Natural Product (NP) Details

General Information of the NP (ID: NP3788)
Name
Rosmarinic acid
Synonyms
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
    Click to Show/Hide
Species Origin Salvia rosmarinus ...     Click to Show/Hide
Salvia rosmarinus
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Lamiaceae
Genus: Salvia
Species: Salvia rosmarinus
Salvia miltiorrhiza
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Lamiaceae
Genus: Salvia
Species: Salvia miltiorrhiza
Mentha canadensis
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Lamiaceae
Genus: Mentha
Species: Mentha canadensis
Salvia flava
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Lamiaceae
Genus: Salvia
Species: Salvia flava
Salvia bowleyana
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Lamiaceae
Genus: Salvia
Species: Salvia bowleyana
Disease Rheumatoid arthritis [ICD-11: FA20] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -6.513
 
MDCK Permeability
 -5.001
 
PAMPA
 +++
 
HIA
 - - -
 
Distribution
VDss
 -0.346
 
PPB
 77.3%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 - -
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 - - -
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 - -
HLM Stability
 - - -
 
Excretion
CLplasma
 13.238
 
T1/2
 1.906
Toxicity
DILI
 +++
 
Rat Oral Acute Toxicity
 -
 
FDAMDD
 +++
 
Respiratory
 - -
 
Human Hepatotoxicity
 +
 
Ototoxicity
 +++
 
Drug-induced Nephrotoxicity
 -
 
Drug-induced Neurotoxicity
 - - -
 
Hematotoxicity
 - - -
 
Genotoxicity
 +++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
    Click to Show/Hide
    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C18H16O8
PubChem CID
5281792
Canonical SMILES
C1=CC(=C(C=C1CC(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O
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
CAS Number
CAS 20283-92-5
Herb ID
HBIN042438
ETMC ID
814
SymMap ID
SMIT00316
TCMSP ID
MOL011865
TTD Drug ID
D05PTT
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Resistance can be Reversed by This NP
          Cisplatin      Bladder cancer     Click to Show/Hide the Molecular Data of This Drug
                 Reversing Drug Resistance     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression FOXM1  Molecule Info 
Pathway MAP
                    In-vitro Model SK-OV-3 CVCL_0532 Ovarian serous cystadenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Rosmarinic acid methyl ester regulates ovarian cancer cell migration and reverses cisplatin resistance by inhibiting the expression of forkhead box M1.
Target and Pathway
Target(s) Bcl-2-like protein 3 (MCL1)  Molecule Info  [3]
Tyrosinase (TYR)  Molecule Info  [1]
BioCyc (S)-reticuline biosynthesis Click to Show/Hide
2 Eumelanin biosynthesis
3 L-dopachrome biosynthesis
KEGG Pathway PI3K-Akt signaling pathway Click to Show/Hide
2 MicroRNAs in cancer
3 Tyrosine metabolism
4 Riboflavin metabolism
5 Metabolic pathways
6 Melanogenesis
NetPath Pathway TCR Signaling Pathway Click to Show/Hide
Panther Pathway Apoptosis signaling pathway Click to Show/Hide
2 CCKR signaling map ST
Pathwhiz Pathway Riboflavin Metabolism Click to Show/Hide
2 Tyrosine Metabolism
Pathway Interaction Database E2F transcription factor network Click to Show/Hide
2 Direct p53 effectors
3 IL6-mediated signaling events
4 HIF-1-alpha transcription factor network
WikiPathways Apoptosis Click to Show/Hide
2 miR-targeted genes in muscle cell - TarBase
3 miR-targeted genes in lymphocytes - TarBase
4 miR-targeted genes in leukocytes - TarBase
5 Apoptosis Modulation and Signaling
6 Dopamine metabolism
References
Reference 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.
Reference 2 Rosmarinic Acid Methyl Ester Regulates Ovarian Cancer Cell Migration and Reverses Cisplatin Resistance by Inhibiting the Expression of Forkhead Box M1. Pharmaceuticals (Basel). 2020 Oct 12;13(10):302.
Reference 3 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.
 Download Picture         KEGG Link