Gentiobiose (Compound)

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ID	2407
Name	Gentiobiose
Synonyms	beta-D-Glucosyl-(1->6)-D-glucose
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE002407 (Gentiobiose) 3D Structure for EE002407 (Gentiobiose) 441422 -OEChem-12292202473D 45 46 0 1 0 0 0 0 0999 V2000 2.1817 -0.8330 0.1909 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3576 1.0353 -0.2823 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3189 0.5711 0.1388 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5172 -2.5577 0.4091 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0122 2.7591 -0.4559 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7369 2.3573 0.5906 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7671 -0.2158 -0.2302 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2206 -1.9074 -0.3813 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9223 0.8185 0.4889 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9774 2.7145 -0.3051 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9988 -3.4159 -0.2745 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9315 -0.2244 0.2396 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9077 -1.3234 -0.1869 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4881 1.5761 0.1856 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9722 1.3896 -0.1302 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6600 0.3932 -0.3162 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4559 0.0001 0.2851 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3330 -0.9811 0.2470 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5173 -1.0840 -0.2498 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7096 0.4427 -0.1632 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5227 -0.4864 -0.2836 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6228 1.4416 0.2342 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9133 -2.4701 0.2491 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 -0.1479 1.3343 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8815 -1.4619 -1.2747 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3438 1.7197 1.2631 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1737 1.5659 -1.1939 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 0.3686 -1.4144 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5210 -0.0510 1.3789 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4584 -1.1170 1.3283 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5234 -1.1043 -1.3481 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9046 0.4792 -1.2417 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5295 -0.5164 -1.3800 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1572 -1.4451 0.0996 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5560 1.5656 1.3213 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8679 -2.5311 1.3416 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9197 -2.7463 -0.0781 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5302 -2.4424 1.3746 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1369 2.6531 -1.4145 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4029 3.2357 0.3399 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7176 -0.1838 -1.2009 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9470 -2.8011 -0.1120 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7709 0.7858 1.4489 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3683 2.5799 -1.1843 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1082 -3.1579 0.0189 H 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 1 19 1 0 0 0 0 2 12 1 0 0 0 0 2 22 1 0 0 0 0 3 16 1 0 0 0 0 3 21 1 0 0 0 0 4 13 1 0 0 0 0 4 38 1 0 0 0 0 5 14 1 0 0 0 0 5 39 1 0 0 0 0 6 15 1 0 0 0 0 6 40 1 0 0 0 0 7 17 1 0 0 0 0 7 41 1 0 0 0 0 8 18 1 0 0 0 0 8 42 1 0 0 0 0 9 20 1 0 0 0 0 9 43 1 0 0 0 0 10 22 1 0 0 0 0 10 44 1 0 0 0 0 11 23 1 0 0 0 0 11 45 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 12 24 1 0 0 0 0 13 18 1 0 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 19 1 0 0 0 0 17 29 1 0 0 0 0 18 20 1 0 0 0 0 18 30 1 0 0 0 0 19 23 1 0 0 0 0 19 31 1 0 0 0 0 20 22 1 0 0 0 0 20 32 1 0 0 0 0 21 33 1 0 0 0 0 21 34 1 0 0 0 0 22 35 1 0 0 0 0 23 36 1 0 0 0 0 23 37 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 441422 > <PUBCHEM_CONFORMER_RMSD> 0.8 > <PUBCHEM_CONFORMER_DIVERSEORDER> 1 68 124 123 113 48 28 103 98 83 120 115 18 114 90 91 74 56 3 102 39 42 46 58 109 11 30 117 75 105 5 121 31 19 88 71 55 22 54 122 106 44 101 60 112 38 34 108 25 40 57 80 4 27 81 77 2 118 13 52 67 97 47 53 32 23 82 100 104 72 89 51 59 125 94 26 79 110 21 41 107 7 76 86 12 61 16 20 64 63 96 17 49 9 36 45 99 92 37 35 10 15 95 85 73 62 24 33 43 70 87 116 84 69 8 66 29 78 50 119 65 111 93 14 6 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 31 1 -0.56 10 -0.68 11 -0.68 12 0.28 13 0.28 14 0.28 15 0.28 16 0.56 17 0.28 18 0.28 19 0.28 2 -0.56 20 0.28 21 0.28 22 0.56 23 0.28 3 -0.56 38 0.4 39 0.4 4 -0.68 40 0.4 41 0.4 42 0.4 43 0.4 44 0.4 45 0.4 5 -0.68 6 -0.68 7 -0.68 8 -0.68 9 -0.68 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 6.4 > <PUBCHEM_PHARMACOPHORE_FEATURES> 21 1 1 acceptor 1 10 acceptor 1 10 donor 1 11 acceptor 1 11 donor 1 2 acceptor 1 3 acceptor 1 4 acceptor 1 4 donor 1 5 acceptor 1 5 donor 1 6 acceptor 1 6 donor 1 7 acceptor 1 7 donor 1 8 acceptor 1 8 donor 1 9 acceptor 1 9 donor 6 1 14 15 16 17 19 rings 6 2 12 13 18 20 22 rings > <PUBCHEM_HEAVY_ATOM_COUNT> 23 > <PUBCHEM_ATOM_DEF_STEREO_COUNT> 10 > <PUBCHEM_ATOM_UDEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_DEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_UDEF_STEREO_COUNT> 0 > <PUBCHEM_ISOTOPIC_ATOM_COUNT> 0 > <PUBCHEM_COMPONENT_COUNT> 1 > <PUBCHEM_CACTVS_TAUTO_COUNT> 1 > <PUBCHEM_CONFORMER_ID> 0006BC4E00000001 > <PUBCHEM_MMFF94_ENERGY> 61.2525 > <PUBCHEM_FEATURE_SELFOVERLAP> 106.716 > <PUBCHEM_SHAPE_FINGERPRINT> 10595046 47 18413106190827377665 10616163 171 18339926042430671871 11405975 8 18341051822320477849 12107183 9 17908145369454675041 12236239 1 17988925591399860124 12596602 18 17418094359968538050 12788726 201 17345761780654823913 13167823 11 18413105056771668151 13533116 47 18343300345068925779 13583140 156 17988356086978354561 14341114 176 18410862078783898545 14790565 3 18047759479862320612 14866123 147 17044580042343992138 15196674 1 18410855468728652385 15250474 111 18271230703569365159 15256400 18 18409449146381365421 15442244 35 18338800005073832464 17492 89 18411419505562793199 17834072 33 18411981373025511814 17844677 252 18411989052458847977 17857418 61 18410007736800608383 1813 80 16877664551998882772 200 152 18131070476081942435 20645477 56 18334013878587736293 20645477 70 18202006516925913286 21065198 57 18410012139031005173 21065199 12 18409449202073288113 21267235 1 18410582807024898110 21421861 104 17751351782246534618 21859007 373 17605538960902217861 23402539 116 18412539934197518701 23559900 14 18411978078690578976 239999 70 18202290195558554454 3004659 81 18188494550029357982 33824 294 18410009966526945042 3421961 26 18339077082642497954 3545911 37 18410857659188632952 4073 2 18187652443669104570 4214541 1 18410575089338055717 5104073 3 18410013225979615235 542803 24 17489593371987350577 543358 83 18339083688080451762 58051976 100 18410857680805855543 59755656 215 18409169904930015222 77779 3 18410292505900885193 8272917 22 18412829075464265598 9709674 26 18408609183885675059 9981440 41 17469045917615533465 9995097 60 18411698764129968772 > <PUBCHEM_SHAPE_MULTIPOLES> 408.77 13.44 3.06 0.65 4.14 0.66 0.01 -0.33 0.56 -1.42 -0.07 -0.01 -0.02 0.15 > <PUBCHEM_SHAPE_SELFOVERLAP> 834.74 > <PUBCHEM_SHAPE_VOLUME> 231.6 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description
Classification	Compounds > Chemical entities > Organic compounds > Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
CAS number	554-91-6
PubChem ID	441422
ChEBI ID	28066
FooDB ID
HMDB ID

Chemical data

MolDBi data

IUPAC Name	(2R,3R,4S,5S,6R)-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol
Traditional IUPAC Name	gentiobiose
Formula	C12H22O11
InChI	InChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1
InChI Key	DLRVVLDZNNYCBX-LIZSDCNHSA-N
Molecular weight	342.297
Exact mass	342.116211528
SMILES	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

ClassyFire Taxonomy

Description	belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	O-glycosyl compounds
Alternative Parents	Disaccharides Oxanes Secondary alcohols Hemiacetals Polyols Oxacyclic compounds Acetals Primary alcohols Hydrocarbon derivatives

Publications with Gentiobiose

ID	Title	First author	Authors	Year	Journal	Volume	Issue	Pages	PubMed ID	DOI	Study design	No. of Biomarkers	No. of Intake values	No. of Concentration values	No. of Reproducibility values	No. of Correlation values	No. of Metabolomic associations	No. of Microbiota associations	No. of Cancer associations

Biomarker data

Measurements of Gentiobiose in biospecimens

Concentration values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Reproducibility values

ID	Excretion ID	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Arithmetic mean	Geometric mean	Median	Unit	Adjusted on	Reproducibility size	ICC	ICC 95% CI lower	ICC 95% CI upper	CV% WS	CV% BS	VAR WS	VAR BS	Publication

Associations of Gentiobiose with exposures

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication

Metabolomic associations

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	Intake Assessment method	Intake	Intervention dose	Biospecimen	Analytical method	Biomarker	Structural identification	Feature selection	Area under curve	Sensitivity	Specificity	PLS-DA VIP	Beta coefficient	Beta coefficient p-value	ANOVA p-value	Publication

Microbiota associations

ID	Biomarker	Experimental evidence	Organism	Biospecimen	Antibiotic	Bacterial source	Substrate	Publication

Associations of Gentiobiose with cancer risk

Cancer associations

ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	No. of cases	No. of controls	Biospecimen	Analytical method	Biomarker	Biomarker detail	Cancer	Study design	Publication

Exposure data

Measurements of Gentiobiose exposures in populations

Intake values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Intake Time definition	Intake assessment tool	Intake food coverage	Intake time coverage	Intake Assessment method	Intake	Intake detail	Food description	Supplement intakes included?	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Associations of Gentiobiose exposures with biomarkers

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication