IMPPAT Phytochemical information: 
Rosmarinic acid
Rosmarinic acid
Summary

SMILES: O=C(O[C@@H](C(=O)O)Cc1ccc(c(c1)O)O)/C=C/c1ccc(c(c1)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
DeepSMILES: O=CO[C@@H]C=O)O))Ccccccc6)O))O))))))))/C=C/cccccc6)O))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OCCc1ccccc1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OCCC1CCCCC1
Scaffold Graph level: CC(CCCC1CCCCC1)CCC1CCCCC1
Functional groups: c/C=C/C(=O)OC; CC(=O)O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Cinnamic acids and derivatives
ClassyFire Subclass: Hydroxycinnamic acids and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acids and derivatives
Synonymous chemical names:
rosmarinic acid, Rosmarinic acid
External chemical identifiers:
CID:CID_5281792; ChEMBL:CHEMBL324842; ChEBI:CHEBI:50371; ZINC:ZINC000000899870; FDASRS:MQE6XG29YI; SureChEMBL:SCHEMBL1650675; MolPort-001-740-341
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Rosmarinic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 360.32
Log P RDKit 1.76
Topological polar surface area (Å2) RDKit 144.52
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.11
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Rosmarinic acid
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.297648
Rosmarinic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -6.82
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Rosmarinic acid
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001360ENSG00000004700RECQL5965ChEMBL, NPASS
TAR_EXP_001485ENSG00000197299BLM641ChEMBL, NPASS
TAR_EXP_000450ENSG00000004487KDM1A23028BindingDB, ChEMBL
TAR_EXP_001551ENSG00000145335SNCA6622ChEMBL, NPASS
TAR_EXP_001128ENSG00000067225PKM5315NPASS
TAR_EXP_001150ENSG00000070501POLB5423ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL, NPASS
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL, NPASS
TAR_EXP_000883ENSG00000196611MMP14312ChEMBL, NPASS
TAR_EXP_001554ENSG00000291971SRC6714ChEMBL, NPASS
TAR_EXP_001567ENSG00000115415STAT16772ChEMBL, NPASS
TAR_EXP_001568ENSG00000168610STAT36774ChEMBL, NPASS
TAR_EXP_000456ENSG00000085662AKR1B1231ChEMBL, NPASS
TAR_EXP_000515ENSG00000010810FYN2534ChEMBL, NPASS
TAR_EXP_000519ENSG00000171298GAA2548NPASS
TAR_EXP_000567ENSG00000177628GBA12629NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000674ENSG00000123636BAZ2B29994ChEMBL, NPASS
TAR_EXP_000706ENSG00000291796APEX1328ChEMBL, NPASS
TAR_EXP_000711ENSG00000086696HSD17B23294BindingDB, ChEMBL, NPASS
TAR_EXP_000740ENSG00000114378HYAL13373BindingDB, NPASS
TAR_EXP_000752ENSG00000142192APP351BindingDB, ChEMBL, NPASS
TAR_EXP_000786ENSG00000177606JUN3725ChEMBL, NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_001868ENSG00000036672USP29099NPASS
TAR_EXP_001728ENSG00000176208ATAD579915NPASS
TAR_EXP_001636ENSG00000118271TTR7276ChEMBL, NPASS
TAR_EXP_001609ENSG00000151090THRB7068ChEMBL, NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000864ENSG00000143384MCL14170BindingDB, ChEMBL, NPASS
TAR_EXP_001569ENSG00000173757STAT5B6777ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000822ENSG00000182866LCK3932ChEMBL, NPASS