MiMeDB: Showing metabocard for carboxy-S-adenosyl-L-methionine (MMDBc0056396)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-25 04:22:04 UTC

Update Date

2025-10-07 16:09:47 UTC

Metabolite ID

MMDBc0056396

Metabolite Identification

Common Name

carboxy-S-adenosyl-L-methionine

Description

Carboxy-S-adenosyl-L-methionine is a member of the class of S-adenosylmethionine derivatives, specifically functioning as a cofactor in various methylation and carboxymethylation reactions. Its chemical structure features a methionine moiety linked to an adenosine, with a carboxymethyl group that can be transferred to specific substrates. In biochemical pathways, carboxy-S-adenosyl-L-methionine (caSAM) plays a crucial role in the modification of nucleic acids. For instance, it is utilized by the DNA methyltransferase M.MedI-N377K to transfer a carboxymethyl group to cytosines, resulting in the formation of 5-carboxymethylcytosine (5camC) (PMID:40276634 ). Additionally, neomorphic variants of DNA methyltransferases, such as M.MpeI-N374K, have adapted to use this metabolite for generating unnatural DNA modifications (PMID:37379458 ). Furthermore, CmoB employs carboxy-S-adenosyl-L-methionine to facilitate carboxymethyl transfer in tRNA modifications in Gram-negative bacteria (PMID:33213836 ). Overall, carboxy-S-adenosyl-L-methionine serves as a versatile metabolite involved in diverse biochemical modifications, highlighting its significance in molecular biology (PMID:23676670 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306252206222D          

 30 32  0  0  1  0            999 V2000
   -2.0806    1.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8908    1.6323    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
   -3.4309    2.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2410    2.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7811    2.7237    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5110    3.5032    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -5.5912    2.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1313    3.1914    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -5.8613    1.7882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1608    0.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6207    0.2291    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7987    0.2995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4778   -0.4605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1014   -1.0006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0311   -1.8226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8078   -0.5744    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5678   -0.8953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6743   -0.6476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3533   -1.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4687   -1.3372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6557   -0.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0506   -0.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0347    0.7173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6876    1.1160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    0.6897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3780   -0.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0844   -0.5613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8106    2.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3507    3.1914    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.0004    2.7237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  2 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  6  0  0  0
 13 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
  1 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
M  CHG  4   2   1   6   1   8  -1  29  -1
M  END


  Mrv1652306252206222D          

 30 32  0  0  1  0            999 V2000
   -2.0806    1.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8908    1.6323    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
   -3.4309    2.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2410    2.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7811    2.7237    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5110    3.5032    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -5.5912    2.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1313    3.1914    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -5.8613    1.7882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1608    0.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6207    0.2291    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7987    0.2995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4778   -0.4605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1014   -1.0006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0311   -1.8226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8078   -0.5744    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5678   -0.8953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6743   -0.6476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3533   -1.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4687   -1.3372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6557   -0.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0506   -0.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0347    0.7173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6876    1.1160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    0.6897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3780   -0.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0844   -0.5613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8106    2.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3507    3.1914    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.0004    2.7237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  2 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  6  0  0  0
 13 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
  1 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
M  CHG  4   2   1   6   1   8  -1  29  -1
M  END
> <DATABASE_ID>
MMDBc0056396

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](C[S+](CC[C@H]([NH3+])C([O-])=O)CC([O-])=O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H22N6O7S/c17-7(16(27)28)1-2-30(4-9(23)24)3-8-11(25)12(26)15(29-8)22-6-21-10-13(18)19-5-20-14(10)22/h5-8,11-12,15,25-26H,1-4,17H2,(H3-,18,19,20,23,24,27,28)/t7-,8+,11+,12+,15+,30?/m0/s1

> <INCHI_KEY>
VFFTYSZNZJBRBG-DYXDMYNLSA-N

> <FORMULA>
C16H22N6O7S

> <MOLECULAR_WEIGHT>
442.45

> <EXACT_MASS>
442.127068246

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.26865602585912

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(carboxymethyl)sulfaniumyl)-2-azaniumylbutanoate

> <JCHEM_LOGP>
-5.814324181249775

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.4811743152205983

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.464992343462125

> <JCHEM_PKA_STRONGEST_BASIC>
9.414369381746813

> <JCHEM_POLAR_SURFACE_AREA>
227.21

> <JCHEM_REFRACTIVITY>
135.43409999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-4-({[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(carboxymethyl)sulfaniumyl)-2-ammoniobutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-JUN-22         0                                  
HETATM    1  C   UNK     0      -3.884   3.338   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0      -5.396   3.047   0.000  0.00  0.00           S+1
HETATM    3  C   UNK     0      -6.404   4.211   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.917   3.920   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.925   5.084   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -8.421   6.539   0.000  0.00  0.00           N+1
HETATM    7  C   UNK     0     -10.437   4.793   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0     -11.445   5.957   0.000  0.00  0.00           O-1
HETATM    9  O   UNK     0     -10.941   3.338   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.900   1.592   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.892   0.428   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.358   0.559   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.759  -0.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.923  -1.868   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.791  -3.402   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.241  -1.072   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.660  -1.671   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      -1.259  -1.209   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -0.660  -2.628   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       0.875  -2.496   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       1.224  -0.996   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.095  -0.201   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      -0.065   1.339   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       1.284   2.083   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       2.602   1.288   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       2.572  -0.252   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       3.891  -1.048   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      -3.380   4.793   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.388   5.957   0.000  0.00  0.00           O-1
HETATM   30  O   UNK     0      -1.868   5.084   0.000  0.00  0.00           O+0
CONECT    1    2   28                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    2   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   11   17                                                  
CONECT   17   16                                                            
CONECT   18   13   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   18   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21   27                                                  
CONECT   27   26                                                            
CONECT   28    1   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

Synonyms

Value	Source
Carboxy-S-adenosyl-L-methionine	ChEBI
Carboxy-sam	ChEBI
CX-SAM	ChEBI
S-Adenosyl-S-carboxymethyl-L-homocystein	ChEBI
4-(((5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(carboxylatomethyl)sulfonio)-2-ammoniobutanoate	MeSH

Molecular Formula

C₁₆H₂₂N₆O₇S

Average Mass

442.45

Monoisotopic Mass

442.127068246

IUPAC Name

(2S)-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(carboxymethyl)sulfaniumyl)-2-azaniumylbutanoate

Traditional Name

(2S)-4-({[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(carboxymethyl)sulfaniumyl)-2-ammoniobutanoate

CAS Registry Number

Not Available

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](C[S+](CC[C@H]([NH3+])C([O-])=O)CC([O-])=O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C16H22N6O7S/c17-7(16(27)28)1-2-30(4-9(23)24)3-8-11(25)12(26)15(29-8)22-6-21-10-13(18)19-5-20-14(10)22/h5-8,11-12,15,25-26H,1-4,17H2,(H3-,18,19,20,23,24,27,28)/t7-,8+,11+,12+,15+,30?/m0/s1

InChI Key

VFFTYSZNZJBRBG-DYXDMYNLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

5'-deoxyribonucleosides

Sub Class

5'-deoxy-5'-thionucleosides

Direct Parent

5'-deoxy-5'-thionucleosides

Alternative Parents

Substituents

5'-deoxy-5'-thionucleoside
Glycosyl compound
N-glycosyl compound
6-aminopurine
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Pentose monosaccharide
Purine
Imidazopyrimidine
Aminopyrimidine
Thia fatty acid
Hydroxy fatty acid
Imidolactam
Monosaccharide
Fatty acyl
Dicarboxylic acid or derivatives
N-substituted imidazole
Pyrimidine
Quaternary ammonium salt
Imidazole
Heteroaromatic compound
Oxolane
Azole
1,2-diol
Amino acid or derivatives
Amino acid
Carboxylic acid salt
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organic salt
Organic zwitterion
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Amine
Primary aliphatic amine
Primary amine
Organosulfur compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-5.8	ChemAxon
pKa (Strongest Acidic)	1.46	ChemAxon
pKa (Strongest Basic)	9.41	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	227.21 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	135.43 m³·mol⁻¹	ChemAxon
Polarizability	42.27 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	396.9
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	314.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	104.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	426.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	311.3
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	198.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1259.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	778.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	1001.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	145.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	296.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	144.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	61.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	403.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	545.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	81.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	189.2
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1326.2
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	645.1

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_1	C[Si](C)(C)O[C@@H]1[C@@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O	standard non polar	2025-10-24	1835.41
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_2	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])O[C@H]1N1C=NC2=C(N)N=CN=C21	standard non polar	2025-10-24	1845.69
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_3	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])[C@@H](O)[C@H]1O	standard non polar	2025-10-24	1860.84
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_4	C[Si](C)(C)O[C@@H]1[C@@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-24	2311.14
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_5	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])[C@@H](O[Si](C)(C)C)[C@H]1O	standard non polar	2025-10-24	1849.08
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_6	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])[C@@H](O)[C@H]1O[Si](C)(C)C	standard non polar	2025-10-24	1908.36
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_7	C[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])[C@@H](O)[C@H]1O)[Si](C)(C)C	standard non polar	2025-10-24	1527.69
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_8	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	standard non polar	2025-10-24	2596.42
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_9	C[Si](C)(C)O[C@@H]1[C@@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H]1O	standard non polar	2025-10-24	1812.92
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_10	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21	standard non polar	2025-10-24	2886.5
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_11	C[Si](C)(C)O[C@@H]1[C@@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-24	899.739
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_1	C[Si](C)(C)O[C@@H]1[C@@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O	standard polar	2025-10-24	689.136
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_2	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])O[C@H]1N1C=NC2=C(N)N=CN=C21	standard polar	2025-10-24	1828.93
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_3	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])[C@@H](O)[C@H]1O	standard polar	2025-10-24	2147.51
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_4	C[Si](C)(C)O[C@@H]1[C@@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-24	1730.66
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_5	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])[C@@H](O[Si](C)(C)C)[C@H]1O	standard polar	2025-10-24	2852.0
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_6	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])[C@@H](O)[C@H]1O[Si](C)(C)C	standard polar	2025-10-24	1042.61
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_7	C[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])[C@@H](O)[C@H]1O)[Si](C)(C)C	standard polar	2025-10-24	1865.47
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_8	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	standard polar	2025-10-24	2023.46
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_9	C[Si](C)(C)O[C@@H]1[C@@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H]1O	standard polar	2025-10-24	1728.66
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_10	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21	standard polar	2025-10-24	1343.09
Gas Chromatography	carboxy-S-adenosyl-L-methionine_TMS_11	C[Si](C)(C)O[C@@H]1[C@@H](C[S+](CC[C@H]([NH3+])C(=O)[O-])CC(=O)[O-])O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-24	1658.09

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0025432	carboxy-S-adenosyl-L-methionine	S-Adenosylhomocysteine	tRNA U34 carboxymethyltransferase	Methylation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria/Eubacteria	Proteobacteria	176	Pig ; Human feces; Cattle ; Human ; River trout ; Lion ; Chicken
Bacteria	Proteobacteria	4	Pig ; Human feces; Cattle ; Human ; River trout ; Lion ; Chicken
Bacteria/Eubacteria	Firmicutes	1	Human
Bacteria/Eubacteria	Cyanobacteria	1

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58837402

KEGG Compound ID

Not Available

BioCyc ID

CPD-15403

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90659115

PDB ID

Not Available

ChEBI ID

134278

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for carboxy-S-adenosyl-L-methionine (MMDBc0056396)

MOL for #<Metabolite:0x00007f9ad03bfe80>

3D MOL for #<Metabolite:0x00007f9ad03bfe80>

3D SDF for #<Metabolite:0x00007f9ad03bfe80>

3D-SDF for #<Metabolite:0x00007f9ad03bfe80>

PDB for #<Metabolite:0x00007f9ad03bfe80>

3D PDB for #<Metabolite:0x00007f9ad03bfe80>

SMILES for #<Metabolite:0x00007f9ad03bfe80>

INCHI for #<Metabolite:0x00007f9ad03bfe80>

Structure for #<Metabolite:0x00007f9ad03bfe80>

3D Structure for #<Metabolite:0x00007f9ad03bfe80>