Hexahydro-6,7-dihydroxy-5-(hydroxymethyl)-3-(2-hydroxyphenyl)-2H-pyrano[2,3-d]oxazol-2-one



Compound IDCDAMM01114
Common nameHexahydro-6,7-dihydroxy-5-(hydroxymethyl)-3-(2-hydroxyphenyl)-2H-pyrano[2,3-d]oxazol-2-one
IUPAC name6,7-dihydroxy-5-(hydroxymethyl)-3-(2-hydroxyphenyl)-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d][1,3]oxazol-2-one
Molecular formulaC13H15NO7

Experimental data

Retention time0.4
Adduct[M+H]+
Actual mz298.091
Theoretical mz298.092
Error2.94
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.9984

Identifiers and class information

Inchi keyXBYMZYWXQBJAJG-UHFFFAOYNA-N
SmilesO=C1OC2C(O)C(O)C(OC2N1C=3C=CC=CC3O)CO
SuperclassBenzenoids
ClassPhenols

Pharmacokinetic properties

Number of descriptor values(#stars)0
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)5
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)297.264
Computed dipole moment(dipole)7.97
Total solvent accessible surface area (SASA)486.28
Hydrophobic component of SASA (FOSA)116.116
Hydrophilic component of SASA (FISA)207.792
Pie component of the SASA (PISA)162.371
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)844.513
Number of hydrogen bond donors (donorHB)4
Number of hydrogen bond acceptors (accptHB)11.05
Free energy of solvation of dipole (dip^2/V)0.0752186
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0454471
Globularity descriptor (glob)0.888553
Predicted polarizability in cubic angstroms (QPpolrz)25.984
Predicted hexadecane/gas partition coefficient (QPlogPC16)9.696
Predicted octanol/gas partition coefficient (QPlogPoct)21.433
Predicted water/gas partition coefficient (QPlogPw)19.047
Predicted octanol/water partition coefficient (QPlogPo/w)-1.008
Predicted aqueous solubility (QPlogS)-1.769
Conformation-independent predicted aqueous solubility (CIQPlogS)-1.836
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.11
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)106.025
Predicted brain/blood partition coefficient (QPlogBB)-1.492
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)43.745
Predicted skin permeability, log Kp (QPlogKp)-4.297
PM3 calculated ionization potential (IP(ev))8.762
PM3 calculated electron affinity (EA(eV))-0.094
Number of likely metabolic reactions (#metab)5
Prediction of binding to human serum albumin (QPlogKhsa)-0.866
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)57.293
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)134.36
Number of nitrogen and oxygen atoms (#NandO)8
Number of violations of Lipinski’s rule of five (RuleOfFive)0
Number of violations of Jorgensen’s rule of three (RuleOfThree)0

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P29274ADORA2AAdenosine A2a receptorT77365SEA
P30542ADORA1Adenosine A1 receptorT92072SEA
O43570CA12Carbonic anhydrase XIIT16987SEA
Q16790CA9Carbonic anhydrase IXT64567SEA
P0DMS8ADORA3Adenosine A3 receptorT36059SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P00491PNPPurine nucleoside phosphorylaseT78198SEA
P04183TK1Thymidine kinase, cytosolicT30081SEA
P11387TOP1DNA topoisomerase IT09826SEA
P32320CDACytidine deaminase (by homology)T79027SEA
P00813ADAAdenosine deaminaseT03661SEA
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P55263ADKAdenosine kinaseT91661SEA
P04406GAPDHGlyceraldehyde-3-phosphate dehydrogenase liverT39321SEA
Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SEA
O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SEA
P01112HRASTransforming protein p21/H-Ras-1T71081SEA
P60568IL2Interleukin-2T61698SEA
P17931LGALS3Galectin-3T72038SEA
P09382LGALS1Galectin-1T09544SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
Q15391P2RY14Purinergic receptor P2Y14T16555SEA
P05231IL6Interleukin-6T32578SEA
Q07108CD69Early activation antigen CD69T48780SEA
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
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
T78198DI0120Diabetes mellitus[ICD-11: 5A10]P00491PNP
T78198DI0167Gout[ICD-11: FA25]P00491PNP
T78198DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P00491PNP
T78198DI0283Mycosis fungoides[ICD-11: 2B01]P00491PNP
T78198DI0351Psoriasis[ICD-11: EA90]P00491PNP
T30081DI0012Acute myeloid leukaemia[ICD-11: 2A60]P04183TK1
T30081DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P04183TK1
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
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
T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
T39321DI0279Muscular atrophy[ICD-11: 8B61]P04406GAPDH
T39321DI0280Muscular dystrophy[ICD-11: 8C70]P04406GAPDH
T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
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
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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