NP-MRD: Showing NP-Card for (2s,4s)-4-{[(1z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-c-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2r,3s,4r,5r)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid (NP0232828)

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Record Information

Version

2.0

Created at

2022-09-06 14:11:46 UTC

Updated at

2022-09-06 14:11:47 UTC

NP-MRD ID

NP0232828

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,4s)-4-{[(1z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-c-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2r,3s,4r,5r)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid

Description

(2S,4S)-4-{[(1Z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-C-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2R,3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. (2s,4s)-4-{[(1z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-c-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2r,3s,4r,5r)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid is found in Hemerocallis fulva. Based on a literature review very few articles have been published on (2S,4S)-4-{[(1Z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-C-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2R,3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062216112D          

 28 28  0  0  1  0            999 V2000
    0.2300    0.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2300    0.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9445   -0.4065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9445   -1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6590   -1.6440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6590   -2.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9445   -2.8815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3734   -2.8815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3734   -3.7065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0879   -2.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8024   -2.8815    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5169   -2.4690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2313   -2.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2313   -3.7065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4189   -3.5632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0438   -3.5632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5741   -4.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2919   -4.9705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8222   -5.6025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4795   -5.1137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1973   -5.8890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9492   -4.4817    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1367   -4.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8024   -3.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5169   -4.1190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0879   -4.1190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6590    0.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3734   -0.4065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  4  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  6  0  0  0
 11 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

     RDKit          3D

 54 54  0  0  0  0  0  0  0  0999 V2000
   -8.0253    0.0811    1.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7655    0.1603    2.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7899    0.4312    1.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4740    0.5259    1.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5305    0.7792    0.6408 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6762    0.8773   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1446    2.1512   -0.4761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0345   -0.2460   -0.9730 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0241    0.2269   -2.2725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6441   -0.3587   -0.4483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2341   -1.4259   -1.0258 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4916   -1.3352   -0.3265 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2993   -0.1972   -0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4019   -0.1283    0.5906 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5942    0.0032    1.7708 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0552   -1.2943    0.7393 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3803   -1.4057    0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2119   -0.1864    0.8519 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5154   -0.4392    0.4699 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6349    0.9653    0.0803 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8208    0.8690   -1.2991 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917    1.1080    0.4433 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1548    1.8267    1.6604 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4527   -1.3761   -2.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5654   -1.2190   -3.0603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6300   -1.5132   -3.3653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1478    0.6356   -0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7674   -0.4985   -0.6624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8635   -0.1198    2.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3614    0.1950    0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5390    0.0269    3.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2478    0.3592    2.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4909    2.4990    0.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5976   -1.1972   -0.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9478    0.2667   -2.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7403   -0.5574    0.6559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1446    0.6195   -0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1997   -2.4412   -0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287   -1.3714    0.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7527    0.7464   -0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8466   -0.2601   -1.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9673    0.7804    1.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7613   -2.2092    1.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6939   -1.7418   -0.4789 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1534    0.0740    1.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6389   -0.2255   -0.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1581    1.8799    0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8962   -0.0674   -1.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6924    1.7996   -0.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9553    1.1968    2.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9096   -2.3844   -3.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9456    1.4458   -0.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3504    1.0481   -0.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7569   -0.5479   -1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
 27  3  1  0
  3  2  1  0
  2  1  2  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11 24  1  0
 24 26  1  0
 24 25  2  0
 22 14  1  0
 28 54  1  0
 27 52  1  0
 27 53  1  0
  2 31  1  0
  1 29  1  0
  1 30  1  0
  4 32  1  0
  7 33  1  0
  8 34  1  6
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  6
 12 39  1  0
 13 40  1  0
 13 41  1  0
 15 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  1
 19 46  1  0
 20 47  1  1
 21 48  1  0
 22 49  1  6
 23 50  1  0
 26 51  1  0
M  END


  Mrv1652309062216112D          

 28 28  0  0  1  0            999 V2000
    0.2300    0.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2300    0.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9445   -0.4065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9445   -1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6590   -1.6440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6590   -2.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9445   -2.8815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3734   -2.8815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3734   -3.7065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0879   -2.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8024   -2.8815    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5169   -2.4690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2313   -2.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2313   -3.7065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4189   -3.5632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0438   -3.5632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5741   -4.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2919   -4.9705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8222   -5.6025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4795   -5.1137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1973   -5.8890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9492   -4.4817    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1367   -4.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8024   -3.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5169   -4.1190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0879   -4.1190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6590    0.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3734   -0.4065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  4  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  6  0  0  0
 11 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0232828

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC\C(C=C)=C/N=C(O)[C@@H](O)C[C@H](NC[C@@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H26N2O10/c1-2-8(5-19)4-17-14(24)10(20)3-9(15(25)26)18-7-16(27)13(23)12(22)11(21)6-28-16/h2,4,9-13,18-23,27H,1,3,5-7H2,(H,17,24)(H,25,26)/b8-4-/t9-,10-,11+,12+,13-,16+/m0/s1

> <INCHI_KEY>
PYEDMQSECHECBB-CEXREEHGSA-N

> <FORMULA>
C16H26N2O10

> <MOLECULAR_WEIGHT>
406.388

> <EXACT_MASS>
406.158745045

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.55076186169549

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4S)-4-{[(1Z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-C-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2R,3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid

> <JCHEM_LOGP>
-7.070251555964

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.3734957019944534

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.372450479326706

> <JCHEM_PKA_STRONGEST_BASIC>
8.379992885694964

> <JCHEM_POLAR_SURFACE_AREA>
212.52999999999997

> <JCHEM_REFRACTIVITY>
92.91850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S)-4-{[(1Z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-C-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2R,3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.429   1.551   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.429   0.011   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.763  -0.759   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.763  -2.299   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       3.097  -3.069   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.097  -4.609   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.763  -5.379   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.430  -5.379   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.430  -6.919   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.764  -4.609   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.098  -5.379   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       8.431  -4.609   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       9.765  -5.379   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.765  -6.919   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.249  -6.651   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      11.282  -6.651   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.272  -7.831   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.745  -9.278   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.735 -10.458   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.228  -9.546   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.702 -10.993   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.238  -8.366   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.722  -8.633   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.098  -6.919   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.431  -7.689   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.764  -7.689   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.097   0.011   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.430  -0.759   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   22                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   14   23                                                  
CONECT   23   22                                                            
CONECT   24   11   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27    3   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   56    0
END

View in JSmol

Synonyms

Value	Source
(2S,4S)-4-{[(1Z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-C-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2R,3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoate	Generator

Chemical Formula

C₁₆H₂₆N₂O₁₀

Average Mass

406.3880 Da

Monoisotopic Mass

406.15875 Da

IUPAC Name

(2S,4S)-4-{[(1Z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-C-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2R,3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid

Traditional Name

(2S,4S)-4-{[(1Z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-C-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2R,3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid

CAS Registry Number

Not Available

SMILES

OC\C(C=C)=C/N=C(O)[C@@H](O)C[C@H](NC[C@@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O)C(O)=O

InChI Identifier

InChI=1S/C16H26N2O10/c1-2-8(5-19)4-17-14(24)10(20)3-9(15(25)26)18-7-16(27)13(23)12(22)11(21)6-28-16/h2,4,9-13,18-23,27H,1,3,5-7H2,(H,17,24)(H,25,26)/b8-4-/t9-,10-,11+,12+,13-,16+/m0/s1

InChI Key

PYEDMQSECHECBB-CEXREEHGSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Hemerocallis fulva	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamine and derivatives

Alternative Parents

Substituents

Glutamine or derivatives
L-alpha-amino acid
Alpha-amino acid
Hydroxy fatty acid
Heterocyclic fatty acid
Short-chain hydroxy acid
Branched fatty acid
Fatty acyl
Fatty amide
Oxane
Monosaccharide
N-acyl-amine
1,3-aminoalcohol
Carboxamide group
Secondary carboxylic acid amide
Hemiacetal
Secondary alcohol
1,2-diol
Amino acid
Oxacycle
Carboxylic acid
Secondary aliphatic amine
Organoheterocyclic compound
Secondary amine
Polyol
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Primary alcohol
Amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
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	-7.1	ChemAxon
pKa (Strongest Acidic)	1.37	ChemAxon
pKa (Strongest Basic)	8.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	212.53 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	92.92 m³·mol⁻¹	ChemAxon
Polarizability	38.55 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

44474558

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,4s)-4-{[(1z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-c-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2r,3s,4r,5r)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid (NP0232828)

MOL for NP0232828 ((2s,4s)-4-{[(1z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-c-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2r,3s,4r,5r)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid)

3D MOL for NP0232828 ((2s,4s)-4-{[(1z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-c-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2r,3s,4r,5r)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid)

3D SDF for NP0232828 ((2s,4s)-4-{[(1z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-c-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2r,3s,4r,5r)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid)

3D-SDF for NP0232828 ((2s,4s)-4-{[(1z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-c-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2r,3s,4r,5r)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid)

PDB for NP0232828 ((2s,4s)-4-{[(1z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-c-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2r,3s,4r,5r)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid)

3D PDB for NP0232828 ((2s,4s)-4-{[(1z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-c-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2r,3s,4r,5r)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid)

SMILES for NP0232828 ((2s,4s)-4-{[(1z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-c-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2r,3s,4r,5r)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid)

INCHI for NP0232828 ((2s,4s)-4-{[(1z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-c-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2r,3s,4r,5r)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid)

Structure for NP0232828 ((2s,4s)-4-{[(1z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-c-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2r,3s,4r,5r)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid)

3D Structure for NP0232828 ((2s,4s)-4-{[(1z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-c-hydroxycarbonimidoyl}-4-hydroxy-2-({[(2r,3s,4r,5r)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid)