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6-O-alpha-L-(4′′-O-p-methoxycinnamoyl) rhamnopyranosylcatalpol
- Family: Plantae - Lamiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Iridoid Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@@H]2OC=CC3C2[C@@]2(CO)O[C@H]2[C@H]3O[C@H]2O[C@H](C)[C@H]([C@@H]([C@@H]2O)O)OC(=O)/C=C/c2ccc(cc2)OC)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C31H40O16/c1-13-25(44-18(34)8-5-14-3-6-15(40-2)7-4-14)22(37)24(39)29(42-13)45-26-16-9-10-41-28(19(16)31(12-33)27(26)47-31)46-30-23(38)21(36)20(35)17(11-32)43-30/h3-10,13,16-17,19-30,32-33,35-39H,11-12H2,1-2H3/b8-5+/t13-,16?,17-,19?,20-,21+,22-,23-,24+,25-,26+,27+,28+,29-,30+,31-/m1/s1 |
| InChIKey | RTCISXKUWWQSRF-SFCWRAENSA-N |
| Formula | C31H40O16 |
| HBA | 16 |
| HBD | 7 |
| MW | 668.65 |
| Rotatable Bonds | 10 |
| TPSA | 235.82 |
| LogP | -2.47 |
| Number Rings | 6 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 47 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.65 |
| Exact Mass | 668.23 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Premna odorata | Lamiaceae | Plantae | 1037421 |
| 2 | Premna odorata | Lamiaceae | Plantae | 1037421 |
Showing of synonyms
6-O-alpha-L-(4′′-O-p-methoxycinnamoyl) rhamnopyranosylcatalpol
- Elmaidomy A.H, Mohyeldin M.M, et al. (2017). Acylated Iridoids and Rhamnopyranoses from Premna odorata (Lamiaceae) as Novel Mesenchymal–Epithelial Transition Factor Receptor Inhibitors for the Control of Breast Cancer.. Phytotherapy research : PTR, 2017, 31(10), 1546-1556. [View] [PubMed]
- Elmaidomy A.H, Mohammed R, et al. (2019). Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco. Metabolites, 2019, 9(10), 223. [View] [PubMed]
No compound-protein relationship available.
SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OC(C(O3)C34)C5C4C(OC=C5)OC6CCCCO6
Level: 3
Mol. Weight: 668.65 g/mol
SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OC(C(O3)C34)C5C4COC=C5
Level: 2
Mol. Weight: 668.65 g/mol
SMILES: O1CCCCC1OC(C(O2)C23)C4C3C(OC=C4)OC5CCCCO5
Level: 2
Mol. Weight: 668.65 g/mol
SMILES: C1=COCC2C1C(C(O3)C23)OC4CCCCO4
Level: 1
Mol. Weight: 668.65 g/mol
SMILES: C12C(O2)CC3C1C(OC=C3)OC4CCCCO4
Level: 1
Mol. Weight: 668.65 g/mol
SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 668.65 g/mol
SMILES: C12C(O2)CC3C1COC=C3
Level: 0
Mol. Weight: 668.65 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 668.65 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 668.65 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.88
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.380
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 124.36
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.720
- Plasma Protein Binding
- 41.93
- 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
- 6.880
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.850
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.620
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.760
- 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
- -227987.270
- Rat (Acute)
- 3.140
- Rat (Chronic Oral)
- 4.400
- Fathead Minnow
- 301.010
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 20442.880
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- -0.450
- Log(P)
- -0.67
- Log S
- -2.34
- Log(Vapor Pressure)
- -661.83
- Melting Point
- 141.84
- pKa Acid
- 3.88
- pKa Basic
- -0.12
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8870 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 2 | 0.8582 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.8028 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7984 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7935 |
| Ephrin type-A receptor 2 | P29317 | EPHA2_HUMAN | Homo sapiens | 3 | 0.7708 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7647 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7621 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7557 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 4 | 0.7549 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7540 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7533 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7477 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7472 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 2 | 0.7442 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7431 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7418 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7403 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7400 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 2 | 0.7395 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7390 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7386 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 2 | 0.7383 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7378 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7378 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7372 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7367 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7366 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 2 | 0.7361 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7336 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7323 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7322 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7315 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7309 |
| Pantothenate synthetase | P9WIL4 | PANC_MYCTO | Mycobacterium tuberculosis | 2 | 0.7303 |
| Purine nucleoside phosphorylase | Q8I3X4 | Q8I3X4_PLAF7 | Plasmodium falciparum | 3 | 0.7302 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7302 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7302 |
| Myosin heavy chain kinase A | P42527 | MHCKA_DICDI | Dictyostelium discoideum | 2 | 0.7292 |
| Pantothenate synthetase | P9WIL4 | PANC_MYCTO | Mycobacterium tuberculosis | 2 | 0.7289 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 2 | 0.7275 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 2 | 0.7247 |
| Aminoglycoside N(3)-acetyltransferase | A0A3P1UCA6 | Q81P86_BACAN | Bacillus anthracis | 2 | 0.7243 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7242 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7232 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 2 | 0.7224 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7216 |
| Biotin carboxylase | P43873 | ACCC_HAEIN | Haemophilus influenzae | 2 | 0.7212 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7211 |
| Single-stranded-DNA-specific exonuclease RecJ | D0EM60 | D0EM60_DEIRD | Deinococcus radiodurans | 2 | 0.7210 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7210 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 2 | 0.7210 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 2 | 0.7204 |
| Ribosome-inactivating protein 3 | P25891 | RIP3_MAIZE | Zea mays | 2 | 0.7204 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 2 | 0.7192 |
| Biotin carboxylase | P24182 | ACCC_ECOLI | Escherichia coli | 2 | 0.7191 |
| Protein kinase C iota type | Q62074 | KPCI_MOUSE | Mus musculus | 2 | 0.7186 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 2 | 0.7173 |
| Serine/threonine-protein kinase toxin HipA | P23874 | HIPA_ECOLI | Escherichia coli | 2 | 0.7169 |
| Tyrosine-protein kinase SYK | P43405 | KSYK_HUMAN | Homo sapiens | 3 | 0.7162 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 2 | 0.7154 |
| RIO-type serine/threonine-protein kinase Rio1 | O28471 | RIO1_ARCFU | Archaeoglobus fulgidus | 2 | 0.7141 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7132 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7127 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7126 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 2 | 0.7123 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 2 | 0.7121 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 2 | 0.7104 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 2 | 0.7098 |
| Chorismate mutase AroH | P19080 | AROH_BACSU | Bacillus subtilis | 2 | 0.7090 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7086 |
| Focal adhesion kinase 1 | Q05397 | FAK1_HUMAN | Homo sapiens | 2 | 0.7085 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 2 | 0.7083 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 2 | 0.7081 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 2 | 0.7077 |
| 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase | P47229 | BPHD_PARXL | Paraburkholderia xenovorans | 2 | 0.7074 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7073 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 2 | 0.7066 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7065 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 2 | 0.7059 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 2 | 0.7057 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7042 |
| Adenosine 5'-monophosphoramidase HINT1 | P80912 | HINT1_RABIT | Oryctolagus cuniculus | 3 | 0.7022 |