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Benzoyl R-(+)-malic acid
- Family: Plantae - Celastraceae
- Kingdom: Plantae
- Class: Dicarboxylic Acid
| Canonical Smiles | O=C(c1ccccc1)O[C@H](C(=O)O)CCC(=O)O |
|---|---|
| InChI | InChI=1S/C12H12O6/c13-10(14)7-6-9(11(15)16)18-12(17)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,14)(H,15,16)/t9-/m0/s1 |
| InChIKey | DARXKQDALRZRMG-VIFPVBQESA-N |
| Formula | C12H12O6 |
| HBA | 4 |
| HBD | 2 |
| MW | 252.22 |
| Rotatable Bonds | 6 |
| TPSA | 100.9 |
| LogP | 1.16 |
| Number Rings | 1 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.25 |
| Exact Mass | 252.06 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Maytenus senegalensis | Celastraceae | Plantae | 256095 |
Showing of synonyms
Benzoyl R-(+)-malic acid
- Okoye FB, Agbo MO, et al. (2014). New neolignan glycoside and an unusual benzoyl malic acid derivative from Maytenus senegalensis leaves. Natural Product Research,2014,29,109-115. [View]
No compound-protein relationship available.
SMILES: c1ccccc1
Level: 0
Mol. Weight: 252.22 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.67
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.17
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.65
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.42
- Plasma Protein Binding
- 59.89
- 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
- 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
- 5.57
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.02
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.94
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 2.66
- 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
- 4.17
- Rat (Acute)
- 1.83
- Rat (Chronic Oral)
- 2.44
- Fathead Minnow
- 3.94
- 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
- 360.73
- Hydration Free Energy
- -6.38
- Log(D) at pH=7.4
- -3.22
- Log(P)
- 1.57
- Log S
- -1.61
- Log(Vapor Pressure)
- -7.96
- Melting Point
- 143.03
- pKa Acid
- 3.68
- pKa Basic
- 4.9
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Geranyl diphosphate synthase large subunit | Q9SBR3 | Q9SBR3_MENPI | Mentha piperita | 3 | 0.9479 |
| Three-prime repair exonuclease 1 | Q91XB0 | TREX1_MOUSE | Mus musculus | 3 | 0.9452 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 3 | 0.9251 |
| 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase | P19992 | HSD_STREX | Streptomyces exfoliatus | 3 | 0.9096 |
| Pantothenate synthetase | P9WIL4 | PANC_MYCTO | Mycobacterium tuberculosis | 3 | 0.8800 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8786 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 3 | 0.8711 |
| Pyrrolysine--tRNA ligase | Q8PWY1 | PYLS_METMA | Methanosarcina mazei | 3 | 0.8707 |
| L-lactate dehydrogenase A chain | P13491 | LDHA_RABIT | Oryctolagus cuniculus | 3 | 0.8667 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 3 | 0.8587 |
| Single-stranded-DNA-specific exonuclease RecJ | D0EM60 | D0EM60_DEIRD | Deinococcus radiodurans | 3 | 0.8303 |
| Plasma membrane ATPase | Q42932 | Q42932_NICPL | Nicotiana plumbaginifolia | 3 | 0.8288 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.8111 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.8014 |
| Phenylpyruvate C(3)-methyltransferase | Q643C8 | MPPJ_STRHY | Streptomyces hygroscopicus | 3 | 0.7978 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7959 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 3 | 0.7734 |
| Malate dehydrogenase | P10584 | MDH_THETH | Thermus thermophilus | 3 | 0.7695 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 3 | 0.7688 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.7677 |
| Polymerase basic protein 2 | P31345 | PB2_I75A3 | Influenza A virus | 3 | 0.7628 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7593 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7575 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7557 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7545 |
| NAD(P) transhydrogenase subunit alpha part 1 | Q2RSB2 | PNTAA_RHORT | Rhodospirillum rubrum | 3 | 0.7490 |
| Pantothenate kinase | P9WPA7 | COAA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7479 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7475 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7459 |
| Ferredoxin--NADP reductase, chloroplastic | P00455 | FENR_SPIOL | Spinacia oleracea | 3 | 0.7445 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7423 |
| 5-formyltetrahydrofolate cyclo-ligase | P75430 | MTHFS_MYCPN | Mycoplasma pneumoniae | 2 | 0.7386 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 2 | 0.7386 |
| Diamine acetyltransferase 1 | P21673 | SAT1_HUMAN | Homo sapiens | 2 | 0.7339 |
| cAMP-dependent protein kinase type II-beta regulatory subunit | P12369 | KAP3_RAT | Rattus norvegicus | 3 | 0.7335 |
| Hydroxymethylglutaryl-CoA synthase | Q9FD71 | HMGCS_ENTFL | Enterococcus faecalis | 2 | 0.7330 |
| Pantothenate kinase | P9WPA7 | COAA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7325 |
| Oxygen-insensitive NAD(P)H nitroreductase | P38489 | NFSB_ECOLI | Escherichia coli | 3 | 0.7310 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7299 |
| Metallophosphoesterase MPPED2 | B1WBP0 | MPPD2_RAT | Rattus norvegicus | 3 | 0.7298 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7293 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7285 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7255 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7254 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 2 | 0.7252 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7226 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7222 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7221 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7219 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 2 | 0.7219 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7219 |
| 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase | P47229 | BPHD_PARXL | Paraburkholderia xenovorans | 3 | 0.7211 |
| ADP-ribosyl-[dinitrogen reductase] hydrolase | A7XNI2 | A7XNI2_AZOBR | Azospirillum brasilense | 2 | 0.7182 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 2 | 0.7169 |
| Aldehyde dehydrogenase, mitochondrial | P05091 | ALDH2_HUMAN | Homo sapiens | 3 | 0.7167 |
| 2'-5'-oligoadenylate synthase 1 | P00973 | OAS1_HUMAN | Homo sapiens | 2 | 0.7164 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7160 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7153 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7152 |
| Multidrug efflux pump subunit AcrB | P31224 | ACRB_ECOLI | Escherichia coli | 3 | 0.7147 |
| Feruloyl esterase A | O42807 | FAEA_ASPNG | Aspergillus niger | 2 | 0.7147 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7141 |
| 3-hydroxy-3-methylglutaryl-coenzyme A reductase | P04035 | HMDH_HUMAN | Homo sapiens | 2 | 0.7105 |
| BH2602 protein | Q9K9P3 | Q9K9P3_BACHD | Bacillus halodurans | 2 | 0.7098 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7098 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 3 | 0.7097 |
| Nucleoside diphosphate kinase | Q5UQL3 | NDK_MIMIV | Acanthamoeba polyphaga mimivirus | 3 | 0.7093 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7090 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7087 |
| Tetracycline repressor protein class B from transposon Tn10 | P04483 | TETR2_ECOLX | Escherichia coli | 2 | 0.7067 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7057 |
| Caffeic acid 3-O-methyltransferase | P28002 | COMT1_MEDSA | Medicago sativa | 2 | 0.7052 |
| Copper-transporting ATPase 1 | Q04656 | ATP7A_HUMAN | Homo sapiens | 3 | 0.7049 |
| 3-hydroxy-3-methylglutaryl-coenzyme A reductase | P13702 | MVAA_PSEMV | Pseudomonas mevalonii | 3 | 0.7045 |
| Cysteine synthase | P45040 | CYSK_HAEIN | Haemophilus influenzae | 3 | 0.7044 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7038 |
| Perakine reductase | Q3L181 | PERR_RAUSE | Rauvolfia serpentina | 2 | 0.7035 |
| Acidic phospholipase A2 3 | P60045 | PA2A3_NAJSG | Naja sagittifera | 2 | 0.7031 |
| Ribonuclease 4 | P15468 | RNAS4_PIG | Sus scrofa | 2 | 0.7025 |
| Mitochondrial dynamics protein MIEF1 | Q9NQG6 | MID51_HUMAN | Homo sapiens | 2 | 0.7019 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7016 |