3,3\'-dihydroxy-4,4\'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1H,1\'H-[2,2\'-bipyridinylidene]-1,1\'-diium-1,1\'-bis(olate)



Compound IDCDAMM00221
Common name3,3\'-dihydroxy-4,4\'-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1H,1\'H-[2,2\'-bipyridinylidene]-1,1\'-diium-1,1\'-bis(olate)
IUPAC name2-[[3-hydroxy-2-[3-hydroxy-1-oxido-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1H-pyridin-1-ium-2-ylidene]-1-oxido-1H-pyridin-1-ium-4-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular formulaC22H30N2O16

Experimental data

Retention time36.55
Adduct[M+H]+
Actual mz579.166
Theoretical mz579.167
Error0.69
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score4.529

Identifiers and class information

Inchi keyZWUNDSBMYWWWEF-UHFFFAOYSA-N
SmilesC1=C[NH+](C(=C2C(=C(C=C[NH+]2[O-])OC3C(C(C(C(O3)CO)O)O)O)O)C(=C1OC4C(C(C(C(O4)CO)O)O)O)O)[O-]
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Pharmacokinetic properties

Number of descriptor values(#stars)12
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)19
Number of reactive functional groups (#rtvFG)4
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)578.483
Computed dipole moment(dipole)9.829
Total solvent accessible surface area (SASA)797.561
Hydrophobic component of SASA (FOSA)234.222
Hydrophilic component of SASA (FISA)437.686
Pie component of the SASA (PISA)125.654
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1507.81
Number of hydrogen bond donors (donorHB)12
Number of hydrogen bond acceptors (accptHB)24.4
Free energy of solvation of dipole (dip^2/V)0.0640668
Index of cohesive interaction in solids (ACxDN^.5/SA)0.105978
Globularity descriptor (glob)0.797319
Predicted polarizability in cubic angstroms (QPpolrz)43.189
Predicted hexadecane/gas partition coefficient (QPlogPC16)18.952
Predicted octanol/gas partition coefficient (QPlogPoct)46.641
Predicted water/gas partition coefficient (QPlogPw)42.888
Predicted octanol/water partition coefficient (QPlogPo/w)-4.53
Predicted aqueous solubility (QPlogS)-1.236
Conformation-independent predicted aqueous solubility (CIQPlogS)-1.944
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.411
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.7
Predicted brain/blood partition coefficient (QPlogBB)-5.172
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.193
Predicted skin permeability, log Kp (QPlogKp)-7.319
PM3 calculated ionization potential (IP(ev))7.411
PM3 calculated electron affinity (EA(eV))0.457
Number of likely metabolic reactions (#metab)11
Prediction of binding to human serum albumin (QPlogKhsa)-1.959
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)282.899
Number of nitrogen and oxygen atoms (#NandO)18
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
P00915CA1Carbonic anhydrase IT13201SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P32320CDACytidine deaminase (by homology)T79027SEA
P00813ADAAdenosine deaminaseT03661SEA
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
O60502OGABifunctional protein NCOATT19567SEA
P60568IL2Interleukin-2T61698SEA
P17931LGALS3Galectin-3T72038SEA
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SEA
P06865HEXABeta-hexosaminidase subunit alphaT63196SEA
P07686HEXBBeta-N-acetyl-D-hexosaminidase-A/BT63197SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
Q15391P2RY14Purinergic receptor P2Y14T16555SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

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
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
T79027DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P32320CDA
T03661DI0016Adaptive immunity immunodeficiency[ICD-11: 4A01]P00813ADA
T03661DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P00813ADA
T03661DI0249Mature B-cell leukaemia[ICD-11: 2A82]P00813ADA
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
T19567DI0025Alzheimer disease[ICD-11: 8A20]O60502OGA
T19567DI0331Parkinsonism[ICD-11: 8A00]O60502OGA
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
T63196DI0242Lysosomal disease[ICD-11: 5C56]P06865HEXA
T63197DI0242Lysosomal disease[ICD-11: 5C56]P07686HEXB
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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