Negletein 6-[rhamnosyl-(1->2)-fucoside]



Compound IDCDAMM00934
Common nameNegletein 6-[rhamnosyl-(1->2)-fucoside]
IUPAC name6-[4,5-dihydroxy-6-methyl-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-5-hydroxy-7-methoxy-2-phenylchromen-4-one
Molecular formulaC28H32O13

Experimental data

Retention time0.47
Adduct[2M+H]+
Actual mz1153.38
Theoretical mz1153.38
Error2.36
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.1128

Identifiers and class information

Inchi keyHKKXKZVCSZYRHK-UHFFFAOYNA-N
SmilesO=C1C=C(OC=2C=C(OC)C(OC3OC(C)C(O)C(O)C3OC4OC(C)C(O)C(O)C4O)=C(O)C12)C=5C=CC=CC5
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

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)11
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)576.553
Computed dipole moment(dipole)9.072
Total solvent accessible surface area (SASA)841.81
Hydrophobic component of SASA (FOSA)343.743
Hydrophilic component of SASA (FISA)228.134
Pie component of the SASA (PISA)269.933
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1607.25
Number of hydrogen bond donors (donorHB)5
Number of hydrogen bond acceptors (accptHB)17.35
Free energy of solvation of dipole (dip^2/V)0.0512059
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0460861
Globularity descriptor (glob)0.788268
Predicted polarizability in cubic angstroms (QPpolrz)53.683
Predicted hexadecane/gas partition coefficient (QPlogPC16)17.844
Predicted octanol/gas partition coefficient (QPlogPoct)35.612
Predicted water/gas partition coefficient (QPlogPw)27.119
Predicted octanol/water partition coefficient (QPlogPo/w)0.613
Predicted aqueous solubility (QPlogS)-3.893
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.921
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.245
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)68
Predicted brain/blood partition coefficient (QPlogBB)-2.547
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)27.066
Predicted skin permeability, log Kp (QPlogKp)-3.717
PM3 calculated ionization potential (IP(ev))9.233
PM3 calculated electron affinity (EA(eV))0.804
Number of likely metabolic reactions (#metab)7
Prediction of binding to human serum albumin (QPlogKhsa)-0.749
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)24.46
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)191.528
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)1

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
Q99720SIGMAR1Sigma opioid receptorT46360SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P22748CA4Carbonic anhydrase IVT53378SEA
P15121AKR1B1Aldose reductaseT26623SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
P09917ALOX5Arachidonate 5-lipoxygenaseT00140SEA
P33527ABCC1Multidrug resistance-associated protein 1T11288SEA
P08183ABCB1P-glycoprotein 1T25258SEA
O95271TNKSTankyrase-1T83059SEA
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P14151SELLLeukocyte adhesion molecule-1T60526SEA
P60568IL2Interleukin-2T61698SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
Q9NPH5NOX4NADPH oxidase 4T29741SEA
Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
P47989XDHXanthine dehydrogenaseT40954SEA
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
Q99417MYCBPMYCBP messenger RNAT37298SEA
P16220CREB1Cyclic AMP-responsive element-binding proteinT92098SEA
Q96HK3CALMCalmodulinT39610SEA
Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T46360DI0105Cough[ICD-11: MD12]Q99720SIGMAR1
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
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
T11288DI0167Gout[ICD-11: FA25]P33527ABCC1
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T83059DI0060Brain cancer[ICD-11: 2A00]O95271TNKS
T83059DI0062Breast cancer[ICD-11: 2C60-2C6Y]O95271TNKS
T83059DI0321Ovarian cancer[ICD-11: 2C73]O95271TNKS
T83059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O95271TNKS
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
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
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T29741DI0146Fibrosis[ICD-11: GA14-GC01]Q9NPH5NOX4
T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
T37298DI0235Liver cancer[ICD-11: 2C12]Q99417MYCBP
T39610DI0068Cardiac arrhythmia[ICD-11: BC9Z]Q96HK3CALM
T39610DI0243Malaria[ICD-11: 1F40-1F45]Q96HK3CALM
T39610DI0370Schizophrenia[ICD-11: 6A20]Q96HK3CALM
T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3

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