Sibiricose A6



Compound IDCDAMM02805
Common nameSibiricose A6
IUPAC name[4-hydroxy-2,5-bis(hydroxymethyl)-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-3-yl] 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
Molecular formulaC23H32O15

Experimental data

Retention time12.08
Adduct[M+H]+
Actual mz549.188
Theoretical mz549.181
Error11.7
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.6559

Identifiers and class information

Inchi keyWTCVROXOIQEIRC-LWISQMTDNA-N
SmilesO=C(OC1C(O)C(OC1(OC2OC(CO)C(O)C(O)C2O)CO)CO)C=CC3=CC(OC)=C(O)C(OC)=C3
SuperclassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)6
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)3
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)548.497
Computed dipole moment(dipole)6.172
Total solvent accessible surface area (SASA)751.04
Hydrophobic component of SASA (FOSA)362.559
Hydrophilic component of SASA (FISA)319.138
Pie component of the SASA (PISA)69.343
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1472.12
Number of hydrogen bond donors (donorHB)8
Number of hydrogen bond acceptors (accptHB)19.35
Free energy of solvation of dipole (dip^2/V)0.025873
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0728723
Globularity descriptor (glob)0.833291
Predicted polarizability in cubic angstroms (QPpolrz)41.223
Predicted hexadecane/gas partition coefficient (QPlogPC16)16.35
Predicted octanol/gas partition coefficient (QPlogPoct)36.361
Predicted water/gas partition coefficient (QPlogPw)30.754
Predicted octanol/water partition coefficient (QPlogPo/w)-1.818
Predicted aqueous solubility (QPlogS)-1.296
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.982
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.56
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)9.322
Predicted brain/blood partition coefficient (QPlogBB)-3.646
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)3.16
Predicted skin permeability, log Kp (QPlogKp)-5.333
PM3 calculated ionization potential (IP(ev))8.719
PM3 calculated electron affinity (EA(eV))0.666
Number of likely metabolic reactions (#metab)10
Prediction of binding to human serum albumin (QPlogKhsa)-1.409
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)235.738
Number of nitrogen and oxygen atoms (#NandO)15
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
P10253GAALysosomal alpha-glucosidase (by homology)T31514SwissTargetPrediction
P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
P29350PTPN6Protein-tyrosine phosphatase 1CT98264SEA
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
P14151SELLLeukocyte adhesion molecule-1T60526SEA
P01112HRASTransforming protein p21/H-Ras-1T71081SwissTargetPrediction
P60568IL2Interleukin-2T61698SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
P17931LGALS3Galectin-3T72038SEA
P14679TYRTyrosinaseT97035SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
P09382LGALS1Galectin-1T09544SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P05231IL6Interleukin-6T32578SEA

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
T31514DI0201Inborn carbohydrate metabolism error[ICD-11: 5C51]P10253GAA
T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
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
T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
T60526DI0037Asthma[ICD-11: CA23]P14151SELL
T60526DI0088Circulatory system disease[ICD-11: BE2Z]P14151SELL
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
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6

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