2-({5-[(2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl)oxy]-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl}oxy)-3-ethenyl-4-({1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl}methyl)-3,4-dihydro-2H-pyran-5-carboxylic acid



Compound IDCDAMM00235
Common name2-({5-[(2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl)oxy]-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl}oxy)-3-ethenyl-4-({1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl}methyl)-3,4-dihydro-2H-pyran-5-carboxylic acid
IUPAC name2-[5-[2-[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-ethenyl-4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-ylmethyl)-3,4-dihydro-2H-pyran-5-carboxylic acid
Molecular formulaC38H52N2O19

Experimental data

Retention time55.68
Adduct[M+H]+
Actual mz841.324
Theoretical mz841.324
Error0.35
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.0863

Identifiers and class information

Inchi keyMXDVXQNMPCXAQC-PYRMWGFRNA-N
SmilesC=CC1C(C(=COC1OC2C(C(C(C(O2)CO)OC3C(C(OC(C3O)OC4(C(C(C(O4)CO)O)O)CO)CO)O)O)O)C(=O)O)CC5C6=C(CCN5)C7=CC=CC=C7N6
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Pharmacokinetic properties

Number of descriptor values(#stars)15
Number of non-conjugated amine groups (#amine)1
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)24
Number of reactive functional groups (#rtvFG)4
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)840.831
Computed dipole moment(dipole)8.955
Total solvent accessible surface area (SASA)1037.87
Hydrophobic component of SASA (FOSA)395.967
Hydrophilic component of SASA (FISA)431.481
Pie component of the SASA (PISA)210.425
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)2163.81
Number of hydrogen bond donors (donorHB)13
Number of hydrogen bond acceptors (accptHB)30.5
Free energy of solvation of dipole (dip^2/V)0.0370609
Index of cohesive interaction in solids (ACxDN^.5/SA)0.105956
Globularity descriptor (glob)0.779531
Predicted polarizability in cubic angstroms (QPpolrz)67.041
Predicted hexadecane/gas partition coefficient (QPlogPC16)25.48
Predicted octanol/gas partition coefficient (QPlogPoct)59.531
Predicted water/gas partition coefficient (QPlogPw)50.371
Predicted octanol/water partition coefficient (QPlogPo/w)-5.265
Predicted aqueous solubility (QPlogS)-0.824
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.127
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.022
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.051
Predicted brain/blood partition coefficient (QPlogBB)-5.218
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.016
Predicted skin permeability, log Kp (QPlogKp)-8.489
PM3 calculated ionization potential (IP(ev))7.928
PM3 calculated electron affinity (EA(eV))0.163
Number of likely metabolic reactions (#metab)16
Prediction of binding to human serum albumin (QPlogKhsa)-2.246
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)326.117
Number of nitrogen and oxygen atoms (#NandO)21
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
P08913ADRA2AAlpha-2a adrenergic receptorT11448SwissTargetPrediction
P18825ADRA2CAdrenergic receptor alpha-2T01777SwissTargetPrediction
P06276BCHEButyrylcholinesteraseT99799SwissTargetPrediction
P41143OPRD1Delta opioid receptorT58992SwissTargetPrediction
P18089ADRA2BAlpha-2b adrenergic receptorT41580SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T11448DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P08913ADRA2A
T11448DI0317Opioid use disorder[ICD-11: 6C43]P08913ADRA2A
T11448DI0396Substance abuse[ICD-11: 6C40]P08913ADRA2A
T01777DI0166Glaucoma[ICD-11: 9C61]P18825ADRA2C
T01777DI0190Hypertension[ICD-11: BA00-BA04]P18825ADRA2C
T01777DI0196Hypotension[ICD-11: BA20-BA21]P18825ADRA2C
T01777DI0308Obesity[ICD-11: 5B80-5B81]P18825ADRA2C
T01777DI0310Ocular disease[ICD-11: N.A.]P18825ADRA2C
T01777DI0396Substance abuse[ICD-11: 6C40]P18825ADRA2C
T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
T58992DI0059Bowel habit change[ICD-11: ME05]P41143OPRD1
T58992DI0218Irritable bowel syndrome[ICD-11: DD91]P41143OPRD1
T58992DI0324Pain[ICD-11: MG30-MG3Z]P41143OPRD1
T41580DI0396Substance abuse[ICD-11: 6C40]P18089ADRA2B
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

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