6-Caffeoylsucrose



Compound IDCDAMM00620
Common name6-Caffeoylsucrose
IUPAC name[6-[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
Molecular formulaC21H28O14

Experimental data

Retention time13.05
Adduct[M+H]+
Actual mz505.153
Theoretical mz505.155
Error4.9
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.7628

Identifiers and class information

Inchi keyUZUDNVXQOKQTDO-DUXPYHPUNA-N
SmilesO=C(OCC1OC(OC2(OC(CO)C(O)C2O)CO)C(O)C(O)C1O)C=CC3=CC=C(O)C(O)=C3
SuperclassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)9
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)18
Number of reactive functional groups (#rtvFG)3
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)504.444
Computed dipole moment(dipole)6.018
Total solvent accessible surface area (SASA)776.831
Hydrophobic component of SASA (FOSA)206.412
Hydrophilic component of SASA (FISA)422.265
Pie component of the SASA (PISA)148.154
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1424.33
Number of hydrogen bond donors (donorHB)9
Number of hydrogen bond acceptors (accptHB)18.6
Free energy of solvation of dipole (dip^2/V)0.0254297
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0718303
Globularity descriptor (glob)0.788094
Predicted polarizability in cubic angstroms (QPpolrz)40.705
Predicted hexadecane/gas partition coefficient (QPlogPC16)17.608
Predicted octanol/gas partition coefficient (QPlogPoct)37.665
Predicted water/gas partition coefficient (QPlogPw)33
Predicted octanol/water partition coefficient (QPlogPo/w)-2.733
Predicted aqueous solubility (QPlogS)-1.835
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.454
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.667
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.981
Predicted brain/blood partition coefficient (QPlogBB)-5.054
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.277
Predicted skin permeability, log Kp (QPlogKp)-7.052
PM3 calculated ionization potential (IP(ev))8.88
PM3 calculated electron affinity (EA(eV))0.761
Number of likely metabolic reactions (#metab)9
Prediction of binding to human serum albumin (QPlogKhsa)-1.534
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)0
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)247.559
Number of nitrogen and oxygen atoms (#NandO)14
Number of violations of Lipinski’s rule of five (RuleOfFive)3
Number of violations of Jorgensen’s rule of three (RuleOfThree)2

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
P02766TTRTransthyretinT86462SEA
P05067APPBeta amyloid A4 proteinT87024SwissTargetPrediction
P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P22748CA4Carbonic anhydrase IVT53378SEA
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction and SEA
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
Q05655PRKCDProtein kinase C deltaT44861SwissTargetPrediction
P52789HK2Hexokinase type IIT96685SEA
P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
P01112HRASTransforming protein p21/H-Ras-1T71081SEA
P60568IL2Interleukin-2T61698SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SwissTargetPrediction
P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SwissTargetPrediction
P04746AMY2APancreatic alpha-amylaseT86918SwissTargetPrediction
P14679TYRTyrosinaseT97035SEA
Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA
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
T86462DI0026Amyloidosis[ICD-11: 5D00]P02766TTR
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
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
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
T44861DI0287Myocardial infarction[ICD-11: BA41-BA43]Q05655PRKCD
T96685DI0133Epidermal dysplasias[ICD-11: EK90]P52789HK2
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
T40111DI0062Breast cancer[ICD-11: 2C60-2C6Y]P20839IMPDH1
T40111DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P20839IMPDH1
T40111DI0250Mature B-cell lymphoma[ICD-11: 2A85]P20839IMPDH1
T40111DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P20839IMPDH1
T40111DI0413Transplant rejection[ICD-11: NE84]P20839IMPDH1
T89360DI0413Transplant rejection[ICD-11: NE84]P12268IMPDH2
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
T45593DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10636MAPT
T45593DI0025Alzheimer disease[ICD-11: 8A20]P10636MAPT
T45593DI0265Mild neurocognitive disorder[ICD-11: 6D71]P10636MAPT
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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