12-Ketolithocholic acid (Compound)

Go to Compound classification

ID	2281
Name	12-Ketolithocholic acid
Synonyms	3alpha-Hydroxy-12-oxo-5beta-cholanoic acid; 3alpha-Hydroxy-12-keto-5beta-cholanic acid; 12-Ketodeoxycholic acid; 12-Dehydrodeoxycholic acid
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE002281 (12-Ketolithocholic acid) 3D Structure for EE002281 (12-Ketolithocholic acid) 3080612 -OEChem-10221911353D 66 69 0 1 0 0 0 0 0999 V2000 0.8706 2.2778 -0.6464 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0229 0.9159 -2.1542 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7934 -1.1969 0.3754 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8552 0.8982 1.2488 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2496 -1.1106 0.4077 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0879 -1.0782 -0.3458 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9646 0.2558 0.1912 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0547 0.0074 0.1704 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3890 0.3266 0.8621 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2462 -0.9415 0.5141 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2653 -0.2771 -0.7471 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1371 -2.2566 -0.0866 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9499 -2.3344 -0.3759 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0494 1.4535 0.5481 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4742 -2.2618 0.6360 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3363 -1.8215 -0.7987 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3410 1.3322 -0.0662 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1094 1.6208 0.3529 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9094 -0.7873 -0.8618 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5929 0.3488 -0.3381 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4220 -0.0950 1.6631 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2786 0.4069 2.4047 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6168 1.4475 0.1768 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9361 0.3525 -0.8467 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7023 -0.0713 -1.3231 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4482 1.8710 -0.2481 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0602 0.5699 -1.0296 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6033 0.1473 0.3168 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0652 -1.2694 1.4755 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1569 -0.8526 -1.3983 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1286 0.3308 -0.8955 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0696 -1.0204 1.2398 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0217 0.0764 -1.7613 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6427 -3.2189 0.0900 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2966 -2.1786 -1.1688 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5705 -3.0794 -1.0825 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0015 -2.8073 0.6113 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9148 1.5559 1.6283 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4902 2.3879 0.1842 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0866 -3.0909 0.2609 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2988 -2.4763 1.6979 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0927 -2.2300 -0.1189 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5817 -2.1607 -1.8113 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7034 1.9239 -0.6212 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9178 2.4612 1.0314 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1566 -0.6158 -1.6408 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4235 -1.7129 -1.1497 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8823 -0.0176 0.6545 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9750 -1.0118 1.8911 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0330 0.7495 1.9949 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5405 -0.0885 2.3110 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7259 -0.4395 2.8224 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7799 1.3237 2.7341 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2720 0.4102 2.8683 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0595 1.1890 1.1463 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0584 2.4006 -0.1368 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9296 -0.0486 -0.6130 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8197 -1.1606 -1.3242 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4087 0.2102 -2.3426 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7811 2.1907 0.5524 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3996 2.3349 0.0308 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1627 2.3094 -1.2090 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2526 0.1971 -2.7676 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7876 0.2535 -1.7874 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0337 1.6613 -1.0862 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1473 -1.4781 1.2460 H 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 24 1 0 0 0 0 2 63 1 0 0 0 0 3 28 1 0 0 0 0 3 66 1 0 0 0 0 4 28 2 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 5 12 1 0 0 0 0 5 29 1 0 0 0 0 6 8 1 0 0 0 0 6 13 1 0 0 0 0 6 30 1 0 0 0 0 7 9 1 0 0 0 0 7 14 1 0 0 0 0 7 31 1 0 0 0 0 8 11 1 0 0 0 0 8 17 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 9 22 1 0 0 0 0 10 15 1 0 0 0 0 10 19 1 0 0 0 0 10 32 1 0 0 0 0 11 16 1 0 0 0 0 11 20 1 0 0 0 0 11 33 1 0 0 0 0 12 15 1 0 0 0 0 12 34 1 0 0 0 0 12 35 1 0 0 0 0 13 16 1 0 0 0 0 13 36 1 0 0 0 0 13 37 1 0 0 0 0 14 17 1 0 0 0 0 14 38 1 0 0 0 0 14 39 1 0 0 0 0 15 40 1 0 0 0 0 15 41 1 0 0 0 0 16 42 1 0 0 0 0 16 43 1 0 0 0 0 18 23 1 0 0 0 0 18 44 1 0 0 0 0 18 45 1 0 0 0 0 19 24 1 0 0 0 0 19 46 1 0 0 0 0 19 47 1 0 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 20 48 1 0 0 0 0 21 49 1 0 0 0 0 21 50 1 0 0 0 0 21 51 1 0 0 0 0 22 52 1 0 0 0 0 22 53 1 0 0 0 0 22 54 1 0 0 0 0 23 24 1 0 0 0 0 23 55 1 0 0 0 0 23 56 1 0 0 0 0 24 57 1 0 0 0 0 25 27 1 0 0 0 0 25 58 1 0 0 0 0 25 59 1 0 0 0 0 26 60 1 0 0 0 0 26 61 1 0 0 0 0 26 62 1 0 0 0 0 27 28 1 0 0 0 0 27 64 1 0 0 0 0 27 65 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 3080612 > <PUBCHEM_CONFORMER_RMSD> 0.8 > <PUBCHEM_CONFORMER_DIVERSEORDER> 5 10 15 6 2 4 11 13 16 3 9 8 1 7 17 12 14 18 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 12 1 -0.57 14 0.06 17 0.45 2 -0.68 24 0.28 27 0.06 28 0.66 3 -0.65 4 -0.57 63 0.4 66 0.5 8 0.06 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 6 > <PUBCHEM_PHARMACOPHORE_FEATURES> 11 1 1 acceptor 1 2 acceptor 1 2 donor 1 26 hydrophobe 1 3 acceptor 1 4 acceptor 3 3 4 28 anion 5 6 8 11 13 16 rings 6 5 6 7 8 14 17 rings 6 5 7 9 10 12 15 rings 6 9 10 18 19 23 24 rings > <PUBCHEM_HEAVY_ATOM_COUNT> 28 > <PUBCHEM_ATOM_DEF_STEREO_COUNT> 9 > <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> 2 > <PUBCHEM_CONFORMER_ID> 002F01A400000005 > <PUBCHEM_MMFF94_ENERGY> 98.6601 > <PUBCHEM_FEATURE_SELFOVERLAP> 55.986 > <PUBCHEM_SHAPE_FINGERPRINT> 10366900 7 17847061069245413211 10554248 39 18260266348321646118 10906281 52 18336283265986575994 11089746 13 18409164424245790236 11315181 36 17703794734110809521 11578080 2 16806714080265673438 11719270 70 18412543193935836590 11796584 16 16515408473813540832 12011746 2 18343584040448601087 12236239 1 17749111119056141846 12422481 6 18260552225544694212 12516196 113 16487257668722368080 12788726 201 18270961224905369105 12838862 33 18338787945507545105 13533116 47 17530963571752635162 13782708 43 16987735519285204198 13914758 101 17458338607395958148 14251752 14 17530961376064530268 14856354 85 14779555594884134411 15131766 46 16663199453957730356 15183329 4 18408328782935111980 15196674 1 18339088206217261532 15238133 3 15140685739614947743 15461852 350 17418092157040620948 15685185 35 12389786911269500098 15788980 27 17022625307487152678 1601671 61 18335704948561009564 17093844 174 18040996279947381984 17349148 13 18273213089111356083 17980427 23 17417828239616318937 18608769 82 18338804515797386955 18681886 176 18271239525188779289 18769570 83 17022619758663960477 200 152 17632578245631337007 20511986 3 18410001135652353626 21150785 3 15769771368828097102 21267235 1 18268164195598266739 21298829 104 18341334375714391809 21709351 56 18335985367228940741 21859007 373 18187909682573196996 22393880 68 18336823195332002695 23402539 116 18407762551494762078 23522609 53 8718261437716365742 23559900 14 18271802475348240953 23569917 315 18341901792102109134 24771293 8 18131353025297168016 2838139 119 18259702294266288549 3004659 81 18261403269430918500 3009799 131 18407755932633862276 335352 9 18409451396764757388 34797466 226 15841559591429057212 34934 24 18408608032781438803 3633792 109 18201154356907516781 484989 97 18196929093100435847 5104073 3 18341346491152424874 559249 180 18334013912546762507 59755656 215 18340211800175143926 59755656 520 16515685571870735507 6328613 192 18260834842877418308 7226269 152 18113903762098219344 > <PUBCHEM_SHAPE_MULTIPOLES> 552.75 15.72 2.16 1.4 13.18 0.55 -0.22 -3.13 2.04 -0.8 0.1 -0.86 -0.23 0.33 > <PUBCHEM_SHAPE_SELFOVERLAP> 1164.715 > <PUBCHEM_SHAPE_VOLUME> 308.8 > <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 > Monohydroxy bile acids, alcohols and derivatives
CAS number	5130-29-0
PubChem ID	3080612
ChEBI ID	139134
FooDB ID	FDB021953
HMDB ID	HMDB0000328

Chemical data

MolDBi data

IUPAC Name	(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional IUPAC Name	12-ketolithocholic acid
Formula	C24H38O4
InChI	InChI=1S/C24H38O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-20,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,23+,24-/m1/s1
InChI Key	CVNYHSDFZXHMMJ-VPUMZWJWSA-N
Molecular weight	390.5561
Exact mass	390.277009704
SMILES	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC(=O)[C@]12C)[C@H](C)CCC(O)=O

ClassyFire Taxonomy

Description	belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Steroids and steroid derivatives
Sub Class	Bile acids, alcohols and derivatives
Direct Parent	Monohydroxy bile acids, alcohols and derivatives
Alternative Parents	Oxosteroids 3-alpha-hydroxysteroids Secondary alcohols Ketones Cyclic alcohols and derivatives Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives

Publications with 12-Ketolithocholic 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 12-Ketolithocholic 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 12-Ketolithocholic 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 12-Ketolithocholic 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 12-Ketolithocholic 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 12-Ketolithocholic 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