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Premnoside H
- 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]2OC(=O)/C=C/c2ccc(cc2)O)OC(=O)/C=C/c2ccc(cc2)O)O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C39H44O18/c1-18-28(46)33(53-25(44)12-6-19-2-8-21(42)9-3-19)34(54-26(45)13-7-20-4-10-22(43)11-5-20)38(51-18)55-32-23-14-15-50-36(27(23)39(17-41)35(32)57-39)56-37-31(49)30(48)29(47)24(16-40)52-37/h2-15,18,23-24,27-38,40-43,46-49H,16-17H2,1H3/b12-6+,13-7+/t18-,23?,24-,27?,28-,29-,30+,31-,32+,33+,34+,35+,36+,37+,38-,39-/m1/s1 |
| InChIKey | ZMPZJQQFJWIGEW-AIWNACMPSA-N |
| Formula | C39H44O18 |
| HBA | 18 |
| HBD | 8 |
| MW | 800.76 |
| Rotatable Bonds | 12 |
| TPSA | 273.12 |
| LogP | -0.8 |
| Number Rings | 7 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 57 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.49 |
| Exact Mass | 800.25 |
| 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
Premnoside H
- 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)OC2C(OC(=O)C=Cc3ccccc3)CCOC2OC(C(O4)C45)C6C5C(OC=C6)OC7CCCCO7
Level: 4
Mol. Weight: 800.76 g/mol
SMILES: c1ccccc1C=CC(=O)OC2C(OC(=O)C=Cc3ccccc3)CCOC2OC(C(O4)C45)C6C5COC=C6
Level: 3
Mol. Weight: 800.76 g/mol
SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)OC(C(O3)C34)C5C4C(OC=C5)OC6CCCCO6
Level: 3
Mol. Weight: 800.76 g/mol
SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)OC(C(O3)C34)C5C4C(OC=C5)OC6CCCCO6
Level: 3
Mol. Weight: 800.76 g/mol
SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)OC(C(O3)C34)C5C4COC=C5
Level: 2
Mol. Weight: 800.76 g/mol
SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)OC(C(O3)C34)C5C4COC=C5
Level: 2
Mol. Weight: 800.76 g/mol
SMILES: c1ccccc1C=CC(=O)OC2C(COCC2)OC(=O)C=Cc3ccccc3
Level: 2
Mol. Weight: 800.76 g/mol
SMILES: O1CCCCC1OC(C(O2)C23)C4C3C(OC=C4)OC5CCCCO5
Level: 2
Mol. Weight: 800.76 g/mol
SMILES: C1=COCC2C1C(C(O3)C23)OC4CCCCO4
Level: 1
Mol. Weight: 800.76 g/mol
SMILES: C12C(O2)CC3C1C(OC=C3)OC4CCCCO4
Level: 1
Mol. Weight: 800.76 g/mol
SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 800.76 g/mol
SMILES: C1COCCC1OC(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 800.76 g/mol
SMILES: C12C(O2)CC3C1COC=C3
Level: 0
Mol. Weight: 800.76 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 800.76 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 800.76 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.99
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 123.320
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 16850.57
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.690
- Plasma Protein Binding
- 49.44
- 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
- Inhibitor
Excretion
- Clearance
- 8.940
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -390.380
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.520
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.110
- 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
- -30586304.940
- Rat (Acute)
- 2.860
- Rat (Chronic Oral)
- 4.910
- Fathead Minnow
- 38616.110
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 3434524.810
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 0.140
- Log(P)
- 0.66
- Log S
- -3.31
- Log(Vapor Pressure)
- -113017.9
- Melting Point
- 183.99
- pKa Acid
- -769.28
- pKa Basic
- -0.02
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9QYJ6 | PDE10_RAT | Rattus norvegicus | 3 | 0.9079 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 3 | 0.9074 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8907 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8427 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.8375 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8179 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 2 | 0.8084 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 4 | 0.8075 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7969 |
| Copper-transporting ATPase | Q97UU7 | Q97UU7_SACS2 | Saccharolobus solfataricus | 4 | 0.7903 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7902 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7695 |
| Protease | O38896 | O38896_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.7570 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7514 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7478 |
| Insulin-degrading enzyme | P14735 | IDE_HUMAN | Homo sapiens | 2 | 0.7450 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7439 |
| Genome polyprotein | C0LMU0 | C0LMU0_9FLAV | dengue virus type 3 | 3 | 0.7435 |
| Antitumor antibiotic C-1027 apoprotein | Q06110 | CAGA_STRGL | Streptomyces globisporus | 3 | 0.7432 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 2 | 0.7410 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7402 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7400 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7380 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 2 | 0.7333 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7300 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7289 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7257 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7257 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.7254 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7235 |
| Bifunctional protein GlmU | P43889 | GLMU_HAEIN | Haemophilus influenzae | 3 | 0.7230 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 2 | 0.7225 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7224 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7211 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7205 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7194 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7156 |
| Kinesin heavy chain | Q41460 | Q41460_SOLTU | Solanum tuberosum | 3 | 0.7135 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7113 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 2 | 0.7108 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7107 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7100 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7091 |
| Myosin heavy chain kinase A | P42527 | MHCKA_DICDI | Dictyostelium discoideum | 2 | 0.7089 |
| Anthranilate phosphoribosyltransferase | P00500 | TRPD_ACIAD | Acinetobacter baylyi | 2 | 0.7080 |
| Purine nucleoside phosphorylase DeoD-type | B1JL34 | DEOD_YERPY | Yersinia pseudotuberculosis serotype O:3 | 2 | 0.7079 |
| Biotin carboxylase | P24182 | ACCC_ECOLI | Escherichia coli | 2 | 0.7075 |
| Protein kinase C iota type | Q62074 | KPCI_MOUSE | Mus musculus | 2 | 0.7065 |
| Phosphoenolpyruvate carboxykinase [GTP] | A5TYT6 | PCKG_MYCTA | Mycobacterium tuberculosis | 3 | 0.7063 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7063 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 4 | 0.7061 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7057 |
| Fructose-1,6-bisphosphatase 1 | P09467 | F16P1_HUMAN | Homo sapiens | 2 | 0.7054 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7051 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 3 | 0.7050 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7049 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7043 |
| Kynurenine--oxoglutarate transaminase 1 | Q16773 | KAT1_HUMAN | Homo sapiens | 2 | 0.7040 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7030 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 2 | 0.7028 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7012 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7011 |
| Formate--tetrahydrofolate ligase | P21164 | FTHS_MOOTH | Moorella thermoacetica | 2 | 0.7008 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7002 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 2 | 0.7001 |