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
• #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: CHEBI:50371
  CAS Number: 20283-92-5
  TTD ID: D05PTT

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
Amine oxidase A (MAOA)	OT8NIWMQ	AOFA_HUMAN	Gene/Protein Processing	[3]
Amine oxidase B (MAOB)	OTTDFM1O	AOFB_HUMAN	Gene/Protein Processing	[3]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[4]
Caspase-8 (CASP8)	OTA8TVI8	CASP8_HUMAN	Gene/Protein Processing	[4]
Catalase (CAT)	OTHEBX9R	CATA_HUMAN	Gene/Protein Processing	[5]
Collagen alpha-1(I) chain (COL1A1)	OTI31178	CO1A1_HUMAN	Gene/Protein Processing	[6]
Disintegrin and metalloproteinase domain-containing protein 17 (ADAM17)	OTTM6KRB	ADA17_HUMAN	Gene/Protein Processing	[7]
DNA cytosine-5)-methyltransferase 1 (DNMT1)	OTM2DGTK	DNMT1_HUMAN	Gene/Protein Processing	[8]
Glutathione peroxidase 1 (GPX1)	OTE2O72Q	GPX1_HUMAN	Gene/Protein Processing	[5]
Glutathione S-transferase omega-1 (GSTO1)	OTUJ93MN	GSTO1_HUMAN	Gene/Protein Processing	[5]

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

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] Combining initro and in silico approaches to evaluate the multifunctional profile of rosmarinic acid from Blechnum brasiliense on targets related to neurodegeneration. Chem Biol Interact. 2016 Jul 25;254:135-45.
• [4] 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.
• [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] 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.
• [7] 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.
• [8] Frequent gene hypermethylation in laryngeal cancer cell lines and the resistance to demethylation induction by plant polyphenols. Toxicol In Vitro. 2011 Feb;25(1):213-21. doi: 10.1016/j.tiv.2010.11.003. Epub 2010 Nov 13.