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3,5-di-O-caffeoylquinic acid 1-methyl ether
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Hydroxycinnamic Acid
| Canonical Smiles | C/C=C(\C(=O)O[C@@H]1C=C(C)CC[C@@]2([C@]1(C)C(=O)CC2C(C)C)O)/C |
|---|---|
| InChI | InChI=1S/C20H30O4/c1-7-14(5)18(22)24-17-10-13(4)8-9-20(23)15(12(2)3)11-16(21)19(17,20)6/h7,10,12,15,17,23H,8-9,11H2,1-6H3/b14-7-/t15?,17-,19-,20-/m1/s1 |
| InChIKey | IVSKJBHOJBAMEK-AKABRVDVSA-N |
| Formula | C20H30O4 |
| HBA | 4 |
| HBD | 1 |
| MW | 334.46 |
| Rotatable Bonds | 3 |
| TPSA | 63.6 |
| LogP | 3.59 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.7 |
| Exact Mass | 334.21 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Inula crithmoides | Asteraceae | Plantae | 119182 |
| 2 | Inula crithmoides | Asteraceae | Plantae | 119182 |
Showing of synonyms
3,5-di-O-caffeoylquinic acid 1-methyl ether
- Mahmoud ZF, Salam NAA, et al. (1981). A carotane derivative and a eudesmanolide from Inula crithmoides. Phytochemistry,1981,20(4),735-738. [View]
- Ela MAA, El-Lakany AM, et al. (2012). New quinic acid derivatives from hepatoprotective Inula crithmoides root extract. Helvetica Chimica Acta,2012,95,61-66. [View]
Pubchem:
162985666
No compound-protein relationship available.
SMILES: O=C1CCC(C12)CCC=CC2
Level: 0
Mol. Weight: 334.46 g/mol
Hepatoprotective
Absorption
- Caco-2 (logPapp)
- -4.49
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.55
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.7
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.58
- Plasma Protein Binding
- 66.05
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- 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
- 7.03
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.34
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.16
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.43
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -2.83
- Rat (Acute)
- 3.11
- Rat (Chronic Oral)
- 1.59
- Fathead Minnow
- 4.07
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 337.46
- Hydration Free Energy
- -6.82
- Log(D) at pH=7.4
- 3.12
- Log(P)
- 4.01
- Log S
- -4.1
- Log(Vapor Pressure)
- -5.59
- Melting Point
- 115.46
- pKa Acid
- 8.9
- pKa Basic
- 3.59
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8961 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8961 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8363 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8363 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7830 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7830 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7272 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7272 |
| Retinol-binding protein 1 | P09455 | RET1_HUMAN | Homo sapiens | 3 | 0.7221 |
| Retinol-binding protein 1 | P09455 | RET1_HUMAN | Homo sapiens | 3 | 0.7221 |