Oleic acid (cis-18:1n-9) (Compound)

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ID	311
Name	Oleic acid (cis-18:1n-9)
Synonyms	cis-9-Octadecenoic acid; Oleate
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE000311 (Oleic acid (cis-18:1n-9)) 3D Structure for EE000311 (Oleic acid (cis-18:1n-9)) 445639 -OEChem-02282313303D 54 53 0 0 0 0 0 0 0999 V2000 7.2438 0.3284 -0.6585 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -0.1564 1.2753 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1503 -1.5706 -0.3069 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4422 -1.3743 0.4892 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0942 -2.3907 0.4411 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0012 1.9226 -0.4319 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2016 1.3600 0.3282 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5251 -0.6197 -0.2917 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2513 1.9525 0.4529 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4597 1.3590 -0.5429 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8105 -2.6942 -0.3381 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1402 0.7880 -0.7626 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4879 2.4841 -0.2779 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6695 0.8265 0.2315 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2198 -3.5599 0.3898 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8401 1.7249 0.3718 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7267 2.4473 0.5696 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9376 0.7868 -0.6213 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4531 -3.8707 -0.4432 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1374 0.2564 0.1255 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7120 -0.6036 -0.5699 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3866 -2.0763 -1.2513 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8429 -2.3555 0.7724 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2198 -0.8479 1.4249 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8271 -1.8633 1.3656 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 -3.3435 0.7481 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2219 2.9375 -0.7821 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1945 1.3077 -1.3192 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3799 1.9612 1.2280 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9826 0.3378 0.6603 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4239 -0.5581 0.3354 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8056 -1.2134 -1.1708 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0555 2.5759 1.3349 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4527 0.9403 0.8253 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6694 2.3772 -0.8922 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2904 0.7391 -1.4316 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0849 -3.1921 -1.2768 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3395 -1.7440 -0.6200 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9916 1.2045 -1.3158 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3225 0.7258 -1.4845 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6205 1.9282 -1.2104 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3101 3.5260 -0.5721 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4503 -0.1828 0.6026 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8442 1.4521 1.1159 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5302 -3.0521 1.3107 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2500 -4.5038 0.6907 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6389 1.8410 1.1029 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7034 3.0866 1.4510 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7734 0.1451 -1.4942 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1730 1.8000 -0.9668 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9701 -2.9499 -0.7317 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1520 -4.4899 0.1278 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1825 -4.4129 -1.3546 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0434 0.0024 -0.1931 H 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 1 54 1 0 0 0 0 2 20 2 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 3 21 1 0 0 0 0 3 22 1 0 0 0 0 4 8 1 0 0 0 0 4 23 1 0 0 0 0 4 24 1 0 0 0 0 5 11 1 0 0 0 0 5 25 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 6 9 1 0 0 0 0 6 27 1 0 0 0 0 6 28 1 0 0 0 0 7 10 1 0 0 0 0 7 29 1 0 0 0 0 7 30 1 0 0 0 0 8 12 1 0 0 0 0 8 31 1 0 0 0 0 8 32 1 0 0 0 0 9 13 1 0 0 0 0 9 33 1 0 0 0 0 9 34 1 0 0 0 0 10 14 1 0 0 0 0 10 35 1 0 0 0 0 10 36 1 0 0 0 0 11 15 1 0 0 0 0 11 37 1 0 0 0 0 11 38 1 0 0 0 0 12 16 1 0 0 0 0 12 39 1 0 0 0 0 12 40 1 0 0 0 0 13 17 1 0 0 0 0 13 41 1 0 0 0 0 13 42 1 0 0 0 0 14 18 1 0 0 0 0 14 43 1 0 0 0 0 14 44 1 0 0 0 0 15 19 1 0 0 0 0 15 45 1 0 0 0 0 15 46 1 0 0 0 0 16 17 2 0 0 0 0 16 47 1 0 0 0 0 17 48 1 0 0 0 0 18 20 1 0 0 0 0 18 49 1 0 0 0 0 18 50 1 0 0 0 0 19 51 1 0 0 0 0 19 52 1 0 0 0 0 19 53 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 445639 > <PUBCHEM_CONFORMER_RMSD> 1.4 > <PUBCHEM_CONFORMER_DIVERSEORDER> 1 17 68 39 4 35 2 30 83 41 74 29 71 63 49 76 89 33 44 52 78 7 69 45 40 77 70 79 37 6 51 28 9 86 88 43 19 5 60 87 18 53 3 20 36 10 58 81 22 62 31 26 38 64 16 72 57 8 75 61 65 32 27 14 55 34 84 82 47 21 67 12 73 50 11 66 15 56 25 24 85 54 48 23 59 80 46 13 42 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 11 1 -0.65 12 0.14 13 0.14 16 -0.29 17 -0.29 18 0.06 2 -0.57 20 0.66 47 0.15 48 0.15 54 0.5 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 15 > <PUBCHEM_PHARMACOPHORE_FEATURES> 4 1 1 acceptor 1 19 hydrophobe 1 2 acceptor 3 1 2 20 anion > <PUBCHEM_HEAVY_ATOM_COUNT> 20 > <PUBCHEM_ATOM_DEF_STEREO_COUNT> 0 > <PUBCHEM_ATOM_UDEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_DEF_STEREO_COUNT> 1 > <PUBCHEM_BOND_UDEF_STEREO_COUNT> 0 > <PUBCHEM_ISOTOPIC_ATOM_COUNT> 0 > <PUBCHEM_COMPONENT_COUNT> 1 > <PUBCHEM_CACTVS_TAUTO_COUNT> 1 > <PUBCHEM_CONFORMER_ID> 0006CCC700000001 > <PUBCHEM_MMFF94_ENERGY> 0.3555 > <PUBCHEM_FEATURE_SELFOVERLAP> 20.354 > <PUBCHEM_SHAPE_FINGERPRINT> 10939801 23 18264205993131333872 11200772 71 17972900312905648404 11513181 2 18058729096576158679 13402501 40 18413673521420763246 14251740 79 18343305889887535969 14251757 5 17976274743443601644 14466204 15 18411700993186262400 14647877 51 18196376909706723006 15183329 4 18333730230246674216 16719943 64 18408885169925804018 20609170 92 18043242454214117013 20721686 56 18336271163460215915 21236236 1 18411983571969847456 23559900 14 18269267036126962521 338550 245 18335145284748167198 373842 8 18336821971177341442 5085150 59 18341322336820639650 559249 180 18334574637971030873 59755656 215 18412829071179880454 6138700 20 18339078294055156679 6437827 68 18410856555761703106 > <PUBCHEM_SHAPE_MULTIPOLES> 399.85 15.31 4.41 0.86 20.96 4.45 -0.04 -4.69 0.16 -2.29 -0.04 0.25 -0.03 -0.25 > <PUBCHEM_SHAPE_SELFOVERLAP> 732.772 > <PUBCHEM_SHAPE_VOLUME> 252.5 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description
Classification	Compounds > Chemical entities > Organic compounds > Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Long-chain fatty acids
CAS number	112-80-1
PubChem ID	445639
ChEBI ID	16196
FooDB ID	FDB012858
HMDB ID	HMDB0000207

Chemical data

MolDBi data

IUPAC Name	(9Z)-octadec-9-enoic acid
Traditional IUPAC Name	oleic acid
Formula	C18H34O2
InChI	InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-
InChI Key	ZQPPMHVWECSIRJ-KTKRTIGZSA-N
Molecular weight	282.4614
Exact mass	282.255880332
SMILES	CCCCCCCC\C=C/CCCCCCCC(O)=O

ClassyFire Taxonomy

Description	belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty acids and conjugates
Direct Parent	Long-chain fatty acids
Alternative Parents	Unsaturated fatty acids Straight chain fatty acids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds

Publications with Oleic acid (cis-18:1n-9)

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 Oleic acid (cis-18:1n-9) 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 Oleic acid (cis-18:1n-9) 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 Oleic acid (cis-18:1n-9) 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 Oleic acid (cis-18:1n-9) 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 Oleic acid (cis-18:1n-9) 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