Exact Mass: 555.356

A marine macrodiolide that is isolated from the sponge Mycale hentscheli and exhibits anticancer and antiviral properties

Cholylphenylalanine

2-[(1-Hydroxy-4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl}pentylidene)amino]-3-phenylpropanoate

Chenodeoxycholyltyrosine

2-(4-{5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)-3-(4-hydroxyphenyl)propanoic acid

Chenodeoxycholyltyrosine belongs to a class of molecules known as bile acid-amino acid conjugates. These are bile acid conjugates that consist of a primary bile acid such as cholic acid, doxycholic acid and chenodeoxycholic acid, conjugated to an amino acid. Chenodeoxycholyltyrosine consists of the bile acid chenodeoxycholic acid conjugated to the amino acid Tyrosine conjugated at the C24 acyl site.Bile acids play an important role in regulating various physiological systems, such as fat digestion, cholesterol metabolism, vitamin absorption, liver function, and enterohepatic circulation through their combined signaling, detergent, and antimicrobial mechanisms (PMID: 34127070). Bile acids also act as detergents in the gut and support the absorption of fats through the intestinal membrane. These same properties allow for the disruption of bacterial membranes, thereby allowing them to serve a bacteriocidal or bacteriostatic function. In humans (and other mammals) bile acids are normally conjugated with the amino acids glycine and taurine by the liver. This conjugation catalyzed by two liver enzymes, bile acid CoA ligase (BAL) and bile acid CoA: amino acid N-acyltransferase (BAT). Glycine and taurine bound BAs are also referred to as bile salts due to their decreased pKa and complete ionization resulting in these compounds being present as anions in vivo. Unlike glycine and taurine-conjugated bile acids, these recently discovered bile acids, such as Chenodeoxycholyltyrosine, are produced by the gut microbiota, making them secondary bile acids (PMID: 32103176) or microbially conjugated bile acids (MCBAs) (PMID: 34127070). Evidence suggests that these bile acid-amino acid conjugates are produced by microbes belonging to Clostridia species (PMID: 32103176). These unusual bile acid-amino acid conjugates are found in higher frequency in patients with inflammatory bowel disease (IBD), cystic fibrosis (CF) and in infants (PMID: 32103176). Chenodeoxycholyltyrosine appears to act as an agonist for the farnesoid X receptor (FXR) and it can also lead to reduced expression of bile acid synthesis genes (PMID: 32103176). It currently appears that microbially conjugated bile acids (MCBAs) or amino acid-bile acid conjugates are only conjugated to cholic acid, deoxycholic acid and chenodeoxycholic acid (PMID: 34127070). It has been estimated that if microbial conjugation of bile acids is very promiscuous and occurs for all potential oxidized, epimerized, and dehydroxylated states of each hydroxyl group present on cholic acid (C3, C7, C12) in addition to ring orientation, the total number of potential human bile acid conjugates could be over 2800 (PMID: 34127070).

Deoxycholyltyrosine

2-[4-(3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoylamino]-3-(4-hydroxyphenyl)propanoic acid

Deoxycholyltyrosine belongs to a class of molecules known as bile acid-amino acid conjugates. These are bile acid conjugates that consist of a primary bile acid such as cholic acid, doxycholic acid and chenodeoxycholic acid, conjugated to an amino acid. Deoxycholyltyrosine consists of the bile acid deoxycholic acid conjugated to the amino acid Tyrosine conjugated at the C24 acyl site.Bile acids play an important role in regulating various physiological systems, such as fat digestion, cholesterol metabolism, vitamin absorption, liver function, and enterohepatic circulation through their combined signaling, detergent, and antimicrobial mechanisms (PMID: 34127070). Bile acids also act as detergents in the gut and support the absorption of fats through the intestinal membrane. These same properties allow for the disruption of bacterial membranes, thereby allowing them to serve a bacteriocidal or bacteriostatic function. In humans (and other mammals) bile acids are normally conjugated with the amino acids glycine and taurine by the liver. This conjugation catalyzed by two liver enzymes, bile acid CoA ligase (BAL) and bile acid CoA: amino acid N-acyltransferase (BAT). Glycine and taurine bound BAs are also referred to as bile salts due to their decreased pKa and complete ionization resulting in these compounds being present as anions in vivo. Unlike glycine and taurine-conjugated bile acids, these recently discovered bile acids, such as Deoxycholyltyrosine, are produced by the gut microbiota, making them secondary bile acids (PMID: 32103176) or microbially conjugated bile acids (MCBAs) (PMID: 34127070). Evidence suggests that these bile acid-amino acid conjugates are produced by microbes belonging to Clostridia species (PMID: 32103176). These unusual bile acid-amino acid conjugates are found in higher frequency in patients with inflammatory bowel disease (IBD), cystic fibrosis (CF) and in infants (PMID: 32103176). Deoxycholyltyrosine appears to act as an agonist for the farnesoid X receptor (FXR) and it can also lead to reduced expression of bile acid synthesis genes (PMID: 32103176). It currently appears that microbially conjugated bile acids (MCBAs) or amino acid-bile acid conjugates are only conjugated to cholic acid, deoxycholic acid and chenodeoxycholic acid (PMID: 34127070). It has been estimated that if microbial conjugation of bile acids is very promiscuous and occurs for all potential oxidized, epimerized, and dehydroxylated states of each hydroxyl group present on cholic acid (C3, C7, C12) in addition to ring orientation, the total number of potential human bile acid conjugates could be over 2800 (PMID: 34127070). D005765 - Gastrointestinal Agents > D001647 - Bile Acids and Salts D005765 - Gastrointestinal Agents > D002793 - Cholic Acids

CONFIDENCE standard compound; INTERNAL_ID 418; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 6831; ORIGINAL_PRECURSOR_SCAN_NO 6826 CONFIDENCE standard compound; INTERNAL_ID 418; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 6849; ORIGINAL_PRECURSOR_SCAN_NO 6848 CONFIDENCE standard compound; INTERNAL_ID 418; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 6877; ORIGINAL_PRECURSOR_SCAN_NO 6875 CONFIDENCE standard compound; INTERNAL_ID 418; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 6885; ORIGINAL_PRECURSOR_SCAN_NO 6883 CONFIDENCE standard compound; INTERNAL_ID 418; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 6879; ORIGINAL_PRECURSOR_SCAN_NO 6877 CONFIDENCE standard compound; INTERNAL_ID 418; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 6892; ORIGINAL_PRECURSOR_SCAN_NO 6890

Lys Pro Arg Arg

(2S)-5-carbamimidamido-2-[(2S)-5-carbamimidamido-2-{[(2S)-1-[(2S)-2,6-diaminohexanoyl]pyrrolidin-2-yl]formamido}pentanamido]pentanoic acid

Lys Arg Pro Arg

(2S)-5-carbamimidamido-2-{[(2S)-1-[(2S)-5-carbamimidamido-2-[(2S)-2,6-diaminohexanamido]pentanoyl]pyrrolidin-2-yl]formamido}pentanoic acid

Lys Arg Arg Pro

(2S)-1-[(2S)-5-carbamimidamido-2-[(2S)-5-carbamimidamido-2-[(2S)-2,6-diaminohexanamido]pentanamido]pentanoyl]pyrrolidine-2-carboxylic acid

Pro Lys Arg Arg

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-pyrrolidin-2-ylformamido]hexanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoic acid

Pro Gln Arg Arg

(2S)-5-carbamimidamido-2-[(2S)-5-carbamimidamido-2-[(2S)-4-carbamoyl-2-[(2S)-pyrrolidin-2-ylformamido]butanamido]pentanamido]pentanoic acid

Pro Arg Lys Arg

(2S)-2-[(2S)-6-amino-2-[(2S)-5-carbamimidamido-2-[(2S)-pyrrolidin-2-ylformamido]pentanamido]hexanamido]-5-carbamimidamidopentanoic acid

Pro Arg Gln Arg

(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-5-carbamimidamido-2-[(2S)-pyrrolidin-2-ylformamido]pentanamido]-4-carbamoylbutanamido]pentanoic acid

Pro Arg Arg Lys

(2S)-6-amino-2-[(2S)-5-carbamimidamido-2-[(2S)-5-carbamimidamido-2-[(2S)-pyrrolidin-2-ylformamido]pentanamido]pentanamido]hexanoic acid

Pro Arg Arg Gln

(2S)-2-[(2S)-5-carbamimidamido-2-[(2S)-5-carbamimidamido-2-[(2S)-pyrrolidin-2-ylformamido]pentanamido]pentanamido]-4-carbamoylbutanoic acid

Gln Pro Arg Arg

(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-amino-4-carbamoylbutanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoic acid

Gln Arg Pro Arg

(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid

Gln Arg Arg Pro

(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carboxylic acid

Arg Lys Pro Arg

(2S)-2-{[(2S)-1-[(2S)-6-amino-2-[(2S)-2-amino-5-carbamimidamidopentanamido]hexanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid

Arg Lys Arg Pro

(2S)-1-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-5-carbamimidamidopentanamido]hexanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carboxylic acid

Arg Pro Lys Arg

(2S)-2-[(2S)-6-amino-2-{[(2S)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}hexanamido]-5-carbamimidamidopentanoic acid

Arg Pro Gln Arg

(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}-4-carbamoylbutanamido]-5-carbamimidamidopentanoic acid

Arg Pro Arg Lys

(2S)-6-amino-2-[(2S)-2-{[(2S)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]hexanoic acid

Arg Pro Arg Gln

(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]-4-carbamoylbutanoic acid

Arg Gln Pro Arg

(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-4-carbamoylbutanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid

Arg Gln Arg Pro

(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carboxylic acid

Arg Arg Lys Pro

(2S)-1-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]hexanoyl]pyrrolidine-2-carboxylic acid

Arg Arg Pro Lys

(2S)-6-amino-2-{[(2S)-1-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}hexanoic acid

Arg Arg Pro Gln

(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}-4-carbamoylbutanoic acid

Arg Arg Gln Pro

(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanoyl]pyrrolidine-2-carboxylic acid

VIVLL

Val-Ile-Val-Leu-Leu

C28H53N5O6 (555.3996)

LPS O-20:0;O

1-(2-methoxy-nonadecanyl)-sn-glycero-3-phosphoserine

C26H54NO9P (555.3536)

Phenylalanocholic Acid

N-(3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oyl)-L-phenylalanine

Solvent Yellow 98

C36H45NO2S (555.3171)

90Yls47brx

C31H45N3O6 (555.3308)

C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C129824 - Antineoplastic Protein Inhibitor

(3R,9R,10S)-16-(dimethylamino)-12-[(2R)-1-hydroxypropan-2-yl]-9-[[(4-methoxyphenyl)methyl-methylamino]methyl]-3,10-dimethyl-2,8-dioxa-12-azabicyclo[12.4.0]octadeca-1(14),15,17-trien-13-one

N-[(2S,3S)-5-[(2S)-1-hydroxypropan-2-yl]-3-methyl-2-[[methyl-[(4-phenylphenyl)methyl]amino]methyl]-6-oxo-2,3,4,7-tetrahydro-1,5-benzoxazonin-9-yl]cyclopropanecarboxamide

N-[(2S,3S)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-2-[[methyl-[(4-phenylphenyl)methyl]amino]methyl]-6-oxo-2,3,4,7-tetrahydro-1,5-benzoxazonin-9-yl]cyclopropanecarboxamide

N-[(2R,3R)-5-[(2S)-1-hydroxypropan-2-yl]-3-methyl-2-[[methyl-[(4-phenylphenyl)methyl]amino]methyl]-6-oxo-2,3,4,7-tetrahydro-1,5-benzoxazonin-9-yl]cyclopropanecarboxamide

N-[(2S,3R)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-2-[[methyl-[(4-phenylphenyl)methyl]amino]methyl]-6-oxo-2,3,4,7-tetrahydro-1,5-benzoxazonin-9-yl]cyclopropanecarboxamide

(3S,9S,10S)-16-(dimethylamino)-12-[(2R)-1-hydroxypropan-2-yl]-9-[[(4-methoxyphenyl)methyl-methylamino]methyl]-3,10-dimethyl-2,8-dioxa-12-azabicyclo[12.4.0]octadeca-1(14),15,17-trien-13-one

N-[(2R,3R)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-2-[[methyl-[(4-phenylphenyl)methyl]amino]methyl]-6-oxo-2,3,4,7-tetrahydro-1,5-benzoxazonin-9-yl]cyclopropanecarboxamide

(3S,9S,10S)-16-(dimethylamino)-12-[(2S)-1-hydroxypropan-2-yl]-9-[[(4-methoxyphenyl)methyl-methylamino]methyl]-3,10-dimethyl-2,8-dioxa-12-azabicyclo[12.4.0]octadeca-1(14),15,17-trien-13-one

(3R,9S,10S)-16-(dimethylamino)-12-[(2R)-1-hydroxypropan-2-yl]-9-[[(4-methoxyphenyl)methyl-methylamino]methyl]-3,10-dimethyl-2,8-dioxa-12-azabicyclo[12.4.0]octadeca-1(14),15,17-trien-13-one

(3R,9R,10R)-16-(dimethylamino)-12-[(2S)-1-hydroxypropan-2-yl]-9-[[(4-methoxyphenyl)methyl-methylamino]methyl]-3,10-dimethyl-2,8-dioxa-12-azabicyclo[12.4.0]octadeca-1(14),15,17-trien-13-one

(3R,9S,10R)-16-(dimethylamino)-12-[(2R)-1-hydroxypropan-2-yl]-9-[[(4-methoxyphenyl)methyl-methylamino]methyl]-3,10-dimethyl-2,8-dioxa-12-azabicyclo[12.4.0]octadeca-1(14),15,17-trien-13-one

(3S,9S,10R)-16-(dimethylamino)-12-[(2R)-1-hydroxypropan-2-yl]-9-[[(4-methoxyphenyl)methyl-methylamino]methyl]-3,10-dimethyl-2,8-dioxa-12-azabicyclo[12.4.0]octadeca-1(14),15,17-trien-13-one

(3S,9R,10R)-16-(dimethylamino)-12-[(2R)-1-hydroxypropan-2-yl]-9-[[(4-methoxyphenyl)methyl-methylamino]methyl]-3,10-dimethyl-2,8-dioxa-12-azabicyclo[12.4.0]octadeca-1(14),15,17-trien-13-one

(3R,9S,10R)-16-(dimethylamino)-12-[(2S)-1-hydroxypropan-2-yl]-9-[[(4-methoxyphenyl)methyl-methylamino]methyl]-3,10-dimethyl-2,8-dioxa-12-azabicyclo[12.4.0]octadeca-1(14),15,17-trien-13-one

(3S,9R,10S)-16-(dimethylamino)-12-[(2R)-1-hydroxypropan-2-yl]-9-[[(4-methoxyphenyl)methyl-methylamino]methyl]-3,10-dimethyl-2,8-dioxa-12-azabicyclo[12.4.0]octadeca-1(14),15,17-trien-13-one

(3R,9R,10R)-16-(dimethylamino)-12-[(2R)-1-hydroxypropan-2-yl]-9-[[(4-methoxyphenyl)methyl-methylamino]methyl]-3,10-dimethyl-2,8-dioxa-12-azabicyclo[12.4.0]octadeca-1(14),15,17-trien-13-one

(3R,9S,10S)-16-(dimethylamino)-12-[(2S)-1-hydroxypropan-2-yl]-9-[[(4-methoxyphenyl)methyl-methylamino]methyl]-3,10-dimethyl-2,8-dioxa-12-azabicyclo[12.4.0]octadeca-1(14),15,17-trien-13-one

globostellatate C(1-)

C33H47O7- (555.3322)

An oxo monocarboxylic acid anion obtained by the deprotonation of the carboxylic group of globostellatic acid C.

globostellatate B(1-)

C33H47O7- (555.3322)

An oxo monocarboxylic acid anion obtained by the deprotonation of the carboxylic group of globostellatic acid B.

HexCer 18:3;2O/6:0

HexCer 22:3;2O/2:0

HexCer 15:3;2O/9:0

HexCer 8:0;2O/16:3

HexCer 16:3;2O/8:0

HexCer 21:3;2O/3:0

HexCer 20:3;2O/4:0

HexCer 17:3;2O/7:0

HexCer 19:3;2O/5:0

HexCer 8:1;2O/16:2

NAGly 16:3/16:3

NAGly 16:4/16:2

NAGly 18:5/14:1

NAGly 22:6/10:0

[3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoxy]-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate

C30H54NO6P (555.3689)

HexCer 14:3;2O/10:0

[3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-hydroxypropyl] (9Z,12Z,15Z,18Z,21Z)-tetracosa-9,12,15,18,21-pentaenoate

(4E,8E,12E)-3-hydroxy-2-[[(Z)-2-hydroxyhexadec-7-enoyl]amino]tetradeca-4,8,12-triene-1-sulfonic acid

(4E,8E)-3-hydroxy-2-[[(10Z,12Z)-2-hydroxyoctadeca-10,12-dienoyl]amino]dodeca-4,8-diene-1-sulfonic acid

(4E,8E,12E)-3-hydroxy-2-[[(Z)-2-hydroxytridec-8-enoyl]amino]heptadeca-4,8,12-triene-1-sulfonic acid

(4E,8E,12E)-3-hydroxy-2-[[(Z)-2-hydroxydodec-5-enoyl]amino]octadeca-4,8,12-triene-1-sulfonic acid

(4E,8E,12E)-3-hydroxy-2-[[(Z)-2-hydroxypentadec-9-enoyl]amino]pentadeca-4,8,12-triene-1-sulfonic acid

(4E,8E,12E)-3-hydroxy-2-[[(Z)-2-hydroxytetradec-9-enoyl]amino]hexadeca-4,8,12-triene-1-sulfonic acid

(4E,8E)-3-hydroxy-2-[[(4Z,7Z)-2-hydroxyhexadeca-4,7-dienoyl]amino]tetradeca-4,8-diene-1-sulfonic acid

(4E,8E,12E)-3-hydroxy-2-(tetradecanoylamino)heptadeca-4,8,12-triene-1-sulfonic acid

(4E,8E,12E)-3-hydroxy-2-(pentadecanoylamino)hexadeca-4,8,12-triene-1-sulfonic acid

(4E,8E)-3-hydroxy-2-[[(Z)-octadec-9-enoyl]amino]trideca-4,8-diene-1-sulfonic acid

(4E,8E)-3-hydroxy-2-[[(Z)-tetradec-9-enoyl]amino]heptadeca-4,8-diene-1-sulfonic acid

(E)-3-hydroxy-2-[[(9Z,12Z)-nonadeca-9,12-dienoyl]amino]dodec-4-ene-1-sulfonic acid

(E)-2-[[(9Z,12Z)-hexadeca-9,12-dienoyl]amino]-3-hydroxypentadec-4-ene-1-sulfonic acid

(4E,8E)-2-[[(Z)-heptadec-9-enoyl]amino]-3-hydroxytetradeca-4,8-diene-1-sulfonic acid

(4E,8E)-2-[[(Z)-hexadec-9-enoyl]amino]-3-hydroxypentadeca-4,8-diene-1-sulfonic acid

(4E,8E,12E)-2-(decanoylamino)-3-hydroxyhenicosa-4,8,12-triene-1-sulfonic acid

(E)-2-[[(11Z,14Z)-henicosa-11,14-dienoyl]amino]-3-hydroxydec-4-ene-1-sulfonic acid

(4E,8E)-3-hydroxy-2-[[(Z)-nonadec-9-enoyl]amino]dodeca-4,8-diene-1-sulfonic acid

(4E,8E,12E)-3-hydroxy-2-(undecanoylamino)icosa-4,8,12-triene-1-sulfonic acid

(4E,8E,12E)-3-hydroxy-2-(tridecanoylamino)octadeca-4,8,12-triene-1-sulfonic acid

(4E,8E,12E)-2-(heptadecanoylamino)-3-hydroxytetradeca-4,8,12-triene-1-sulfonic acid

(E)-3-hydroxy-2-[[(9Z,12Z)-octadeca-9,12-dienoyl]amino]tridec-4-ene-1-sulfonic acid

3-hydroxy-2-[[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]amino]tridecane-1-sulfonic acid

(E)-2-[[(9Z,12Z)-heptadeca-9,12-dienoyl]amino]-3-hydroxytetradec-4-ene-1-sulfonic acid

(4E,8E,12E)-2-(hexadecanoylamino)-3-hydroxypentadeca-4,8,12-triene-1-sulfonic acid

3-hydroxy-2-[[(11Z,14Z,17Z)-icosa-11,14,17-trienoyl]amino]undecane-1-sulfonic acid

2-[[(7Z,10Z,13Z)-hexadeca-7,10,13-trienoyl]amino]-3-hydroxypentadecane-1-sulfonic acid

(4E,8E)-3-hydroxy-2-[[(Z)-pentadec-9-enoyl]amino]hexadeca-4,8-diene-1-sulfonic acid

(4E,8E)-3-hydroxy-2-[[(Z)-tridec-9-enoyl]amino]octadeca-4,8-diene-1-sulfonic acid

(E)-3-hydroxy-2-[[(11Z,14Z)-icosa-11,14-dienoyl]amino]undec-4-ene-1-sulfonic acid

(4E,8E,12E)-2-(dodecanoylamino)-3-hydroxynonadeca-4,8,12-triene-1-sulfonic acid

[3-[(3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaenoxy]-2-propanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate

[1-[2-aminoethoxy(hydroxy)phosphoryl]oxy-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoxy]propan-2-yl] butanoate

[1-[2-aminoethoxy(hydroxy)phosphoryl]oxy-3-[(3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaenoxy]propan-2-yl] hexanoate

[1-[2-aminoethoxy(hydroxy)phosphoryl]oxy-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoxy]propan-2-yl] acetate

2-[[(E)-2-[[(4Z,7Z,10Z,13Z)-hexadeca-4,7,10,13-tetraenoyl]amino]-3-hydroxyoct-4-enoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

C29H52N2O6P+ (555.3563)

pateamine A

1-(2-methoxy-nonadecanyl)-sn-glycero-3-phosphoserine

C26H54NO9P (555.3536)

PC(21:5)

PC(10:1(1)_11:4)

LdMePE(22:5)

DGCC 20:2

DGTS 19:3;O2

C29H49NO9 (555.3407)

DGTS 20:2;O

LPE 24:5

HexCer 8:0;O2/16:3

Phe-alphaMCA

Phe-betaMCA

Phe-CA

Phe-HCA

Tyr-CDCA

Tyr-DCA

Tyr-HDCA

Tyr-UDCA

ST 27:1;O7;Gly

C29H49NO9 (555.3407)

ST 28:0;O6;Gly

ST 21:0;O4;HexNAc

C29H49NO9 (555.3407)

ST 24:5;O2;HexNAc

ST 25:4;O;HexNAc

ST 27:2;O4;Tau

C29H49NO7S (555.323)

ST 28:1;O3;Tau

ST 29:0;O2;Tau

(2s)-2-{[(2s)-2-{[(3r)-1,3-dihydroxydodecylidene]amino}-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-n-(4-methyl-1-oxopentan-2-yl)pentanediimidic acid

C27H49N5O7 (555.3632)

(3s,6z,8e,11s,15r,17s)-15-amino-3-[(1e,3e,5e)-7-(dimethylamino)-2,5-dimethylhepta-1,3,5-trien-1-yl]-9,11,17-trimethyl-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]henicosa-1(21),6,8,18-tetraene-5,13-dione

(2s)-2-{[(2s)-2-{[(3r)-1,3-dihydroxydodecylidene]amino}-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-n-[(2s)-4-methyl-1-oxopentan-2-yl]pentanediimidic acid

C27H49N5O7 (555.3632)

{11-ethyl-16-hydroxy-4,6,8-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl}methyl 2-methoxybenzoate

2-({2-[(1,3-dihydroxydodecylidene)amino]-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene}amino)-n-(4-methyl-1-oxopentan-2-yl)pentanediimidic acid

C27H49N5O7 (555.3632)

(1s,2r,5s,7s,8r,9r,11s,12s,15s)-21-(2,3-dihydroxy-3-methylbutyl)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6,10-dioxa-24-azaheptacyclo[13.10.0.0²,¹².0⁵,¹¹.0⁹,¹¹.0¹⁷,²⁵.0¹⁸,²³]pentacosa-17(25),18,20,22-tetraene-8,12-diol

(1s,2r,5s,7s,8r,9r,11s,12s,15s)-21-(2,3-dihydroxy-3-methylbutyl)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6,10-dioxa-24-azaheptacyclo[13.10.0.0²,¹².0⁵,¹¹.0⁹,¹¹.0¹⁷,²⁵.0¹⁸,²³]pentacosa-17(25),18,20,22-tetraene-8,12-diol

(1s,2r,5s,7s,8r,9r,11s,12s,15s)-19-[(2r)-2,3-dihydroxy-3-methylbutyl]-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6,10-dioxa-24-azaheptacyclo[13.10.0.0²,¹².0⁵,¹¹.0⁹,¹¹.0¹⁷,²⁵.0¹⁸,²³]pentacosa-17(25),18,20,22-tetraene-8,12-diol

(1s,2r,5s,7s,8r,9r,11s,12s,15s)-19-[(2r)-2,3-dihydroxy-3-methylbutyl]-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6,10-dioxa-24-azaheptacyclo[13.10.0.0²,¹².0⁵,¹¹.0⁹,¹¹.0¹⁷,²⁵.0¹⁸,²³]pentacosa-17(25),18,20,22-tetraene-8,12-diol

19-(2,3-dihydroxy-3-methylbutyl)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6,10-dioxa-24-azaheptacyclo[13.10.0.0²,¹².0⁵,¹¹.0⁹,¹¹.0¹⁷,²⁵.0¹⁸,²³]pentacosa-17(25),18,20,22-tetraene-8,12-diol

19-(2,3-dihydroxy-3-methylbutyl)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6,10-dioxa-24-azaheptacyclo[13.10.0.0²,¹².0⁵,¹¹.0⁹,¹¹.0¹⁷,²⁵.0¹⁸,²³]pentacosa-17(25),18,20,22-tetraene-8,12-diol

[(1s,2r,3r,4s,5r,6s,8s,9s,10r,13s,16s,17r)-11-ethyl-16-hydroxy-4,6,8-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-methoxybenzoate

15-amino-3-[7-(dimethylamino)-2,5-dimethylhepta-1,3,5-trien-1-yl]-9,11,17-trimethyl-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]henicosa-1(21),6,8,18-tetraene-5,13-dione