IMPPAT Phytochemical information: 
Carnosic acid
Carnosic acid
Summary

SMILES: OC(=O)[C@@]12CCCC([C@@H]2CCc2c1c(O)c(c(c2)C(C)C)O)(C)C
InChI: InChI=1S/C20H28O4/c1-11(2)13-10-12-6-7-14-19(3,4)8-5-9-20(14,18(23)24)15(12)17(22)16(13)21/h10-11,14,21-22H,5-9H2,1-4H3,(H,23,24)/t14-,20+/m0/s1
InChIKey: QRYRORQUOLYVBU-VBKZILBWSA-N
DeepSMILES: OC=O)[C@]CCCC[C@@H]6CCcc%10cO)ccc6)CC)C)))O))))))))C)C
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CCC1CCCCC21
Scaffold Graph/Node level: C1CCC2C(C1)CCC1CCCCC12
Scaffold Graph level: C1CCC2C(C1)CCC1CCCCC12
Functional groups: CC(=O)O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Abietane diterpenoids
Synonymous chemical names:
carnosic acid, salvin, Salvin
External chemical identifiers:
CID:CID_65126; ChEMBL:CHEMBL484853; ChEBI:CHEBI:65585; ZINC:ZINC000003984016; FDASRS:LI791SXT24; SureChEMBL:SCHEMBL9923661; MolPort-005-943-409
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Carnosic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 332.44
Log P RDKit 4.32
Topological polar surface area (Å2) RDKit 77.76
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.65
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Carnosic 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 Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.705018
Carnosic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.86
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Carnosic 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_001907ENSG00000148834GSTO19446BindingDB, ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576BindingDB, ChEMBL, NPASS
TAR_EXP_000270ENSG00000197408CYP2B61555ChEMBL, NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL, NPASS
TAR_EXP_000277ENSG00000130649CYP2E11571ChEMBL, NPASS
TAR_EXP_001145ENSG00000175535PNLIP5406BindingDB, ChEMBL, NPASS
TAR_EXP_000499ENSG00000108839ALOX12239NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL, NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559BindingDB, ChEMBL, NPASS
TAR_EXP_000272ENSG00000138115CYP2C81558ChEMBL, NPASS
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL, NPASS
TAR_EXP_000504ENSG00000179593ALOX15B247NPASS
TAR_EXP_001914ENSG00000148344PTGES9536BindingDB, ChEMBL, NPASS
TAR_EXP_000242ENSG00000168036CTNNB11499BindingDB, ChEMBL, NPASS
TAR_EXP_000701ENSG00000164120HPGD3248ChEMBL, NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216ChEMBL, NPASS
TAR_EXP_001374ENSG00000116128BCL9607BindingDB, ChEMBL, NPASS
TAR_EXP_001665ENSG00000111424VDR7421ChEMBL, NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000430ENSG00000160752FDPS2224BindingDB, ChEMBL, NPASS