NP-MRD: Showing NP-Card for N-Acetyl-9-O-lactoylneuraminic acid (NP0086642)

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Record Information

Version

2.0

Created at

2022-05-11 16:26:54 UTC

Updated at

2022-05-11 16:26:54 UTC

NP-MRD ID

NP0086642

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetyl-9-O-lactoylneuraminic acid

Description

N-Acetyl-9-O-lactoylneuraminic acid, also known as 9-O-lactoyl-N-acetylneuraminic acid or neu5,8ac29, belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N-Acetyl-9-O-lactoylneuraminic acid is a sialic acid produced by sialate 9-O-lactoyltransferases. N-Acetyl-9-O-lactoylneuraminic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-9-O-lactoylneuraminic acid was first documented in 1993 (PMID: 8358222). A sialic acid produced by sialate 9-O-lactoyltransferases.

Structure

MOL 3D MOL SDF PDB SMILES InChI

N-Acetyl-9-O-lactoylneuraminic acid.mol
  Mrv1652305231920012D          

 26 26  0  0  0  0            999 V2000
    0.6394    2.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    1.5651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1697    1.4219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.7401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.3276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3572   -0.4974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0717   -0.9099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.9099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3572   -1.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.9099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.7401    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7862    0.3276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.5651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7862    1.9776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4519    2.4836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1091    2.9724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -2.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -1.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -2.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -2.1474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    1.5651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    0.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  2 16  1  0  0  0  0
  1 17  2  0  0  0  0
  1 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 19 23  2  0  0  0  0
 11 19  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 13 24  1  0  0  0  0
M  END

     RDKit          3D

 49 49  0  0  0  0  0  0  0  0999 V2000
   -3.8984   -3.7332    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9178   -2.6918    0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1447   -3.0247    1.5681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8532   -1.4223    0.0013 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8996   -0.4371    0.4258 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5503    0.8221    0.9396 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9715    1.2310    2.1268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5529    1.9323   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1856    2.2213   -0.6304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2641    2.4262   -2.0027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5414    3.3823   -0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1732    4.3375   -0.7370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083    3.4958    1.3565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3371    1.1236   -0.4297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347   -0.0843   -0.6870 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1059   -1.1647   -0.7256 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8174   -1.2308    0.4535 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539   -1.0290   -1.9607 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7554   -2.1776   -1.9848 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7562    0.2260   -1.9009 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5386    0.3952   -0.7695 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5883   -0.3757   -0.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9527   -1.3736   -0.9910 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3056   -0.0365    0.9135 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8446    1.3931    0.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3130   -0.9450    1.1415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4227   -4.4840   -0.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3563   -4.2519    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7099   -3.2200   -0.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5088   -1.2078   -0.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3012   -0.8672    1.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6243    0.5614    1.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6194    1.1800    2.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2191    1.6371   -0.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0143    2.8158    0.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8185    1.7640   -2.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9850    3.8247    2.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4942   -0.0848   -1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4852   -2.1364   -0.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8473   -0.3436    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3686   -1.0275   -2.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2335   -2.9763   -1.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4860    0.2516   -2.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1639    1.1447   -2.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6280   -0.0150    1.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3285    1.7233    1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9854    2.0445    0.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5117    1.3907   -0.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6072   -0.9837    2.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 26  1  0
 24 22  1  0
 22 23  2  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  1  0
 18 16  1  0
 16 17  1  0
 16 15  1  0
 15 14  1  0
 14  9  1  0
  9 10  1  6
  9  8  1  0
  8  6  1  0
  6  7  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  9 11  1  0
 11 13  1  0
 11 12  2  0
  5 15  1  0
 25 46  1  0
 25 47  1  0
 25 48  1  0
 24 45  1  1
 26 49  1  0
 20 43  1  0
 20 44  1  0
 18 41  1  6
 19 42  1  0
 16 39  1  6
 17 40  1  0
 15 38  1  6
 10 36  1  0
  8 34  1  0
  8 35  1  0
  6 32  1  1
  7 33  1  0
  5 31  1  1
  4 30  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 13 37  1  0
M  END

N-Acetyl-9-O-lactoylneuraminic acid.mol
  Mrv1652305231920012D          

 26 26  0  0  0  0            999 V2000
    0.6394    2.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    1.5651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1697    1.4219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.7401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.3276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3572   -0.4974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0717   -0.9099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.9099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3572   -1.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.9099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.7401    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7862    0.3276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.5651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7862    1.9776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4519    2.4836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1091    2.9724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -2.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -1.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -2.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -2.1474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    1.5651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    0.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  2 16  1  0  0  0  0
  1 17  2  0  0  0  0
  1 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 19 23  2  0  0  0  0
 11 19  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 13 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086642

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C(=O)OC[C@@H](O)[C@@H](O)[C@@H]1O[C@@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H23NO11/c1-5(16)12(21)25-4-8(19)10(20)11-9(15-6(2)17)7(18)3-14(24,26-11)13(22)23/h5,7-11,16,18-20,24H,3-4H2,1-2H3,(H,15,17)(H,22,23)/t5?,7-,8+,9+,10+,11+,14-/m0/s1

> <INCHI_KEY>
XXNWSGSWDRDYLR-NVZZXFSUSA-N

> <FORMULA>
C14H23NO11

> <MOLECULAR_WEIGHT>
381.3325

> <EXACT_MASS>
381.127110583

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.589700176790075

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4S,5R,6R)-6-[(1R,2R)-1,2-dihydroxy-3-[(2-hydroxypropanoyl)oxy]propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
-2.44

> <JCHEM_LOGP>
-3.371295912333333

> <ALOGPS_LOGS>
-0.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.10088884434343

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.836081708227458

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3430942462579258

> <JCHEM_POLAR_SURFACE_AREA>
203.07999999999998

> <JCHEM_REFRACTIVITY>
79.12899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.73e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S,5R,6R)-6-[(1R,2R)-1,2-dihydroxy-3-[(2-hydroxypropanoyl)oxy]propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: N-Acetyl-9-O-lactoylneuraminic acid.mol           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAY-19         0                                  
HETATM    1  C   UNK     0       1.194   4.369   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.667   2.922   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.183   2.654   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.667   1.382   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.667   0.612   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.667  -0.928   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.001  -1.698   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.667  -1.698   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.667  -3.238   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.001  -0.928   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.334  -1.698   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.001   1.382   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -3.334   0.612   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -2.001   2.922   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.334   3.692   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.667   3.692   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.710   4.636   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.204   5.548   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.334  -3.238   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.668  -4.008   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.002  -3.238   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.668  -5.548   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.001  -4.008   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.668   1.382   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.668   2.922   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.002   0.612   0.000  0.00  0.00           C+0
CONECT    1    2   17   18                                                  
CONECT    2    1    3    4   16                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   19                                                       
CONECT   12    5   13   14                                                  
CONECT   13   12   24                                                       
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    2                                                       
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19   20   23   11                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19                                                            
CONECT   24   25   26   13                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

View in JSmol

Synonyms

Value	Source
N-Acetyl-9-O-lactoylneuraminate	Generator
5-(Acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoate	HMDB
5-(Acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoate) D-glycero-D-galacto-2-nonulosonate	HMDB
5-(Acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoate) D-glycero-D-galacto-2-nonulosonic acid	HMDB
5-(Acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoic acid	HMDB
9-O-Lactoyl-N-acetylneuraminic acid	HMDB
Neu5,8ac29	HMDB
Neu5ac9LT	HMDB
(2S,4S,5R,6R)-6-[(1R,2R)-1,2-Dihydroxy-3-[(2-hydroxypropanoyl)oxy]propyl]-2,4-dihydroxy-5-[(1-hydroxyethylidene)amino]oxane-2-carboxylate	HMDB
N-Acetyl-9-O-lactoylneuraminic acid	MeSH

Chemical Formula

C₁₄H₂₃NO₁₁

Average Mass

381.3325 Da

Monoisotopic Mass

381.12711 Da

IUPAC Name

(2S,4S,5R,6R)-6-[(1R,2R)-1,2-dihydroxy-3-[(2-hydroxypropanoyl)oxy]propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,4S,5R,6R)-6-[(1R,2R)-1,2-dihydroxy-3-[(2-hydroxypropanoyl)oxy]propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(O)C(=O)OC[C@@H](O)[C@@H](O)[C@@H]1O[C@@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O

InChI Identifier

InChI=1S/C14H23NO11/c1-5(16)12(21)25-4-8(19)10(20)11-9(15-6(2)17)7(18)3-14(24,26-11)13(22)23/h5,7-11,16,18-20,24H,3-4H2,1-2H3,(H,15,17)(H,22,23)/t5?,7-,8+,9+,10+,11+,14-/m0/s1

InChI Key

XXNWSGSWDRDYLR-NVZZXFSUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Alanine or derivatives
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

L-alanine derivative (CHEBI:40992 )
N-acetyl-L-amino acid (CHEBI:40992 )

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	-2.4	ALOGPS
logP	-3.4	ChemAxon
logS	-0.69	ALOGPS
pKa (Strongest Acidic)	2.84	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.08 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	79.13 m³·mol⁻¹	ChemAxon
Polarizability	34.59 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000768

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022232

KNApSAcK ID

Not Available

Chemspider ID

166877

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5735

PubChem Compound

192236

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kleineidam RG, Hofmann O, Reuter G, Schauer R: Indications for the enzymatic synthesis of 9-O-lactoyl-N-acetylneuraminic acid in equine liver. Glycoconj J. 1993 Feb;10(1):116-9. doi: 10.1007/BF00731195. [PubMed:8358222 ]

Showing NP-Card for N-Acetyl-9-O-lactoylneuraminic acid (NP0086642)

MOL for NP0086642 (N-Acetyl-9-O-lactoylneuraminic acid)

3D MOL for NP0086642 (N-Acetyl-9-O-lactoylneuraminic acid)

3D SDF for NP0086642 (N-Acetyl-9-O-lactoylneuraminic acid)

3D-SDF for NP0086642 (N-Acetyl-9-O-lactoylneuraminic acid)

PDB for NP0086642 (N-Acetyl-9-O-lactoylneuraminic acid)

3D PDB for NP0086642 (N-Acetyl-9-O-lactoylneuraminic acid)

SMILES for NP0086642 (N-Acetyl-9-O-lactoylneuraminic acid)

INCHI for NP0086642 (N-Acetyl-9-O-lactoylneuraminic acid)

Structure for NP0086642 (N-Acetyl-9-O-lactoylneuraminic acid)

3D Structure for NP0086642 (N-Acetyl-9-O-lactoylneuraminic acid)