Diosbulbinoside D



Compound IDCDAMM02796
Common nameDiosbulbinoside D
IUPAC name8-(furan-3-yl)-10-methyl-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,14-dioxatetracyclo[11.2.1.02,11.05,10]hexadec-2-ene-6,15-dione
Molecular formulaC25H30O11

Experimental data

Retention time13.57
Adduct[M+H]+
Actual mz507.18
Theoretical mz507.186
Error13.36
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.7638

Identifiers and class information

Inchi keyKXNADXBKEHOTDP-UHFFFAOYNA-N
SmilesO=C1OC2CC1C3=C(OC4OC(CO)C(O)C(O)C4O)CC5C(=O)OC(C6=COC=C6)CC5(C)C3C2
SuperclassOrganoheterocyclic compounds
ClassNaphthopyrans

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)7
Number of reactive functional groups (#rtvFG)3
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)506.505
Computed dipole moment(dipole)10.625
Total solvent accessible surface area (SASA)664.072
Hydrophobic component of SASA (FOSA)290.509
Hydrophilic component of SASA (FISA)235.117
Pie component of the SASA (PISA)138.447
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1334.42
Number of hydrogen bond donors (donorHB)4
Number of hydrogen bond acceptors (accptHB)15.75
Free energy of solvation of dipole (dip^2/V)0.0845912
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0474346
Globularity descriptor (glob)0.882698
Predicted polarizability in cubic angstroms (QPpolrz)44.077
Predicted hexadecane/gas partition coefficient (QPlogPC16)14.119
Predicted octanol/gas partition coefficient (QPlogPoct)30.638
Predicted water/gas partition coefficient (QPlogPw)23.686
Predicted octanol/water partition coefficient (QPlogPo/w)-0.23
Predicted aqueous solubility (QPlogS)-2.55
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.873
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.09
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)58.383
Predicted brain/blood partition coefficient (QPlogBB)-1.87
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)22.954
Predicted skin permeability, log Kp (QPlogKp)-4.693
PM3 calculated ionization potential (IP(ev))9.584
PM3 calculated electron affinity (EA(eV))-0.129
Number of likely metabolic reactions (#metab)10
Prediction of binding to human serum albumin (QPlogKhsa)-0.7
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)31.296
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)180.557
Number of nitrogen and oxygen atoms (#NandO)11
Number of violations of Lipinski’s rule of five (RuleOfFive)2
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
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
P13726F3Coagulation factor VII/tissue factorT72702SwissTargetPrediction
P35372OPRM1Mu opioid receptorT47768SEA
P41145OPRK1Kappa Opioid receptorT60693SEA
P41143OPRD1Delta opioid receptorT58992SEA
Q02750MAP2K1Dual specificity mitogen-activated protein kinase kinase 1T99057SwissTargetPrediction
P28482MAPK1MAP kinase ERK2T58970SwissTargetPrediction
P55263ADKAdenosine kinaseT91661SwissTargetPrediction
Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
P52789HK2Hexokinase type IIT96685SwissTargetPrediction
O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SwissTargetPrediction
Q9NY91SLC5A4Low affinity sodium-glucose cotransporterT22583SwissTargetPrediction
P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
P60568IL2Interleukin-2T61698SEA
P15056BRAFSerine/threonine-protein kinase B-rafT99089SwissTargetPrediction
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
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
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
T20401DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P00918CA2
T20401DI0137Essential hypertension[ICD-11: BA00]P00918CA2
T20401DI0166Glaucoma[ICD-11: 9C61]P00918CA2
T20401DI0175Heart failure[ICD-11: BD10-BD1Z]P00918CA2
T20401DI0214Insomnia[ICD-11: 7A00-7A0Z]P00918CA2
T20401DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00918CA2
T54771DI0120Diabetes mellitus[ICD-11: 5A10]P13866SLC5A1
T54771DI0175Heart failure[ICD-11: BD10-BD1Z]P13866SLC5A1
T54771DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P13866SLC5A1
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
T47768DI0013Acute pain[ICD-11: MG31]P35372OPRM1
T47768DI0059Bowel habit change[ICD-11: ME05]P35372OPRM1
T47768DI0087Chronic pain[ICD-11: MG30]P35372OPRM1
T47768DI0101Corneal disease[ICD-11: 9A76-9A78]P35372OPRM1
T47768DI0105Cough[ICD-11: MD12]P35372OPRM1
T47768DI0117Depression[ICD-11: 6A70-6A7Z]P35372OPRM1
T47768DI0124Digestive system disease[ICD-11: DE2Z]P35372OPRM1
T47768DI0218Irritable bowel syndrome[ICD-11: DD91]P35372OPRM1
T47768DI0228Large intestine motility disorder[ICD-11: DB32]P35372OPRM1
T47768DI0317Opioid use disorder[ICD-11: 6C43]P35372OPRM1
T47768DI0324Pain[ICD-11: MG30-MG3Z]P35372OPRM1
T47768DI0349Pruritus[ICD-11: EC90]P35372OPRM1
T47768DI0374Sensation disturbance[ICD-11: MB40]P35372OPRM1
T60693DI0304Non-specific cutaneous vascular symptom[ICD-11: ME64]P41145OPRK1
T60693DI0324Pain[ICD-11: MG30-MG3Z]P41145OPRK1
T60693DI0349Pruritus[ICD-11: EC90]P41145OPRK1
T58992DI0059Bowel habit change[ICD-11: ME05]P41143OPRD1
T58992DI0218Irritable bowel syndrome[ICD-11: DD91]P41143OPRD1
T58992DI0324Pain[ICD-11: MG30-MG3Z]P41143OPRD1
T99057DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]Q02750MAP2K1
T99057DI0336Phakomatoses/hamartoneoplastic syndrome[ICD-11: LD2D]Q02750MAP2K1
T58970DI0036Arteries/arterioles disorder[ICD-11: BD52]P28482MAPK1
T58970DI0252Melanoma[ICD-11: 2C30]P28482MAPK1
T58970DI0326Pancreatic cancer[ICD-11: 2C10]P28482MAPK1
T58970DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28482MAPK1
T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
T96685DI0133Epidermal dysplasias[ICD-11: EK90]P52789HK2
T22583DI0009Acute diabete complication[ICD-11: 5A2Y]Q9NY91SLC5A4
T22583DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q9NY91SLC5A4
T30085DI0120Diabetes mellitus[ICD-11: 5A10]P31639SLC5A2
T30085DI0175Heart failure[ICD-11: BD10-BD1Z]P31639SLC5A2
T30085DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P31639SLC5A2
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T99089DI0252Melanoma[ICD-11: 2C30]P15056BRAF
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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