769.79
- Rat (Acute)
- 3.06
- Rat (Chronic Oral)
- 5.61
- Fathead Minnow
- 525497.07
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 46815681.5
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- -12.19
- Log(P)
- 0.41
- Log S
- -3.02
- Log(Vapor Pressure)
- -1541528.41
- Melting Point
- 205.61
- pKa Acid
- -11153.57
- pKa Basic
- -66.8
| 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 | 0.9359 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9064 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.9060 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8934 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8875 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8684 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8563 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8497 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8485 |
| Caffeic acid O-methyltransferase | Q9ZTU2 | Q9ZTU2_LOLPR | Lolium perenne | 4 | 0.8453 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8346 |
| Aminoglycoside N(3)-acetyltransferase | A0A3P1UCA6 | Q81P86_BACAN | Bacillus anthracis | 3 | 0.8258 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8219 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8164 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.8101 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8073 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8054 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7999 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7927 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 3 | 0.7862 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 3 | 0.7818 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7808 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7800 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7766 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7721 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7694 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7694 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7634 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7605 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7597 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7520 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7495 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7493 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7471 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7414 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7345 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7325 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7307 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7288 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7284 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7278 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.7217 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7216 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7212 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 3 | 0.7205 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7198 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7193 |
| ADP compounds hydrolase NudE | P45799 | NUDE_ECOLI | Escherichia coli | 2 | 0.7184 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7181 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7179 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7168 |
| Class 10 plant pathogenesis-related protein 2B | Q9LLQ2 | P102B_LUPLU | Lupinus luteus | 2 | 0.7167 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7165 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7157 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 2 | 0.7156 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7135 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7130 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7122 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7120 |
| DNA polymerase III subunit epsilon | P03007 | DPO3E_ECOLI | Escherichia coli | 3 | 0.7117 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7113 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7112 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7098 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | P0AF12 | MTNN_ECOLI | Escherichia coli | 2 | 0.7084 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7068 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 2 | 0.7066 |
| Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 | Q8GZB6 | SUVH4_ARATH | Arabidopsis thaliana | 3 | 0.7057 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7051 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 2 | 0.7046 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 2 | 0.7045 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.7041 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7022 |
| RIO-type serine/threonine-protein kinase Rio1 | O28471 | RIO1_ARCFU | Archaeoglobus fulgidus | 2 | 0.7020 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7019 |
| Anthranilate phosphoribosyltransferase | P00500 | TRPD_ACIAD | Acinetobacter baylyi | 2 | 0.7016 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7009 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7001 |