Details of the Drug

General Information of Drug (ID: DMQ6SJT)

Drug Name
ROSMARINIC ACID
Synonyms
rosmarinic acid; 20283-92-5; Rosemary acid; (R)-rosmarinic acid; UNII-MQE6XG29YI; Rosmarinate; MQE6XG29YI; CHEMBL324842; CHEBI:50371; Labiatenic acid; C18H16O8; (R)-O-(3,4-Dihydroxycinnamoyl)-3-(3,4- dihydroxyphenyl)lactic acid; 3,4-Dihydroxycinnamic acid (R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethyl ester; (2R)-3-(3,4-dihydroxyphenyl)-2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]propanoic acid; 537-15-5; Rosemaric acid; (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-propanoic acid
Indication
Disease Entry ICD 11 Status REF
Rheumatoid arthritis FA20 Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 360.3
Logarithm of the Partition Coefficient (xlogp) 2.4
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 8
Chemical Identifiers
Formula
C18H16O8
IUPAC Name
(2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoic acid
Canonical SMILES
C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O
InChI
InChI=1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+/t16-/m1/s1
InChIKey
DOUMFZQKYFQNTF-WUTVXBCWSA-N
Cross-matching ID
PubChem CID
5281792
ChEBI ID
CHEMBL50371
CAS Number
20283-92-5
UNII
MQE6XG29YI
DrugBank ID
DB16865
TTD ID
D05PTT
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Induced myeloid leukemia cell differentiation protein Mcl-1 (MCL1) TTL53M6 MCL1_HUMAN Inhibitor [2]
Tyrosinase (TYR) TTULVH8 TYRO_HUMAN Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Collagen alpha-1(I) chain (COL1A1) OTI31178 CO1A1_HUMAN Gene/Protein Processing [3]
Disintegrin and metalloproteinase domain-containing protein 17 (ADAM17) OTTM6KRB ADA17_HUMAN Gene/Protein Processing [4]
Kelch-like ECH-associated protein 1 (KEAP1) OTFHOD0C KEAP1_HUMAN Gene/Protein Processing [5]
NACHT, LRR and PYD domains-containing protein 3 (NLRP3) OTZM6MHU NLRP3_HUMAN Gene/Protein Processing [6]
Plasminogen activator inhibitor 1 (SERPINE1) OTT0MPQ3 PAI1_HUMAN Gene/Protein Processing [7]
Poly(ADP-ribose) glycohydrolase (PARG) OT10JTIO PARG_HUMAN Gene/Protein Processing [8]
Potassium channel subfamily U member 1 (KCNU1) OTEGV1XY KCNU1_HUMAN Gene/Protein Processing [9]
Superoxide dismutase , mitochondrial (SOD2) OTIWXGZ9 SODM_HUMAN Gene/Protein Processing [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Rheumatoid arthritis
ICD Disease Classification FA20
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Tyrosinase (TYR) DTT TYR 6.68E-04 2.54 1.15
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 A novel ring-expanded product with enhanced tyrosinase inhibitory activity from classical Fe-catalyzed oxidation of rosmarinic acid, a potent antio... Bioorg Med Chem Lett. 2010 Dec 15;20(24):7393-6.
2 In silico identification and biochemical evaluation of novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2). Bioorg Med Chem Lett. 2010 Dec 15;20(24):7331-6.
3 Human precision-cut liver slices as a model to test antifibrotic drugs in the early onset of liver fibrosis. Toxicol In Vitro. 2016 Sep;35:77-85. doi: 10.1016/j.tiv.2016.05.012. Epub 2016 May 26.
4 Rosmarinic acid down-regulates endothelial protein C receptor shedding in vitro and in vivo. Food Chem Toxicol. 2013 Sep;59:311-5. doi: 10.1016/j.fct.2013.06.003. Epub 2013 Jun 14.
5 Identification of lead-produced lipid hydroperoxides in human HepG2 cells and protection using rosmarinic and ascorbic acids with a reference to their regulatory roles on Nrf2-Keap1 antioxidant pathway. Chem Biol Interact. 2019 Dec 1;314:108847. doi: 10.1016/j.cbi.2019.108847. Epub 2019 Oct 11.
6 Rosmarinic acid decreases viability, inhibits migration and modulates expression of apoptosis-related CASP8/CASP3/NLRP3 genes in human metastatic melanoma cells. Chem Biol Interact. 2023 Apr 25;375:110427. doi: 10.1016/j.cbi.2023.110427. Epub 2023 Feb 28.
7 Organ- and species-specific biological activity of rosmarinic acid. Toxicol In Vitro. 2016 Apr;32:261-8. doi: 10.1016/j.tiv.2016.01.009. Epub 2016 Jan 19.
8 The effect of dietary polyphenols on the epigenetic regulation of gene expression in MCF7 breast cancer cells. Toxicol Lett. 2010 Feb 1;192(2):119-25.
9 Rosmarinic acid compromises human sperm functions by an intracellular Ca(2+) concentration-related mechanism. Reprod Toxicol. 2018 Oct;81:58-63. doi: 10.1016/j.reprotox.2018.07.079. Epub 2018 Jul 20.