omega-Muricholic acid (Compound)

Go to Compound classification

ID	1833
Name	omega-Muricholic acid
Synonyms	3alpha,6alpha,7beta-Trihydroxy-5beta-cholanoic acid; omega-Muricholate; omega-MCA
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE001833 (omega-Muricholic acid) 3D Structure for EE001833 (omega-Muricholic acid) 5283851 -OEChem-09232115463D 69 72 0 1 0 0 0 0 0999 V2000 -1.4020 -3.2202 -0.2116 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0515 -2.7595 -0.9601 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7584 2.0908 -2.6726 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5440 0.8785 -2.8133 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3661 -0.3600 -1.0967 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0919 -0.9152 0.5090 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4046 -0.8410 0.1403 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2119 0.0944 1.0714 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6866 0.5245 0.4178 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2353 0.5919 0.7039 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6210 -0.0879 0.4561 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0076 -0.4807 -0.1405 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6414 1.5116 0.9345 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8616 1.5450 1.2510 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8734 -1.8833 -0.3975 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2537 -2.1106 0.1043 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3651 -1.8755 -0.0717 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7060 -1.6053 0.1831 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7429 2.0294 0.3417 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1951 -0.3339 2.5607 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2355 0.0266 -1.5763 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7948 0.4333 1.2729 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5418 0.3325 2.1990 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1376 2.0415 -0.2780 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1592 1.2523 -1.5905 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1220 0.1358 0.5454 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6161 1.9290 1.5537 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1945 0.7183 -0.8675 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4791 0.3376 -1.5685 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1755 -1.2862 1.5367 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4450 -0.4287 -0.8822 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5541 0.8333 -0.6308 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5967 0.4235 -0.5152 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0157 -0.6077 0.2837 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7940 1.8887 -0.0848 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1097 2.2277 1.6097 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0029 1.3644 2.3211 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2201 2.5634 1.0640 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7145 -1.6426 -1.4549 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0936 -2.6859 -0.8131 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0348 -2.7655 0.9548 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5092 -2.2946 0.9319 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2342 -2.1433 0.9786 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2350 -1.8033 -0.7556 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0646 2.5037 -0.3796 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7362 2.6756 1.2282 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1820 -0.4162 2.9631 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6741 -1.3048 2.7214 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7165 0.3908 3.1935 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2787 0.2567 -2.0607 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6977 -0.7454 -2.2028 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8531 -0.0835 2.2389 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6228 0.3254 2.3803 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1458 -0.6277 2.5414 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1225 1.1107 2.8445 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8502 1.6056 0.4323 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4479 3.0788 -0.4498 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1882 0.9347 -1.7959 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5066 -3.4475 0.7282 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9541 0.5344 1.1413 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2904 -0.9476 0.5054 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9872 -2.7726 -0.6953 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2554 2.4820 0.6810 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9626 2.1057 2.4100 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5784 2.3738 1.8351 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3786 2.8387 -2.7100 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3908 0.3370 -1.5023 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1403 1.8111 -0.8307 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3767 0.6384 -3.2730 H 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 1 59 1 0 0 0 0 2 17 1 0 0 0 0 2 62 1 0 0 0 0 3 25 1 0 0 0 0 3 66 1 0 0 0 0 4 29 1 0 0 0 0 4 69 1 0 0 0 0 5 29 2 0 0 0 0 6 7 1 0 0 0 0 6 9 1 0 0 0 0 6 15 1 0 0 0 0 6 30 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 7 31 1 0 0 0 0 8 11 1 0 0 0 0 8 13 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 9 32 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 10 23 1 0 0 0 0 11 18 1 0 0 0 0 11 22 1 0 0 0 0 11 33 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 12 34 1 0 0 0 0 13 14 1 0 0 0 0 13 35 1 0 0 0 0 13 36 1 0 0 0 0 14 37 1 0 0 0 0 14 38 1 0 0 0 0 15 17 1 0 0 0 0 15 39 1 0 0 0 0 16 18 1 0 0 0 0 16 40 1 0 0 0 0 16 41 1 0 0 0 0 17 42 1 0 0 0 0 18 43 1 0 0 0 0 18 44 1 0 0 0 0 19 24 1 0 0 0 0 19 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 20 49 1 0 0 0 0 21 25 1 0 0 0 0 21 50 1 0 0 0 0 21 51 1 0 0 0 0 22 26 1 0 0 0 0 22 27 1 0 0 0 0 22 52 1 0 0 0 0 23 53 1 0 0 0 0 23 54 1 0 0 0 0 23 55 1 0 0 0 0 24 25 1 0 0 0 0 24 56 1 0 0 0 0 24 57 1 0 0 0 0 25 58 1 0 0 0 0 26 28 1 0 0 0 0 26 60 1 0 0 0 0 26 61 1 0 0 0 0 27 63 1 0 0 0 0 27 64 1 0 0 0 0 27 65 1 0 0 0 0 28 29 1 0 0 0 0 28 67 1 0 0 0 0 28 68 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 5283851 > <PUBCHEM_CONFORMER_RMSD> 0.8 > <PUBCHEM_CONFORMER_DIVERSEORDER> 3 5 1 4 2 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 14 1 -0.68 15 0.28 17 0.28 2 -0.68 25 0.28 28 0.06 29 0.66 3 -0.68 4 -0.65 5 -0.57 59 0.4 62 0.4 66 0.4 69 0.5 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 6.2 > <PUBCHEM_PHARMACOPHORE_FEATURES> 14 1 1 acceptor 1 1 donor 1 2 acceptor 1 2 donor 1 27 hydrophobe 1 3 acceptor 1 3 donor 1 4 acceptor 1 5 acceptor 3 4 5 29 anion 5 7 8 11 16 18 rings 6 10 12 19 21 24 25 rings 6 6 7 8 9 13 14 rings 6 6 9 10 12 15 17 rings > <PUBCHEM_HEAVY_ATOM_COUNT> 29 > <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> 0050A00B00000003 > <PUBCHEM_MMFF94_ENERGY> 108.9489 > <PUBCHEM_FEATURE_SELFOVERLAP> 71.218 > <PUBCHEM_SHAPE_FINGERPRINT> 10498660 4 18340757200332849177 10670039 82 18410296878716234500 11135926 11 18271252621130003846 1200032 147 18194412082776015137 12011746 2 18060132137457212545 12236239 1 17894910733233949874 12596602 18 15357698569686748784 12788726 201 16916503628478547921 12954195 1 17703242715207885312 13540713 4 17986381411613666882 13690498 29 18126570252083505286 13782708 43 15698001825731146940 13911987 19 18338514145500015245 14211702 104 12031795772971308164 14251751 18 13830122897647340484 14790565 3 18056760919491889569 14840074 17 17894351059839909541 14931854 50 18130208386410596189 15052358 14 18272371953952326796 15064981 194 18411425029560538589 15183329 4 18271813406693668878 15188451 53 11671773875783706301 15575132 122 18040157318548298060 17913733 40 14129053725592989560 18608769 82 18341321293623511011 19958102 18 18272660004835308534 20567600 247 15051733067279557804 21267235 1 18201727309475923355 21279426 13 18202281424971299304 21637258 2 14333405632363179716 21709351 56 18409447020367298628 21756936 100 17240490247108212528 22122407 14 16588319284459070420 22393880 68 18272364308673156674 23379529 103 16484131886187784983 23559900 14 17988357161348036952 23569914 152 16625467169213187932 2838139 119 17240488035374460172 350125 39 18340200895395441571 4015057 19 16773510074926604200 4058900 60 18115589231940644931 4258327 124 17821449067332210829 5364581 5 11386659558551083934 56638632 10 15286499806394487142 59755656 215 18201720613980078630 59755656 520 17988375810048641315 6608658 132 18113615655697863676 > <PUBCHEM_SHAPE_MULTIPOLES> 567.46 14.54 2.5 2.09 17.74 1.25 0.79 -4.24 10.77 -2.67 0.07 0.73 -0.9 0.62 > <PUBCHEM_SHAPE_SELFOVERLAP> 1190.501 > <PUBCHEM_SHAPE_VOLUME> 318.4 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description
Classification	Compounds > Chemical entities > Organic compounds > Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives > Trihydroxy bile acids, alcohols and derivatives
CAS number	6830-03-1
PubChem ID	5283851
ChEBI ID	81299
FooDB ID	FDB021983
HMDB ID	HMDB0000364

Chemical data

MolDBi data

IUPAC Name	(4R)-4-[(1S,2R,5R,7R,8R,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional IUPAC Name	(4R)-4-[(1S,2R,5R,7R,8R,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Formula	C24H40O5
InChI	InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21-,22-,23-,24-/m1/s1
InChI Key	DKPMWHFRUGMUKF-NTPBNISXSA-N
Molecular weight	408.5714
Exact mass	408.28757439
SMILES	[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)[C@H](O)[C@]2([H])C[C@H](O)CC[C@]12C

ClassyFire Taxonomy

Description	belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Steroids and steroid derivatives
Sub Class	Bile acids, alcohols and derivatives
Direct Parent	Trihydroxy bile acids, alcohols and derivatives
Alternative Parents	7-alpha-hydroxysteroids 6-hydroxysteroids 3-alpha-hydroxysteroids Secondary alcohols Cyclic alcohols and derivatives Polyols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds

Publications with omega-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 omega-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 omega-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 omega-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 omega-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 omega-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