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Phillyrin
- Family: Plantae - Thymelaeaceae
- Kingdom: Plantae
-
Class: Lignan
- Subclass: Tetrahydrofurofuran Lignan Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](Oc2ccc(cc2OC)[C@H]2OC[C@H]3[C@@H]2CO[C@H]3c2ccc(c(c2)OC)OC)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C27H34O11/c1-32-17-6-4-13(8-19(17)33-2)25-15-11-36-26(16(15)12-35-25)14-5-7-18(20(9-14)34-3)37-27-24(31)23(30)22(29)21(10-28)38-27/h4-9,15-16,21-31H,10-12H2,1-3H3/t15-,16-,21+,22+,23-,24+,25-,26+,27+/m0/s1 |
| InChIKey | KFFCKOBAHMGTMW-LGQRSHAYSA-N |
| Formula | C27H34O11 |
| HBA | 11 |
| HBD | 4 |
| MW | 534.56 |
| Rotatable Bonds | 8 |
| TPSA | 145.53 |
| LogP | 0.97 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 38 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.56 |
| Exact Mass | 534.21 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Eremophila maculata | Scrophulariaceae | Plantae | 1214565 |
| 2 | Thymelaea microphylla | Thymelaeaceae | Plantae | 224056 |
Showing of synonyms
Phillyrin
Phyllyrin
UNII-VE9P4964MG
VE9P4964MG
PHILLYRIN [MI]
PHILLYROSIDE, (+)-
(2S,3R,4S,5S,6R)-2-[4-[(3R,3aR,6S,6aR)-3-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
DTXSID40197589
4-(4-(3,4-Dimethoxyphenyl)tetrahydro-1H,3H-furo(3,4-c)furan-1-yl)-2-methoxyphenyl, (1S-(1alpha,3aalpha,4beta,6aalpha))-beta-D-glucopyranoside
.BETA.-D-GLUCOPYRANOSIDE, 4-((1S,3AR,4R,6AR)-4-(3,4-DIMETHOXYPHENYL)TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1-YL)-2-METHOXYPHENYL
4-((1S,3AR,4R,6AR))-4-(4-(3,4-DIMETHOXYPHENYL)TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1-YL)-2-METHOXYPHENYL-.BETA.-D-GLUCOPYRANOSIDE
Beta-D-Glucopyranoside, 4-(4-(3,4-dimethoxyphenyl)tetrahydro-1H,3H-furo(3,4-c)furan-1-yl)-2-methoxyphenyl, (1S-(1alpha,3aalpha,4beta,6aalpha))-
(2S,3R,4S,5S,6R)-2-(4-((3R,3aR,6S,6aR)-3-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro(3,4-c)furan-6-yl)-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
(2S,3R,4S,5S,6R)-2-(4-((3S,3aR,6R,6aR)-3-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro(3,4-c)furan-6-yl)-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
(2S,3R,4S,5S,6R)-2-[4-[(3S,3aR,6R,6aR)-3-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
DTXCID50120080
Beta-D-Glucopyranoside, 4-((1S,3aR,4R,6aR)-4-(3,4-dimethoxyphenyl)tetrahydro-1H,3H-furo(3,4-c)furan-1-yl)-2-methoxyphenyl
4-((1S,3AR,4R,6AR))-4-(4-(3,4-DIMETHOXYPHENYL)TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1-YL)-2-METHOXYPHENYL-BETA-D-GLUCOPYRANOSIDE
Forsythin
Phillyroside
Phillyrin (Standard)
Phillygenin-O-glucoside
SCHEMBL710957
Phillyrin, >=98% (HPLC)
CHEBI:80888
HY-N0482R
HY-N0482
MSK000538
S3926
AKOS037514776
CCG-269935
1ST000538
CS-0009002
C17048
Q27151384
- Kerbab K, Mekhelfi T, et al. (2015). Chemical composition and antioxidant activity of a polar extract of Thymelaea microphylla Coss. Et Dur. Nat Prod Res,2015,29(7),671-5. [View] [PubMed]
- Youssef F.S, Ashour M.L, et al. (2016). Eremophila maculata —Isolation of a rare naturally-occurring lignan glycoside and the hepatoprotective activity of the leaf extract. Phytomedicine : international journal of phytotherapy and phytopharmacology, 2016, 23(12), 1484-1493. [View] [PubMed]
Pubchem:
101712
Gnps:
CCMSLIB00006529551
Zinc:
ZINC000056874329
Kegg Ligand:
C17048
Chebi:
80888
Nmrshiftdb2:
60030564
Comptox:
DTXSID40197589
CPRiL:
82741
SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccc(cc4)OC5CCCCO5
Level: 3
Mol. Weight: 534.56 g/mol
SMILES: C1OCC(C12)COC2c3ccc(cc3)OC4CCCCO4
Level: 2
Mol. Weight: 534.56 g/mol
SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4
Level: 2
Mol. Weight: 534.56 g/mol
SMILES: C1OCC(C12)COC2c3ccccc3
Level: 1
Mol. Weight: 534.56 g/mol
SMILES: c1ccccc1OC2CCCCO2
Level: 1
Mol. Weight: 534.56 g/mol
SMILES: C1OCC(C12)COC2
Level: 0
Mol. Weight: 534.56 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 534.56 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 534.56 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.04
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.860
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 0.33
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.940
- Plasma Protein Binding
- 90.25
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.280
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.390
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.220
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.750
- 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
- -3040.680
- Rat (Acute)
- 2.800
- Rat (Chronic Oral)
- 3.660
- Fathead Minnow
- 9.870
- 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
- 454.700
- Hydration Free Energy
- -2.830
- Log(D) at pH=7.4
- 1.550
- Log(P)
- 0.44
- Log S
- -3.43
- Log(Vapor Pressure)
- -10.57
- Melting Point
- 186.51
- pKa Acid
- 6.91
- pKa Basic
- 1.81
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.9727 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.9548 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.9431 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9180 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9175 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.9161 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.9120 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.9108 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9089 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9005 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8975 |
| ALK tyrosine kinase receptor | Q9UM73 | ALK_HUMAN | Homo sapiens | 3 | 0.8870 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.8767 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8647 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8367 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8247 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.8240 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8231 |
| Decaprenylphosphoryl-beta-D-ribose oxidase | I6X8C4 | I6X8C4_MYCTU | Mycobacterium tuberculosis | 3 | 0.8214 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8142 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8088 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8067 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8040 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.8026 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7995 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7992 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7954 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 3 | 0.7932 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7929 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7813 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7796 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.7786 |
| High affinity 3',5'-cyclic-AMP phosphodiesterase 7A | Q13946 | PDE7A_HUMAN | Homo sapiens | 3 | 0.7771 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7756 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7756 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.7734 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7734 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7731 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.7661 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7659 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7649 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7645 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7597 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7583 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7527 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7522 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7513 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7489 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7468 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7460 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7428 |
| Glycogen phosphorylase, liver form | P06737 | PYGL_HUMAN | Homo sapiens | 3 | 0.7417 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7411 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7396 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7385 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7382 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7365 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7360 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7332 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7328 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 2 | 0.7327 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7326 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7303 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7288 |
| Orf1ab polyprotein | Q6T1E9 | Q6T1E9_CVHSA | SARS coronavirus CUHK-L2 | 3 | 0.7284 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7280 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7279 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7277 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7262 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7237 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7223 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 2 | 0.7219 |
| Lactoylglutathione lyase | Q04760 | LGUL_HUMAN | Homo sapiens | 2 | 0.7217 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7215 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 2 | 0.7212 |
| UDP-3-O-acyl-N-acetylglucosamine deacetylase | P47205 | LPXC_PSEAE | Pseudomonas aeruginosa | 4 | 0.7200 |
| ALK tyrosine kinase receptor | Q9UM73 | ALK_HUMAN | Homo sapiens | 3 | 0.7193 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7182 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7158 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.7151 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7150 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7148 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 2 | 0.7136 |
| Aspartokinase 1, chloroplastic | Q9LYU8 | AK1_ARATH | Arabidopsis thaliana | 3 | 0.7126 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7118 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7111 |
| D-alanyl-D-alanine carboxypeptidase | P15555 | DAC_STRSR | Streptomyces sp | 2 | 0.7103 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 3 | 0.7094 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7094 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9QYJ6 | PDE10_RAT | Rattus norvegicus | 3 | 0.7094 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 2 | 0.7092 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7079 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7068 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7047 |
| 6-phosphogluconate dehydrogenase, decarboxylating | P96789 | 6PGD_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7036 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7027 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7025 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7024 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7024 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7015 |
| Cystathionine gamma-synthase | P56069 | METB_HELPY | Helicobacter pylori | 3 | 0.7006 |