NP-MRD: Showing NP-Card for 13-hydroxystreptazolin (NP0003593)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2020-12-09 00:48:03 UTC

Updated at

2021-07-15 16:46:50 UTC

NP-MRD ID

NP0003593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-hydroxystreptazolin

Provided By

NPAtlas

Description

(4S,5S,6Z,11S)-5-hydroxy-6-(2-hydroxyethylidene)-3-oxa-1-azatricyclo[5.3.1.0⁴,¹¹]Undec-7-en-2-one belongs to the class of organic compounds known as oxazolidinones. Oxazolidinones are compounds containing an oxazolidinone moiety, which is an oxazolidine bearing a ketone group. 13-hydroxystreptazolin is found in Streptomyces and Streptomyces sp.A1. 13-hydroxystreptazolin was first documented in 2001 (PMID: 11170664). Based on a literature review very few articles have been published on (4S,5S,6Z,11S)-5-hydroxy-6-(2-hydroxyethylidene)-3-oxa-1-azatricyclo[5.3.1.0⁴,¹¹]Undec-7-en-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117483D          

 29 31  0  0  0  0            999 V2000
   -3.3477   -2.0261    1.5932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3154   -1.5595    1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0204   -2.0687    1.0057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3982   -1.7210   -0.2206 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0409   -1.3527   -0.0784 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7457   -1.7765   -1.2252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1092    0.1301   -0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042    0.8353    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5265    0.1655    0.1152 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3191    0.5663   -0.9732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2200    0.6615   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7848    1.8255    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    2.0482   -0.0694 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0756    0.8460    0.2151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2831   -0.3594    0.2978 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1260   -0.4462   -0.5751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6017   -2.5020   -0.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5337   -1.8228    0.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1190   -2.2274   -1.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1680    1.9204    0.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0247    0.4749    1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147   -0.9167    0.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1854    0.1016   -0.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1765    2.6536    0.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5584    2.8959    0.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    2.3244   -1.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8225    0.6626   -0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649    1.0148    1.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3637   -0.3477   -1.6330 H   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  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
 15 16  1  0  0  0  0
 15  2  1  0  0  0  0
 16  4  1  0  0  0  0
 16 11  1  0  0  0  0
  4 17  1  6  0  0  0
  5 18  1  1  0  0  0
  6 19  1  0  0  0  0
  8 20  1  0  0  0  0
  9 21  1  0  0  0  0
  9 22  1  0  0  0  0
 10 23  1  0  0  0  0
 12 24  1  0  0  0  0
 13 25  1  0  0  0  0
 13 26  1  0  0  0  0
 14 27  1  0  0  0  0
 14 28  1  0  0  0  0
 16 29  1  6  0  0  0
M  END

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -3.3477   -2.0261    1.5932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3154   -1.5595    1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0204   -2.0687    1.0057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3982   -1.7210   -0.2206 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0409   -1.3527   -0.0784 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7457   -1.7765   -1.2252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1092    0.1301   -0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042    0.8353    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5265    0.1655    0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3191    0.5663   -0.9732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2200    0.6615   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7848    1.8255    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    2.0482   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0756    0.8460    0.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2831   -0.3594    0.2978 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1260   -0.4462   -0.5751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6017   -2.5020   -0.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5337   -1.8228    0.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1190   -2.2274   -1.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1680    1.9204    0.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0247    0.4749    1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147   -0.9167    0.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1854    0.1016   -0.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1765    2.6536    0.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5584    2.8959    0.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    2.3244   -1.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8225    0.6626   -0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649    1.0148    1.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3637   -0.3477   -1.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15  2  1  0
 16  4  1  0
 16 11  1  0
  4 17  1  6
  5 18  1  1
  6 19  1  0
  8 20  1  0
  9 21  1  0
  9 22  1  0
 10 23  1  0
 12 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 16 29  1  6
M  END


  Mrv1652306242117483D          

 29 31  0  0  0  0            999 V2000
   -3.3477   -2.0261    1.5932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3154   -1.5595    1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0204   -2.0687    1.0057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3982   -1.7210   -0.2206 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0409   -1.3527   -0.0784 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7457   -1.7765   -1.2252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1092    0.1301   -0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042    0.8353    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5265    0.1655    0.1152 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3191    0.5663   -0.9732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2200    0.6615   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7848    1.8255    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    2.0482   -0.0694 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0756    0.8460    0.2151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2831   -0.3594    0.2978 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1260   -0.4462   -0.5751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6017   -2.5020   -0.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5337   -1.8228    0.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1190   -2.2274   -1.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1680    1.9204    0.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0247    0.4749    1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147   -0.9167    0.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1854    0.1016   -0.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1765    2.6536    0.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5584    2.8959    0.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    2.3244   -1.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8225    0.6626   -0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649    1.0148    1.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3637   -0.3477   -1.6330 H   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  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
 15 16  1  0  0  0  0
 15  2  1  0  0  0  0
 16  4  1  0  0  0  0
 16 11  1  0  0  0  0
  4 17  1  6  0  0  0
  5 18  1  1  0  0  0
  6 19  1  0  0  0  0
  8 20  1  0  0  0  0
  9 21  1  0  0  0  0
  9 22  1  0  0  0  0
 10 23  1  0  0  0  0
 12 24  1  0  0  0  0
 13 25  1  0  0  0  0
 13 26  1  0  0  0  0
 14 27  1  0  0  0  0
 14 28  1  0  0  0  0
 16 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0003593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C(\[H])=C1\C2=C([H])C([H])([H])C([H])([H])N3C(=O)O[C@]([H])([C@@]1([H])O[H])[C@]23[H]

> <INCHI_IDENTIFIER>
InChI=1S/C11H13NO4/c13-5-3-7-6-2-1-4-12-8(6)10(9(7)14)16-11(12)15/h2-3,8-10,13-14H,1,4-5H2/b7-3-/t8-,9-,10-/m0/s1

> <INCHI_KEY>
XGUFQWYNNZVQCB-ABBOFZCMSA-N

> <FORMULA>
C11H13NO4

> <MOLECULAR_WEIGHT>
223.228

> <EXACT_MASS>
223.084457903

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
22.061575006464572

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,5S,6Z,11S)-5-hydroxy-6-(2-hydroxyethylidene)-3-oxa-1-azatricyclo[5.3.1.0^{4,11}]undec-7-en-2-one

> <ALOGPS_LOGP>
-0.25

> <JCHEM_LOGP>
-1.0306458990000005

> <ALOGPS_LOGS>
-0.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.616059074642362

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.452628112530295

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5369349339496674

> <JCHEM_POLAR_SURFACE_AREA>
70.0

> <JCHEM_REFRACTIVITY>
56.4921

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.68e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5S,6Z,11S)-5-hydroxy-6-(2-hydroxyethylidene)-3-oxa-1-azatricyclo[5.3.1.0^{4,11}]undec-7-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -3.3477   -2.0261    1.5932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3154   -1.5595    1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0204   -2.0687    1.0057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3982   -1.7210   -0.2206 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0409   -1.3527   -0.0784 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7457   -1.7765   -1.2252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1092    0.1301   -0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042    0.8353    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5265    0.1655    0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3191    0.5663   -0.9732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2200    0.6615   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7848    1.8255    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    2.0482   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0756    0.8460    0.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2831   -0.3594    0.2978 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1260   -0.4462   -0.5751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6017   -2.5020   -0.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5337   -1.8228    0.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1190   -2.2274   -1.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1680    1.9204    0.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0247    0.4749    1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147   -0.9167    0.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1854    0.1016   -0.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1765    2.6536    0.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5584    2.8959    0.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    2.3244   -1.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8225    0.6626   -0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649    1.0148    1.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3637   -0.3477   -1.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15  2  1  0
 16  4  1  0
 16 11  1  0
  4 17  1  6
  5 18  1  1
  6 19  1  0
  8 20  1  0
  9 21  1  0
  9 22  1  0
 10 23  1  0
 12 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 16 29  1  6
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -3.348  -2.026   1.593  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.315  -1.560   1.037  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.020  -2.069   1.006  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.398  -1.721  -0.221  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.041  -1.353  -0.078  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.746  -1.777  -1.225  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.109   0.130  -0.043  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.204   0.835   0.043  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.527   0.166   0.115  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.319   0.566  -0.973  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.220   0.662  -0.118  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.785   1.825   0.111  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.234   2.048  -0.069  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.076   0.846   0.215  0.00  0.00           C+0
HETATM   15  N   UNK     0      -2.283  -0.359   0.298  0.00  0.00           N+0
HETATM   16  C   UNK     0      -1.126  -0.446  -0.575  0.00  0.00           C+0
HETATM   17  H   UNK     0      -0.602  -2.502  -0.962  0.00  0.00           H+0
HETATM   18  H   UNK     0       1.534  -1.823   0.798  0.00  0.00           H+0
HETATM   19  H   UNK     0       1.119  -2.227  -1.851  0.00  0.00           H+0
HETATM   20  H   UNK     0       2.168   1.920   0.064  0.00  0.00           H+0
HETATM   21  H   UNK     0       4.025   0.475   1.075  0.00  0.00           H+0
HETATM   22  H   UNK     0       3.415  -0.917   0.165  0.00  0.00           H+0
HETATM   23  H   UNK     0       5.185   0.102  -0.904  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.177   2.654   0.442  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.558   2.896   0.560  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.398   2.324  -1.152  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.822   0.663  -0.612  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.665   1.015   1.153  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.364  -0.348  -1.633  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16   17                                             
CONECT    5    4    6    7   18                                             
CONECT    6    5   19                                                       
CONECT    7    5    8   11                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   21   22                                             
CONECT   10    9   23                                                       
CONECT   11    7   12   16                                                  
CONECT   12   11   13   24                                                  
CONECT   13   12   14   25   26                                             
CONECT   14   13   15   27   28                                             
CONECT   15   14   16    2                                                  
CONECT   16   15    4   11   29                                             
CONECT   17    4                                                            
CONECT   18    5                                                            
CONECT   19    6                                                            
CONECT   20    8                                                            
CONECT   21    9                                                            
CONECT   22    9                                                            
CONECT   23   10                                                            
CONECT   24   12                                                            
CONECT   25   13                                                            
CONECT   26   13                                                            
CONECT   27   14                                                            
CONECT   28   14                                                            
CONECT   29   16                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

RDKit          3D

29 31  0  0  0  0  0  0  0  0999 V2000
   -3.3477   -2.0261    1.5932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3154   -1.5595    1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0204   -2.0687    1.0057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3982   -1.7210   -0.2206 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0409   -1.3527   -0.0784 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7457   -1.7765   -1.2252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1092    0.1301   -0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042    0.8353    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5265    0.1655    0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3191    0.5663   -0.9732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2200    0.6615   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7848    1.8255    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    2.0482   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0756    0.8460    0.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2831   -0.3594    0.2978 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1260   -0.4462   -0.5751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6017   -2.5020   -0.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5337   -1.8228    0.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1190   -2.2274   -1.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1680    1.9204    0.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0247    0.4749    1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147   -0.9167    0.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1854    0.1016   -0.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1765    2.6536    0.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5584    2.8959    0.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    2.3244   -1.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8225    0.6626   -0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649    1.0148    1.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3637   -0.3477   -1.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15  2  1  0
 16  4  1  0
 16 11  1  0
  4 17  1  6
  5 18  1  1
  6 19  1  0
  8 20  1  0
  9 21  1  0
  9 22  1  0
 10 23  1  0
 12 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 16 29  1  6
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₁H₁₃NO₄

Average Mass

223.2280 Da

Monoisotopic Mass

223.08446 Da

IUPAC Name

(4S,5S,6Z,11S)-5-hydroxy-6-(2-hydroxyethylidene)-3-oxa-1-azatricyclo[5.3.1.0^{4,11}]undec-7-en-2-one

Traditional Name

(4S,5S,6Z,11S)-5-hydroxy-6-(2-hydroxyethylidene)-3-oxa-1-azatricyclo[5.3.1.0^{4,11}]undec-7-en-2-one

CAS Registry Number

Not Available

SMILES

OC\C=C1/[C@H](O)[C@H]2OC(=O)N3CCC=C1[C@@H]23

InChI Identifier

InChI=1S/C11H13NO4/c13-5-3-7-6-2-1-4-12-8(6)10(9(7)14)16-11(12)15/h2-3,8-10,13-14H,1,4-5H2/b7-3-/t8-,9-,10-/m0/s1

InChI Key

XGUFQWYNNZVQCB-ABBOFZCMSA-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
Streptomyces	NPAtlas	11170664
Streptomyces sp.A1	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxazolidinones. Oxazolidinones are compounds containing an oxazolidinone moiety, which is an oxazolidine bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Oxazolidines

Direct Parent

Oxazolidinones

Alternative Parents

Substituents

Oxazolidinone
Cyclic alcohol
Carbamic acid ester
Carbonic acid derivative
Secondary alcohol
Oxacycle
Azacycle
Organopnictogen compound
Primary alcohol
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	-0.25	ALOGPS
logP	-1	ChemAxon
logS	-0.68	ALOGPS
pKa (Strongest Acidic)	13.45	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	56.49 m³·mol⁻¹	ChemAxon
Polarizability	22.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA012916

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8712434

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10537043

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Puder C, Loya S, Hizi A, Zeeck A: New co-metabolites of the streptazolin pathway. J Nat Prod. 2001 Jan;64(1):42-5. doi: 10.1021/np000377i. [PubMed:11170664 ]

Showing NP-Card for 13-hydroxystreptazolin (NP0003593)

MOL for NP0003593 (13-hydroxystreptazolin)

3D MOL for NP0003593 (13-hydroxystreptazolin)

3D SDF for NP0003593 (13-hydroxystreptazolin)

3D-SDF for NP0003593 (13-hydroxystreptazolin)

PDB for NP0003593 (13-hydroxystreptazolin)

3D PDB for NP0003593 (13-hydroxystreptazolin)

SMILES for NP0003593 (13-hydroxystreptazolin)

INCHI for NP0003593 (13-hydroxystreptazolin)

Structure for NP0003593 (13-hydroxystreptazolin)

3D Structure for NP0003593 (13-hydroxystreptazolin)