1-O-Caffeoylglucose



Compound IDCDAMM00845
Common name1-O-Caffeoylglucose
IUPAC name[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 3-(3,4-dihydroxyphenyl)prop-2-enoate
Molecular formulaC15H18O9

Experimental data

Retention time0.46
Adduct[M+H]+
Actual mz343.1
Theoretical mz343.102
Error7.22
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.5519

Identifiers and class information

Inchi keyWQSDYZZEIBAPIN-DUXPYHPUNA-N
SmilesO=C(OC1OC(CO)C(O)C(O)C1O)C=CC2=CC=C(O)C(O)=C2
SuperclassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)1
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)11
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)342.302
Computed dipole moment(dipole)3.84
Total solvent accessible surface area (SASA)613.592
Hydrophobic component of SASA (FOSA)140.531
Hydrophilic component of SASA (FISA)326.642
Pie component of the SASA (PISA)146.418
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1040.8
Number of hydrogen bond donors (donorHB)6
Number of hydrogen bond acceptors (accptHB)12
Free energy of solvation of dipole (dip^2/V)0.0141653
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0479046
Globularity descriptor (glob)0.809461
Predicted polarizability in cubic angstroms (QPpolrz)29.834
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.523
Predicted octanol/gas partition coefficient (QPlogPoct)25.519
Predicted water/gas partition coefficient (QPlogPw)22.595
Predicted octanol/water partition coefficient (QPlogPo/w)-1.522
Predicted aqueous solubility (QPlogS)-2.15
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.042
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.313
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)7.913
Predicted brain/blood partition coefficient (QPlogBB)-3.423
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)2.647
Predicted skin permeability, log Kp (QPlogKp)-5.968
PM3 calculated ionization potential (IP(ev))8.955
PM3 calculated electron affinity (EA(eV))0.789
Number of likely metabolic reactions (#metab)6
Prediction of binding to human serum albumin (QPlogKhsa)-1.068
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)21.152
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)172.253
Number of nitrogen and oxygen atoms (#NandO)9
Number of violations of Lipinski’s rule of five (RuleOfFive)1
Number of violations of Jorgensen’s rule of three (RuleOfThree)1

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
O43570CA12Carbonic anhydrase XIIT16987SEA
Q16790CA9Carbonic anhydrase IXT64567SEA
Q07820MCL1Induced myeloid leukemia cell differentiation protein Mcl-1T14912SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SEA
P02766TTRTransthyretinT86462SEA
P05067APPBeta amyloid A4 proteinT87024SwissTargetPrediction and SEA
P00918CA2Carbonic anhydrase IIT20401SEA
P10253GAALysosomal alpha-glucosidase (by homology)T31514SwissTargetPrediction
P27487DPP4Dipeptidyl peptidase IVT31391SwissTargetPrediction
P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P22748CA4Carbonic anhydrase IVT53378SEA
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction and SEA
P00491PNPPurine nucleoside phosphorylaseT78198SwissTargetPrediction
P14920DAOD-amino-acid oxidaseT33124SwissTargetPrediction
P04183TK1Thymidine kinase, cytosolicT30081SwissTargetPrediction
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
P14780MMP9Matrix metalloproteinase 9T54156SEA
P03956MMP1Matrix metalloproteinase 1T52450SEA
P11309PIM1Serine/threonine-protein kinase PIM1T50594SwissTargetPrediction
P24941CDK2Cyclin-dependent kinase 2T70176SwissTargetPrediction
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
P78536ADAM17ADAM17T82393SwissTargetPrediction
P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P49841GSK3BGlycogen synthase kinase-3 betaT70977SwissTargetPrediction
Q09472EP300Histone acetyltransferase p300T25956SEA
P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
P32320CDACytidine deaminase (by homology)T79027SwissTargetPrediction
P00813ADAAdenosine deaminaseT03661SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P04062GBABeta-glucocerebrosidaseT84173SwissTargetPrediction
P55263ADKAdenosine kinaseT91661SwissTargetPrediction
O60502OGABifunctional protein NCOATT19567SwissTargetPrediction
P11142HSPA8Heat shock cognate 71 kDa proteinT12817SwissTargetPrediction
P06493CDK1Cyclin-dependent kinase 1/cyclin B1T49898SwissTargetPrediction
P04406GAPDHGlyceraldehyde-3-phosphate dehydrogenase liverT39321SwissTargetPrediction
Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
P52789HK2Hexokinase type IIT96685SEA
P11021HSPA578 kDa glucose-regulated proteinT77594SwissTargetPrediction
P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
P23526AHCYAdenosylhomocysteinaseT68698SwissTargetPrediction
P01112HRASTransforming protein p21/H-Ras-1T71081SEA
P60568IL2Interleukin-2T61698SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
P17931LGALS3Galectin-3T72038SEA
P19971TYMPThymidine phosphorylaseT59929SwissTargetPrediction
P14679TYRTyrosinaseT97035SEA
Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
P47989XDHXanthine dehydrogenaseT40954SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
P09382LGALS1Galectin-1T09544SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
Q15391P2RY14Purinergic receptor P2Y14T16555SEA
P05231IL6Interleukin-6T32578SEA
Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA
O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA
P10809HSPD1Mitochondrial matrix protein P1T11283SEA
P01100FOSProto-oncogene c-FosT28025SEA
Q07108CD69Early activation antigen CD69T48780SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
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
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
T86462DI0026Amyloidosis[ICD-11: 5D00]P02766TTR
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
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
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
T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
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
T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
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
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
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
T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
T50594DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11309PIM1
T50594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11309PIM1
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
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T82393DI0062Breast cancer[ICD-11: 2C60-2C6Y]P78536ADAM17
T82393DI0366Rheumatoid arthritis[ICD-11: FA20]P78536ADAM17
T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T70977DI0288Myotonic disorder[ICD-11: 8C71]P49841GSK3B
T25956DI0346Prostate cancer[ICD-11: 2C82]Q09472EP300
T25956DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q09472EP300
T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
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
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
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
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
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
T45593DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10636MAPT
T45593DI0025Alzheimer disease[ICD-11: 8A20]P10636MAPT
T45593DI0265Mild neurocognitive disorder[ICD-11: 6D71]P10636MAPT
T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1
T11283DI0120Diabetes mellitus[ICD-11: 5A10]P10809HSPD1
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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