Cistanoside C



Compound IDCDAMM02971
Common nameCistanoside C
IUPAC name[5-hydroxy-6-[2-(4-hydroxy-3-methoxyphenyl)ethoxy]-2-(hydroxymethyl)-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl] 3-(3,4-dihydroxyphenyl)prop-2-enoate
Molecular formulaC30H38O15

Experimental data

Retention time3.5
Adduct[M+Na]+
Actual mz661.212
Theoretical mz661.21
Error2.7
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.2667

Identifiers and class information

Inchi keySUNMCVVGOLDIKD-KVEOLEFTNA-N
SmilesO=C(OC1C(OC(OCCC2=CC=C(O)C(OC)=C2)C(O)C1OC3OC(C)C(O)C(O)C3O)CO)C=CC4=CC=C(O)C(O)=C4
SuperclassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives

Plant source

  • Clitoria ternatea L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)10
    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)20
    Number of reactive functional groups (#rtvFG)3
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)638.621
    Computed dipole moment(dipole)5.846
    Total solvent accessible surface area (SASA)986.459
    Hydrophobic component of SASA (FOSA)370.288
    Hydrophilic component of SASA (FISA)338.201
    Pie component of the SASA (PISA)277.97
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1853.03
    Number of hydrogen bond donors (donorHB)8
    Number of hydrogen bond acceptors (accptHB)20.3
    Free energy of solvation of dipole (dip^2/V)0.0184421
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0582052
    Globularity descriptor (glob)0.739619
    Predicted polarizability in cubic angstroms (QPpolrz)57.817
    Predicted hexadecane/gas partition coefficient (QPlogPC16)22.056
    Predicted octanol/gas partition coefficient (QPlogPoct)42.635
    Predicted water/gas partition coefficient (QPlogPw)33.585
    Predicted octanol/water partition coefficient (QPlogPo/w)-0.334
    Predicted aqueous solubility (QPlogS)-3.631
    Conformation-independent predicted aqueous solubility (CIQPlogS)-4.568
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-7.071
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)6.148
    Predicted brain/blood partition coefficient (QPlogBB)-4.764
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)2.015
    Predicted skin permeability, log Kp (QPlogKp)-4.853
    PM3 calculated ionization potential (IP(ev))8.593
    PM3 calculated electron affinity (EA(eV))1.014
    Number of likely metabolic reactions (#metab)10
    Prediction of binding to human serum albumin (QPlogKhsa)-1.236
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)0.23
    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)236.673
    Number of nitrogen and oxygen atoms (#NandO)15
    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 proteinT87024SEA
    P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
    P43166CA7Carbonic anhydrase VIIT37541SEA
    P23280CA6Carbonic anhydrase VIT06569SEA
    Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
    P15121AKR1B1Aldose reductaseT26623SEA
    P11926ODC1Ornithine decarboxylaseT60366SEA
    P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
    P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
    Q09472EP300Histone acetyltransferase p300T25956SEA
    P08581METHepatocyte growth factor receptorT40474SEA
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
    P16109SELPP-selectinT10965SEA
    P14151SELLLeukocyte adhesion molecule-1T60526SEA
    P01112HRASTransforming protein p21/H-Ras-1T71081SEA
    P60568IL2Interleukin-2T61698SEA
    P17931LGALS3Galectin-3T72038SEA
    P04746AMY2APancreatic alpha-amylaseT86918SEA
    P14679TYRTyrosinaseT97035SEA
    Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
    P10636MAPTMicrotubule-associated protein tauT45593SEA
    Q04760GLO1Glyoxalase IT88285SEA
    Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    Q99417MYCBPMYCBP messenger RNAT37298SEA
    Q8N183NDUFAF2HUMAN NADH:ubiquinone oxidoreductase complex assembly factor 2T01453SEA
    Q9P0J0NDUFA13Mitochondrial complex IT82391SEA
    Q9Y6M9NDUFB9HUMAN NADH:ubiquinone oxidoreductase subunit B9T01465SEA
    Q8N183NDUFAF2HUMAN NADH:ubiquinone oxidoreductase complex assembly factor 2T01453SEA
    P03897MT-ND3NADH dehydrogenaseT77195SEA

    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
    T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
    T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
    T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
    T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
    T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
    T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
    T25956DI0346Prostate cancer[ICD-11: 2C82]Q09472EP300
    T25956DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q09472EP300
    T40474DI0238Lung cancer[ICD-11: 2C25]P08581MET
    T40474DI0303Non-small-cell lung cancer[ICD-11: 2C25]P08581MET
    T40474DI0407Thyroid cancer[ICD-11: 2D10]P08581MET
    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
    T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
    T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
    T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
    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
    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
    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
    T37298DI0235Liver cancer[ICD-11: 2C12]Q99417MYCBP
    T82391DI0069Cardiomyopathy[ICD-11: BC43]Q9P0J0NDUFA13
    T77195DI0331Parkinsonism[ICD-11: 8A00]P03897MT-ND3

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