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Methyl citrate
- Family: Plantae - Commelinaceae
- Kingdom: Plantae
-
Class: Tricarboxylic Acid
- Subclass: Hydroxy Fatty Acid
| Canonical Smiles | COC(=O)CC(C(=O)O)(CC(=O)O)O |
|---|---|
| InChI | InChI=1S/C7H10O7/c1-14-5(10)3-7(13,6(11)12)2-4(8)9/h13H,2-3H2,1H3,(H,8,9)(H,11,12) |
| InChIKey | YUTUUOJFXIMELV-UHFFFAOYSA-N |
| Formula | C7H10O7 |
| HBA | 5 |
| HBD | 3 |
| MW | 206.15 |
| Rotatable Bonds | 5 |
| TPSA | 121.13 |
| LogP | -1.16 |
| Number Rings | 0 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 14 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.57 |
| Exact Mass | 206.04 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Symphonia globulifera | Guttiferae | Plantae | 156483 |
| 2 | Callisia fragrans | Commelinaceae | Plantae | 428217 |
Showing of synonyms
Methyl citrate
2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid
26163-61-1
Citric acid methyl ester
SCHEMBL454845
CHEMBL4217399
CHEBI:182319
HY-N9540
AKOS040757905
DA-55394
MS-23119
CS-0200245
F82976
1-Methyl 2-hydroxy-1,2,3-propanetricarboxylate
NCGC00385398-01!2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid
- Ngouela S, Lenta BN, et al. (2006). Anti-plasmodial and antioxidant activities of constituents of the seed shells of Symphonia globulifera Linn f.. Phytochemistry,2006, 67(3), 302-306. [View] [PubMed]
- El Sohafy S.M, Nassra R.A, et al. (2021). Chemical profiling and biological screening with potential anti-inflammatory activity of Callisia fragrans grown in Egypt. Natural product research, 2021, 35(23), 5521-5524. [View] [PubMed]
Pubchem:
378532
Cas:
26163-61-1
Gnps:
CCMSLIB00000848116
Chebi:
182319
Nmrshiftdb2:
70068740
Chembl:
CHEMBL4217399
CPRiL:
419711
No scaffolds available.
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.01
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.050
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -4.38
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- -0.040
- Plasma Protein Binding
- 1.6
- 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
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- -0.640
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -0.480
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Toxic
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.540
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 2.720
- 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
- 10.470
- Rat (Acute)
- 1.920
- Rat (Chronic Oral)
- 2.830
- Fathead Minnow
- 2.800
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 268.430
- Hydration Free Energy
- -8.730
- Log(D) at pH=7.4
- -2.390
- Log(P)
- -1.21
- Log S
- -0.29
- Log(Vapor Pressure)
- -6.99
- Melting Point
- 118.13
- pKa Acid
- 2.57
- pKa Basic
- 6.07
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Mexicain | P84346 | MEX1_JACME | Jacaratia mexicana | 3 | 0.9058 |
| Geranyl diphosphate synthase large subunit | Q9SBR3 | Q9SBR3_MENPI | Mentha piperita | 3 | 0.8756 |
| Putative choline kinase | Q5CUP2 | Q5CUP2_CRYPI | Cryptosporidium parvum | 3 | 0.8340 |
| 3-hydroxy-3-methylglutaryl-coenzyme A reductase | P13702 | MVAA_PSEMV | Pseudomonas mevalonii | 3 | 0.8158 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8064 |
| Ditrans,polycis-undecaprenyl-diphosphate synthase ((2E,6E)-farnesyl-diphosphate specific) | P60472 | UPPS_ECOLI | Escherichia coli | 3 | 0.8023 |
| Geranylgeranyl pyrophosphate synthase BTS1 | Q12051 | GGPPS_YEAST | Saccharomyces cerevisiae | 3 | 0.7934 |
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.7903 |
| Farnesyl pyrophosphate synthase | P14324 | FPPS_HUMAN | Homo sapiens | 3 | 0.7851 |
| Pyridoxal kinase, putative | C4LVZ4 | C4LVZ4_ENTHI | Entamoeba histolytica | 3 | 0.7770 |
| N-acetylglutamate synthase, mitochondrial | Q8N159 | NAGS_HUMAN | Homo sapiens | 3 | 0.7646 |
| D-3-phosphoglycerate dehydrogenase | P9WNX3 | SERA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7465 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7408 |
| 2-dehydro-3-deoxygluconokinase | Q53W83 | KDGK_THET8 | Thermus thermophilus | 4 | 0.7346 |