(E)-1-O-Cinnamoyl-beta-D-glucose



Compound IDCDAMM02149
Common name(E)-1-O-Cinnamoyl-beta-D-glucose
IUPAC name[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 3-phenylprop-2-enoate
Molecular formulaC15H18O7

Experimental data

Retention time9.57
Adduct[M+Na]+
Actual mz333.095
Theoretical mz333.094
Error2.05
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.206

Identifiers and class information

Inchi keyCJGRGYBLAHPYOM-VOTSOKGWNA-N
SmilesO=C(OC1OC(CO)C(O)C(O)C1O)C=CC=2C=CC=CC2
SuperclassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives

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)0
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)9
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)310.303
Computed dipole moment(dipole)3.316
Total solvent accessible surface area (SASA)567.824
Hydrophobic component of SASA (FOSA)143.526
Hydrophilic component of SASA (FISA)200.162
Pie component of the SASA (PISA)224.135
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)973.234
Number of hydrogen bond donors (donorHB)4
Number of hydrogen bond acceptors (accptHB)10.5
Free energy of solvation of dipole (dip^2/V)0.0113003
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0369833
Globularity descriptor (glob)0.83643
Predicted polarizability in cubic angstroms (QPpolrz)29.156
Predicted hexadecane/gas partition coefficient (QPlogPC16)11.103
Predicted octanol/gas partition coefficient (QPlogPoct)21.172
Predicted water/gas partition coefficient (QPlogPw)18.187
Predicted octanol/water partition coefficient (QPlogPo/w)-0.151
Predicted aqueous solubility (QPlogS)-2.105
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.024
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.248
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)125.245
Predicted brain/blood partition coefficient (QPlogBB)-1.886
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)52.376
Predicted skin permeability, log Kp (QPlogKp)-3.555
PM3 calculated ionization potential (IP(ev))9.408
PM3 calculated electron affinity (EA(eV))0.72
Number of likely metabolic reactions (#metab)4
Prediction of binding to human serum albumin (QPlogKhsa)-0.882
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)63.608
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)129.041
Number of nitrogen and oxygen atoms (#NandO)7
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
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
O43570CA12Carbonic anhydrase XIIT16987SEA
Q16790CA9Carbonic anhydrase IXT64567SEA
Q07820MCL1Induced myeloid leukemia cell differentiation protein Mcl-1T14912SwissTargetPrediction
P04818TYMSThymidylate synthase (by homology)T98397SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SEA
P00918CA2Carbonic anhydrase IIT20401SEA
P10253GAALysosomal alpha-glucosidase (by homology)T31514SwissTargetPrediction
P06280GLAAlpha-galactosidase AT61339SEA
P27487DPP4Dipeptidyl peptidase IVT31391SwissTargetPrediction
P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P15121AKR1B1Aldose reductaseT26623SEA
P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
P00491PNPPurine nucleoside phosphorylaseT78198SwissTargetPrediction
P14920DAOD-amino-acid oxidaseT33124SwissTargetPrediction
P04183TK1Thymidine kinase, cytosolicT30081SwissTargetPrediction
O14684PTGESProstaglandin E synthaseT02562SwissTargetPrediction
P08253MMP2Matrix metalloproteinase 2T68251SEA
P08254MMP3Matrix metalloproteinase 3T86702SwissTargetPrediction
Q13547HDAC1Histone deacetylase 1T68547SwissTargetPrediction
P13726F3Coagulation factor VII/tissue factorT72702SEA
P08183ABCB1P-glycoprotein 1T25258SEA
P24941CDK2Cyclin-dependent kinase 2T70176SwissTargetPrediction
P78536ADAM17ADAM17T82393SwissTargetPrediction
P49841GSK3BGlycogen synthase kinase-3 betaT70977SwissTargetPrediction
P24385CCND1Cyclin-dependent kinase 4/cyclin D1T12355SwissTargetPrediction
P32320CDACytidine deaminase (by homology)T79027SwissTargetPrediction and SEA
P00813ADAAdenosine deaminaseT03661SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
Q9Y251HPSEHeparanaseT47623SEA
P04062GBABeta-glucocerebrosidaseT84173SwissTargetPrediction
P55263ADKAdenosine kinaseT91661SwissTargetPrediction and SEA
O60502OGABifunctional protein NCOATT19567SwissTargetPrediction
P11142HSPA8Heat shock cognate 71 kDa proteinT12817SwissTargetPrediction
P06493CDK1Cyclin-dependent kinase 1/cyclin B1T49898SwissTargetPrediction
P04406GAPDHGlyceraldehyde-3-phosphate dehydrogenase liverT39321SwissTargetPrediction and SEA
Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
P52789HK2Hexokinase type IIT96685SwissTargetPrediction and SEA
P11021HSPA578 kDa glucose-regulated proteinT77594SwissTargetPrediction
P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
P23526AHCYAdenosylhomocysteinaseT68698SwissTargetPrediction
P50750CDK9Cyclin-dependent kinase 9T44458SwissTargetPrediction
P16109SELPP-selectinT10965SEA
P14151SELLLeukocyte adhesion molecule-1T60526SEA
P01112HRASTransforming protein p21/H-Ras-1T71081SEA
P60568IL2Interleukin-2T61698SEA
P68400CSNK2A1Casein kinase II alphaT51565SwissTargetPrediction
P17931LGALS3Galectin-3T72038SEA
P19971TYMPThymidine phosphorylaseT59929SwissTargetPrediction
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SEA
Q13526PIN1Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1T16308SwissTargetPrediction
P63316TNNC1Troponin, cardiac muscleT12966SEA
P19438TNFRSF1ATumor necrosis factor receptor R1T86552SEA
P09382LGALS1Galectin-1T09544SEA
P01111NRASGTPase NRasT35486SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
Q15391P2RY14Purinergic receptor P2Y14T16555SEA
P05231IL6Interleukin-6T32578SEA
O75884RBBP9Putative hydrolase RBBP9T12084SEA
O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA
P55011SLC12A2Na-K-Cl cotransporterT85581SEA
Q07108CD69Early activation antigen CD69T48780SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA
P19429TNNI3Cardiac troponin IT20186SEA
P45379TNNT2Cardiac muscle troponin TT05887SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
T14912DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q07820MCL1
T14912DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]Q07820MCL1
T14912DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q07820MCL1
T14912DI0252Melanoma[ICD-11: 2C30]Q07820MCL1
T14912DI0274Multiple myeloma[ICD-11: 2A83]Q07820MCL1
T14912DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q07820MCL1
T98397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P04818TYMS
T98397DI0395Stomach cancer[ICD-11: 2B72]P04818TYMS
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
T20401DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P00918CA2
T20401DI0137Essential hypertension[ICD-11: BA00]P00918CA2
T20401DI0166Glaucoma[ICD-11: 9C61]P00918CA2
T20401DI0175Heart failure[ICD-11: BD10-BD1Z]P00918CA2
T20401DI0214Insomnia[ICD-11: 7A00-7A0Z]P00918CA2
T20401DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00918CA2
T31514DI0201Inborn carbohydrate metabolism error[ICD-11: 5C51]P10253GAA
T61339DI0201Inborn carbohydrate metabolism error[ICD-11: 5C51]P06280GLA
T31391DI0009Acute diabete complication[ICD-11: 5A2Y]P27487DPP4
T31391DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P27487DPP4
T54771DI0120Diabetes mellitus[ICD-11: 5A10]P13866SLC5A1
T54771DI0175Heart failure[ICD-11: BD10-BD1Z]P13866SLC5A1
T54771DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P13866SLC5A1
T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
T78198DI0120Diabetes mellitus[ICD-11: 5A10]P00491PNP
T78198DI0167Gout[ICD-11: FA25]P00491PNP
T78198DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P00491PNP
T78198DI0283Mycosis fungoides[ICD-11: 2B01]P00491PNP
T78198DI0351Psoriasis[ICD-11: EA90]P00491PNP
T33124DI0038Ataxic disorder[ICD-11: 8A03]P14920DAO
T33124DI0370Schizophrenia[ICD-11: 6A20]P14920DAO
T30081DI0012Acute myeloid leukaemia[ICD-11: 2A60]P04183TK1
T30081DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P04183TK1
T02562DI0025Alzheimer disease[ICD-11: 8A20]O14684PTGES
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T86702DI0101Corneal disease[ICD-11: 9A76-9A78]P08254MMP3
T86702DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P08254MMP3
T86702DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P08254MMP3
T86702DI0275Multiple sclerosis[ICD-11: 8A40]P08254MMP3
T86702DI0287Myocardial infarction[ICD-11: BA41-BA43]P08254MMP3
T86702DI0320Osteoarthritis[ICD-11: FA00-FA05]P08254MMP3
T86702DI0366Rheumatoid arthritis[ICD-11: FA20]P08254MMP3
T68547DI0274Multiple myeloma[ICD-11: 2A83]Q13547HDAC1
T68547DI0283Mycosis fungoides[ICD-11: 2B01]Q13547HDAC1
T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T70176DI0060Brain cancer[ICD-11: 2A00]P24941CDK2
T70176DI0062Breast cancer[ICD-11: 2C60-2C6Y]P24941CDK2
T70176DI0238Lung cancer[ICD-11: 2C25]P24941CDK2
T70176DI0241Lymphoma[ICD-11: 2A80-2A86]P24941CDK2
T70176DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P24941CDK2
T70176DI0303Non-small-cell lung cancer[ICD-11: 2C25]P24941CDK2
T70176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P24941CDK2
T70176DI0406Thymoma[ICD-11: 2C27]P24941CDK2
T82393DI0062Breast cancer[ICD-11: 2C60-2C6Y]P78536ADAM17
T82393DI0366Rheumatoid arthritis[ICD-11: FA20]P78536ADAM17
T70977DI0288Myotonic disorder[ICD-11: 8C71]P49841GSK3B
T12355DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P24385CCND1
T79027DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P32320CDA
T03661DI0016Adaptive immunity immunodeficiency[ICD-11: 4A01]P00813ADA
T03661DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P00813ADA
T03661DI0249Mature B-cell leukaemia[ICD-11: 2A82]P00813ADA
T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
T18639DI0081Chronic arterial occlusive disease[ICD-11: BD4Z]P05230FGF1
T18639DI0102Coronary atherosclerosis[ICD-11: BA52]P05230FGF1
T31621DI0005Acne vulgaris[ICD-11: ED80]P09038FGF2
T47623DI0020African trypanosomiasis[ICD-11: 1F51]Q9Y251HPSE
T47623DI0310Ocular disease[ICD-11: N.A.]Q9Y251HPSE
T84173DI0257Metabolic disorder[ICD-11: 5C50-5D2Z]P04062GBA
T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
T19567DI0025Alzheimer disease[ICD-11: 8A20]O60502OGA
T19567DI0331Parkinsonism[ICD-11: 8A00]O60502OGA
T49898DI0062Breast cancer[ICD-11: 2C60-2C6Y]P06493CDK1
T49898DI0238Lung cancer[ICD-11: 2C25]P06493CDK1
T49898DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P06493CDK1
T49898DI0250Mature B-cell lymphoma[ICD-11: 2A85]P06493CDK1
T49898DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06493CDK1
T39321DI0279Muscular atrophy[ICD-11: 8B61]P04406GAPDH
T39321DI0280Muscular dystrophy[ICD-11: 8C70]P04406GAPDH
T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
T96685DI0133Epidermal dysplasias[ICD-11: EK90]P52789HK2
T77594DI0252Melanoma[ICD-11: 2C30]P11021HSPA5
T77594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11021HSPA5
T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
T44458DI0012Acute myeloid leukaemia[ICD-11: 2A60]P50750CDK9
T44458DI0241Lymphoma[ICD-11: 2A80-2A86]P50750CDK9
T44458DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P50750CDK9
T44458DI0249Mature B-cell leukaemia[ICD-11: 2A82]P50750CDK9
T44458DI0250Mature B-cell lymphoma[ICD-11: 2A85]P50750CDK9
T44458DI0302Non-alcoholic fatty liver disease[ICD-11: DB92]P50750CDK9
T44458DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P50750CDK9
T10965DI0088Circulatory system disease[ICD-11: BE2Z]P16109SELP
T10965DI0381Sickle-cell disorder[ICD-11: 3A51]P16109SELP
T60526DI0037Asthma[ICD-11: CA23]P14151SELL
T60526DI0088Circulatory system disease[ICD-11: BE2Z]P14151SELL
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T51565DI0104Coronavirus infection[ICD-11: 1D92]P68400CSNK2A1
T51565DI0235Liver cancer[ICD-11: 2C12]P68400CSNK2A1
T51565DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P68400CSNK2A1
T72038DI0190Hypertension[ICD-11: BA00-BA04]P17931LGALS3
T72038DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P17931LGALS3
T72038DI0252Melanoma[ICD-11: 2C30]P17931LGALS3
T72038DI0302Non-alcoholic fatty liver disease[ICD-11: DB92]P17931LGALS3
T72038DI0351Psoriasis[ICD-11: EA90]P17931LGALS3
T59929DI0117Depression[ICD-11: 6A70-6A7Z]P19971TYMP
T86918DI0110Cystic fibrosis[ICD-11: CA25]P04746AMY2A
T86918DI0328Pancreatic malfunction[ICD-11: DC30-DC3Z]P04746AMY2A
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T16308DI0238Lung cancer[ICD-11: 2C25]Q13526PIN1
T12966DI0006Acquired cutaneous blood vessel malformation[ICD-11: EF20]P63316TNNC1
T12966DI0175Heart failure[ICD-11: BD10-BD1Z]P63316TNNC1
T86552DI0060Brain cancer[ICD-11: 2A00]P19438TNFRSF1A
T86552DI0321Ovarian cancer[ICD-11: 2C73]P19438TNFRSF1A
T35486DI0095Colorectal cancer[ICD-11: 2B91]P01111NRAS
T35486DI0172Head and neck cancer[ICD-11: 2D42]P01111NRAS
T35486DI0238Lung cancer[ICD-11: 2C25]P01111NRAS
T35486DI0326Pancreatic cancer[ICD-11: 2C10]P01111NRAS
T35486DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P01111NRAS
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
T85581DI0175Heart failure[ICD-11: BD10-BD1Z]P55011SLC12A2
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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