NP-MRD: Showing NP-Card for S-adenosyl-L-methioninamine (NP0334382)

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Record Information

Version

2.0

Created at

2024-09-09 23:25:35 UTC

Updated at

2024-09-09 23:25:36 UTC

NP-MRD ID

NP0334382

Secondary Accession Numbers

None

Natural Product Identification

Common Name

S-adenosyl-L-methioninamine

Description

Decarboxy-sam, also known as S-adenosyl 3-(methylthio)propylamine or dcsam, is a member of the class of compounds known as 5'-deoxy-5'-thionucleosides. 5'-Deoxy-5'-thionucleosides are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group. Decarboxy-sam is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Decarboxy-sam can be found in a number of food items such as caraway, celeriac, prunus (cherry, plum), and sparkleberry, which makes decarboxy-sam a potential biomarker for the consumption of these food products. Decarboxy-sam may be a unique E.Coli metabolite.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08131209392D          

 28 30  0  0  0  0            999 V2000
    0.1684    5.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2606    6.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9750    7.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5461    7.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8828    7.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8567    4.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1360    7.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5973    6.5971    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0292    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6836    5.7766    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4905    5.6051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6967    5.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755    5.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9030    6.3196    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6895    6.5971    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.4503    5.9789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6104    4.8229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1893    4.9722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9430    6.9487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7235    6.4058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0705    5.2246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    4.8514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510    6.9327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684    6.5971    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
    1.1008    5.9382    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8587    5.7910    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9713    4.9639    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3524    5.6277    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  8  5  1  1  0  0  0
 10  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15  3  1  0  0  0  0
 16 12  1  0  0  0  0
 17  6  2  0  0  0  0
 17 12  1  0  0  0  0
 18  6  1  0  0  0  0
 18 13  2  0  0  0  0
 19  7  2  0  0  0  0
 19  9  1  0  0  0  0
 20  7  1  0  0  0  0
 20 13  1  0  0  0  0
 14 20  1  1  0  0  0
 10 21  1  6  0  0  0
 11 22  1  6  0  0  0
 23  8  1  0  0  0  0
 23 14  1  0  0  0  0
 24  1  1  0  0  0  0
 24  4  1  0  0  0  0
 24  5  1  0  0  0  0
  8 25  1  6  0  0  0
 10 26  1  1  0  0  0
 11 27  1  1  0  0  0
 14 28  1  6  0  0  0
M  CHG  2  15   1  24   1
M  END


  Mrv0541 08131209392D          

 28 30  0  0  0  0            999 V2000
    0.1684    5.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2606    6.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9750    7.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5461    7.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8828    7.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8567    4.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1360    7.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5973    6.5971    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0292    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6836    5.7766    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4905    5.6051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6967    5.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755    5.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9030    6.3196    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6895    6.5971    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.4503    5.9789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6104    4.8229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1893    4.9722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9430    6.9487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7235    6.4058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0705    5.2246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    4.8514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510    6.9327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684    6.5971    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
    1.1008    5.9382    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8587    5.7910    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9713    4.9639    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3524    5.6277    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  8  5  1  1  0  0  0
 10  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15  3  1  0  0  0  0
 16 12  1  0  0  0  0
 17  6  2  0  0  0  0
 17 12  1  0  0  0  0
 18  6  1  0  0  0  0
 18 13  2  0  0  0  0
 19  7  2  0  0  0  0
 19  9  1  0  0  0  0
 20  7  1  0  0  0  0
 20 13  1  0  0  0  0
 14 20  1  1  0  0  0
 10 21  1  6  0  0  0
 11 22  1  6  0  0  0
 23  8  1  0  0  0  0
 23 14  1  0  0  0  0
 24  1  1  0  0  0  0
 24  4  1  0  0  0  0
 24  5  1  0  0  0  0
  8 25  1  6  0  0  0
 10 26  1  1  0  0  0
 11 27  1  1  0  0  0
 14 28  1  6  0  0  0
M  CHG  2  15   1  24   1
M  END
> <DATABASE_ID>
NP0334382

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(C[S+](C)CCC[NH3+])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C14H23N6O3S/c1-24(4-2-3-15)5-8-10(21)11(22)14(23-8)20-7-19-9-12(16)17-6-18-13(9)20/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18)/q+1/p+1/t8-,10-,11-,14-,24?/m1/s1

> <INCHI_KEY>
ZUNBITIXDCPNSD-LSRJEVITSA-O

> <FORMULA>
C14H24N6O3S

> <MOLECULAR_WEIGHT>
356.444

> <EXACT_MASS>
356.163059354

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
37.339144530747674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
2

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.73

> <JCHEM_LOGP>
-2.750104969875945

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
13.949691544589712

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.445729441899676

> <JCHEM_PKA_STRONGEST_BASIC>
10.09131159991071

> <JCHEM_POLAR_SURFACE_AREA>
146.95

> <JCHEM_REFRACTIVITY>
101.69779999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
S-adenosylmethioninaminium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+1
HETATM   16  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+1
HETATM   25  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   24                                                            
CONECT    2    3    4                                                       
CONECT    3    2   15                                                       
CONECT    4    2   24                                                       
CONECT    5    8   24                                                       
CONECT    6   17   18                                                       
CONECT    7   19   20                                                       
CONECT    8    5   10   23   25                                             
CONECT    9   12   13   19                                                  
CONECT   10    8   11   21   26                                             
CONECT   11   10   14   22   27                                             
CONECT   12    9   16   17                                                  
CONECT   13    9   18   20                                                  
CONECT   14   11   20   23   28                                             
CONECT   15    3                                                            
CONECT   16   12                                                            
CONECT   17    6   12                                                       
CONECT   18    6   13                                                       
CONECT   19    7    9                                                       
CONECT   20    7   13   14                                                  
CONECT   21   10                                                            
CONECT   22   11                                                            
CONECT   23    8   14                                                       
CONECT   24    1    4    5                                                  
CONECT   25    8                                                            
CONECT   26   10                                                            
CONECT   27   11                                                            
CONECT   28   14                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
S-Adenosyl 3-(methylsulfanyl)propylamine	ChEBI
S-Adenosyl 3-(methylsulphanyl)propylamine	Generator
S-Adenosyl 3-(methylthio)propylamine	ChEBI

Chemical Formula

C₁₄H₂₄N₆O₃S

Average Mass

356.4440 Da

Monoisotopic Mass

356.16306 Da

IUPAC Name

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

Traditional Name

S-adenosylmethioninaminium

CAS Registry Number

Not Available

SMILES

[H][C@]1(C[S+](C)CCC[NH3+])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C14H23N6O3S/c1-24(4-2-3-15)5-8-10(21)11(22)14(23-8)20-7-19-9-12(16)17-6-18-13(9)20/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18)/q+1/p+1/t8-,10-,11-,14-,24?/m1/s1

InChI Key

ZUNBITIXDCPNSD-LSRJEVITSA-O

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Pentose monosaccharide
Purine
Imidazopyrimidine
Aminopyrimidine
Imidolactam
Pyrimidine
Monosaccharide
N-substituted imidazole
Heteroaromatic compound
Tetrahydrofuran
Azole
Imidazole
Secondary alcohol
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Primary aliphatic amine
Organooxygen compound
Organosulfur compound
Organic oxygen compound
Organic nitrogen compound
Primary amine
Amine
Alcohol
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

ammonium ion (CHEBI:57443 )
sulfonium compound (CHEBI:57443 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-1.7	ALOGPS
logP	-2.8	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.45	ChemAxon
pKa (Strongest Basic)	10.09	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	146.95 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	101.7 m³·mol⁻¹	ChemAxon
Polarizability	37.34 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB031151

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

25203490

PDB ID

Not Available

ChEBI ID

57443

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for S-adenosyl-L-methioninamine (NP0334382)

MOL for NP0334382 (S-adenosyl-L-methioninamine)

3D MOL for NP0334382 (S-adenosyl-L-methioninamine)

3D SDF for NP0334382 (S-adenosyl-L-methioninamine)

3D-SDF for NP0334382 (S-adenosyl-L-methioninamine)

PDB for NP0334382 (S-adenosyl-L-methioninamine)

3D PDB for NP0334382 (S-adenosyl-L-methioninamine)

SMILES for NP0334382 (S-adenosyl-L-methioninamine)

INCHI for NP0334382 (S-adenosyl-L-methioninamine)

Structure for NP0334382 (S-adenosyl-L-methioninamine)

3D Structure for NP0334382 (S-adenosyl-L-methioninamine)