NP-MRD: Showing NP-Card for 3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid (NP0244057)

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Record Information

Version

2.0

Created at

2022-09-07 04:45:09 UTC

Updated at

2022-09-07 04:45:09 UTC

NP-MRD ID

NP0244057

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid

Description

3-{6-[(Acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. 3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid is found in Streptomyces paulus. Based on a literature review very few articles have been published on 3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072206452D          

 48 50  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -3.5692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3309   -3.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8006   -4.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0118   -4.0580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0828   -4.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5525   -5.6085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8953   -5.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1774   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9899   -6.0382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471   -6.5270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256   -4.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2380   -4.6310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282   -2.3317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9979   -3.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4676   -3.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8104   -3.3935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  2  0  0  0  0
  3  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 26 30  2  0  0  0  0
 19 30  1  0  0  0  0
 30 31  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 10 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 41 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 36 48  1  0  0  0  0
M  END


  Mrv1652309072206452D          

 48 50  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -3.5692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3309   -3.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8006   -4.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0118   -4.0580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0828   -4.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5525   -5.6085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8953   -5.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1774   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9899   -6.0382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471   -6.5270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256   -4.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2380   -4.6310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282   -2.3317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9979   -3.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4676   -3.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8104   -3.3935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  2  0  0  0  0
  3  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 26 30  2  0  0  0  0
 19 30  1  0  0  0  0
 30 31  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 10 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 41 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 36 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244057

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CC(OC2C(O)C(OC(COC(C)=O)C2OC(=O)C(=CC)N=C=S)C2(O)CC(=O)C(=N)C(C(O)=O)=C2O)OC(C)C1(O)C(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C29H38N2O16S/c1-6-14(31-10-48)27(39)47-22-16(9-43-13(4)33)45-25(28(40)8-15(34)20(30)19(24(28)36)26(37)38)21(35)23(22)46-18-7-17(42-5)29(41,11(2)32)12(3)44-18/h6,11-12,16-18,21-23,25,30,32,35-36,40-41H,7-9H2,1-5H3,(H,37,38)

> <INCHI_KEY>
HPQDYNPAMCQCMI-UHFFFAOYSA-N

> <FORMULA>
C29H38N2O16S

> <MOLECULAR_WEIGHT>
702.68

> <EXACT_MASS>
702.194204326

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
67.06283714329902

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid

> <JCHEM_LOGP>
-1.0810479947194884

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.1980422478634

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.596481499568874

> <JCHEM_PKA_STRONGEST_BASIC>
2.4947859265659726

> <JCHEM_POLAR_SURFACE_AREA>
281.24999999999994

> <JCHEM_REFRACTIVITY>
172.7403

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0       6.668   0.770   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.518  -6.663   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.484  -6.663   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.495  -7.842   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.022  -7.575   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.021  -9.289   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       1.031 -10.469   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       3.538  -9.557   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.065 -11.004   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.581 -11.271   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       3.075 -12.184   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.528  -8.377   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.044  -8.645   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      12.186  -4.353   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      11.196  -6.067   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      10.206  -7.247   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      12.713  -6.335   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    3    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   34                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   11   18                                                       
CONECT   18   17   19   32                                                  
CONECT   19   18   20   21   30                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   30                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   26   19   31                                                  
CONECT   31   30                                                            
CONECT   32   18   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   10   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   48                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   38   42   43   46                                             
CONECT   42   41                                                            
CONECT   43   41   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   41   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   36                                                       
MASTER        0    0    0    0    0    0    0    0   48    0  100    0
END

View in JSmol

Synonyms

Value	Source
3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylate	Generator

Chemical Formula

C₂₉H₃₈N₂O₁₆S

Average Mass

702.6800 Da

Monoisotopic Mass

702.19420 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1CC(OC2C(O)C(OC(COC(C)=O)C2OC(=O)C(=CC)N=C=S)C2(O)CC(=O)C(=N)C(C(O)=O)=C2O)OC(C)C1(O)C(C)O

InChI Identifier

InChI=1S/C29H38N2O16S/c1-6-14(31-10-48)27(39)47-22-16(9-43-13(4)33)45-25(28(40)8-15(34)20(30)19(24(28)36)26(37)38)21(35)23(22)46-18-7-17(42-5)29(41,11(2)32)12(3)44-18/h6,11-12,16-18,21-23,25,30,32,35-36,40-41H,7-9H2,1-5H3,(H,37,38)

InChI Key

HPQDYNPAMCQCMI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces paulus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Disaccharide
C-glycosyl compound
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
Cyclohexenone
Fatty acid ester
Fatty acyl
Oxane
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Cyclic ketone
Secondary alcohol
Ketone
Ketimine
Isothiocyanate
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Enol
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Imine
Carbonyl group
Alcohol
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	-1.1	ChemAxon
pKa (Strongest Acidic)	3.6	ChemAxon
pKa (Strongest Basic)	2.49	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	281.25 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	172.74 m³·mol⁻¹	ChemAxon
Polarizability	67.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

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

162818431

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid (NP0244057)

MOL for NP0244057 (3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid)

3D MOL for NP0244057 (3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid)

3D SDF for NP0244057 (3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid)

3D-SDF for NP0244057 (3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid)

PDB for NP0244057 (3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid)

3D PDB for NP0244057 (3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid)

SMILES for NP0244057 (3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid)

INCHI for NP0244057 (3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid)

Structure for NP0244057 (3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid)

3D Structure for NP0244057 (3-{6-[(acetyloxy)methyl]-3-hydroxy-4-{[5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy}-5-[(2-isothiocyanatobut-2-enoyl)oxy]oxan-2-yl}-2,3-dihydroxy-6-imino-5-oxocyclohex-1-ene-1-carboxylic acid)