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Sinapaldehyde
- Family: Plantae - Lamiaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Cinnamaldehyde
| Canonical Smiles | COc1cc(/C=C/C=O)cc(c1O)OC |
|---|---|
| InChI | InChI=1S/C11H12O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-7,13H,1-2H3/b4-3+ |
| InChIKey | CDICDSOGTRCHMG-ONEGZZNKSA-N |
| Formula | C11H12O4 |
| HBA | 4 |
| HBD | 1 |
| MW | 208.21 |
| Rotatable Bonds | 4 |
| TPSA | 55.76 |
| LogP | 1.62 |
| Number Rings | 1 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 15 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.18 |
| Exact Mass | 208.07 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Dracaena cinnabari | Dracaenaceae | Plantae | 1142948 |
| 2 | Premna odorata | Lamiaceae | Plantae | 1037421 |
Showing of synonyms
Sinapaldehyde
Trans-3,5-Dimethoxy-4-Hydroxy Cinnamaldehyde
2-Propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)-, (2E)-
3,5-Dimethoxy-4-hydroxycinnamaldehyde (E)
2-Propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)-, (E)-
627-731-3
4206-58-0
Sinapinaldehyde
Sinapyl aldehyde
Sinapoyl aldehyde
(E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylaldehyde
20649-43-8
Sinapic aldehyde
Trans-Sinapaldehyde
Trans-3,5-Dimethoxy-4-hydroxycinnamaldehyde
3,5-Dimethoxy-4-hydroxycinnamaldehyde
(E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenal
(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enal
(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enal
(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)acrylaldehyde
4VB87UV6WG
CHEBI:27949
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenal
Cinnamaldehyde, 4-hydroxy-3,5-dimethoxy-
(E)-3,5-Dimethoxy-4-hydroxyphenylpropenaldehyde
(E)-sinapaldehyde
4-Hydroxy-3,5-dimethoxy-cinnemaldehyde
(E)-Sinapinaldehyde
(E)-sinapoaldehyde
MFCD00075980
(E)-sinapoyl aldehyde
Bmse000606
Bmse010085
UNII-4VB87UV6WG
SCHEMBL197270
CHEMBL225067
MEGxp0_001085
ACon1_001103
DTXSID10863340
HY-N1312
MSK168185
3,4-dimethoxy-4-hydroxycinnamaldehyde
AKOS015999009
FS65543
NCGC00169673-01
BS-42317
DA-68299
1ST168185
CS-0016716
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenal
C05610
G12202
3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylaldehyde
EN300-1860016
Trans-3,5-Dimethoxy-4-hydroxycinnamaldehyde, 98%
(E)-3-(4-hydroxy-3,5-dimethoxy-phenyl)prop-2-enal
BRD-K19027245-001-01-0
Q63392287
072ADBB5-241A-428F-B856-9EF1F076A5A6
Retention index: SEE J. Agric. Food Chem. 2009, 57, 3217-3227
SNY
- Helal I.E, Elsbaey M, et al. (2022). A new homoisoflavan from Dracaena cinnabari Balf. f. resin: a-glucosidase and COX-II inhibitory activity. Natural product research, 2022, 36(5), 1224-1229. [View] [PubMed]
- Elmaidomy A.H, Mohammed R, et al. (2019). Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco. Metabolites, 2019, 9(10), 223. [View] [PubMed]
Pubchem:
5280802
Cas:
4206-58-0
Gnps:
CCMSLIB00000217497
Zinc:
ZINC000001530242
Kegg Ligand:
C05610
Chebi:
27949
Nmrshiftdb2:
60022313
Metabolights:
MTBLC27949
Chembl:
CHEMBL225067
Pdb Ligand:
SNY
CPRiL:
238139
SMILES: c1ccccc1
Level: 0
Mol. Weight: 208.21 g/mol
Anti-alpha-glucosidase
Absorption
- Caco-2 (logPapp)
- -4.35
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -3.920
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.96
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.380
- Plasma Protein Binding
- 28.77
- 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
- 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
- 7.180
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.510
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Toxic
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.130
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 7.010
- Micronucleos
- Safe
- 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
- 4.250
- Rat (Acute)
- 1.920
- Rat (Chronic Oral)
- 2.140
- Fathead Minnow
- 4.270
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 321.730
- Hydration Free Energy
- -9.220
- Log(D) at pH=7.4
- 1.070
- Log(P)
- 0.84
- Log S
- -2.12
- Log(Vapor Pressure)
- -4.34
- Melting Point
- 117.4
- pKa Acid
- 7.05
- pKa Basic
- 0.9
| 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 | 0.9743 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9464 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9460 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9376 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.9243 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.9236 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 4 | 0.9072 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 4 | 0.9068 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.9066 |
| Uracil-DNA glycosylase | P20536 | UNG_VACCC | Vaccinia virus | 4 | 0.9048 |
| Caffeic acid O-methyltransferase | Q9ZTU2 | Q9ZTU2_LOLPR | Lolium perenne | 4 | 0.8934 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.8889 |
| Uracil-DNA glycosylase | P13051 | UNG_HUMAN | Homo sapiens | 4 | 0.8742 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8732 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.8689 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8685 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8621 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8609 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8590 |
| Uracil-DNA glycosylase | P9WFQ9 | UNG_MYCTU | Mycobacterium tuberculosis | 4 | 0.8584 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.8505 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.8410 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8388 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.8342 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.8201 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.8146 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8121 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.8051 |
| Thymidylate kinase | Q9KQI2 | KTHY_VIBCH | Vibrio cholerae serotype O1 | 4 | 0.7995 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7932 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.7816 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7802 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7795 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7749 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7742 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7720 |
| Uridine phosphorylase | Q9KT71 | Q9KT71_VIBCH | Vibrio cholerae serotype O1 | 4 | 0.7715 |
| Aminoglycoside N(3)-acetyltransferase | A0A3P1UCA6 | Q81P86_BACAN | Bacillus anthracis | 3 | 0.7710 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7636 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 4 | 0.7602 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7601 |
| Glucose-1-phosphate thymidylyltransferase | Q9AGY4 | Q9AGY4_ANETH | Aneurinibacillus thermoaerophilus | 4 | 0.7587 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7577 |
| Uridine phosphorylase | P0A1F6 | UDP_SALTY | Salmonella typhimurium | 4 | 0.7561 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7550 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7541 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7540 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7518 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.7514 |
| Putative glycosyl transferase | Q9RN61 | Q9RN61_STRNO | Streptomyces nogalater | 5 | 0.7476 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7475 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7460 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7403 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7401 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7399 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7386 |
| Beta-glucosidase 12 | B8AVF0 | BGL12_ORYSI | Oryza sativa subsp. indica | 2 | 0.7382 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7320 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7311 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7297 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7291 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7260 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7232 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7221 |
| 3'-5' exoribonuclease Rv2179c | P9WJ73 | EXRBN_MYCTU | Mycobacterium tuberculosis | 2 | 0.7207 |
| DNA-binding transcriptional dual regulator CRP | P0ACJ8 | CRP_ECOLI | Escherichia coli | 3 | 0.7185 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7156 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 2 | 0.7141 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7133 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 2 | 0.7127 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7118 |
| DNA-binding transcriptional dual regulator CRP | P0ACJ8 | CRP_ECOLI | Escherichia coli | 3 | 0.7116 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7110 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7108 |
| Purine nucleoside phosphorylase DeoD-type | B1JL34 | DEOD_YERPY | Yersinia pseudotuberculosis serotype O:3 | 2 | 0.7089 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 4 | 0.7088 |
| dTDP-4-dehydrorhamnose 3,5-epimerase | A0A6L7H6N0 | A0A1S0QLH9_BACAN | Bacillus anthracis | 3 | 0.7080 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7064 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 3 | 0.7059 |
| Uridine phosphorylase | P0A1F6 | UDP_SALTY | Salmonella typhimurium | 3 | 0.7045 |
| Single-strand selective monofunctional uracil DNA glycosylase | Q9YGN6 | SMUG1_XENLA | Xenopus laevis | 4 | 0.7022 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 2 | 0.7007 |
| dTDP-4-dehydro-6-deoxyglucose 3-epimerase | Q5SFD1 | CHMJ_STRBI | Streptomyces bikiniensis | 3 | 0.7006 |