Glyco-beta-muricholic acid (Compound)

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ID	2329
Name	Glyco-beta-muricholic acid
Synonyms	N-(3alpha,6beta,7beta-Trihydroxy-5beta-cholanoyl)-glycine; beta-Glycomuricholic acid; Gly-beta-MCA
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE002329 (Glyco-beta-muricholic acid) 3D Structure for EE002329 (Glyco-beta-muricholic acid) 137333454 -OEChem-12292204373D 76 79 0 1 0 0 0 0 0999 V2000 -1.8817 -3.1418 0.2760 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2848 -2.6402 1.5398 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0302 0.4463 -3.4458 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5529 1.7500 -1.0093 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9769 -1.2951 0.8603 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7564 -2.1241 -0.2771 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7302 -0.4090 -1.2575 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6352 -0.3920 0.1924 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0882 -0.7185 0.5952 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0721 0.8516 0.9191 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9832 0.5241 0.2480 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5036 0.2867 0.5855 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3612 0.8632 0.3338 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9990 -1.0304 -0.1163 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9246 2.0616 0.5200 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4101 1.8390 0.8421 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6225 -1.9843 -0.1078 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4662 -1.4337 0.3839 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1053 -2.2510 0.1779 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7748 -0.6239 0.3517 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4120 1.4634 0.1121 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0434 0.7196 2.4628 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1515 -0.8654 -1.6452 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3730 1.7669 1.0240 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7152 0.2015 2.1205 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5153 1.6067 -1.3996 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0292 0.3195 -2.0278 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8072 1.2889 0.7179 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1485 3.2231 0.6034 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1765 1.3583 -0.7644 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6183 0.9536 -1.0214 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9908 -1.0635 -1.5229 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6739 -1.5509 -0.2711 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6583 -0.1783 -0.8896 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1043 -0.9125 1.6722 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9100 0.6498 -0.8412 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2932 1.1519 -0.7262 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0029 -1.2486 0.2770 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6084 2.9666 1.0439 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8222 2.2638 -0.5538 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5473 1.8578 1.9279 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9588 2.6997 0.4458 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4758 -1.8692 -1.1881 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4582 -2.1877 -0.4098 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3637 -1.9541 1.3428 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4316 -3.1124 -0.4179 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3444 -0.9003 1.2451 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3637 -0.9012 -0.5273 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0841 2.4153 0.5433 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4278 1.3056 0.5024 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6463 -0.0579 2.8059 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2618 1.6617 2.9318 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0234 0.4780 2.8826 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1768 -0.7592 -2.1359 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5849 -1.7798 -2.0719 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2814 1.7138 2.1135 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0096 -0.4665 2.6179 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7260 -0.1508 2.3572 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6053 1.1840 2.5931 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1961 2.4297 -1.6497 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5493 1.8878 -1.8353 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0627 0.1401 -1.7083 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2272 -3.8950 -0.2327 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5016 1.9426 1.2653 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0181 0.2933 1.1203 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2247 -2.8564 1.6635 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9518 3.3270 -0.4684 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0294 3.8308 0.8399 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3195 3.6718 1.1534 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3786 -0.3831 -3.8150 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0752 2.3849 -1.1360 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5208 0.7458 -1.3891 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8992 -0.9916 -1.2144 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6585 -0.3638 -2.0342 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7805 -1.9238 -2.1643 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4418 -1.6215 1.6600 H 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 1 63 1 0 0 0 0 2 19 1 0 0 0 0 2 66 1 0 0 0 0 3 27 1 0 0 0 0 3 70 1 0 0 0 0 4 31 2 0 0 0 0 5 33 1 0 0 0 0 5 76 1 0 0 0 0 6 33 2 0 0 0 0 7 31 1 0 0 0 0 7 32 1 0 0 0 0 7 73 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 8 34 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 9 35 1 0 0 0 0 10 13 1 0 0 0 0 10 15 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 11 36 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 12 25 1 0 0 0 0 13 20 1 0 0 0 0 13 24 1 0 0 0 0 13 37 1 0 0 0 0 14 19 1 0 0 0 0 14 23 1 0 0 0 0 14 38 1 0 0 0 0 15 16 1 0 0 0 0 15 39 1 0 0 0 0 15 40 1 0 0 0 0 16 41 1 0 0 0 0 16 42 1 0 0 0 0 17 19 1 0 0 0 0 17 43 1 0 0 0 0 18 20 1 0 0 0 0 18 44 1 0 0 0 0 18 45 1 0 0 0 0 19 46 1 0 0 0 0 20 47 1 0 0 0 0 20 48 1 0 0 0 0 21 26 1 0 0 0 0 21 49 1 0 0 0 0 21 50 1 0 0 0 0 22 51 1 0 0 0 0 22 52 1 0 0 0 0 22 53 1 0 0 0 0 23 27 1 0 0 0 0 23 54 1 0 0 0 0 23 55 1 0 0 0 0 24 28 1 0 0 0 0 24 29 1 0 0 0 0 24 56 1 0 0 0 0 25 57 1 0 0 0 0 25 58 1 0 0 0 0 25 59 1 0 0 0 0 26 27 1 0 0 0 0 26 60 1 0 0 0 0 26 61 1 0 0 0 0 27 62 1 0 0 0 0 28 30 1 0 0 0 0 28 64 1 0 0 0 0 28 65 1 0 0 0 0 29 67 1 0 0 0 0 29 68 1 0 0 0 0 29 69 1 0 0 0 0 30 31 1 0 0 0 0 30 71 1 0 0 0 0 30 72 1 0 0 0 0 32 33 1 0 0 0 0 32 74 1 0 0 0 0 32 75 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 137333454 > <PUBCHEM_CONFORMER_RMSD> 1 > <PUBCHEM_CONFORMER_DIVERSEORDER> 4 11 33 56 45 55 59 58 62 21 37 29 51 20 47 2 31 53 40 13 52 17 54 43 10 12 30 5 24 44 14 57 19 34 39 36 9 38 48 42 28 35 32 60 8 46 18 15 61 1 25 7 41 49 50 6 16 27 63 26 22 23 3 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 19 1 -0.68 17 0.28 19 0.28 2 -0.68 27 0.28 3 -0.68 30 0.06 31 0.57 32 0.36 33 0.66 4 -0.57 5 -0.65 6 -0.57 63 0.4 66 0.4 7 -0.73 70 0.4 73 0.37 76 0.5 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 9.2 > <PUBCHEM_PHARMACOPHORE_FEATURES> 16 1 1 acceptor 1 1 donor 1 2 acceptor 1 2 donor 1 29 hydrophobe 1 3 acceptor 1 3 donor 1 4 acceptor 1 5 acceptor 1 6 acceptor 1 7 donor 3 5 6 33 anion 5 8 10 13 18 20 rings 6 12 14 21 23 26 27 rings 6 8 9 10 11 15 16 rings 6 9 11 12 14 17 19 rings > <PUBCHEM_HEAVY_ATOM_COUNT> 33 > <PUBCHEM_ATOM_DEF_STEREO_COUNT> 11 > <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> 082F8ACE00000004 > <PUBCHEM_MMFF94_ENERGY> 112.6645 > <PUBCHEM_FEATURE_SELFOVERLAP> 81.393 > <PUBCHEM_SHAPE_FINGERPRINT> 10 15 9295290542803704628 10369192 42 14418140603811367097 11135926 11 18336549322073359867 11578080 2 17314217865880098191 12166972 35 18187939395604947236 12760667 363 17846504720587984904 13583140 156 17095793404855544977 13690498 29 18120938571154239855 13782708 43 17418376913198343340 13811026 1 18343299272097072728 14068700 675 17346597461316656784 14251752 14 18187365415726720300 14664723 55 17967811609878639445 14904525 67 15792014523544462916 14931854 50 18270099285435908925 15052358 14 18408599262421251765 15183329 4 18334577928305967022 19377110 9 10952048974657781432 19958102 18 18410572890346241126 21267235 1 18269002049813777827 21279426 13 18410294735458429786 21315764 119 17967814955562638614 21792961 116 18260831488555367835 22393880 68 18336821017567299441 23522609 53 17912120323487215416 23559900 14 18270960262321043680 23569914 152 17697587797735364293 3004659 81 18335147488693948854 32027 91 18272369814990197760 335352 9 18412261701673293865 3383291 50 17917994983790967582 397830 11 13039182620037643556 4015057 19 17631168761460354457 4093350 32 14851882505378653538 444769 64 18341343214207818187 5085150 59 18202562852762100262 5364581 5 9871751295181676135 59755656 520 16805613576494924146 6086070 43 18410283739930669481 6697151 62 17988634225393769552 > <PUBCHEM_SHAPE_MULTIPOLES> 638.93 20.15 2.83 1.91 34.93 0.29 0.83 7.66 10.17 0.83 -0.55 -2.87 -0.16 0.71 > <PUBCHEM_SHAPE_SELFOVERLAP> 1333.853 > <PUBCHEM_SHAPE_VOLUME> 359.6 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description	Glycine conjugate of beta-muricholic acid.
Classification	Compounds > Chemical entities > Organic compounds > Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Glycinated bile acids and derivatives
CAS number
PubChem ID	137333454
ChEBI ID
FooDB ID
HMDB ID

Chemical data

MolDBi data

IUPAC Name	2-[(4R)-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid
Traditional IUPAC Name	[(4R)-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid
Formula	C26H43NO6
InChI	InChI=1S/C26H43NO6/c1-14(4-7-20(29)27-13-21(30)31)16-5-6-17-22-18(9-11-25(16,17)2)26(3)10-8-15(28)12-19(26)23(32)24(22)33/h14-19,22-24,28,32-33H,4-13H2,1-3H3,(H,27,29)(H,30,31)/t14-,15-,16-,17+,18+,19+,22+,23+,24-,25-,26-/m1/s1
InChI Key	ZQYUKJFJPJDMMR-IIWZPVADSA-N
Molecular weight	465.631
Exact mass	465.309038109
SMILES	C[C@H](CCC(=O)NCC(O)=O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)[C@@H](O)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

Publications with Glyco-beta-muricholic acid

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 Glyco-beta-muricholic acid 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 Glyco-beta-muricholic acid 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 Glyco-beta-muricholic acid 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 Glyco-beta-muricholic acid 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 Glyco-beta-muricholic acid 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