NP-MRD: Showing NP-Card for Lacto-N-biose I (NP0087552)

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Record Information

Version

2.0

Created at

2022-05-11 16:52:50 UTC

Updated at

2022-05-11 16:52:50 UTC

NP-MRD ID

NP0087552

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lacto-N-biose I

Description

Lacto-N-biose I, also known as gal(b1-3)a-glcnac, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. Lacto-N-biose I is an extremely weak basic (essentially neutral) compound (based on its pKa). Lacto-N-biose I was first documented in 2004 (PMID: 14993226). A beta-D-Galp-(1->3)-D-GlcpNAc in which the N-acetylaminoglucose moiety has alpha configuration (PMID: 19420691) (PMID: 23270920) (PMID: 24065834) (PMID: 24936348).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231220432D          

 26 27  0  0  1  0            999 V2000
   18.9309   -5.6513    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2163   -5.2388    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2163   -4.4138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.9309   -4.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6454   -4.4138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6454   -5.2388    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5019   -8.1263    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5019   -6.4763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7874   -6.8888    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2163   -6.8888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.2163   -7.7138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7874   -7.7138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.9308   -8.1263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5019   -8.9513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0729   -8.1263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0729   -6.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9308   -6.4763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3599   -5.6513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3599   -6.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0743   -6.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6454   -6.8888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5019   -5.6513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5019   -4.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5019   -3.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3599   -4.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0729   -5.6513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  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  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  1  6  0  0  0
  7 14  1  1  0  0  0
 12 15  1  1  0  0  0
  9 16  1  1  0  0  0
 10 17  1  1  0  0  0
  1 17  1  1  0  0  0
  6 18  1  6  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 19  2  0  0  0  0
  2 22  1  6  0  0  0
  3 23  1  1  0  0  0
 24 23  1  0  0  0  0
  5 25  1  6  0  0  0
 26 16  1  0  0  0  0
M  END

     RDKit          3D

 51 52  0  0  0  0  0  0  0  0999 V2000
   -2.3040   -4.0406    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1021   -2.9328   -0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7964   -3.2131   -1.3460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2410   -1.5723    0.2354 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0567   -0.4716   -0.6545 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3230    0.3543   -0.8322 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4646   -0.4173   -0.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3738    1.4280    0.0186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4414    2.4167   -0.2552 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0021    3.5472   -1.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9778    4.4689   -1.2750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2453    1.7968   -0.9620 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1448    2.6427   -0.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9736    0.4796   -0.2250 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2953    0.0157   -0.4336 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0516   -0.0843    0.7491 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0717    0.8144    0.6800 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3095    0.2930    0.9875 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3680    1.3590    0.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4704    1.9387   -0.3216 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5675   -0.8219   -0.0060 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0703   -0.4459   -1.2661 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6941   -1.9730    0.4701 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5209   -2.9369   -0.5230 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4260   -1.4860    1.0680 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4040   -1.7028    2.4655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4145   -4.7225    0.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3675   -3.5943    1.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2388   -4.5827    0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4928   -1.3794    1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7950   -0.8751   -1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3637    0.7308   -1.8696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2366    0.1585   -0.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0689    2.8199    0.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3931    3.1593   -2.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7780    4.0476   -0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3527    5.3747   -1.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4806    1.5403   -1.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292    2.9589   -1.7604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1161    0.6756    0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573    0.2651    1.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2588   -0.0903    2.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3499    0.8385    1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2321    2.0646    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3693    2.2676   -0.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6336   -1.1022   -0.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6019   -0.9266   -1.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2986   -2.4790    1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2854   -3.5959   -0.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5965   -2.1481    0.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1832   -0.8622    2.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 14  5  1  0
 25 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  6
  6 32  1  6
  7 33  1  0
  9 34  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  6
 13 39  1  0
 14 40  1  1
 16 41  1  1
 18 42  1  1
 19 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  6
 22 47  1  0
 23 48  1  1
 24 49  1  0
 25 50  1  6
 26 51  1  0
M  END


  Mrv0541 02231220432D          

 26 27  0  0  1  0            999 V2000
   18.9309   -5.6513    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2163   -5.2388    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2163   -4.4138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.9309   -4.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6454   -4.4138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6454   -5.2388    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5019   -8.1263    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5019   -6.4763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7874   -6.8888    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2163   -6.8888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.2163   -7.7138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7874   -7.7138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.9308   -8.1263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5019   -8.9513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0729   -8.1263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0729   -6.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9308   -6.4763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3599   -5.6513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3599   -6.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0743   -6.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6454   -6.8888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5019   -5.6513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5019   -4.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5019   -3.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3599   -4.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0729   -5.6513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  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  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  1  6  0  0  0
  7 14  1  1  0  0  0
 12 15  1  1  0  0  0
  9 16  1  1  0  0  0
 10 17  1  1  0  0  0
  1 17  1  1  0  0  0
  6 18  1  6  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 19  2  0  0  0  0
  2 22  1  6  0  0  0
  3 23  1  1  0  0  0
 24 23  1  0  0  0  0
  5 25  1  6  0  0  0
 26 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087552

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H25NO11/c1-4(18)15-7-12(9(20)6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8+,9-,10+,11-,12-,13+,14+/m1/s1

> <INCHI_KEY>
HMQPEDMEOBLSQB-RCBHQUQDSA-N

> <FORMULA>
C14H25NO11

> <MOLECULAR_WEIGHT>
383.3484

> <EXACT_MASS>
383.142760647

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
35.89910380011098

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2S,3R,4R,5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide

> <ALOGPS_LOGP>
-2.80

> <JCHEM_LOGP>
-4.991410057333334

> <ALOGPS_LOGS>
-0.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.205563776562057

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.494146945668488

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981030798011294

> <JCHEM_POLAR_SURFACE_AREA>
198.39999999999998

> <JCHEM_REFRACTIVITY>
79.43799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.62e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2S,3R,4R,5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      35.338 -10.549   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      34.004  -9.779   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      34.004  -8.239   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      35.338  -7.469   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      36.671  -8.239   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      36.671  -9.779   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.670 -15.169   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      32.670 -12.089   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      31.336 -12.859   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.004 -12.859   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      34.004 -14.399   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.336 -14.399   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      35.337 -15.169   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      32.670 -16.709   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      30.003 -15.169   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      30.003 -12.089   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      35.337 -12.089   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      38.005 -10.549   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      38.005 -12.089   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      39.339 -12.859   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      36.671 -12.859   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      32.670 -10.549   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      32.670  -7.469   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      32.670  -5.929   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      38.005  -7.469   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      30.003 -10.549   0.000  0.00  0.00           O+0
CONECT    1    2    6   17                                                  
CONECT    2    1    3   22                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    1    5   18                                                  
CONECT    7   11   12   14                                                  
CONECT    8    9   10                                                       
CONECT    9    8   12   16                                                  
CONECT   10    8   11   17                                                  
CONECT   11    7   10   13                                                  
CONECT   12    7    9   15                                                  
CONECT   13   11                                                            
CONECT   14    7                                                            
CONECT   15   12                                                            
CONECT   16    9   26                                                       
CONECT   17   10    1                                                       
CONECT   18    6   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    2                                                            
CONECT   23    3   24                                                       
CONECT   24   23                                                            
CONECT   25    5                                                            
CONECT   26   16                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
Gal(b1-3)a-glcnac	ChEBI
WURCS=2.0/2,2,1/[a2122h-1a_1-5_2*ncc/3=o][a2112h-1b_1-5]/1-2/a3-b1	ChEBI
2-Acetamido-2-deoxy-3-O-b-D-galactopyranosyl-D-glucose	HMDB
2-Acetamido-2-deoxy-3-O-beta-D-galactopyranosyl-D-glucopyranose	HMDB
2-Acetamido-2-deoxy-3-O-beta-D-galactopyranosyl-D-glucose	HMDB
2-Acetamido-2-deoxy-3-O-beta-delta-galactopyranosyl-delta-glucopyranose	HMDB
2-Acetamido-2-deoxy-3-O-beta-delta-galactopyranosyl-delta-glucose	HMDB
beta-D-Gal-(1->3)-D-glcnac	HMDB
beta-D-Galactopyranosyl-(1->3)-N-acetyl-D-glucosamine	HMDB
beta-delta-Gal-(1->3)-delta-glcnac	HMDB
beta-delta-Galactopyranosyl-(1->3)-N-acetyl-delta-glucosamine	HMDB
Gal(beta1-3)glcnac	HMDB
Lacto-N-biose	HMDB
O-beta-D-Galactopyranosyl-(1->3)-N-acetylglucosamine	HMDB
O-beta-delta-Galactopyranosyl-(1->3)-N-acetylglucosamine	HMDB
Gal-1,3-glcnac	HMDB
Galactosyl-1,3-N-acetylglucosamine	HMDB
N-[(2S,3R,4R,5S,6R)-2,5-Dihydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]ethanimidate	HMDB
Lacto-N-biose I	MeSH

Chemical Formula

C₁₄H₂₅NO₁₁

Average Mass

383.3484 Da

Monoisotopic Mass

383.14276 Da

IUPAC Name

N-[(2S,3R,4R,5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide

Traditional Name

N-[(2S,3R,4R,5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C14H25NO11/c1-4(18)15-7-12(9(20)6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8+,9-,10+,11-,12-,13+,14+/m1/s1

InChI Key

HMQPEDMEOBLSQB-RCBHQUQDSA-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 acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

Acylaminosugar
N-acyl-alpha-hexosamine
Disaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Acetamide
Carboxamide group
Hemiacetal
Secondary carboxylic acid amide
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Alcohol
Primary alcohol
Organonitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	-2.8	ALOGPS
logP	-5	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Acidic)	11.49	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	198.4 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.44 m³·mol⁻¹	ChemAxon
Polarizability	35.9 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

External Links

HMDB ID

HMDB0006575

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023977

KNApSAcK ID

Not Available

Chemspider ID

4450965

KEGG Compound ID

C06372

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5288905

PDB ID

Not Available

ChEBI ID

27707

Good Scents ID

Not Available

References

General References

Kakuda S, Shiba T, Ishiguro M, Tagawa H, Oka S, Kajihara Y, Kawasaki T, Wakatsuki S, Kato R: Structural basis for acceptor substrate recognition of a human glucuronyltransferase, GlcAT-P, an enzyme critical in the biosynthesis of the carbohydrate epitope HNK-1. J Biol Chem. 2004 May 21;279(21):22693-703. doi: 10.1074/jbc.M400622200. Epub 2004 Mar 1. [PubMed:14993226 ]
Kiyohara M, Tachizawa A, Nishimoto M, Kitaoka M, Ashida H, Yamamoto K: Prebiotic effect of lacto-N-biose I on bifidobacterial growth. Biosci Biotechnol Biochem. 2009 May;73(5):1175-9. doi: 10.1271/bbb.80697. Epub 2009 May 7. [PubMed:19420691 ]
Satoh T, Odamaki T, Namura M, Shimizu T, Iwatsuki K, Nishimoto M, Kitaoka M, Xiao JZ: In vitro comparative evaluation of the impact of lacto-N-biose I, a major building block of human milk oligosaccharides, on the fecal microbiota of infants. Anaerobe. 2013 Feb;19:50-7. doi: 10.1016/j.anaerobe.2012.12.007. Epub 2012 Dec 25. [PubMed:23270920 ]
Koyama Y, Hidaka M, Nishimoto M, Kitaoka M: Directed evolution to enhance thermostability of galacto-N-biose/lacto-N-biose I phosphorylase. Protein Eng Des Sel. 2013 Nov;26(11):755-61. doi: 10.1093/protein/gzt049. Epub 2013 Sep 24. [PubMed:24065834 ]
Goto M, Takano-Ishikawa Y, Nishimoto M, Kitaoka M: Effect of Lacto-N-biose I on the Antigen-specific Immune Responses of Splenocytes. Biosci Microbiota Food Health. 2012;31(2):47-50. doi: 10.12938/bmfh.31.47. Epub 2012 Apr 20. [PubMed:24936348 ]

Showing NP-Card for Lacto-N-biose I (NP0087552)

MOL for NP0087552 (Lacto-N-biose I)

3D MOL for NP0087552 (Lacto-N-biose I)

3D SDF for NP0087552 (Lacto-N-biose I)

3D-SDF for NP0087552 (Lacto-N-biose I)

PDB for NP0087552 (Lacto-N-biose I)

3D PDB for NP0087552 (Lacto-N-biose I)

SMILES for NP0087552 (Lacto-N-biose I)

INCHI for NP0087552 (Lacto-N-biose I)

Structure for NP0087552 (Lacto-N-biose I)

3D Structure for NP0087552 (Lacto-N-biose I)