Stenophylline B 3-O-beta-D-glucopyranoside



Compound IDCDAMM01791
Common nameStenophylline B 3-O-beta-D-glucopyranoside
IUPAC name2-(hydroxymethyl)-6-[[17-[1-hydroxy-1-(5-methylpiperidin-2-yl)ethyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-3,4,5-triol
Molecular formulaC33H55NO7

Experimental data

Retention time16
Adduct[M+H]+
Actual mz578.406
Theoretical mz578.405
Error1.77
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.6665

Identifiers and class information

Inchi keyRJBTVSPVEZZAHJ-UHFFFAOYNA-N
SmilesOCC1OC(OC2CC3=CCC4C(CCC5(C)C4CCC5C(O)(C)C6NCC(C)CC6)C3(C)CC2)C(O)C(O)C1O
SuperclassLipids and lipid-like molecules
ClassSteroids and steroid derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)1
Number of non-conjugated amine groups (#amine)1
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)10
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)577.8
Computed dipole moment(dipole)2.925
Total solvent accessible surface area (SASA)893.341
Hydrophobic component of SASA (FOSA)674.539
Hydrophilic component of SASA (FISA)194.802
Pie component of the SASA (PISA)24
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1767.45
Number of hydrogen bond donors (donorHB)6
Number of hydrogen bond acceptors (accptHB)12.45
Free energy of solvation of dipole (dip^2/V)0.0048391
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0341372
Globularity descriptor (glob)0.79137
Predicted polarizability in cubic angstroms (QPpolrz)58.388
Predicted hexadecane/gas partition coefficient (QPlogPC16)17.473
Predicted octanol/gas partition coefficient (QPlogPoct)34.991
Predicted water/gas partition coefficient (QPlogPw)22.202
Predicted octanol/water partition coefficient (QPlogPo/w)2.631
Predicted aqueous solubility (QPlogS)-4.782
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.698
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.748
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)35.115
Predicted brain/blood partition coefficient (QPlogBB)-1.714
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)14.658
Predicted skin permeability, log Kp (QPlogKp)-6.128
PM3 calculated ionization potential (IP(ev))9.228
PM3 calculated electron affinity (EA(eV))-1.229
Number of likely metabolic reactions (#metab)7
Prediction of binding to human serum albumin (QPlogKhsa)0.366
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)44.093
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)129.097
Number of nitrogen and oxygen atoms (#NandO)8
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
Q15125EBPAnti-estrogen binding site (AEBS)T25317SEA
P31213SRD5A2Steroid 5-alpha-reductase 2T71390SEA
P10275ARAndrogen ReceptorT11211SEA
Q92731ESR2Estrogen receptor betaT80896SEA
P08185SERPINA6Corticosteroid binding globulinT88452SEA
Q9UHC9NPC1L1Niemann-Pick C1-like protein 1T33901SEA
Q13133NR1H3LXR-alphaT52297SEA
Q15465SHHSonic hedgehog protein (by homology)T12075SEA
P11413G6PDGlucose-6-phosphate 1-dehydrogenaseT63484SEA
P05093CYP17A1Cytochrome P450 17A1T89041SEA
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P60568IL2Interleukin-2T61698SEA
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SEA
O15439ABCC4Multidrug resistance protein 4T39919SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T25317DI0366Rheumatoid arthritis[ICD-11: FA20]Q15125EBP
T71390DI0348Prostate hyperplasia[ICD-11: GA90]P31213SRD5A2
T11211DI0005Acne vulgaris[ICD-11: ED80]P10275AR
T11211DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10275AR
T11211DI0021Alcoholic liver disease[ICD-11: DB94]P10275AR
T11211DI0062Breast cancer[ICD-11: 2C60-2C6Y]P10275AR
T11211DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P10275AR
T11211DI0145Female pelvic pain[ICD-11: GA34]P10275AR
T11211DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P10275AR
T11211DI0237Low bone mass disorder[ICD-11: FB83]P10275AR
T11211DI0247Mammary tumour[ICD-11: 2C60-2C6Z]P10275AR
T11211DI0346Prostate cancer[ICD-11: 2C82]P10275AR
T11211DI0401Testicular dysfunction[ICD-11: 5A81]P10275AR
T80896DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q92731ESR2
T80896DI0108Cushing syndrome[ICD-11: 5A70]Q92731ESR2
T80896DI0254Menopausal disorder[ICD-11: GA30]Q92731ESR2
T80896DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]Q92731ESR2
T88452DI0037Asthma[ICD-11: CA23]P08185SERPINA6
T88452DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P08185SERPINA6
T88452DI0362Respiratory system disease[ICD-11: CB40-CB7Z]P08185SERPINA6
T33901DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q9UHC9NPC1L1
T52297DI0117Depression[ICD-11: 6A70-6A7Z]Q13133NR1H3
T63484DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P11413G6PD
T89041DI0346Prostate cancer[ICD-11: 2C82]P05093CYP17A1
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
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

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