Lippioside I



Compound IDCDAMM01818
Common nameLippioside I
IUPAC name6,7-dihydroxy-7-methyl-1-[3,4,5-trihydroxy-6-[3-(4-hydroxyphenyl)prop-2-enoyloxymethyl]oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
Molecular formulaC25H30O13

Experimental data

Retention time2.88
Adduct[M+H]+
Actual mz539.183
Theoretical mz539.176
Error11.91
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.7231

Identifiers and class information

Inchi keyQCPZTWAULZJVIK-QPJJXVBHNA-N
SmilesO=C(O)C1=COC(OC2OC(COC(=O)C=CC3=CC=C(O)C=C3)C(O)C(O)C2O)C4C1CC(O)C4(O)C
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Pharmacokinetic properties

Number of descriptor values(#stars)6
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)14
Number of reactive functional groups (#rtvFG)3
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)538.504
Computed dipole moment(dipole)6.113
Total solvent accessible surface area (SASA)815.979
Hydrophobic component of SASA (FOSA)245.481
Hydrophilic component of SASA (FISA)349.409
Pie component of the SASA (PISA)221.089
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1518.58
Number of hydrogen bond donors (donorHB)7
Number of hydrogen bond acceptors (accptHB)17.4
Free energy of solvation of dipole (dip^2/V)0.0246105
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0564182
Globularity descriptor (glob)0.783028
Predicted polarizability in cubic angstroms (QPpolrz)47.741
Predicted hexadecane/gas partition coefficient (QPlogPC16)18.047
Predicted octanol/gas partition coefficient (QPlogPoct)36.461
Predicted water/gas partition coefficient (QPlogPw)29.866
Predicted octanol/water partition coefficient (QPlogPo/w)-0.512
Predicted aqueous solubility (QPlogS)-3.119
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.64
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.29
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)1.219
Predicted brain/blood partition coefficient (QPlogBB)-4.08
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.446
Predicted skin permeability, log Kp (QPlogKp)-5.836
PM3 calculated ionization potential (IP(ev))9.107
PM3 calculated electron affinity (EA(eV))0.715
Number of likely metabolic reactions (#metab)7
Prediction of binding to human serum albumin (QPlogKhsa)-1.23
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)230.347
Number of nitrogen and oxygen atoms (#NandO)13
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
P08473MMENeprilysinT05409SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9UHC9NPC1L1Niemann-Pick C1-like protein 1T33901SwissTargetPrediction
Q04609FOLH1Glutamate carboxypeptidase IIT97071SwissTargetPrediction
P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SwissTargetPrediction and SEA
P42892ECE1Endothelin-converting enzyme 1T50970SwissTargetPrediction
P16109SELPP-selectinT10965SwissTargetPrediction
P60568IL2Interleukin-2T61698SwissTargetPrediction and SEA
P17931LGALS3Galectin-3T72038SwissTargetPrediction
P16885PLCG2Phospholipase C-gamma-2T93922SEA
P20273CD22CD22T37539SwissTargetPrediction
O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T05409DI0175Heart failure[ICD-11: BD10-BD1Z]P08473MME
T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
T33901DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q9UHC9NPC1L1
T97071DI0122Diagnostic imaging[ICD-11: N.A.]Q04609FOLH1
T97071DI0346Prostate cancer[ICD-11: 2C82]Q04609FOLH1
T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
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
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
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
T37539DI0240Lyme borreliosis[ICD-11: 1C1G]P20273CD22
T37539DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P20273CD22
T37539DI0249Mature B-cell leukaemia[ICD-11: 2A82]P20273CD22
T37539DI0250Mature B-cell lymphoma[ICD-11: 2A85]P20273CD22

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