3-Dehydrochenodeoxycholic acid (Compound)

Go to Compound classification

ID	2188
Name	3-Dehydrochenodeoxycholic acid
Synonyms	7alpha-Hydroxy-3-oxo-5beta-cholanoic acid; 3-Oxochenodeoxycholic acid; 3-Ketochenodeoxycholic acid; 3-Keto-CDCA
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE002188 (3-Dehydrochenodeoxycholic acid) 3D Structure for EE002188 (3-Dehydrochenodeoxycholic acid) 5283932 -OEChem-12242201103D 66 69 0 1 0 0 0 0 0999 V2000 -2.2210 -2.3547 -0.9388 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7868 0.3722 -1.5651 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9421 -0.8661 0.7055 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9801 1.3960 0.8998 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1921 0.1664 0.1033 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2236 -1.0177 -0.1033 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1239 -0.8294 0.6106 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7999 0.4619 0.0550 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2107 0.7441 0.7001 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4173 -0.3767 -0.6724 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5414 1.4113 -0.5148 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8419 1.6870 0.0994 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0735 -2.2389 0.2362 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1141 -0.5381 0.6699 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0403 -2.0517 0.4408 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4840 -1.8645 -0.2555 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3913 -1.8220 1.1090 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9025 1.9019 -0.0964 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5490 0.4417 1.5855 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7350 0.3561 -0.4650 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0770 1.1897 2.1778 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8241 -0.6904 -0.6832 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4195 1.7698 -0.1756 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7735 0.4751 -0.8753 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8579 -0.3320 -1.2680 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5799 1.8328 -0.8434 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2080 0.3816 -1.1754 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7423 0.3945 0.2392 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0051 -1.0921 -1.1818 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9463 -0.7093 1.6848 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9784 0.2757 -1.0151 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1806 -0.3551 -1.7477 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4243 1.2803 -1.5982 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1222 2.3214 -0.3714 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7041 2.0259 1.1305 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2888 2.5292 -0.4413 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7081 -3.1437 -0.2601 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0838 -2.4333 1.3146 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9186 -0.4008 1.4095 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5682 -2.9279 0.9002 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2074 -2.0407 0.5488 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7753 -2.4911 -1.1060 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2357 -1.7798 2.1946 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0455 -2.6837 0.9263 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5244 1.9188 -1.1276 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6451 2.8767 0.3356 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0870 -0.3927 2.0466 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1798 1.3295 1.6912 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6659 0.6219 2.2041 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0225 0.3108 0.5925 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5413 2.1390 2.2744 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0633 1.3436 2.6309 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5515 0.4484 2.7864 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4145 -1.6130 -0.7028 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1235 -0.7024 -1.5227 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8320 2.6031 -0.7541 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8766 1.7759 0.8186 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9818 -1.3686 -0.9349 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5716 -0.3777 -2.3266 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7942 -3.1381 -0.9954 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0678 1.9590 -1.8025 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0589 2.3899 -0.0640 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5369 2.3523 -0.9200 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9432 -0.1525 -1.7908 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1900 1.3995 -1.5709 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2905 -0.8654 1.6225 H 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 1 60 1 0 0 0 0 2 24 2 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 10 1 0 0 0 0 5 11 1 0 0 0 0 5 19 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 6 29 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 7 30 1 0 0 0 0 8 9 1 0 0 0 0 8 12 1 0 0 0 0 8 31 1 0 0 0 0 9 14 1 0 0 0 0 9 18 1 0 0 0 0 9 21 1 0 0 0 0 10 16 1 0 0 0 0 10 20 1 0 0 0 0 10 32 1 0 0 0 0 11 12 1 0 0 0 0 11 33 1 0 0 0 0 11 34 1 0 0 0 0 12 35 1 0 0 0 0 12 36 1 0 0 0 0 13 16 1 0 0 0 0 13 37 1 0 0 0 0 13 38 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 14 39 1 0 0 0 0 15 17 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 43 1 0 0 0 0 17 44 1 0 0 0 0 18 23 1 0 0 0 0 18 45 1 0 0 0 0 18 46 1 0 0 0 0 19 47 1 0 0 0 0 19 48 1 0 0 0 0 19 49 1 0 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 20 50 1 0 0 0 0 21 51 1 0 0 0 0 21 52 1 0 0 0 0 21 53 1 0 0 0 0 22 24 1 0 0 0 0 22 54 1 0 0 0 0 22 55 1 0 0 0 0 23 24 1 0 0 0 0 23 56 1 0 0 0 0 23 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 61 1 0 0 0 0 26 62 1 0 0 0 0 26 63 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> 5283932 > <PUBCHEM_CONFORMER_RMSD> 0.8 > <PUBCHEM_CONFORMER_DIVERSEORDER> 4 15 8 14 11 12 7 6 13 18 17 5 3 10 1 16 2 9 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 12 1 -0.68 15 0.28 2 -0.57 22 0.06 23 0.06 24 0.45 27 0.06 28 0.66 3 -0.65 4 -0.57 60 0.4 66 0.5 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 6 > <PUBCHEM_PHARMACOPHORE_FEATURES> 11 1 1 acceptor 1 1 donor 1 2 acceptor 1 26 hydrophobe 1 3 acceptor 1 4 acceptor 3 3 4 28 anion 5 5 6 10 13 16 rings 6 5 6 7 8 11 12 rings 6 7 8 9 14 15 17 rings 6 9 14 18 22 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> 3 > <PUBCHEM_CONFORMER_ID> 0050A05C00000004 > <PUBCHEM_MMFF94_ENERGY> 98.401 > <PUBCHEM_FEATURE_SELFOVERLAP> 55.984 > <PUBCHEM_SHAPE_FINGERPRINT> 10366900 7 18060137626646904875 10554248 39 17967814947052092174 11089746 13 18260265261114436852 11135609 187 18339078182391197257 11315181 36 18272938244894542832 11719270 70 18408319969820982562 12011746 2 18342175561948369797 12236239 1 17458065993142520350 12422481 6 17822015294192652596 12516196 113 16487256564973795344 12596602 18 13686306751001053878 12616971 3 17022911176822010566 12633257 1 13045953416936552951 12788726 201 17916310425024642505 12838862 33 18336251384903546685 13914758 101 17095516271320279516 14856354 85 14129068023138172019 15131766 46 15576997392618321934 15183329 4 18260554415988304668 15461852 350 17846779641813958356 15788980 27 17022908973118795300 18335252 98 9583519829067769292 18608769 82 18335427915525105467 18681886 176 18339919415221904400 200 152 17917710185152192593 20511986 3 18336255791381704282 21150785 3 16415476064929774556 21859007 373 18041262319266045924 23402539 116 18041000661246462420 23559900 14 18270958050428677953 23569917 315 18409455782170187106 2838139 119 18113335302139808989 335352 9 18334860519894956364 34797466 226 16773804714384420764 34934 24 18261114041146714099 3633792 109 18339075974403558325 484989 97 18267300027748285479 5104073 3 18263657189940447194 59755656 215 18410015399665680606 59755656 520 16153708747378074059 6371009 1 18409730660213748540 9981440 41 18260557718312526683 > <PUBCHEM_SHAPE_MULTIPOLES> 552.75 16.1 2.2 1.32 14.94 0.59 -0.29 -4.54 2.72 -1.03 -0.04 -0.49 -0.18 0.11 > <PUBCHEM_SHAPE_SELFOVERLAP> 1163.094 > <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
PubChem ID	5283932
ChEBI ID	88097
FooDB ID	FDB022081
HMDB ID	HMDB0000503

Chemical data

MolDBi data

IUPAC Name	(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional IUPAC Name	(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Formula	C24H38O4
InChI	InChI=1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-15,17-20,22,26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,17-,18+,19+,20-,22+,23+,24-/m1/s1
InChI Key	KNVADAPHVNKTEP-CIGXQKLNSA-N
Molecular weight	390.564
Exact mass	390.277009704
SMILES	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[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	7-hydroxysteroids 3-oxo-5-beta-steroids Secondary alcohols Cyclic ketones Cyclic alcohols and derivatives Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives

Publications with 3-Dehydrochenodeoxycholic 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 3-Dehydrochenodeoxycholic 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 3-Dehydrochenodeoxycholic 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 3-Dehydrochenodeoxycholic 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 3-Dehydrochenodeoxycholic 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 3-Dehydrochenodeoxycholic 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