Cichorioside B



Compound IDCDAMM01090
Common nameCichorioside B
IUPAC name4-hydroxy-3,6-dimethyl-9-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
Molecular formulaC21H28O10

Experimental data

Retention time11.41
Adduct[M+H]+
Actual mz441.179
Theoretical mz441.175
Error8.21
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.7504

Identifiers and class information

Inchi keyZEMSXERQBUSFBA-KWBPDTRHNA-N
SmilesO=C1C=C(COC2OC(CO)C(O)C(O)C2O)C3C1=C(C)CC(O)C4C3OC(=O)C4C
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

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)9
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)440.446
Computed dipole moment(dipole)10.695
Total solvent accessible surface area (SASA)646.605
Hydrophobic component of SASA (FOSA)319.883
Hydrophilic component of SASA (FISA)289.231
Pie component of the SASA (PISA)37.491
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1227.83
Number of hydrogen bond donors (donorHB)5
Number of hydrogen bond acceptors (accptHB)16.9
Free energy of solvation of dipole (dip^2/V)0.0931666
Index of cohesive interaction in solids (ACxDN^.5/SA)0.058443
Globularity descriptor (glob)0.857598
Predicted polarizability in cubic angstroms (QPpolrz)37.563
Predicted hexadecane/gas partition coefficient (QPlogPC16)13.069
Predicted octanol/gas partition coefficient (QPlogPoct)30.444
Predicted water/gas partition coefficient (QPlogPw)25.482
Predicted octanol/water partition coefficient (QPlogPo/w)-1.79
Predicted aqueous solubility (QPlogS)-1.99
Conformation-independent predicted aqueous solubility (CIQPlogS)-1.909
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.015
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)17.911
Predicted brain/blood partition coefficient (QPlogBB)-2.601
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)6.4
Predicted skin permeability, log Kp (QPlogKp)-5.854
PM3 calculated ionization potential (IP(ev))10.119
PM3 calculated electron affinity (EA(eV))0.758
Number of likely metabolic reactions (#metab)10
Prediction of binding to human serum albumin (QPlogKhsa)-1.109
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)38.895
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)185.601
Number of nitrogen and oxygen atoms (#NandO)10
Number of violations of Lipinski’s rule of five (RuleOfFive)0
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
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P06239LCKTyrosine-protein kinase LCKT12499SwissTargetPrediction
P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
P08473MMENeprilysinT05409SwissTargetPrediction
P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction
P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
Q9H3R0KDM4CLysine-specific demethylase 4CT73863SwissTargetPrediction
Q6B0I6KDM4DLysine-specific demethylase 4DT17036SwissTargetPrediction
P10275ARAndrogen ReceptorT11211SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
Q9Y4C1KDM3ALysine-specific demethylase 3AT25362SwissTargetPrediction
P00519ABL1Tyrosine-protein kinase ABLT63505SwissTargetPrediction
O14965AURKASerine/threonine-protein kinase Aurora-AT87675SwissTargetPrediction
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
O14746TERTTelomerase reverse transcriptaseT86052SwissTargetPrediction
P24723PRKCHProtein kinase C etaT40149SwissTargetPrediction
P11387TOP1DNA topoisomerase IT09826SwissTargetPrediction
Q02156PRKCEProtein kinase C epsilonT00895SwissTargetPrediction
P12931SRCTyrosine-protein kinase SRCT85943SwissTargetPrediction
P40763STAT3Signal transducer and activator of transcription 3T29130SwissTargetPrediction
P32320CDACytidine deaminase (by homology)T79027SEA
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
Q05655PRKCDProtein kinase C deltaT44861SwissTargetPrediction
P42892ECE1Endothelin-converting enzyme 1T50970SwissTargetPrediction
Q9UGL1KDM5BLysine-specific demethylase 5BT56871SwissTargetPrediction
P11362FGFR1Fibroblast growth factor receptor 1T47101SwissTargetPrediction
O60502OGABifunctional protein NCOATT19567SwissTargetPrediction
Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
P23415GLRA1Glycine receptor subunit alpha-1T50269SwissTargetPrediction
P48167GLRBGlycine receptorT55285SwissTargetPrediction
P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
P06737PYGLLiver glycogen phosphorylaseT19184SwissTargetPrediction
Q15172PPP2R5ASerine/threonine protein phosphatase 2A, 56 kDa regulatory subunit, alpha isoformT57291SwissTargetPrediction
P67775PPP2CASerine/threonine protein phosphatase 2A, catalytic subunit, alpha isoformT40491SwissTargetPrediction
P50281MMP14Matrix metalloproteinase 14T65019SwissTargetPrediction
P17936IGFBP3Insulin-like growth factor binding protein 3T33455SwissTargetPrediction
Q13976PRKG1cGMP-dependent protein kinase 1 betaT78543SwissTargetPrediction
Q04759PRKCQProtein kinase C thetaT23995SwissTargetPrediction
P60568IL2Interleukin-2T61698SEA
P08151GLI1Zinc finger protein GLI1T40890SwissTargetPrediction
Q06187BTKTyrosine-protein kinase BTKT97719SwissTargetPrediction
P80192MAP3K9Mitogen-activated protein kinase kinase kinase 9T19760SwissTargetPrediction
P17931LGALS3Galectin-3T72038SwissTargetPrediction and SEA
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SwissTargetPrediction and SEA
P29317EPHA2Ephrin type-A receptor 2T57278SwissTargetPrediction
P41252IARSIsoleucyl-tRNA synthetaseT46515SwissTargetPrediction
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
Q15391P2RY14Purinergic receptor P2Y14T16555SEA
P05231IL6Interleukin-6T32578SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

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
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T12499DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P06239LCK
T54771DI0120Diabetes mellitus[ICD-11: 5A10]P13866SLC5A1
T54771DI0175Heart failure[ICD-11: BD10-BD1Z]P13866SLC5A1
T54771DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P13866SLC5A1
T05409DI0175Heart failure[ICD-11: BD10-BD1Z]P08473MME
T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
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
T16347DI0009Acute diabete complication[ICD-11: 5A2Y]P18031PTPN1
T16347DI0062Breast cancer[ICD-11: 2C60-2C6Y]P18031PTPN1
T16347DI0308Obesity[ICD-11: 5B80-5B81]P18031PTPN1
T16347DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P18031PTPN1
T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
T63505DI0062Breast cancer[ICD-11: 2C60-2C6Y]P00519ABL1
T63505DI0220Ischemia[ICD-11: 8B10-8B11]P00519ABL1
T63505DI0250Mature B-cell lymphoma[ICD-11: 2A85]P00519ABL1
T63505DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P00519ABL1
T87675DI0009Acute diabete complication[ICD-11: 5A2Y]O14965AURKA
T87675DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O14965AURKA
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
T86052DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]O14746TERT
T86052DI0284Myelodysplastic syndrome[ICD-11: 2A37]O14746TERT
T86052DI0326Pancreatic cancer[ICD-11: 2C10]O14746TERT
T40149DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P24723PRKCH
T09826DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P11387TOP1
T09826DI0095Colorectal cancer[ICD-11: 2B91]P11387TOP1
T09826DI0238Lung cancer[ICD-11: 2C25]P11387TOP1
T09826DI0321Ovarian cancer[ICD-11: 2C73]P11387TOP1
T09826DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11387TOP1
T00895DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]Q02156PRKCE
T00895DI0243Malaria[ICD-11: 1F40-1F45]Q02156PRKCE
T85943DI0062Breast cancer[ICD-11: 2C60-2C6Y]P12931SRC
T85943DI0220Ischemia[ICD-11: 8B10-8B11]P12931SRC
T85943DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P12931SRC
T85943DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P12931SRC
T29130DI0351Psoriasis[ICD-11: EA90]P40763STAT3
T79027DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P32320CDA
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
T44861DI0287Myocardial infarction[ICD-11: BA41-BA43]Q05655PRKCD
T47101DI0095Colorectal cancer[ICD-11: 2B91]P11362FGFR1
T47101DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P11362FGFR1
T47101DI0235Liver cancer[ICD-11: 2C12]P11362FGFR1
T47101DI0403Thrombocytopenia[ICD-11: 3B64]P11362FGFR1
T19567DI0025Alzheimer disease[ICD-11: 8A20]O60502OGA
T19567DI0331Parkinsonism[ICD-11: 8A00]O60502OGA
T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
T50269DI0411Tonus and reflex abnormality[ICD-11: MB47]P23415GLRA1
T55285DI0411Tonus and reflex abnormality[ICD-11: MB47]P48167GLRB
T30085DI0120Diabetes mellitus[ICD-11: 5A10]P31639SLC5A2
T30085DI0175Heart failure[ICD-11: BD10-BD1Z]P31639SLC5A2
T30085DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P31639SLC5A2
T40491DI0268Molluscum contagiosum[ICD-11: 1E76]P67775PPP2CA
T65019DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P50281MMP14
T33455DI0115Dementia[ICD-11: 6D80-6D8Z]P17936IGFBP3
T23995DI0413Transplant rejection[ICD-11: NE84]Q04759PRKCQ
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T97719DI0231Leukaemia[ICD-11: 2A60-2B33]Q06187BTK
T19760DI0037Asthma[ICD-11: CA23]P80192MAP3K9
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
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
T57278DI0060Brain cancer[ICD-11: 2A00]P29317EPHA2
T57278DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P29317EPHA2
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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