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(-)-syringaresinol
- Family: Plantae - Rhizophoraceae
- Kingdom: Plantae
- Class: Phenolic
| Canonical Smiles | COc1cc(cc(c1O)OC)[C@@H]1OC[C@@H]2[C@H]1CO[C@H]2c1cc(OC)c(c(c1)OC)O |
|---|---|
| InChI | InChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3/t13-,14-,21+,22+/m1/s1 |
| InChIKey | KOWMJRJXZMEZLD-WRMVBYCNSA-N |
| Formula | C22H26O8 |
| HBA | 8 |
| HBD | 2 |
| MW | 418.44 |
| Rotatable Bonds | 6 |
| TPSA | 95.84 |
| LogP | 3.21 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.45 |
| Exact Mass | 418.16 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cassipourea congoensis | Rhizophoraceae | Plantae | 2708747 |
Showing of synonyms
(-)-syringaresinol
6216-81-5
(-)-Lirioresinol B
Syringaresinol, (-)-
QD6NNG8CM5
CHEBI:49212
4,4'-((1R,3aS,4R,6aS)-Tetrahydro-1H,3H-furo(3,4-C)furan-1,4-diyl)bis(2,6-dimethoxyphenol)
Phenol, 4,4'-((1R,3aS,4R,6aS)-tetrahydro-1H,3H-furo(3,4-C)furan-1,4-diyl)bis(2,6-dimethoxy-
4-[(3R,3aS,6R,6aS)-6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenol
(7beta,7'beta,8beta,8'beta)-3,3',5,5'-tetramethoxy-7,9':7',9-diepoxylignane-4,4'-diol
Phenol, 4,4'-(tetrahydro-1H,3H-furo(3,4-C)furan-1,4-diyl)bis(2,6-dimethoxy-, (1R-(1alpha,3aalpha,4alpha,6aalpha))-
PHENOL, 4,4'-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS(2,6-DIMETHOXY-, (1R-(1.ALPHA.,3A.ALPHA.,4.ALPHA.,6A.ALPHA.))-
4,4'-((1R,3aS,4R,6aS)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis(2,6-dimethoxyphenol)
4-((3R,3aS,6R,6aS)-6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro(3,4-c)furan-3-yl)-2,6-dimethoxyphenol
DL-Syringaresinol
Syringaresinol - 93%
UNII-QD6NNG8CM5
Lirioresinol b
Minus Syringaresinol
()-Syringaresinol
(-)-Syringaresinol - 98%
CHEMBL402653
SCHEMBL16562875
KOWMJRJXZMEZLD-WRMVBYCNSA-N
DTXSID901316029
AKOS030231411
FS74040
DA-59414
MS-27314
XS164035
HY-126066
CS-0090357
Q27121535
4,4'-(1R,3aS,4R,6aS)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(2,6-dimethoxyphenol)
4-[(3R,3aS,6R,6aS)-6-(4-hydroxy-3,5-dimethoxy-phenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxy-phenol
- Takou DM, Waffo AFK, et al. (2019). Melanin Production Inhibitors from the West African Cassipourea congoensis. Planta Medica International Open 2019; 6(02): e50-e56. [View]
Pubchem:
11604108
Cas:
6216-81-5
Zinc:
ZINC000029041899
Chebi:
49212
Nmrshiftdb2:
60021824
Metabolights:
MTBLC49212
Chembl:
CHEMBL402653
No compound-protein relationship available.
SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4
Level: 2
Mol. Weight: 418.44 g/mol
SMILES: C1OCC(C12)COC2c3ccccc3
Level: 1
Mol. Weight: 418.44 g/mol
SMILES: C1OCC(C12)COC2
Level: 0
Mol. Weight: 418.44 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 418.44 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.0
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.960
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.06
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.930
- Plasma Protein Binding
- 76.91
- 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
- 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
- 10.880
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.420
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.710
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.360
- Micronucleos
- Toxic
- 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
- Toxic
- T. Pyriformis
- -48.920
- Rat (Acute)
- 2.150
- Rat (Chronic Oral)
- 2.330
- Fathead Minnow
- 4.180
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 452.390
- Hydration Free Energy
- -3.570
- Log(D) at pH=7.4
- 2.860
- Log(P)
- 1.43
- Log S
- -4.25
- Log(Vapor Pressure)
- -8.58
- Melting Point
- 174.4
- pKa Acid
- 8.35
- pKa Basic
- 2.31
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.9642 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9475 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9418 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.9282 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.9109 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 4 | 0.9080 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8947 |
| Caffeic acid O-methyltransferase | Q9ZTU2 | Q9ZTU2_LOLPR | Lolium perenne | 4 | 0.8883 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.8740 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8718 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8630 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8464 |
| Uracil-DNA glycosylase | P13051 | UNG_HUMAN | Homo sapiens | 4 | 0.8389 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8284 |
| HTH-type transcriptional regulator EthR | P9WMC1 | ETHR_MYCTU | Mycobacterium tuberculosis | 3 | 0.8203 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8144 |
| Uridine phosphorylase | Q5XA29 | Q5XA29_STRP6 | Streptococcus pyogenes serotype M6 | 4 | 0.8143 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.8122 |
| Single-strand selective monofunctional uracil DNA glycosylase | Q9YGN6 | SMUG1_XENLA | Xenopus laevis | 4 | 0.8109 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8107 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8092 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.8073 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.8001 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 4 | 0.7956 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9QYJ6 | PDE10_RAT | Rattus norvegicus | 3 | 0.7956 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7925 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7905 |
| Uridine phosphorylase | Q9KT71 | Q9KT71_VIBCH | Vibrio cholerae serotype O1 | 4 | 0.7887 |
| ALK tyrosine kinase receptor | Q9UM73 | ALK_HUMAN | Homo sapiens | 3 | 0.7839 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7837 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7833 |
| Uridine phosphorylase 2 | O95045 | UPP2_HUMAN | Homo sapiens | 4 | 0.7819 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7801 |
| Uracil-DNA glycosylase | P20536 | UNG_VACCC | Vaccinia virus | 4 | 0.7783 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 4 | 0.7767 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7676 |
| Histone deacetylase 8 | Q9BY41 | HDAC8_HUMAN | Homo sapiens | 3 | 0.7676 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 4 | 0.7659 |
| Glucose-1-phosphate thymidylyltransferase | Q9AGY4 | Q9AGY4_ANETH | Aneurinibacillus thermoaerophilus | 4 | 0.7620 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7619 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7592 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7565 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7526 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7506 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 4 | 0.7504 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7481 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7470 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7414 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.7390 |
| Uridine phosphorylase | Q9KT71 | Q9KT71_VIBCH | Vibrio cholerae serotype O1 | 4 | 0.7384 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7374 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.7357 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7347 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 4 | 0.7344 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7337 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7335 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7329 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7310 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7308 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 3 | 0.7300 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7288 |
| Peroxidase C1A | P00433 | PER1A_ARMRU | Armoracia rusticana | 2 | 0.7269 |
| Thymidylate kinase | Q9KQI2 | KTHY_VIBCH | Vibrio cholerae serotype O1 | 4 | 0.7262 |
| HTH-type transcriptional regulator EthR | P9WMC1 | ETHR_MYCTU | Mycobacterium tuberculosis | 4 | 0.7260 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7241 |
| Aspartokinase 1, chloroplastic | Q9LYU8 | AK1_ARATH | Arabidopsis thaliana | 3 | 0.7227 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7222 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7214 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7209 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 4 | 0.7199 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7189 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7172 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.7172 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 2 | 0.7167 |
| Nucleoside phosphorylase, putative | Q57VZ2 | Q57VZ2_TRYB2 | Trypanosoma brucei brucei | 4 | 0.7162 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7151 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7142 |
| Aminoglycoside N(3)-acetyltransferase | A0A3P1UCA6 | Q81P86_BACAN | Bacillus anthracis | 3 | 0.7109 |
| Histone deacetylase 8 | Q9BY41 | HDAC8_HUMAN | Homo sapiens | 3 | 0.7097 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 3 | 0.7092 |
| Uridine phosphorylase | P0A1F6 | UDP_SALTY | Salmonella typhimurium | 3 | 0.7089 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7074 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7054 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7053 |
| Virulence sensor histidine kinase PhoQ | P0DM80 | PHOQ_SALTY | Salmonella typhimurium | 3 | 0.7044 |
| Uracil-DNA glycosylase | P9WFQ9 | UNG_MYCTU | Mycobacterium tuberculosis | 4 | 0.7042 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7040 |
| Histidine kinase 4 | Q9C5U0 | AHK4_ARATH | Arabidopsis thaliana | 3 | 0.7037 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7036 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7035 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7022 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 2 | 0.7017 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7016 |