Methyl rosmarinate

Details

• Internal ID: d3eb179b-58cd-46f6-a2d2-e2513edbe2ba
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: methyl (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoate
• SMILES (Canonical): COC(=O)C(CC1=CC(=C(C=C1)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O
• SMILES (Isomeric): COC(=O)[C@@H](CC1=CC(=C(C=C1)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O
• InChI: InChI=1S/C19H18O8/c1-26-19(25)17(10-12-3-6-14(21)16(23)9-12)27-18(24)7-4-11-2-5-13(20)15(22)8-11/h2-9,17,20-23H,10H2,1H3/b7-4+/t17-/m1/s1
• InChI Key: XHALVRQBZGZHFE-BBOMDTFKSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₈
• Molecular Weight: 374.30 g/mol
• Exact Mass: 374.10016753 g/mol
• Topological Polar Surface Area (TPSA): 134.00 Ų
• XlogP: 2.70

Synonyms

• 99353-00-1
• methyl (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoate
• CHEMBL241405
• (R)-3-(3,4-Dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl (E)-3-(3,4-dihydroxyphenyl)acrylate
• Benzenepropanoic acid,a-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-,methyl ester, (aR)-
• Methylrosmarinic acid
• (+)-Methyl rosmarinate
• Boc-L-Lysinyl-L-Proline
• SCHEMBL12410151
• CHEBI:175804
• DTXSID901316093
• HY-N3266
• BDBM50210054
• AKOS037515147
• AS-83668
• CS-0023747
• F82128
• (R,E)-3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl 3-(3,4-dihydroxyphenyl)acrylate
• (R)-3-(3,4-Dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl(E)-3-(3,4-dihydroxyphenyl)acrylate
• 3-(3,4-dihydroxy-phenyl)-acrylic acid 2-(3,4-dihydroxy-phenyl)-1-methoxy carbonyl-ethyl ester
• Benzenepropanoic acid, .alpha.-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-, methyl ester, (.alpha.R)-
• methyl (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-propanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4393	P39900	Matrix metalloproteinase 12	2750 nM	IC50	PMID: 22658537
CHEMBL280	P45452	Matrix metalloproteinase 13	29030 nM	IC50	PMID: 22658537
CHEMBL283	P08254	Matrix metalloproteinase 3	28260 nM	IC50	PMID: 22658537
CHEMBL321	P14780	Matrix metalloproteinase 9	610 nM; 610 nM	IC50; IC50	via Super-PRED; PMID: 22658537
CHEMBL332	P03956	Matrix metalloproteinase-1	14740 nM; 14700 nM	IC50; IC50	PMID: 22658537; PMID: 23353736
CHEMBL333	P08253	Matrix metalloproteinase-2	3580 nM	IC50	PMID: 22658537

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.23%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.69%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.58%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.48%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.22%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.89%	86.33%
CHEMBL2581	P07339	Cathepsin D	92.35%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.58%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.67%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.01%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	83.96%	90.17%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	83.88%	100.00%
CHEMBL4208	P20618	Proteasome component C5	82.07%	90.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.44%	95.17%
CHEMBL3194	P02766	Transthyretin	81.29%	90.71%
CHEMBL2535	P11166	Glucose transporter	80.05%	98.75%

Plants that contains it

• Angelica keiskei
• Angelica ursina
• Ardisia macrocarpa
• Arnebia guttata
• Bourreria pulchra
• Cenchrus americanus
• Chlorophytum malayense
• Clausena indica
• Cordia sebestena
• Empetrum nigrum
• Ephedra lomatolepis
• Erigeron breviscapus
• Euonymus maackii
• Gentiana olivieri
• Glechoma grandis
• Glechoma hederacea
• Glechoma longituba
• Isodon coetsa
• Isodon serra
• Jateorhiza palmata
• Lindera umbellata
• Lycopus lucidus
• Melissa officinalis
• Morus notabilis
• Nicotiana gossei
• Origanum dictamnus
• Orthosiphon aristatus var. aristatus
• Physalis angulata
• Picradeniopsis oppositifolia
• Pinus halepensis
• Pinus thunbergii
• Pterocaulon rugosum
• Rauvolfia tetraphylla
• Ruta chalepensis
• Salvia miltiorrhiza
• Salvia prionitis
• Salvia sonchifolia
• Satureja montana
• Saussurea triangulata
• Senecio grandiflorus
• Stephania succifera
• Stevia salicifolia
• Tetraria capillaris
• Teucrium alyssifolium
• Vernonanthura serratuloides
• Zephyranthes carinata

Cross-Links

• PubChem: 6479915
• NPASS: NPC168799
• ChEMBL: CHEMBL241405
• LOTUS: LTS0224323
• wikiData: Q105007084