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Galloyl shikimic acid
- Family: Plantae - Myrtaceae
- Kingdom: Plantae
-
Class: Tannin
- Subclass: Hydrolyzable Tannin
| Canonical Smiles | O[C@@H]1CC(=C([C@H]([C@H]1O)O)C(=O)c1cc(O)c(c(c1)O)O)C(=O)O |
|---|---|
| InChI | InChI=1S/C14H14O9/c15-6-1-4(2-7(16)11(6)19)10(18)9-5(14(22)23)3-8(17)12(20)13(9)21/h1-2,8,12-13,15-17,19-21H,3H2,(H,22,23)/t8-,12+,13-/m1/s1 |
| InChIKey | PNBAIKSYIZXAEP-OXHMUOHRSA-N |
| Formula | C14H14O9 |
| HBA | 8 |
| HBD | 7 |
| MW | 326.26 |
| Rotatable Bonds | 3 |
| TPSA | 175.75 |
| LogP | -1.15 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.29 |
| Exact Mass | 326.06 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Eucalyptus camaledulensis | Myrtaceae | Plantae | 34316 |
Showing of synonyms
Galloyl shikimic acid
- Singab A-N, Ayoub N, et al. (2011). Phenolic Constituents of Eucalyptus camaldulensis Dehnh, with Potential Antioxidant and Cytotoxic Activities. Records of Natural Products,2011,5(4),271-280. [View]
No compound-protein relationship available.
SMILES: C1CCCC=C1C(=O)c2ccccc2
Level: 1
Mol. Weight: 326.26 g/mol
SMILES: C1=CCCCC1
Level: 0
Mol. Weight: 326.26 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 326.26 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.51
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.77
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -0.58
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.43
- Plasma Protein Binding
- 58.31
- 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
- 8.91
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -2.16
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.81
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.24
- 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
- -0.75
- Rat (Acute)
- 1.79
- Rat (Chronic Oral)
- 3.88
- Fathead Minnow
- 3.58
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 547.11
- Hydration Free Energy
- -15.25
- Log(D) at pH=7.4
- -3.11
- Log(P)
- -1.4
- Log S
- -1.83
- Log(Vapor Pressure)
- -11.83
- Melting Point
- 183.67
- pKa Acid
- 2.91
- pKa Basic
- 8.29
| 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 | 0.8862 |
| Thiazole tautomerase | P25053 | TENI_BACSU | Bacillus subtilis | 3 | 0.8808 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8732 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.8685 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.8509 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8455 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 4 | 0.8391 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.8213 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8193 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8107 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8027 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7951 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7930 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.7805 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 4 | 0.7804 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 4 | 0.7611 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7580 |
| GMP synthase [glutamine-hydrolyzing] | Q8IJR9 | Q8IJR9_PLAF7 | Plasmodium falciparum | 5 | 0.7358 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7290 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7267 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7235 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 4 | 0.7205 |
| Glucose-1-phosphate thymidylyltransferase | Q9AGY4 | Q9AGY4_ANETH | Aneurinibacillus thermoaerophilus | 5 | 0.7188 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7147 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7059 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 3 | 0.7026 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 3 | 0.7021 |