MiMeDB: Showing metabocard for N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide (MMDBc0031624)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:41:51 UTC

Update Date

2022-08-31 18:22:36 UTC

Metabolite ID

MMDBc0031624

Metabolite Identification

Common Name

N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide

Description

N-acetyl-D-glucosamine(anhydrous)N-acetylmuramyl-tripeptide is an intermediate in peptidoglycan synthesis and turnover. Peptidoglycan can be described as a fisherman's net that encloses bacteria. The mesh of the net is made of two segments of parallel, somewhat inextensible glycan threads, held together by two small elastic peptide crosslinks allowing the net to expand or shrink. The glycan moiety of the peptidoglycan is very uniform among all bacteria, and is made up of alternating Œ≤-1,4-linked N-acetylglucosamine and N-acetyl muramate residues, with an average chain lengthof 10 to 65 disaccharide units (depending on the organism). The peptidoglycan synthesis pathway starts in the cytoplasm, where in six steps the peptidoglycan precursor a UDP-N-acetylmuramoyl-pentapeptide is synthesized. This precursor is then attached to the memberane acceptor all-trans-undecaprenyl phosphate, generating a N-acetylmuramoyl-pentapeptide-diphosphoundecaprenol, also known as lipid I. Another transferase then adds UDP-N-acetyl-Œ±-D-glucosamine, yielding the complete monomeric unit a lipid II, also known as lipid II. This final lipid intermediate is transferred by an as yet unknown mechanism through the membrane. The peptidoglycan monomers are then polymerized on the outside surface by glycosyltransferases, which form the linear glycan chains, and transpeptidases, which catalyze the formation of peptide crosslinks. Peptide crosslinks form between different parts of the peptides depending on the organism. For example, in Mycobacteria and in E. coli most links form between the carboxyl group of the penultimate D-alanine (residue 4) of one peptide to the amino group at the D-center of meso-diaminopimelate (residue 3) of an adjacent peptide of a second glycan chain (as in E. coli). The crosslinking reaction is catalyzed by transpeptidases and involves the cleavage of the D-alanyl-D-alanine bond of the donor peptide, providing the energy to drive the reaction. As a result, the peptides in the peptidoglycan polymers are one or two amino acids shorter than the peptides in the monomers.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08141218152D          

 59 60  0  0  0  0            999 V2000
   14.9760   -0.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2460    2.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5963    4.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4654    2.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3051    0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4949    0.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8452   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2756   -1.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8156   -2.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2756    6.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3557    5.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2460    4.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4359    0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4359    2.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3262    3.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7355    3.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9548    0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5456   -1.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6553    0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9760    3.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0055    6.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8958    5.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5456   -3.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4654    4.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1954    5.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9253    5.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1659    3.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6258    4.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6258   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1659    1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0055   -0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9253    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2756    4.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2249    1.7605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7060    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5161    3.1637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1954    3.7873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3557   -0.8900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1954   -0.5782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0857    7.0614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6258    6.4378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8663    2.6959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5456    3.3196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7355   -3.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0857   -3.8523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6553    6.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1152    5.0346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0857    0.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3557    1.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2756    0.3573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6046    1.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8747    0.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7355    0.9809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3852    1.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7060    5.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8958    2.8518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5456    5.5023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8156    4.0991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  1  0  0  0  0
 13  1  1  0  0  0  0
 14  2  1  0  0  0  0
 15  3  1  0  0  0  0
 16  4  1  0  0  0  0
 17  6  1  0  0  0  0
 18  8  1  0  0  0  0
 19  7  1  0  0  0  0
 20 12  2  0  0  0  0
 21 10  1  0  0  0  0
 22 11  1  0  0  0  0
 23  9  1  0  0  0  0
 25 21  1  0  0  0  0
 26 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 20  1  0  0  0  0
 28 22  1  0  0  0  0
 28 27  1  0  0  0  0
 29 13  1  0  0  0  0
 30 14  1  0  0  0  0
 31 18  1  0  0  0  0
 32 17  1  0  0  0  0
 33 19  1  0  0  0  0
 34 24  1  0  0  0  0
 35 17  1  0  0  0  0
 36 13  1  4  0  0  0
 36 30  2  0  0  0  0
 37 15  2  0  0  0  0
 37 20  1  4  0  0  0
 38 16  2  0  0  0  0
 38 24  1  4  0  0  0
 39 18  1  4  0  0  0
 39 29  2  0  0  0  0
 40 19  1  4  0  0  0
 40 31  2  0  0  0  0
 41 10  1  0  0  0  0
 42 11  1  0  0  0  0
 43 15  1  0  0  0  0
 44 16  1  0  0  0  0
 45 23  2  0  0  0  0
 46 23  1  0  0  0  0
 47 25  1  0  0  0  0
 48 26  1  0  0  0  0
 49 29  1  0  0  0  0
 50 30  1  0  0  0  0
 51 31  1  0  0  0  0
 52 32  2  0  0  0  0
 53 32  1  0  0  0  0
 54 33  2  0  0  0  0
 55 33  1  0  0  0  0
 56 12  1  0  0  0  0
 56 22  1  0  0  0  0
 57 14  1  0  0  0  0
 57 27  1  0  0  0  0
 58 21  1  0  0  0  0
 58 34  1  0  0  0  0
 59 28  1  0  0  0  0
 59 34  1  0  0  0  0
M  END


  Mrv0541 08141218152D          

 59 60  0  0  0  0            999 V2000
   14.9760   -0.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2460    2.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5963    4.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4654    2.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3051    0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4949    0.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8452   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2756   -1.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8156   -2.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2756    6.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3557    5.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2460    4.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4359    0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4359    2.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3262    3.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7355    3.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9548    0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5456   -1.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6553    0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9760    3.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0055    6.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8958    5.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5456   -3.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4654    4.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1954    5.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9253    5.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1659    3.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6258    4.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6258   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1659    1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0055   -0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9253    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2756    4.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2249    1.7605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7060    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5161    3.1637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1954    3.7873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3557   -0.8900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1954   -0.5782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0857    7.0614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6258    6.4378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8663    2.6959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5456    3.3196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7355   -3.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0857   -3.8523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6553    6.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1152    5.0346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0857    0.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3557    1.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2756    0.3573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6046    1.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8747    0.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7355    0.9809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3852    1.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7060    5.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8958    2.8518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5456    5.5023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8156    4.0991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  1  0  0  0  0
 13  1  1  0  0  0  0
 14  2  1  0  0  0  0
 15  3  1  0  0  0  0
 16  4  1  0  0  0  0
 17  6  1  0  0  0  0
 18  8  1  0  0  0  0
 19  7  1  0  0  0  0
 20 12  2  0  0  0  0
 21 10  1  0  0  0  0
 22 11  1  0  0  0  0
 23  9  1  0  0  0  0
 25 21  1  0  0  0  0
 26 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 20  1  0  0  0  0
 28 22  1  0  0  0  0
 28 27  1  0  0  0  0
 29 13  1  0  0  0  0
 30 14  1  0  0  0  0
 31 18  1  0  0  0  0
 32 17  1  0  0  0  0
 33 19  1  0  0  0  0
 34 24  1  0  0  0  0
 35 17  1  0  0  0  0
 36 13  1  4  0  0  0
 36 30  2  0  0  0  0
 37 15  2  0  0  0  0
 37 20  1  4  0  0  0
 38 16  2  0  0  0  0
 38 24  1  4  0  0  0
 39 18  1  4  0  0  0
 39 29  2  0  0  0  0
 40 19  1  4  0  0  0
 40 31  2  0  0  0  0
 41 10  1  0  0  0  0
 42 11  1  0  0  0  0
 43 15  1  0  0  0  0
 44 16  1  0  0  0  0
 45 23  2  0  0  0  0
 46 23  1  0  0  0  0
 47 25  1  0  0  0  0
 48 26  1  0  0  0  0
 49 29  1  0  0  0  0
 50 30  1  0  0  0  0
 51 31  1  0  0  0  0
 52 32  2  0  0  0  0
 53 32  1  0  0  0  0
 54 33  2  0  0  0  0
 55 33  1  0  0  0  0
 56 12  1  0  0  0  0
 56 22  1  0  0  0  0
 57 14  1  0  0  0  0
 57 27  1  0  0  0  0
 58 21  1  0  0  0  0
 58 34  1  0  0  0  0
 59 28  1  0  0  0  0
 59 34  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031624

> <DATABASE_NAME>
MIME

> <SMILES>
CC(OC1C(OC2OC(CO)C(O)C(O)C2N=C(C)O)C(CO)OC=C1N=C(C)O)C(O)=NC(C)C(O)=NC(CCC(O)=O)C(O)=NC(CCCC(N)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H54N6O19/c1-13(29(49)39-18(8-9-23(45)46)31(51)40-19(33(54)55)7-5-6-17(35)32(52)53)36-30(50)14(2)57-27-20(37-15(3)43)12-56-22(11-42)28(27)59-34-24(38-16(4)44)26(48)25(47)21(10-41)58-34/h12-14,17-19,21-22,24-28,34,41-42,47-48H,5-11,35H2,1-4H3,(H,36,50)(H,37,43)(H,38,44)(H,39,49)(H,40,51)(H,45,46)(H,52,53)(H,54,55)

> <INCHI_KEY>
ZWZMFRJKRXDGBE-UHFFFAOYSA-N

> <FORMULA>
C34H54N6O19

> <MOLECULAR_WEIGHT>
850.8214

> <EXACT_MASS>
850.344373576

> <JCHEM_ACCEPTOR_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
82.91109912437385

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6-{[4-carboxy-2-({2-[(2-{[3-({4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene}amino)-1-hydroxybutylidene]amino}heptanedioic acid

> <ALOGPS_LOGP>
-1.59

> <JCHEM_LOGP>
-2.8021662306666677

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.761508843425881

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2332558620588396

> <JCHEM_POLAR_SURFACE_AREA>
418.7100000000001

> <JCHEM_REFRACTIVITY>
194.0502000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-6-{[4-carboxy-2-({2-[(2-{[3-({4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene}amino)-1-hydroxybutylidene]amino}heptanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-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  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   38  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   39  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   40  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   41  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   16                                                            
CONECT    5    6    7                                                       
CONECT    6    5   17                                                       
CONECT    7    5   19                                                       
CONECT    8    9   18                                                       
CONECT    9    8   23                                                       
CONECT   10   21   41                                                       
CONECT   11   22   42                                                       
CONECT   12   20   56                                                       
CONECT   13    1   29   36                                                  
CONECT   14    2   30   57                                                  
CONECT   15    3   37   43                                                  
CONECT   16    4   38   44                                                  
CONECT   17    6   32   35                                                  
CONECT   18    8   31   39                                                  
CONECT   19    7   33   40                                                  
CONECT   20   12   27   37                                                  
CONECT   21   10   25   58                                                  
CONECT   22   11   28   56                                                  
CONECT   23    9   45   46                                                  
CONECT   24   26   34   38                                                  
CONECT   25   21   26   47                                                  
CONECT   26   24   25   48                                                  
CONECT   27   20   28   57                                                  
CONECT   28   22   27   59                                                  
CONECT   29   13   39   49                                                  
CONECT   30   14   36   50                                                  
CONECT   31   18   40   51                                                  
CONECT   32   17   52   53                                                  
CONECT   33   19   54   55                                                  
CONECT   34   24   58   59                                                  
CONECT   35   17                                                            
CONECT   36   13   30                                                       
CONECT   37   15   20                                                       
CONECT   38   16   24                                                       
CONECT   39   18   29                                                       
CONECT   40   19   31                                                       
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   23                                                            
CONECT   46   23                                                            
CONECT   47   25                                                            
CONECT   48   26                                                            
CONECT   49   29                                                            
CONECT   50   30                                                            
CONECT   51   31                                                            
CONECT   52   32                                                            
CONECT   53   32                                                            
CONECT   54   33                                                            
CONECT   55   33                                                            
CONECT   56   12   22                                                       
CONECT   57   14   27                                                       
CONECT   58   21   34                                                       
CONECT   59   28   34                                                       
MASTER        0    0    0    0    0    0    0    0   59    0  120    0
END

Synonyms

Value	Source
2-Amino-6-{[4-carboxy-2-({2-[(2-{[3-({4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene}amino)-1-hydroxybutylidene]amino}heptanedioate	Generator

Molecular Formula

C₃₄H₅₄N₆O₁₉

Average Mass

850.8214

Monoisotopic Mass

850.344373576

IUPAC Name

2-amino-6-{[4-carboxy-2-({2-[(2-{[3-({4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene}amino)-1-hydroxybutylidene]amino}heptanedioic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(OC1C(OC2OC(CO)C(O)C(O)C2N=C(C)O)C(CO)OC=C1N=C(C)O)C(O)=NC(C)C(O)=NC(CCC(O)=O)C(O)=NC(CCCC(N)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C34H54N6O19/c1-13(29(49)39-18(8-9-23(45)46)31(51)40-19(33(54)55)7-5-6-17(35)32(52)53)36-30(50)14(2)57-27-20(37-15(3)43)12-56-22(11-42)28(27)59-34-24(38-16(4)44)26(48)25(47)21(10-41)58-34/h12-14,17-19,21-22,24-28,34,41-42,47-48H,5-11,35H2,1-4H3,(H,36,50)(H,37,43)(H,38,44)(H,39,49)(H,40,51)(H,45,46)(H,52,53)(H,54,55)

InChI Key

ZWZMFRJKRXDGBE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
Saccharolipid
N-acyl-alpha-hexosamine
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Glycosyl compound
O-glycosyl compound
Alpha-amino acid
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
Amino fatty acid
Hydroxy fatty acid
Oxane
Fatty acyl
Monosaccharide
Secondary alcohol
Amino acid
Amino acid or derivatives
Acetal
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Primary aliphatic amine
Organic oxide
Carbonyl group
Alcohol
Primary amine
Primary alcohol
Organonitrogen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

a small molecule (CPD0-2155 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.2 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-2.8	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.23	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	25	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	418.71 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	194.05 m³·mol⁻¹	ChemAxon
Polarizability	82.91 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-0205010390-85cd3c5657158613899a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-0938145230-e508f2d59123ebfe6784	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1915010000-8ee2356690ba5b763312	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01qj-4101004970-f5bbca7c644c4263aed7	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001r-2022053590-506c0fdb246d34764b03	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000l-8397480000-91222a57edd94b56d00b	2015-09-15	View Spectrum

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

Metabolic Reactions

Not Available

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	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	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

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

45479614

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sajed T, Marcu A, Ramirez M, Pon A, Guo AC, Knox C, Wilson M, Grant JR, Djoumbou Y, Wishart DS: ECMDB 2.0: A richer resource for understanding the biochemistry of E. coli. Nucleic Acids Res. 2016 Jan 4;44(D1):D495-501. doi: 10.1093/nar/gkv1060. Epub 2015 Oct 19. [PubMed:26481353 ]

Showing metabocard for N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide (MMDBc0031624)

MOL for #<Metabolite:0x00007fece534c5e0>

3D MOL for #<Metabolite:0x00007fece534c5e0>

3D SDF for #<Metabolite:0x00007fece534c5e0>

3D-SDF for #<Metabolite:0x00007fece534c5e0>

PDB for #<Metabolite:0x00007fece534c5e0>

3D PDB for #<Metabolite:0x00007fece534c5e0>

SMILES for #<Metabolite:0x00007fece534c5e0>

INCHI for #<Metabolite:0x00007fece534c5e0>

Structure for #<Metabolite:0x00007fece534c5e0>

3D Structure for #<Metabolite:0x00007fece534c5e0>