1-O-Caffeoyl-(b-D-glucose 6-O-sulfate)



Compound IDCDAMM01785
Common name1-O-Caffeoyl-(b-D-glucose 6-O-sulfate)
IUPAC name[3,4,5-trihydroxy-6-(sulfooxymethyl)oxan-2-yl] 3-(3,4-dihydroxyphenyl)prop-2-enoate
Molecular formulaC15H18O12S

Experimental data

Retention time3.74
Adduct[M+H]+
Actual mz423.058
Theoretical mz423.059
Error3.73
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.9067

Identifiers and class information

Inchi keyGAIBMNYWJJJOQO-DUXPYHPUNA-N
SmilesO=C(OC1OC(COS(=O)(=O)O)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)3
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)13
Number of reactive functional groups (#rtvFG)3
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)422.36
Computed dipole moment(dipole)5.869
Total solvent accessible surface area (SASA)651.139
Hydrophobic component of SASA (FOSA)126.923
Hydrophilic component of SASA (FISA)376.9
Pie component of the SASA (PISA)145.062
Weakly polar component of the SASA (WPSA)2.253
Total solvent accesible volume (volume)1146.59
Number of hydrogen bond donors (donorHB)6
Number of hydrogen bond acceptors (accptHB)14.3
Free energy of solvation of dipole (dip^2/V)0.0300448
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0537946
Globularity descriptor (glob)0.813638
Predicted polarizability in cubic angstroms (QPpolrz)32.771
Predicted hexadecane/gas partition coefficient (QPlogPC16)13.921
Predicted octanol/gas partition coefficient (QPlogPoct)28.24
Predicted water/gas partition coefficient (QPlogPw)24.843
Predicted octanol/water partition coefficient (QPlogPo/w)-1.516
Predicted aqueous solubility (QPlogS)-1.93
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.604
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.432
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.669
Predicted brain/blood partition coefficient (QPlogBB)-4.01
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.24
Predicted skin permeability, log Kp (QPlogKp)-6.707
PM3 calculated ionization potential (IP(ev))8.959
PM3 calculated electron affinity (EA(eV))0.773
Number of likely metabolic reactions (#metab)5
Prediction of binding to human serum albumin (QPlogKhsa)-1.367
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)219.985
Number of nitrogen and oxygen atoms (#NandO)12
Number of violations of Lipinski’s rule of five (RuleOfFive)2
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
P07327ADH1AAlcohol dehydrogenase alpha chainT65570SwissTargetPrediction
O43570CA12Carbonic anhydrase XIIT16987SEA
Q16790CA9Carbonic anhydrase IXT64567SEA
P02766TTRTransthyretinT86462SEA
P05067APPBeta amyloid A4 proteinT87024SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P15121AKR1B1Aldose reductaseT26623SEA
P00491PNPPurine nucleoside phosphorylaseT78198SwissTargetPrediction
P14780MMP9Matrix metalloproteinase 9T54156SEA
P07195LDHBL-lactate dehydrogenase B chainT88057SwissTargetPrediction
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P52789HK2Hexokinase type IIT96685SEA
P16109SELPP-selectinT10965SEA
P60568IL2Interleukin-2T61698SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SwissTargetPrediction
P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SwissTargetPrediction
Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
P33316DUTdUTP pyrophosphataseT39054SwissTargetPrediction
O94759TRPM2Transient receptor potential cation channel subfamily M member 2T78205SwissTargetPrediction
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T65570DI0139Exposure to noxious substances harmful effect[ICD-11: NE61]P07327ADH1A
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
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
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
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
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T18639DI0081Chronic arterial occlusive disease[ICD-11: BD4Z]P05230FGF1
T18639DI0102Coronary atherosclerosis[ICD-11: BA52]P05230FGF1
T31621DI0005Acne vulgaris[ICD-11: ED80]P09038FGF2
T96685DI0133Epidermal dysplasias[ICD-11: EK90]P52789HK2
T10965DI0088Circulatory system disease[ICD-11: BE2Z]P16109SELP
T10965DI0381Sickle-cell disorder[ICD-11: 3A51]P16109SELP
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
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
T39054DI0238Lung cancer[ICD-11: 2C25]P33316DUT
T39054DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P33316DUT

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