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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-08-30 22:33:41 UTC

Update Date

2022-11-15 17:47:03 UTC

HMDB ID

HMDB0242435

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Deoxycholylmethionine

Description

Deoxycholylmethionine 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. Deoxycholylmethionine consists of the bile acid deoxycholic acid conjugated to the amino acid Methionine 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 Deoxycholylmethionine, 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 ). Deoxycholylmethionine 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 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652308302122372D          

 36 39  0  0  0  0            999 V2000
    9.2792    0.0320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5648   -0.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8503    0.0320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5648   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8503   -1.6180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1358   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1358   -0.3805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4214   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7069   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -2.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5243   -1.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9722   -0.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3847   -0.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1298    0.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3228    0.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0679    1.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6199    2.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3650    2.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9170    3.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6621    4.3227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7240    3.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9789    2.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4269    1.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2339    1.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6818    1.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4888    1.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7437    0.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5507    0.0565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9763   -0.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2792   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9937   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7082   -1.6180    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.4227   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 12 31  1  0  0  0  0
 15 31  1  0  0  0  0
 31 32  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END

HMDB0242435
     RDKit          3D
Deoxycholylmethionine
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.6460   -1.8348   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6869   -1.0771    0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3194   -0.8077    1.7935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958   -1.4691    2.7811 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3998    0.2493    1.8320 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5737    0.8660    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6869   -0.2653   -0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6500   -1.2193   -0.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2671   -1.7420    0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6952   -1.7204   -0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2992   -2.9476   -0.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4676   -0.6715   -0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0282    0.6091    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4941    1.5484   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253    2.4035   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7961    3.9042   -0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1623    2.2611    1.4348 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8457    2.0928    0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3044   -2.3720    0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8370   -1.9688   -1.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6939    1.1424    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1745    0.0808   -1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1000   -0.8755   -1.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001   -2.1281   -1.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0900   -2.8327    0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2893   -1.2539    1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5123   -3.5692   -1.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0177   -2.6543   -1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8838   -3.5179   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5077   -0.7038   -0.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2730    0.5170    1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9135    1.0747    1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2613    1.0378   -1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4282    2.1172   -0.8687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7699    4.0115    0.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0466    4.5272    0.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7974    4.1648   -1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5117    3.0232    0.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  7  2  1  0
 18 15  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
M  END


  Mrv1652308302122372D          

 36 39  0  0  0  0            999 V2000
    9.2792    0.0320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5648   -0.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8503    0.0320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5648   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8503   -1.6180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1358   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1358   -0.3805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4214   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7069   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -2.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5243   -1.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9722   -0.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3847   -0.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1298    0.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3228    0.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0679    1.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6199    2.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3650    2.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9170    3.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6621    4.3227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7240    3.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9789    2.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4269    1.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2339    1.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6818    1.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4888    1.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7437    0.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5507    0.0565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9763   -0.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2792   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9937   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7082   -1.6180    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.4227   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 12 31  1  0  0  0  0
 15 31  1  0  0  0  0
 31 32  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242435

> <DATABASE_NAME>
hmdb

> <SMILES>
CSCCC(NC(=O)CCC(C)C1CCC2C3CCC4CC(O)CCC4(C)C3CC(O)C12C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H49NO5S/c1-17(5-10-26(33)30-24(27(34)35)12-14-36-4)21-8-9-22-20-7-6-18-15-19(31)11-13-28(18,2)23(20)16-25(32)29(21,22)3/h17-25,31-32H,5-16H2,1-4H3,(H,30,33)(H,34,35)

> <INCHI_KEY>
LKUHGQIXJRDHNR-UHFFFAOYSA-N

> <FORMULA>
C29H49NO5S

> <MOLECULAR_WEIGHT>
523.77

> <EXACT_MASS>
523.333144856

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
61.015446287032944

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)-4-(methylsulfanyl)butanoic acid

> <ALOGPS_LOGP>
3.58

> <JCHEM_LOGP>
3.9061686346666673

> <ALOGPS_LOGS>
-5.29

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.430657817963176

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.877079524627175

> <JCHEM_PKA_STRONGEST_BASIC>
-0.28460523469223575

> <JCHEM_POLAR_SURFACE_AREA>
106.86000000000001

> <JCHEM_REFRACTIVITY>
143.5829

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.68e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)-4-(methylsulfanyl)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242435
     RDKit          3D
Deoxycholylmethionine
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.6460   -1.8348   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6869   -1.0771    0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3194   -0.8077    1.7935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958   -1.4691    2.7811 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3998    0.2493    1.8320 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5737    0.8660    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6869   -0.2653   -0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6500   -1.2193   -0.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2671   -1.7420    0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6952   -1.7204   -0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2992   -2.9476   -0.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4676   -0.6715   -0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0282    0.6091    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4941    1.5484   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253    2.4035   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7961    3.9042   -0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1623    2.2611    1.4348 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8457    2.0928    0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3044   -2.3720    0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8370   -1.9688   -1.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6939    1.1424    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1745    0.0808   -1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1000   -0.8755   -1.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001   -2.1281   -1.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0900   -2.8327    0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2893   -1.2539    1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5123   -3.5692   -1.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0177   -2.6543   -1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8838   -3.5179   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5077   -0.7038   -0.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2730    0.5170    1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9135    1.0747    1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2613    1.0378   -1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4282    2.1172   -0.8687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7699    4.0115    0.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0466    4.5272    0.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7974    4.1648   -1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5117    3.0232    0.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  7  2  1  0
 18 15  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
M  END

HEADER    PROTEIN                                 30-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-AUG-21         0                                  
HETATM    1  O   UNK     0      17.321   0.060   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      15.988  -0.710   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      14.654   0.060   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      15.988  -2.250   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      14.654  -3.020   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      13.320  -2.250   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.320  -0.710   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.987  -3.020   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.653  -2.250   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.319  -3.020   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.319  -4.560   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.986  -2.250   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.579  -2.877   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.548  -1.732   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.318  -0.399   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.842   1.066   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.336   1.386   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.860   2.851   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.891   3.995   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.415   5.460   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.445   6.604   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.969   8.069   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.951   6.284   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.427   4.820   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.397   3.675   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.903   3.355   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.873   2.211   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.379   1.890   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.855   0.426   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.361   0.106   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.825  -0.719   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.289  -1.195   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.321  -3.020   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      18.655  -2.250   0.000  0.00  0.00           C+0
HETATM   35  S   UNK     0      19.989  -3.020   0.000  0.00  0.00           S+0
HETATM   36  C   UNK     0      21.322  -2.250   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   31                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   31                                                  
CONECT   16   15   17   27                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   19   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   16   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   12   15   32                                             
CONECT   32   31                                                            
CONECT   33    4   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

COMPND    HMDB0242435
HETATM    1  C1  UNL     1       3.646  -1.835  -0.041  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.687  -1.077   0.414  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.319  -0.808   1.794  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.796  -1.469   2.781  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.400   0.249   1.832  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.574   0.866   0.539  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.687  -0.265  -0.362  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.650  -1.219  -0.707  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.267  -1.742   0.300  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.695  -1.720  -0.185  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.299  -2.948  -0.825  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.468  -0.672  -0.084  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.028   0.609   0.517  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.494   1.548  -0.551  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.425   2.404  -0.023  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.796   3.904  -0.202  1.00  0.00           C  
HETATM   17  O3  UNL     1      -0.162   2.261   1.435  1.00  0.00           O  
HETATM   18  C15 UNL     1       0.846   2.093   0.314  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.304  -2.372   0.625  1.00  0.00           H  
HETATM   20  H2  UNL     1       3.837  -1.969  -1.097  1.00  0.00           H  
HETATM   21  H3  UNL     1       2.694   1.142   0.664  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.175   0.081  -1.323  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.100  -0.875  -1.611  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.200  -2.128  -1.134  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.090  -2.833   0.555  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.289  -1.254   1.284  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.512  -3.569  -1.293  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.018  -2.654  -1.621  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.884  -3.518  -0.053  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.508  -0.704  -0.454  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.273   0.517   1.308  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.914   1.075   1.051  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.261   1.038  -1.514  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.428   2.117  -0.869  1.00  0.00           H  
HETATM   35  H17 UNL     1      -1.770   4.012   0.300  1.00  0.00           H  
HETATM   36  H18 UNL     1      -0.047   4.527   0.308  1.00  0.00           H  
HETATM   37  H19 UNL     1      -0.797   4.165  -1.267  1.00  0.00           H  
HETATM   38  H20 UNL     1       1.512   3.023   0.486  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   18   21
CONECT    7    8   22
CONECT    8    9   23   24
CONECT    9   10   25   26
CONECT   10   11   12   12
CONECT   11   27   28   29
CONECT   12   13   30
CONECT   13   14   31   32
CONECT   14   15   33   34
CONECT   15   16   17   18
CONECT   16   35   36   37
CONECT   17   18
CONECT   18   38
END

HMDB0242435
     RDKit          3D
Deoxycholylmethionine
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.6460   -1.8348   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6869   -1.0771    0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3194   -0.8077    1.7935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958   -1.4691    2.7811 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3998    0.2493    1.8320 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5737    0.8660    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6869   -0.2653   -0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6500   -1.2193   -0.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2671   -1.7420    0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6952   -1.7204   -0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2992   -2.9476   -0.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4676   -0.6715   -0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0282    0.6091    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4941    1.5484   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253    2.4035   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7961    3.9042   -0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1623    2.2611    1.4348 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8457    2.0928    0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3044   -2.3720    0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8370   -1.9688   -1.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6939    1.1424    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1745    0.0808   -1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1000   -0.8755   -1.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001   -2.1281   -1.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0900   -2.8327    0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2893   -1.2539    1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5123   -3.5692   -1.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0177   -2.6543   -1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8838   -3.5179   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5077   -0.7038   -0.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2730    0.5170    1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9135    1.0747    1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2613    1.0378   -1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4282    2.1172   -0.8687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7699    4.0115    0.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0466    4.5272    0.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7974    4.1648   -1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5117    3.0232    0.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  7  2  1  0
 18 15  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-[(4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl}-1-hydroxypentylidene)amino]-4-(methylsulfanyl)butanoate	HMDB
2-[(4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl}-1-hydroxypentylidene)amino]-4-(methylsulphanyl)butanoate	HMDB
2-[(4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl}-1-hydroxypentylidene)amino]-4-(methylsulphanyl)butanoic acid	HMDB

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.322

Monoisotopic Molecular Weight

248.141244504

IUPAC Name

2-(4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)-4-(methylsulfanyl)butanoic acid

Traditional Name

2-(4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)-4-(methylsulfanyl)butanoic acid

CAS Registry Number

Not Available

SMILES

CC1=CCCC2(C)OC2C2OC(=O)C(=C)C2CC1

InChI Identifier

InChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3

InChI Key

KTEXNACQROZXEV-UHFFFAOYSA-N

Chemical Taxonomy

Classification

Not classified

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.58	ALOGPS
logP	3.91	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	3.88	ChemAxon
pKa (Strongest Basic)	-0.28	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	143.58 m³·mol⁻¹	ChemAxon
Polarizability	61.02 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	159.3	32859911
AllCCS	[M+H-H2O]+	155.5	32859911
AllCCS	[M+NH4]+	162.8	32859911
AllCCS	[M+Na]+	163.8	32859911
AllCCS	[M-H]-	164.4	32859911
AllCCS	[M+Na-2H]-	164.3	32859911
AllCCS	[M+HCOO]-	164.3	32859911

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholylmethionine 10V, Positive-QTOF	splash10-0002-0090000000-308c6024b53a399d0d74	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholylmethionine 20V, Positive-QTOF	splash10-0002-0190000000-0d8aac5015201d73c601	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholylmethionine 40V, Positive-QTOF	splash10-0032-1980000000-e5680ba3528f930ffa42	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholylmethionine 10V, Negative-QTOF	splash10-0002-0090000000-7b3a58b796a0e4263959	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholylmethionine 20V, Negative-QTOF	splash10-0002-0090000000-717909ee4df9ba3b89f8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholylmethionine 40V, Negative-QTOF	splash10-002g-1090000000-e822bc693a6fb3c5c561	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Intestine

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Guzior DV, Quinn RA: Review: microbial transformations of human bile acids. Microbiome. 2021 Jun 14;9(1):140. doi: 10.1186/s40168-021-01101-1. [PubMed:34127070 ]
Quinn RA, Melnik AV, Vrbanac A, Fu T, Patras KA, Christy MP, Bodai Z, Belda-Ferre P, Tripathi A, Chung LK, Downes M, Welch RD, Quinn M, Humphrey G, Panitchpakdi M, Weldon KC, Aksenov A, da Silva R, Avila-Pacheco J, Clish C, Bae S, Mallick H, Franzosa EA, Lloyd-Price J, Bussell R, Thron T, Nelson AT, Wang M, Leszczynski E, Vargas F, Gauglitz JM, Meehan MJ, Gentry E, Arthur TD, Komor AC, Poulsen O, Boland BS, Chang JT, Sandborn WJ, Lim M, Garg N, Lumeng JC, Xavier RJ, Kazmierczak BI, Jain R, Egan M, Rhee KE, Ferguson D, Raffatellu M, Vlamakis H, Haddad GG, Siegel D, Huttenhower C, Mazmanian SK, Evans RM, Nizet V, Knight R, Dorrestein PC: Global chemical effects of the microbiome include new bile-acid conjugations. Nature. 2020 Mar;579(7797):123-129. doi: 10.1038/s41586-020-2047-9. Epub 2020 Feb 26. [PubMed:32103176 ]

Showing metabocard for Deoxycholylmethionine (HMDB0242435)

MOL for HMDB0242435 (Deoxycholylmethionine)

3D MOL for HMDB0242435 (Deoxycholylmethionine)

3D SDF for HMDB0242435 (Deoxycholylmethionine)

3D-SDF for HMDB0242435 (Deoxycholylmethionine)

PDB for HMDB0242435 (Deoxycholylmethionine)

3D PDB for HMDB0242435 (Deoxycholylmethionine)

SMILES for HMDB0242435 (Deoxycholylmethionine)

INCHI for HMDB0242435 (Deoxycholylmethionine)

Structure for HMDB0242435 (Deoxycholylmethionine)

3D Structure for HMDB0242435 (Deoxycholylmethionine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra