Vitecannaside B



Compound IDCDAMM01829
Common nameVitecannaside B
IUPAC name6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4-dihydronaphthalene-2-carbaldehyde
Molecular formulaC26H30O11

Experimental data

Retention time10.3
Adduct[M+H]+
Actual mz519.18
Theoretical mz519.186
Error12.47
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.2035

Identifiers and class information

Inchi keyHEUDOTUCVGDCHH-BHMRDVGONA-N
SmilesO=CC1=CC=2C=C(OC)C(O)=CC2C(C3=CC=C(O)C(OC)=C3)C1COC4OC(CO)C(O)C(O)C4O
SuperclassLignans, neolignans and related compounds
ClassLignan glycosides

Pharmacokinetic properties

Number of descriptor values(#stars)2
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)13
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)518.516
Computed dipole moment(dipole)4.762
Total solvent accessible surface area (SASA)775.765
Hydrophobic component of SASA (FOSA)314.159
Hydrophilic component of SASA (FISA)318.707
Pie component of the SASA (PISA)142.899
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1472.58
Number of hydrogen bond donors (donorHB)6
Number of hydrogen bond acceptors (accptHB)15.2
Free energy of solvation of dipole (dip^2/V)0.0154022
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0479942
Globularity descriptor (glob)0.806902
Predicted polarizability in cubic angstroms (QPpolrz)45.796
Predicted hexadecane/gas partition coefficient (QPlogPC16)16.51
Predicted octanol/gas partition coefficient (QPlogPoct)32.867
Predicted water/gas partition coefficient (QPlogPw)25.618
Predicted octanol/water partition coefficient (QPlogPo/w)-0.209
Predicted aqueous solubility (QPlogS)-3.231
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.425
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.338
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)9.41
Predicted brain/blood partition coefficient (QPlogBB)-3.483
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)3.192
Predicted skin permeability, log Kp (QPlogKp)-5.642
PM3 calculated ionization potential (IP(ev))8.65
PM3 calculated electron affinity (EA(eV))0.614
Number of likely metabolic reactions (#metab)10
Prediction of binding to human serum albumin (QPlogKhsa)-0.752
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)4.272
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)195.68
Number of nitrogen and oxygen atoms (#NandO)11
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
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P34913EPHX2Epoxide hydrataseT35734SwissTargetPrediction
P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
P11387TOP1DNA topoisomerase IT09826SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SwissTargetPrediction and SEA
P14151SELLLeukocyte adhesion molecule-1T60526SEA
P60568IL2Interleukin-2T61698SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SEA
Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P05231IL6Interleukin-6T32578SEA
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
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
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T35734DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P34913EPHX2
T35734DI0190Hypertension[ICD-11: BA00-BA04]P34913EPHX2
T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
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
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
T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
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
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
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
T82391DI0069Cardiomyopathy[ICD-11: BC43]Q9P0J0NDUFA13
T77195DI0331Parkinsonism[ICD-11: 8A00]P03897MT-ND3
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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