Exact Mass: 489.3566382

A macrolide that is isolated from several Streptomyces species and displays antibiotic, antineoplastic and antimalarial properties.

Chenodeoxycholylproline

1-(4-{5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanoyl)pyrrolidine-2-carboxylic acid

Chenodeoxycholylproline 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. Chenodeoxycholylproline consists of the bile acid chenodeoxycholic acid conjugated to the amino acid Proline 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 Chenodeoxycholylproline, 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). Chenodeoxycholylproline 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).

Deoxycholylproline

1-(4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanoyl)pyrrolidine-2-carboxylic acid

C27H56NO4P (489.3946746000001)

Deoxycholylproline 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. Deoxycholylproline consists of the bile acid deoxycholic acid conjugated to the amino acid Proline 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 Deoxycholylproline, 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). Deoxycholylproline 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).

Vertilmicin

2-[(4-amino-3-{[3-amino-6-(1-aminoethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-6-(ethylamino)-2-hydroxycyclohexyl)oxy]-5-methyl-4-(methylamino)oxane-3,5-diol

C22H43N5O7 (489.3162328)

Erucylphosphocholine

Docos-13-en-1-yl 2-(trimethylazaniumyl)ethyl phosphoric acid

Nirogacestat

2-[(6,8-Difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)amino]-N-(1-{1-[(2,2-dimethylpropyl)amino]-2-methylpropan-2-yl}-1H-imidazol-4-yl)pentanimidate

C27H41F2N5O (489.32790000000006)

D004791 - Enzyme Inhibitors > D000091062 - Gamma Secretase Inhibitors and Modulators

Lys Lys Lys Ser

(2S)-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2,6-diaminohexanamido]hexanamido]hexanamido]-3-hydroxypropanoic acid

Lys Lys Ser Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2,6-diaminohexanamido]hexanamido]-3-hydroxypropanamido]hexanoic acid

Lys Ser Lys Lys

(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-3-hydroxypropanamido]hexanamido]hexanoic acid

Ser Lys Lys Lys

(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-amino-3-hydroxypropanamido]hexanamido]hexanamido]hexanoic acid

C27H55NO4S (489.38515900000004)

2-pentacosanamidoethanesulfonic acid

NAT 25:0

N-pentacosanoyl taurine

C27H55NO4S (489.38515900000004)

tributylhexadecylammonium bromide

C28H60BrN (489.390886)

Carboprost tromethamine

D012102 - Reproductive Control Agents > D010120 - Oxytocics C78568 - Prostaglandin Analogue

2-[bis(2-hydroxyethyl)amino]ethanol,4-tridecan-3-ylbenzenesulfonic acid

C27H41F2N5O (489.32790000000006)

Etisomicin

C22H43N5O7 (489.3162328)

N,N,N-Triheptyl-1-heptanaminium bromide

C28H60BrN (489.390886)

Poly(diallyldimethylammonium chloride)

C24H54Cl3N3 (489.3383094)

Nirogacestat

D004791 - Enzyme Inhibitors > D000091062 - Gamma Secretase Inhibitors and Modulators C471 - Enzyme Inhibitor

1,3-Dihydroxy-2-(hydroxymethyl)propan-2-aminium (5Z,9alpha,11beta,13E,15S)-9,11,15-trihydroxy-15-methylprosta-5,13-dien-1-Oate

(1R,2R)-2-[(4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid

Deoxycholylproline

Chenodeoxycholylproline

C27H56NO4P (489.3946746000001)

[(E)-docos-13-enyl] 2-(trimethylazaniumyl)ethyl phosphate

(-)-borrelidin

(1R,2R)-2-[(2R,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]cyclopentanecarboxylic acid

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

N-[(4S,7R,8S)-5-(cyclohexylmethyl)-8-methoxy-4,7,10-trimethyl-11-oxo-2-oxa-5,10-diazabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl]-2-methoxyacetamide

N-[(2S)-4-methyl-1-[[(2S)-4-methyl-1-[[(3S)-5-methyl-2-oxohexan-3-yl]amino]-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]carbamic acid (phenylmethyl) ester

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

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

N-[(5R,6S,9R)-5-methoxy-3,6,9-trimethyl-8-(4-oxanylmethyl)-2-oxo-11-oxa-3,8-diazabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl]butanamide

N-[(4S,7S,8S)-5-(cyclohexylmethyl)-8-methoxy-4,7,10-trimethyl-11-oxo-2-oxa-5,10-diazabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl]-2-methoxyacetamide

N-[(4R,7R,8R)-5-(cyclohexylmethyl)-8-methoxy-4,7,10-trimethyl-11-oxo-2-oxa-5,10-diazabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl]-2-methoxyacetamide

N-[(4R,7R,8S)-5-(cyclohexylmethyl)-8-methoxy-4,7,10-trimethyl-11-oxo-2-oxa-5,10-diazabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl]-2-methoxyacetamide

N-[(5R,6R,9R)-5-methoxy-3,6,9-trimethyl-8-(4-oxanylmethyl)-2-oxo-11-oxa-3,8-diazabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl]butanamide

N-[(5S,6S,9S)-5-methoxy-3,6,9-trimethyl-8-(4-oxanylmethyl)-2-oxo-11-oxa-3,8-diazabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl]butanamide

N-[(5S,6S,9R)-5-methoxy-3,6,9-trimethyl-8-(4-oxanylmethyl)-2-oxo-11-oxa-3,8-diazabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl]butanamide

N-[(5R,6R,9S)-5-methoxy-3,6,9-trimethyl-8-(4-oxanylmethyl)-2-oxo-11-oxa-3,8-diazabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl]butanamide

N-[(5S,6R,9S)-5-methoxy-3,6,9-trimethyl-8-(4-oxanylmethyl)-2-oxo-11-oxa-3,8-diazabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl]butanamide

N-[(4S,7R,8R)-5-(cyclohexylmethyl)-8-methoxy-4,7,10-trimethyl-11-oxo-2-oxa-5,10-diazabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl]-2-methoxyacetamide

N-[(4R,7S,8S)-5-(cyclohexylmethyl)-8-methoxy-4,7,10-trimethyl-11-oxo-2-oxa-5,10-diazabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl]-2-methoxyacetamide

N-[(4S,7S,8R)-5-(cyclohexylmethyl)-8-methoxy-4,7,10-trimethyl-11-oxo-2-oxa-5,10-diazabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl]-2-methoxyacetamide

N-[(4R,7S,8R)-5-(cyclohexylmethyl)-8-methoxy-4,7,10-trimethyl-11-oxo-2-oxa-5,10-diazabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl]-2-methoxyacetamide

Ldgcc 16:0

C26H51NO7 (489.3665336)

HexCer 8:1;2O/11:0

HexCer 12:1;2O/7:0

HexCer 17:1;2O/2:0

HexCer 15:1;2O/4:0

HexCer 16:1;2O/3:0

HexCer 11:1;2O/8:0

HexCer 10:1;2O/9:0

HexCer 13:1;2O/6:0

HexCer 14:1;2O/5:0

HexCer 9:1;2O/10:0

NAGly 16:4/11:0

2-aminoethyl [2-hydroxy-3-[(11Z,14Z,17Z)-icosa-11,14,17-trienoxy]propyl] hydrogen phosphate

(E)-3-hydroxy-2-[[(Z)-2-hydroxypentadec-9-enoyl]amino]dec-4-ene-1-sulfonic acid

(E)-3-hydroxy-2-[[(Z)-2-hydroxytetradec-9-enoyl]amino]undec-4-ene-1-sulfonic acid

(4E,8E)-3-hydroxy-2-(2-hydroxydodecanoylamino)trideca-4,8-diene-1-sulfonic acid

(E)-3-hydroxy-2-[[(Z)-2-hydroxytridec-8-enoyl]amino]dodec-4-ene-1-sulfonic acid

(4E,8E)-3-hydroxy-2-(2-hydroxytridecanoylamino)dodeca-4,8-diene-1-sulfonic acid

(E)-3-hydroxy-2-[[(Z)-2-hydroxydodec-5-enoyl]amino]tridec-4-ene-1-sulfonic acid

3-hydroxy-2-[[(Z)-tetradec-9-enoyl]amino]dodecane-1-sulfonic acid

(E)-3-hydroxy-2-(undecanoylamino)pentadec-4-ene-1-sulfonic acid

3-hydroxy-2-[[(Z)-tridec-9-enoyl]amino]tridecane-1-sulfonic acid

(E)-3-hydroxy-2-(pentadecanoylamino)undec-4-ene-1-sulfonic acid

(E)-2-(decanoylamino)-3-hydroxyhexadec-4-ene-1-sulfonic acid

2-[[(Z)-hexadec-9-enoyl]amino]-3-hydroxydecane-1-sulfonic acid

(E)-3-hydroxy-2-(tridecanoylamino)tridec-4-ene-1-sulfonic acid

(E)-3-hydroxy-2-(tetradecanoylamino)dodec-4-ene-1-sulfonic acid

(E)-2-(hexadecanoylamino)-3-hydroxydec-4-ene-1-sulfonic acid

(E)-2-(dodecanoylamino)-3-hydroxytetradec-4-ene-1-sulfonic acid

3-hydroxy-2-[[(Z)-pentadec-9-enoyl]amino]undecane-1-sulfonic acid

Cer-AS d30:5

Cer-BS d30:5

2-[[(4E,8E,12E)-2-(butanoylamino)-3-hydroxypentadeca-4,8,12-trienoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

2-[hydroxy-[(4E,8E,12E)-3-hydroxy-2-(pentanoylamino)tetradeca-4,8,12-trienoxy]phosphoryl]oxyethyl-trimethylazanium

2-[hydroxy-[(4E,8E,12E)-3-hydroxy-2-(propanoylamino)hexadeca-4,8,12-trienoxy]phosphoryl]oxyethyl-trimethylazanium

2-[[(4E,8E,12E)-2-acetamido-3-hydroxyheptadeca-4,8,12-trienoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

NA-Cit 22:4(7Z,10Z,13Z,16Z)

NA-DOPA 20:1(11Z)

C27H55NO4S (489.38515900000004)

NA-Taurine 25:0

NA-Tyr 21:0

CAR 22:5;OH

MGCC 16:0

C26H51NO7 (489.3665336)

LPE O-20:3

LPE P-20:2

LPE P-20:2 or LPE O-20:3

CerP 14:2;O2/11:0

CerP 15:2;O2/10:0

CerP 25:2;O2

ST 26:3;O4;Gly

ST 27:2;O3;Gly

ST 28:1;O2;Gly

ST 20:2;O;HexNAc

7-hydroxy-1-[1-(3-hydroxy-5-methylpiperidin-2-yl)ethyl]-9a,11a-dimethyl-6-oxo-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate

(2r)-2-(2-{[(3r,4r,5s,7s,16s)-17-amino-4,16-dihydroxy-3,7-dimethylheptadecan-5-yl]oxy}-2-oxoethyl)butanedioic acid

(1r,2r)-2-[(2s,4z,6e,8s,9s,11r,13s,15s,16s)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid

2-[(3r,4as,8s,10ar,10bs)-7,7,10b-trimethyl-8-{[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-1h,2h,3h,4ah,5h,8h,9h,10h,10ah-naphtho[2,1-b]pyran-3-yl]propan-2-ol

C33H47NO2 (489.3606602)

n-[3-(17-amino-1-hydroxy-1,5,9,14-tetraazaheptadecan-1-yl)propyl]-2-(1h-indol-3-yl)ethanimidic acid

C26H47N7O2 (489.3791042)

(1r,2r,3as,3br,5ar,7s,9ar,9bs,11as)-7-hydroxy-1-[(1s)-1-[(2r,3s,5r)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-9a,11a-dimethyl-6-oxo-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate

2-[(3s,4as,8s,10ar,10bs)-7,7,10b-trimethyl-8-{[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-1h,2h,3h,4ah,5h,8h,9h,10h,10ah-naphtho[2,1-b]pyran-3-yl]propan-2-ol

C33H47NO2 (489.3606602)

5-(1,2-dihydroxy-4-oxocyclohexyl)-3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-1-methylpyridin-2-one

(1s,2s)-2-[(2r,4z,6e,8s,9r,13r,15r,16r)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid

(4s,5s,7s,9r,11s,12s,13e,15e,18s)-18-[(1r,2r)-2-carboxycyclopentyl]-4,12-dihydroxy-13-isocyano-5,7,9,11-tetramethyl-1-oxacyclooctadeca-13,15-dien-2-one