Carnosic acid



Compound IDCDAMM01048
Common nameCarnosic acid
IUPAC name5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid
Molecular formulaC20H28O4

Experimental data

Retention time16.53
Adduct[M+H]+
Actual mz333.209
Theoretical mz333.206
Error9.38
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.9965

Identifiers and class information

Inchi keyQRYRORQUOLYVBU-YBMSBYLISA-N
SmilesO=C(O)C12C=3C(O)=C(O)C(=CC3CCC1C(C)(C)CCC2)C(C)C
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Pharmacokinetic properties

Number of descriptor values(#stars)0
Number of non-conjugated amine groups (#amine)0
Number of amidine and guanidine groups (#amidine)0
Number of carboxylic acid groups (#acid)1
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)4
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-1
Molecular weight (mol_MW)332.439
Computed dipole moment(dipole)8.173
Total solvent accessible surface area (SASA)570.953
Hydrophobic component of SASA (FOSA)426.581
Hydrophilic component of SASA (FISA)117.827
Pie component of the SASA (PISA)26.546
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1053.32
Number of hydrogen bond donors (donorHB)3
Number of hydrogen bond acceptors (accptHB)3.5
Free energy of solvation of dipole (dip^2/V)0.0634109
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0106176
Globularity descriptor (glob)0.876878
Predicted polarizability in cubic angstroms (QPpolrz)33.685
Predicted hexadecane/gas partition coefficient (QPlogPC16)9.794
Predicted octanol/gas partition coefficient (QPlogPoct)17.835
Predicted water/gas partition coefficient (QPlogPw)9.034
Predicted octanol/water partition coefficient (QPlogPo/w)3.765
Predicted aqueous solubility (QPlogS)-4.41
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.659
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-1.843
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)191.491
Predicted brain/blood partition coefficient (QPlogBB)-0.699
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)105.409
Predicted skin permeability, log Kp (QPlogKp)-3.213
PM3 calculated ionization potential (IP(ev))8.985
PM3 calculated electron affinity (EA(eV))0.152
Number of likely metabolic reactions (#metab)4
Prediction of binding to human serum albumin (QPlogKhsa)0.315
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)89.837
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)0
Van der Waals surface area (PSA)75.679
Number of nitrogen and oxygen atoms (#NandO)4
Number of violations of Lipinski’s rule of five (RuleOfFive)0
Number of violations of Jorgensen’s rule of three (RuleOfThree)0

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
Q8TDS4HCAR2Hydroxycarboxylic acid receptor 2T88185SwissTargetPrediction
P12821ACEAngiotensin-converting enzymeT98311SwissTargetPrediction
P09960LTA4HLeukotriene A4 hydrolaseT03691SwissTargetPrediction
P11940PABPC1Polyadenylate-binding protein 1T58679SwissTargetPrediction
P08473MMENeprilysinT05409SwissTargetPrediction
P10275ARAndrogen ReceptorT11211SwissTargetPrediction
P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
O14684PTGESProstaglandin E synthaseT02562SwissTargetPrediction
P15090FABP4Fatty acid binding protein adipocyteT07217SwissTargetPrediction
Q01469FABP5Fatty acid binding protein epidermalT21507SwissTargetPrediction
P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
Q13133NR1H3LXR-alphaT52297SwissTargetPrediction and SEA
P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
Q9HC97GPR35G-protein coupled receptor 35T56143SwissTargetPrediction
P35372OPRM1Mu opioid receptorT47768SwissTargetPrediction
P30559OXTROxytocin receptor (by homology)T84486SwissTargetPrediction
P41143OPRD1Delta opioid receptorT58992SwissTargetPrediction
P37231PPARGPeroxisome proliferator-activated receptor gammaT58921SwissTargetPrediction
P49356FNTBFarnesyl protein transferaseT13127SwissTargetPrediction
P35222CTNNB1Axin1/beta-cateninT82795SEA
P32246CCR1C-C chemokine receptor type 1T16016SwissTargetPrediction
P30556AGTR1Type-1 angiotensin II receptorT74456SwissTargetPrediction
P08842STSSteryl-sulfataseT33489SwissTargetPrediction
Q9UNA0ADAMTS5ADAMTS5T98896SwissTargetPrediction
P42892ECE1Endothelin-converting enzyme 1T50970SwissTargetPrediction
P05556ITGB1Integrin alpha2/beta1T01851SwissTargetPrediction
P23109AMPD1AMP deaminase 1T84553SwissTargetPrediction
P11362FGFR1Fibroblast growth factor receptor 1T47101SwissTargetPrediction
P15085CPA1Carboxypeptidase A1T33966SwissTargetPrediction
Q13258PTGDRProstanoid DP receptorT68782SwissTargetPrediction
P10619CTSALysosomal protective proteinT37154SwissTargetPrediction
P50052AGTR2Angiotensin II receptorT09909SwissTargetPrediction
Q00987MDM2p53-binding protein Mdm-2T00176SwissTargetPrediction
P50281MMP14Matrix metalloproteinase 14T65019SwissTargetPrediction
P51686CCR9C-C chemokine receptor type 9T97873SwissTargetPrediction
P23109AMPD1AMP deaminase 1T84553SwissTargetPrediction
P26010ITGB7Integrin alpha-4/beta-7T07403SwissTargetPrediction
P10415BCL2Apoptosis regulator Bcl-2T31309SwissTargetPrediction
Q16548BCL2A1Bcl-2-related protein A1 (by homology)T12797SwissTargetPrediction
P23109AMPD1AMP deaminase 1T84553SwissTargetPrediction
Q92843BCL2L2Apoptosis regulator Bcl-WT03755SwissTargetPrediction
P55055NR1H2LXR-betaT13714SwissTargetPrediction and SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T88185DI0203Inborn lipid metabolism error[ICD-11: 5C52]Q8TDS4HCAR2
T98311DI0175Heart failure[ICD-11: BD10-BD1Z]P12821ACE
T98311DI0190Hypertension[ICD-11: BA00-BA04]P12821ACE
T03691DI0012Acute myeloid leukaemia[ICD-11: 2A60]P09960LTA4H
T58679DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11940PABPC1
T05409DI0175Heart failure[ICD-11: BD10-BD1Z]P08473MME
T11211DI0005Acne vulgaris[ICD-11: ED80]P10275AR
T11211DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10275AR
T11211DI0021Alcoholic liver disease[ICD-11: DB94]P10275AR
T11211DI0062Breast cancer[ICD-11: 2C60-2C6Y]P10275AR
T11211DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P10275AR
T11211DI0145Female pelvic pain[ICD-11: GA34]P10275AR
T11211DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P10275AR
T11211DI0237Low bone mass disorder[ICD-11: FB83]P10275AR
T11211DI0247Mammary tumour[ICD-11: 2C60-2C6Z]P10275AR
T11211DI0346Prostate cancer[ICD-11: 2C82]P10275AR
T11211DI0401Testicular dysfunction[ICD-11: 5A81]P10275AR
T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
T02562DI0025Alzheimer disease[ICD-11: 8A20]O14684PTGES
T54156DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P14780MMP9
T54156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P14780MMP9
T54156DI0395Stomach cancer[ICD-11: 2B72]P14780MMP9
T54156DI0419Ulcerative colitis[ICD-11: DD71]P14780MMP9
T52297DI0117Depression[ICD-11: 6A70-6A7Z]Q13133NR1H3
T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
T47768DI0013Acute pain[ICD-11: MG31]P35372OPRM1
T47768DI0059Bowel habit change[ICD-11: ME05]P35372OPRM1
T47768DI0087Chronic pain[ICD-11: MG30]P35372OPRM1
T47768DI0101Corneal disease[ICD-11: 9A76-9A78]P35372OPRM1
T47768DI0105Cough[ICD-11: MD12]P35372OPRM1
T47768DI0117Depression[ICD-11: 6A70-6A7Z]P35372OPRM1
T47768DI0124Digestive system disease[ICD-11: DE2Z]P35372OPRM1
T47768DI0218Irritable bowel syndrome[ICD-11: DD91]P35372OPRM1
T47768DI0228Large intestine motility disorder[ICD-11: DB32]P35372OPRM1
T47768DI0317Opioid use disorder[ICD-11: 6C43]P35372OPRM1
T47768DI0324Pain[ICD-11: MG30-MG3Z]P35372OPRM1
T47768DI0349Pruritus[ICD-11: EC90]P35372OPRM1
T47768DI0374Sensation disturbance[ICD-11: MB40]P35372OPRM1
T84486DI0009Acute diabete complication[ICD-11: 5A2Y]P30559OXTR
T84486DI0041Autism spectrum disorder[ICD-11: 6A02]P30559OXTR
T84486DI0340Postpartum haemorrhage[ICD-11: JA43]P30559OXTR
T58992DI0059Bowel habit change[ICD-11: ME05]P41143OPRD1
T58992DI0218Irritable bowel syndrome[ICD-11: DD91]P41143OPRD1
T58992DI0324Pain[ICD-11: MG30-MG3Z]P41143OPRD1
T58921DI0009Acute diabete complication[ICD-11: 5A2Y]P37231PPARG
T58921DI0025Alzheimer disease[ICD-11: 8A20]P37231PPARG
T58921DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P37231PPARG
T13127DI0342Premature ageing appearance[ICD-11: LD2B]P49356FNTB
T82795DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35222CTNNB1
T16016DI0120Diabetes mellitus[ICD-11: 5A10]P32246CCR1
T16016DI0366Rheumatoid arthritis[ICD-11: FA20]P32246CCR1
T74456DI0137Essential hypertension[ICD-11: BA00]P30556AGTR1
T74456DI0190Hypertension[ICD-11: BA00-BA04]P30556AGTR1
T74456DI0373Secondary hypertension[ICD-11: BA04]P30556AGTR1
T74456DI0425Urinary system clinical symptom[ICD-11: MF8Y]P30556AGTR1
T33489DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P08842STS
T98896DI0320Osteoarthritis[ICD-11: FA00-FA05]Q9UNA0ADAMTS5
T01851DI0060Brain cancer[ICD-11: 2A00]P05556ITGB1
T01851DI0238Lung cancer[ICD-11: 2C25]P05556ITGB1
T01851DI0365Retinopathy[ICD-11: 9B71]P05556ITGB1
T47101DI0095Colorectal cancer[ICD-11: 2B91]P11362FGFR1
T47101DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P11362FGFR1
T47101DI0235Liver cancer[ICD-11: 2C12]P11362FGFR1
T47101DI0403Thrombocytopenia[ICD-11: 3B64]P11362FGFR1
T68782DI0102Coronary atherosclerosis[ICD-11: BA52]Q13258PTGDR
T37154DI0009Acute diabete complication[ICD-11: 5A2Y]P10619CTSA
T09909DI0190Hypertension[ICD-11: BA00-BA04]P50052AGTR2
T09909DI0373Secondary hypertension[ICD-11: BA04]P50052AGTR2
T00176DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q00987MDM2
T00176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q00987MDM2
T65019DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P50281MMP14
T97873DI0107Crohn disease[ICD-11: DD70]P51686CCR9
T07403DI0107Crohn disease[ICD-11: DD70]P26010ITGB7
T31309DI0062Breast cancer[ICD-11: 2C60-2C6Y]P10415BCL2
T31309DI0249Mature B-cell leukaemia[ICD-11: 2A82]P10415BCL2
T31309DI0273Motor neuron disease[ICD-11: 8B60]P10415BCL2
T31309DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P10415BCL2
T03755DI0286Myeloproliferative neoplasm[ICD-11: 2A20]Q92843BCL2L2
T13714DI0039Atopic eczema[ICD-11: EA80]P55055NR1H2

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