NP-MRD: Showing NP-Card for N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6+ (NP0033119)

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Record Information

Version

2.0

Created at

2021-06-19 23:45:16 UTC

Updated at

2021-06-30 00:02:43 UTC

NP-MRD ID

NP0033119

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6+

Provided By

JEOL Database JEOL Logo

Description

4-[[(5S,10R)-7,9-Dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]Deca-2,6,8-triene-3-yl]carbonylamino]butanoic acid belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6+ is found in Aplysina fulva. N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6+ was first documented in 2007 (Rogers, E. W., et al.). Based on a literature review very few articles have been published on 4-[[(5S,10R)-7,9-Dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]Deca-2,6,8-triene-3-yl]carbonylamino]butanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101453D          

 40 41  0  0  0  0            999 V2000
    3.4627   -5.0264   -3.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6195   -3.8310   -4.0927 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6386   -2.9066   -3.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5087   -2.7902   -4.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105   -3.8689   -5.9883 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.4549   -1.7539   -4.1839 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6063   -0.6634   -5.1054 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5312   -1.2435   -2.7124 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9517   -1.2021   -2.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9307   -1.9648   -2.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6734   -1.8327   -2.0244 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2022    0.0819   -2.5363 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8391   -0.2018   -1.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4642    0.9077   -0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891    2.0595   -0.8177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0731    0.4746    0.7282 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7545    1.3677    1.6374 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7926    2.1381    2.5445 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9383    1.2465    3.4465 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7457    0.5407    4.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9289    0.6890    4.7520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9972   -0.3269    5.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8615   -1.4396   -0.8531 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954   -2.1743   -1.8662 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425   -4.8277   -2.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5072   -5.5139   -3.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2674   -5.7124   -3.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5443   -2.1798   -4.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6968   -1.0499   -5.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619   -0.5406   -1.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4536    0.9553   -2.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0004    0.2379   -3.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.5268    0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4605    0.7657    2.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3370    2.0808    1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1206    2.7460    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3739    2.8360    3.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2007    1.8713    3.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019    0.4998    2.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6195   -0.7067    5.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0  0  0  0
 19 18  1  0  0  0  0
 14 13  1  0  0  0  0
  8 24  1  1  0  0  0
 17 16  1  0  0  0  0
  4  3  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  3  1  0  0  0  0
  4  5  1  0  0  0  0
 16 14  1  0  0  0  0
 10 11  1  0  0  0  0
 18 17  1  0  0  0  0
  3  2  1  0  0  0  0
 24 23  1  0  0  0  0
  2  1  1  0  0  0  0
 23 13  2  0  0  0  0
  6  7  1  0  0  0  0
 13 12  1  0  0  0  0
 19 20  1  0  0  0  0
  8 12  1  0  0  0  0
 20 22  1  0  0  0  0
  4  6  1  0  0  0  0
 20 21  2  0  0  0  0
 19 38  1  0  0  0  0
 19 39  1  0  0  0  0
 18 36  1  0  0  0  0
 18 37  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
 16 33  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
  6 28  1  1  0  0  0
  9 30  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  7 29  1  0  0  0  0
 22 40  1  0  0  0  0
M  END

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    3.4627   -5.0264   -3.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6195   -3.8310   -4.0927 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6386   -2.9066   -3.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5087   -2.7902   -4.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105   -3.8689   -5.9883 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.4549   -1.7539   -4.1839 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6063   -0.6634   -5.1054 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5312   -1.2435   -2.7124 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9517   -1.2021   -2.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9307   -1.9648   -2.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6734   -1.8327   -2.0244 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2022    0.0819   -2.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8391   -0.2018   -1.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4642    0.9077   -0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891    2.0595   -0.8177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0731    0.4746    0.7282 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7545    1.3677    1.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7926    2.1381    2.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9383    1.2465    3.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457    0.5407    4.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9289    0.6890    4.7520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9972   -0.3269    5.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8615   -1.4396   -0.8531 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954   -2.1743   -1.8662 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425   -4.8277   -2.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5072   -5.5139   -3.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2674   -5.7124   -3.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5443   -2.1798   -4.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6968   -1.0499   -5.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619   -0.5406   -1.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4536    0.9553   -2.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0004    0.2379   -3.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.5268    0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4605    0.7657    2.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3370    2.0808    1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1206    2.7460    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3739    2.8360    3.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2007    1.8713    3.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019    0.4998    2.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6195   -0.7067    5.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
 19 18  1  0
 14 13  1  0
  8 24  1  1
 17 16  1  0
  4  3  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10  3  1  0
  4  5  1  0
 16 14  1  0
 10 11  1  0
 18 17  1  0
  3  2  1  0
 24 23  1  0
  2  1  1  0
 23 13  2  0
  6  7  1  0
 13 12  1  0
 19 20  1  0
  8 12  1  0
 20 22  1  0
  4  6  1  0
 20 21  2  0
 19 38  1  0
 19 39  1  0
 18 36  1  0
 18 37  1  0
 17 34  1  0
 17 35  1  0
 16 33  1  0
 12 31  1  0
 12 32  1  0
  6 28  1  1
  9 30  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  7 29  1  0
 22 40  1  0
M  END


  Mrv1652306202101453D          

 40 41  0  0  0  0            999 V2000
    3.4627   -5.0264   -3.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6195   -3.8310   -4.0927 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6386   -2.9066   -3.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5087   -2.7902   -4.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105   -3.8689   -5.9883 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.4549   -1.7539   -4.1839 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6063   -0.6634   -5.1054 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5312   -1.2435   -2.7124 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9517   -1.2021   -2.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9307   -1.9648   -2.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6734   -1.8327   -2.0244 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2022    0.0819   -2.5363 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8391   -0.2018   -1.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4642    0.9077   -0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891    2.0595   -0.8177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0731    0.4746    0.7282 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7545    1.3677    1.6374 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7926    2.1381    2.5445 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9383    1.2465    3.4465 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7457    0.5407    4.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9289    0.6890    4.7520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9972   -0.3269    5.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8615   -1.4396   -0.8531 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954   -2.1743   -1.8662 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425   -4.8277   -2.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5072   -5.5139   -3.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2674   -5.7124   -3.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5443   -2.1798   -4.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6968   -1.0499   -5.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619   -0.5406   -1.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4536    0.9553   -2.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0004    0.2379   -3.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.5268    0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4605    0.7657    2.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3370    2.0808    1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1206    2.7460    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3739    2.8360    3.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2007    1.8713    3.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019    0.4998    2.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6195   -0.7067    5.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0  0  0  0
 19 18  1  0  0  0  0
 14 13  1  0  0  0  0
  8 24  1  1  0  0  0
 17 16  1  0  0  0  0
  4  3  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  3  1  0  0  0  0
  4  5  1  0  0  0  0
 16 14  1  0  0  0  0
 10 11  1  0  0  0  0
 18 17  1  0  0  0  0
  3  2  1  0  0  0  0
 24 23  1  0  0  0  0
  2  1  1  0  0  0  0
 23 13  2  0  0  0  0
  6  7  1  0  0  0  0
 13 12  1  0  0  0  0
 19 20  1  0  0  0  0
  8 12  1  0  0  0  0
 20 22  1  0  0  0  0
  4  6  1  0  0  0  0
 20 21  2  0  0  0  0
 19 38  1  0  0  0  0
 19 39  1  0  0  0  0
 18 36  1  0  0  0  0
 18 37  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
 16 33  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
  6 28  1  1  0  0  0
  9 30  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  7 29  1  0  0  0  0
 22 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033119

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C([H])([H])C([H])([H])N([H])C(=O)C1=NO[C@]2(C([H])=C(Br)C(OC([H])([H])[H])=C(Br)[C@]2([H])O[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H16Br2N2O6/c1-23-11-7(15)5-14(12(21)10(11)16)6-8(18-24-14)13(22)17-4-2-3-9(19)20/h5,12,21H,2-4,6H2,1H3,(H,17,22)(H,19,20)/t12-,14+/m0/s1

> <INCHI_KEY>
QIRBPXLEOLCMDX-GXTWGEPZSA-N

> <FORMULA>
C14H16Br2N2O6

> <MOLECULAR_WEIGHT>
468.098

> <EXACT_MASS>
465.937512

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
37.37179269132211

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[(5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}butanoic acid

> <ALOGPS_LOGP>
1.46

> <JCHEM_LOGP>
0.29307675399999994

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.379942881971985

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.917084630982626

> <JCHEM_PKA_STRONGEST_BASIC>
-0.20529813871010705

> <JCHEM_POLAR_SURFACE_AREA>
117.45

> <JCHEM_REFRACTIVITY>
92.59429999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    3.4627   -5.0264   -3.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6195   -3.8310   -4.0927 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6386   -2.9066   -3.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5087   -2.7902   -4.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105   -3.8689   -5.9883 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.4549   -1.7539   -4.1839 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6063   -0.6634   -5.1054 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5312   -1.2435   -2.7124 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9517   -1.2021   -2.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9307   -1.9648   -2.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6734   -1.8327   -2.0244 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2022    0.0819   -2.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8391   -0.2018   -1.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4642    0.9077   -0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891    2.0595   -0.8177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0731    0.4746    0.7282 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7545    1.3677    1.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7926    2.1381    2.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9383    1.2465    3.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457    0.5407    4.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9289    0.6890    4.7520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9972   -0.3269    5.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8615   -1.4396   -0.8531 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954   -2.1743   -1.8662 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425   -4.8277   -2.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5072   -5.5139   -3.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2674   -5.7124   -3.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5443   -2.1798   -4.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6968   -1.0499   -5.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619   -0.5406   -1.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4536    0.9553   -2.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0004    0.2379   -3.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.5268    0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4605    0.7657    2.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3370    2.0808    1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1206    2.7460    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3739    2.8360    3.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2007    1.8713    3.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019    0.4998    2.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6195   -0.7067    5.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
 19 18  1  0
 14 13  1  0
  8 24  1  1
 17 16  1  0
  4  3  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10  3  1  0
  4  5  1  0
 16 14  1  0
 10 11  1  0
 18 17  1  0
  3  2  1  0
 24 23  1  0
  2  1  1  0
 23 13  2  0
  6  7  1  0
 13 12  1  0
 19 20  1  0
  8 12  1  0
 20 22  1  0
  4  6  1  0
 20 21  2  0
 19 38  1  0
 19 39  1  0
 18 36  1  0
 18 37  1  0
 17 34  1  0
 17 35  1  0
 16 33  1  0
 12 31  1  0
 12 32  1  0
  6 28  1  1
  9 30  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  7 29  1  0
 22 40  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       3.463  -5.026  -3.326  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.619  -3.831  -4.093  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.639  -2.907  -3.782  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.509  -2.790  -4.507  0.00  0.00           C+0
HETATM    5 Br   UNK     0       1.111  -3.869  -5.988  0.00  0.00          Br+0
HETATM    6  C   UNK     0       0.455  -1.754  -4.184  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.606  -0.663  -5.105  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.531  -1.244  -2.712  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.952  -1.202  -2.186  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.931  -1.965  -2.703  0.00  0.00           C+0
HETATM   11 Br   UNK     0       4.673  -1.833  -2.024  0.00  0.00          Br+0
HETATM   12  C   UNK     0      -0.202   0.082  -2.536  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.839  -0.202  -1.234  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.464   0.908  -0.424  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.389   2.059  -0.818  0.00  0.00           O+0
HETATM   16  N   UNK     0      -2.073   0.475   0.728  0.00  0.00           N+0
HETATM   17  C   UNK     0      -2.755   1.368   1.637  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.793   2.138   2.545  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.938   1.246   3.446  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.746   0.541   4.501  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.929   0.689   4.752  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.997  -0.327   5.209  0.00  0.00           O+0
HETATM   23  N   UNK     0      -0.862  -1.440  -0.853  0.00  0.00           N+0
HETATM   24  O   UNK     0      -0.195  -2.174  -1.866  0.00  0.00           O+0
HETATM   25  H   UNK     0       3.543  -4.828  -2.252  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.507  -5.514  -3.546  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.267  -5.712  -3.606  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.544  -2.180  -4.344  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.697  -1.050  -5.996  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.162  -0.541  -1.350  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.454   0.955  -2.505  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.000   0.238  -3.269  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.063  -0.527   0.907  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.461   0.766   2.216  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.337   2.081   1.043  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.121   2.746   1.926  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.374   2.836   3.159  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.201   1.871   3.963  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.402   0.500   2.852  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.619  -0.707   5.865  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    3    1                                                       
CONECT    3    4   10    2                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    8    7    4   28                                             
CONECT    7    6   29                                                       
CONECT    8   24    6    9   12                                             
CONECT    9    8   10   30                                                  
CONECT   10    9    3   11                                                  
CONECT   11   10                                                            
CONECT   12   13    8   31   32                                             
CONECT   13   14   23   12                                                  
CONECT   14   15   13   16                                                  
CONECT   15   14                                                            
CONECT   16   17   14   33                                                  
CONECT   17   16   18   34   35                                             
CONECT   18   19   17   36   37                                             
CONECT   19   18   20   38   39                                             
CONECT   20   19   22   21                                                  
CONECT   21   20                                                            
CONECT   22   20   40                                                       
CONECT   23   24   13                                                       
CONECT   24    8   23                                                       
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    6                                                            
CONECT   29    7                                                            
CONECT   30    9                                                            
CONECT   31   12                                                            
CONECT   32   12                                                            
CONECT   33   16                                                            
CONECT   34   17                                                            
CONECT   35   17                                                            
CONECT   36   18                                                            
CONECT   37   18                                                            
CONECT   38   19                                                            
CONECT   39   19                                                            
CONECT   40   22                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   82    0
END

RDKit          3D

40 41  0  0  0  0  0  0  0  0999 V2000
    3.4627   -5.0264   -3.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6195   -3.8310   -4.0927 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6386   -2.9066   -3.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5087   -2.7902   -4.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105   -3.8689   -5.9883 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.4549   -1.7539   -4.1839 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6063   -0.6634   -5.1054 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5312   -1.2435   -2.7124 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9517   -1.2021   -2.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9307   -1.9648   -2.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6734   -1.8327   -2.0244 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2022    0.0819   -2.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8391   -0.2018   -1.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4642    0.9077   -0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891    2.0595   -0.8177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0731    0.4746    0.7282 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7545    1.3677    1.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7926    2.1381    2.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9383    1.2465    3.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457    0.5407    4.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9289    0.6890    4.7520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9972   -0.3269    5.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8615   -1.4396   -0.8531 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954   -2.1743   -1.8662 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425   -4.8277   -2.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5072   -5.5139   -3.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2674   -5.7124   -3.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5443   -2.1798   -4.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6968   -1.0499   -5.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619   -0.5406   -1.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4536    0.9553   -2.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0004    0.2379   -3.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.5268    0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4605    0.7657    2.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3370    2.0808    1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1206    2.7460    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3739    2.8360    3.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2007    1.8713    3.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019    0.4998    2.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6195   -0.7067    5.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
 19 18  1  0
 14 13  1  0
  8 24  1  1
 17 16  1  0
  4  3  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10  3  1  0
  4  5  1  0
 16 14  1  0
 10 11  1  0
 18 17  1  0
  3  2  1  0
 24 23  1  0
  2  1  1  0
 23 13  2  0
  6  7  1  0
 13 12  1  0
 19 20  1  0
  8 12  1  0
 20 22  1  0
  4  6  1  0
 20 21  2  0
 19 38  1  0
 19 39  1  0
 18 36  1  0
 18 37  1  0
 17 34  1  0
 17 35  1  0
 16 33  1  0
 12 31  1  0
 12 32  1  0
  6 28  1  1
  9 30  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  7 29  1  0
 22 40  1  0
M  END

View in JSmol

Synonyms

Value	Source
4-[[(5S,10R)-7,9-Dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-yl]carbonylamino]butanoate	Generator

Chemical Formula

C₁₄H₁₆Br₂N₂O₆

Average Mass

468.0980 Da

Monoisotopic Mass

465.93751 Da

IUPAC Name

4-{[(5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}butanoic acid

Traditional Name

4-{[(5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}butanoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])C([H])([H])C([H])([H])N([H])C(=O)C1=NO[C@]2(C([H])=C(Br)C(OC([H])([H])[H])=C(Br)[C@]2([H])O[H])C1([H])[H]

InChI Identifier

InChI=1S/C14H16Br2N2O6/c1-23-11-7(15)5-14(12(21)10(11)16)6-8(18-24-14)13(22)17-4-2-3-9(19)20/h5,12,21H,2-4,6H2,1H3,(H,17,22)(H,19,20)/t12-,14+/m0/s1

InChI Key

QIRBPXLEOLCMDX-GXTWGEPZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aplysina fulva	JEOL database	Rogers, E. W., et al, J. Nat. Prod. 70, 1191 (2007)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
Halogenated fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Fatty acyl
Isoxazoline
Bromohydrin
Carboxamide group
Halohydrin
Oxime ether
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid
Oxacycle
Azacycle
Bromoalkene
Monocarboxylic acid or derivatives
Haloalkene
Organoheterocyclic compound
Vinyl halide
Vinyl bromide
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Organohalogen compound
Organobromide
Organonitrogen compound
Organooxygen compound
Alcohol
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
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	1.46	ALOGPS
logP	0.29	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	3.92	ChemAxon
pKa (Strongest Basic)	-0.21	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.45 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	92.59 m³·mol⁻¹	ChemAxon
Polarizability	37.37 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

10480933

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16756891

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rogers, E. W., et al. (2007). Rogers, E. W., et al, J. Nat. Prod. 70, 1191 (2007). J. Nat. Prod..

Showing NP-Card for N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6+ (NP0033119)

MOL for NP0033119 (N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6+)

3D MOL for NP0033119 (N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6+)

3D SDF for NP0033119 (N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6+)

3D-SDF for NP0033119 (N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6+)

PDB for NP0033119 (N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6+)

3D PDB for NP0033119 (N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6+)

SMILES for NP0033119 (N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6+)

INCHI for NP0033119 (N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6+)

Structure for NP0033119 (N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6+)

3D Structure for NP0033119 (N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6+)