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Citrusin E
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Phenolic Glycoside
| Canonical Smiles | OCC1OC(Oc2ccc(cc2OC)CCC(=O)OC)C(C(C1O)O)O |
|---|---|
| InChI | InChI=1S/C17H24O9/c1-23-11-7-9(4-6-13(19)24-2)3-5-10(11)25-17-16(22)15(21)14(20)12(8-18)26-17/h3,5,7,12,14-18,20-22H,4,6,8H2,1-2H3 |
| InChIKey | GPJDWVYEUMEYKE-UHFFFAOYSA-N |
| Formula | C17H24O9 |
| HBA | 9 |
| HBD | 4 |
| MW | 372.37 |
| Rotatable Bonds | 7 |
| TPSA | 134.91 |
| LogP | -1.02 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.59 |
| Exact Mass | 372.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Euphorbia gaditana | Euphorbiaceae | Plantae | 3990 |
Showing of synonyms
Citrusin E
CHEBI:168372
Methyl 3-[3-methoxy-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]propanoate
- Badaoui M, Magid A, et al. (2020). Antioxidant activity-guided isolation of constituents from Euphorbia gaditana Coss. and their antioxidant and tyrosinase inhibitory activities. Phytochemistry Letters, 2020, 39, 99-104. [View]
No compound-protein relationship available.
SMILES: c1ccccc1OC2CCCCO2
Level: 1
Mol. Weight: 372.37 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 372.37 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 372.37 g/mol
Antioxidant
Absorption
- Caco-2 (logPapp)
- -5.46
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.87
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.01
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.67
- Plasma Protein Binding
- 0.2
- 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
- 4.36
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.07
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.07
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.33
- 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
- -1.24
- Rat (Acute)
- 2.08
- Rat (Chronic Oral)
- 3.5
- Fathead Minnow
- 4.04
- 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
- 430.25
- Hydration Free Energy
- -14.24
- Log(D) at pH=7.4
- 0.09
- Log(P)
- -0.89
- Log S
- -1.73
- Log(Vapor Pressure)
- -9.12
- Melting Point
- 143.97
- pKa Acid
- 7.29
- pKa Basic
- 2.67
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.9466 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.9126 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8875 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8836 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8761 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8686 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8385 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8362 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8341 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.8335 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8246 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.8116 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.8114 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8046 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8010 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7969 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7925 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7841 |
| DNA polymerase theta | O75417 | DPOLQ_HUMAN | Homo sapiens | 4 | 0.7832 |
| Phenolphthiocerol/phthiocerol polyketide synthase subunit C | P96202 | PPSC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7715 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7707 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7660 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7660 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7657 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7606 |
| Laminarinase | Q9WXN1 | Q9WXN1_THEMA | Thermotoga maritima | 3 | 0.7606 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 2 | 0.7598 |
| 14-3-3 protein gamma | P61981 | 1433G_HUMAN | Homo sapiens | 3 | 0.7592 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 4 | 0.7527 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7520 |
| Raucaffricine-O-beta-D-glucosidase | Q9SPP9 | RG1_RAUSE | Rauvolfia serpentina | 4 | 0.7504 |
| Oxygenase | Q194P4 | Q194P4_STRAA | Streptomyces argillaceus | 3 | 0.7468 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7463 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7456 |
| IAG-nucleoside hydrolase | Q9GPQ4 | Q9GPQ4_TRYVI | Trypanosoma vivax | 4 | 0.7425 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.7420 |
| Cyclic nucleotide-gated potassium channel mll3241 | Q98GN8 | CNGK1_RHILO | Mesorhizobium japonicum) | 3 | 0.7387 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7383 |
| 3'-5' exoribonuclease Rv2179c | P9WJ73 | EXRBN_MYCTU | Mycobacterium tuberculosis | 2 | 0.7376 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7362 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7337 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7320 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7290 |
| Nucleoside diphosphate kinase | Q5UQL3 | NDK_MIMIV | Acanthamoeba polyphaga mimivirus | 2 | 0.7279 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7274 |
| Metallophosphoesterase | A3DJ38 | A3DJ38_HUNT2 | Clostridium thermocellum | 2 | 0.7266 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7266 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7254 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7252 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 3 | 0.7252 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7238 |
| 6-phosphogluconate dehydrogenase, decarboxylating | P96789 | 6PGD_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7214 |
| L-lactate dehydrogenase A chain | P13491 | LDHA_RABIT | Oryctolagus cuniculus | 2 | 0.7192 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7187 |
| Pyridoxal kinase | O00764 | PDXK_HUMAN | Homo sapiens | 2 | 0.7185 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7176 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 4 | 0.7173 |
| L-methionine gamma-lyase | Q84AR1 | Q84AR1_CITFR | Citrobacter freundii | 3 | 0.7170 |
| Cyclic AMP receptor protein | Q5SID7 | CRP_THET8 | Thermus thermophilus | 2 | 0.7148 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7138 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7137 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7119 |
| Nucleoside 2-deoxyribosyltransferase | Q8RLY5 | Q8RLY5_LACHE | Lactobacillus helveticus | 3 | 0.7115 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7112 |
| Angiotensin-converting enzyme | Q10714 | ACE_DROME | Drosophila melanogaster | 3 | 0.7111 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7100 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7087 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 2 | 0.7072 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.7044 |
| DNA polymerase III subunit epsilon | P03007 | DPO3E_ECOLI | Escherichia coli | 2 | 0.7041 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 3 | 0.7027 |
| Methionine--tRNA ligase | P00959 | SYM_ECOLI | Escherichia coli | 4 | 0.7013 |
| 1-deoxy-D-xylulose 5-phosphate reductoisomerase | P45568 | DXR_ECOLI | Escherichia coli | 2 | 0.7004 |