NP-MRD: Showing NP-Card for Mycosporine-ornithine (NP0008681)

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Record Information

Version

2.0

Created at

2020-12-09 06:12:59 UTC

Updated at

2021-07-15 17:01:06 UTC

NP-MRD ID

NP0008681

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mycosporine-ornithine

Provided By

NPAtlas

Description

Mycosporine-ornithine is found in Nodularia spumigena. Mycosporine-ornithine was first documented in 2016 (PMID: 27520810). Based on a literature review very few articles have been published on 2-amino-5-{[5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}pentanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106123D          

 43 43  0  0  0  0            999 V2000
   -0.9747   -3.1844   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0388   -1.8490   -1.6455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8598   -0.9815   -0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590   -0.0126   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1562    0.1004   -0.3017 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0471   -0.4351    0.6727 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4785   -0.1217    0.2948 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3755   -0.7121    1.3605 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8378   -0.4494    1.0693 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2676   -1.0046   -0.1748 N   0  0  1  0  0  0  0  0  0  0  0  0
    5.1728    0.9822    1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8685    1.6389    2.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8142    1.5942    0.0788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1153    0.9187    0.5236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3980    1.2459   -0.1921 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0641    2.1265   -1.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2866    2.0090    0.7678 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4477    2.4457    0.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1375    0.0507   -0.6806 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3061   -1.1429   -0.9056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8410   -2.2575   -1.0777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9737   -3.6579   -1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2820   -3.8039   -1.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5882   -3.2314   -0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5447    0.6178   -1.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8419   -0.0496    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9137   -1.5428    0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7007   -0.4903   -0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6347    0.9820    0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1659   -0.2582    2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2458   -1.7961    1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4054   -0.9897    1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7991   -1.8924   -0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2874   -0.3107   -0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5879    2.5662   -0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4062    0.4207    1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495    1.8338    0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9389    3.0150   -0.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7309    2.8964    1.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5679    1.3143    1.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7238    3.3364    0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9475   -0.2611    0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7084    0.3402   -1.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20  3  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  5 25  1  0  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
  8 30  1  0  0  0  0
  8 31  1  0  0  0  0
  9 32  1  1  0  0  0
 10 33  1  0  0  0  0
 10 34  1  0  0  0  0
 13 35  1  0  0  0  0
 14 36  1  0  0  0  0
 14 37  1  0  0  0  0
 16 38  1  0  0  0  0
 17 39  1  0  0  0  0
 17 40  1  0  0  0  0
 18 41  1  0  0  0  0
 19 42  1  0  0  0  0
 19 43  1  0  0  0  0
M  END

     RDKit          3D

 43 43  0  0  0  0  0  0  0  0999 V2000
   -0.9747   -3.1844   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0388   -1.8490   -1.6455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8598   -0.9815   -0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590   -0.0126   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1562    0.1004   -0.3017 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0471   -0.4351    0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785   -0.1217    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3755   -0.7121    1.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8378   -0.4494    1.0693 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2676   -1.0046   -0.1748 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1728    0.9822    1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8685    1.6389    2.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8142    1.5942    0.0788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1153    0.9187    0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980    1.2459   -0.1921 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0641    2.1265   -1.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2866    2.0090    0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4477    2.4457    0.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1375    0.0507   -0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3061   -1.1429   -0.9056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8410   -2.2575   -1.0777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9737   -3.6579   -1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2820   -3.8039   -1.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5882   -3.2314   -0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5447    0.6178   -1.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8419   -0.0496    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9137   -1.5428    0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7007   -0.4903   -0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6347    0.9820    0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1659   -0.2582    2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2458   -1.7961    1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4054   -0.9897    1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7991   -1.8924   -0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2874   -0.3107   -0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5879    2.5662   -0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4062    0.4207    1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495    1.8338    0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9389    3.0150   -0.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7309    2.8964    1.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5679    1.3143    1.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7238    3.3364    0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9475   -0.2611    0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7084    0.3402   -1.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  4 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 15 19  1  0
 19 20  1  0
 20 21  2  0
 20  3  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  1
 10 33  1  0
 10 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
M  END


  Mrv1652306242106123D          

 43 43  0  0  0  0            999 V2000
   -0.9747   -3.1844   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0388   -1.8490   -1.6455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8598   -0.9815   -0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590   -0.0126   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1562    0.1004   -0.3017 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0471   -0.4351    0.6727 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4785   -0.1217    0.2948 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3755   -0.7121    1.3605 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8378   -0.4494    1.0693 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2676   -1.0046   -0.1748 N   0  0  1  0  0  0  0  0  0  0  0  0
    5.1728    0.9822    1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8685    1.6389    2.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8142    1.5942    0.0788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1153    0.9187    0.5236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3980    1.2459   -0.1921 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0641    2.1265   -1.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2866    2.0090    0.7678 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4477    2.4457    0.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1375    0.0507   -0.6806 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3061   -1.1429   -0.9056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8410   -2.2575   -1.0777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9737   -3.6579   -1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2820   -3.8039   -1.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5882   -3.2314   -0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5447    0.6178   -1.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8419   -0.0496    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9137   -1.5428    0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7007   -0.4903   -0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6347    0.9820    0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1659   -0.2582    2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2458   -1.7961    1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4054   -0.9897    1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7991   -1.8924   -0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2874   -0.3107   -0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5879    2.5662   -0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4062    0.4207    1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495    1.8338    0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9389    3.0150   -0.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7309    2.8964    1.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5679    1.3143    1.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7238    3.3364    0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9475   -0.2611    0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7084    0.3402   -1.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20  3  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  5 25  1  0  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
  8 30  1  0  0  0  0
  8 31  1  0  0  0  0
  9 32  1  1  0  0  0
 10 33  1  0  0  0  0
 10 34  1  0  0  0  0
 13 35  1  0  0  0  0
 14 36  1  0  0  0  0
 14 37  1  0  0  0  0
 16 38  1  0  0  0  0
 17 39  1  0  0  0  0
 17 40  1  0  0  0  0
 18 41  1  0  0  0  0
 19 42  1  0  0  0  0
 19 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0008681

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]([H])(N([H])[H])C([H])([H])C([H])([H])C([H])([H])N([H])C1=C(OC([H])([H])[H])C(=O)C([H])([H])[C@@](O[H])(C([H])([H])O[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H22N2O6/c1-21-11-9(5-13(20,7-16)6-10(11)17)15-4-2-3-8(14)12(18)19/h8,15-16,20H,2-7,14H2,1H3,(H,18,19)/t8-,13-/m1/s1

> <INCHI_KEY>
AERJYLRVJRRKIZ-UHFFFAOYSA-N

> <FORMULA>
C13H22N2O6

> <MOLECULAR_WEIGHT>
302.327

> <EXACT_MASS>
302.147786436

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
30.766399652607774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-5-{[(5R)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}pentanoic acid

> <ALOGPS_LOGP>
-2.83

> <JCHEM_LOGP>
-4.813444110355704

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.580035131103163

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7132371110369928

> <JCHEM_PKA_STRONGEST_BASIC>
9.325108638535593

> <JCHEM_POLAR_SURFACE_AREA>
142.11

> <JCHEM_REFRACTIVITY>
75.48119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-amino-5-{[(5R)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 43  0  0  0  0  0  0  0  0999 V2000
   -0.9747   -3.1844   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0388   -1.8490   -1.6455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8598   -0.9815   -0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590   -0.0126   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1562    0.1004   -0.3017 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0471   -0.4351    0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785   -0.1217    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3755   -0.7121    1.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8378   -0.4494    1.0693 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2676   -1.0046   -0.1748 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1728    0.9822    1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8685    1.6389    2.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8142    1.5942    0.0788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1153    0.9187    0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980    1.2459   -0.1921 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0641    2.1265   -1.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2866    2.0090    0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4477    2.4457    0.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1375    0.0507   -0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3061   -1.1429   -0.9056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8410   -2.2575   -1.0777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9737   -3.6579   -1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2820   -3.8039   -1.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5882   -3.2314   -0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5447    0.6178   -1.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8419   -0.0496    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9137   -1.5428    0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7007   -0.4903   -0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6347    0.9820    0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1659   -0.2582    2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2458   -1.7961    1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4054   -0.9897    1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7991   -1.8924   -0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2874   -0.3107   -0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5879    2.5662   -0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4062    0.4207    1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495    1.8338    0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9389    3.0150   -0.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7309    2.8964    1.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5679    1.3143    1.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7238    3.3364    0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9475   -0.2611    0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7084    0.3402   -1.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  4 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 15 19  1  0
 19 20  1  0
 20 21  2  0
 20  3  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  1
 10 33  1  0
 10 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
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  C   UNK     0      -0.975  -3.184  -1.182  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.039  -1.849  -1.646  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.860  -0.982  -0.921  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.259  -0.013  -0.253  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.156   0.100  -0.302  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.047  -0.435   0.673  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.478  -0.122   0.295  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.376  -0.712   1.361  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.838  -0.449   1.069  0.00  0.00           C+0
HETATM   10  N   UNK     0       5.268  -1.005  -0.175  0.00  0.00           N+0
HETATM   11  C   UNK     0       5.173   0.982   1.135  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.869   1.639   2.162  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.814   1.594   0.079  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.115   0.919   0.524  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.398   1.246  -0.192  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.064   2.127  -1.243  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.287   2.009   0.768  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.448   2.446   0.120  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.138   0.051  -0.681  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.306  -1.143  -0.906  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.841  -2.257  -1.078  0.00  0.00           O+0
HETATM   22  H   UNK     0      -1.974  -3.658  -1.195  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.282  -3.804  -1.784  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.588  -3.231  -0.127  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.545   0.618  -1.120  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.842  -0.050   1.694  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.914  -1.543   0.680  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.701  -0.490  -0.705  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.635   0.982   0.277  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.166  -0.258   2.349  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.246  -1.796   1.441  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.405  -0.990   1.881  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.799  -1.892  -0.439  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.287  -0.311  -0.958  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.588   2.566  -0.159  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.406   0.421   1.491  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.550   1.834   0.717  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.939   3.015  -0.821  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.731   2.896   1.137  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.568   1.314   1.601  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.724   3.336   0.456  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.947  -0.261   0.036  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.708   0.340  -1.610  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6   25                                                  
CONECT    6    5    7   26   27                                             
CONECT    7    6    8   28   29                                             
CONECT    8    7    9   30   31                                             
CONECT    9    8   10   11   32                                             
CONECT   10    9   33   34                                                  
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   35                                                       
CONECT   14    4   15   36   37                                             
CONECT   15   14   16   17   19                                             
CONECT   16   15   38                                                       
CONECT   17   15   18   39   40                                             
CONECT   18   17   41                                                       
CONECT   19   15   20   42   43                                             
CONECT   20   19   21    3                                                  
CONECT   21   20                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
CONECT   29    7                                                            
CONECT   30    8                                                            
CONECT   31    8                                                            
CONECT   32    9                                                            
CONECT   33   10                                                            
CONECT   34   10                                                            
CONECT   35   13                                                            
CONECT   36   14                                                            
CONECT   37   14                                                            
CONECT   38   16                                                            
CONECT   39   17                                                            
CONECT   40   17                                                            
CONECT   41   18                                                            
CONECT   42   19                                                            
CONECT   43   19                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   86    0
END

RDKit          3D

43 43  0  0  0  0  0  0  0  0999 V2000
   -0.9747   -3.1844   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0388   -1.8490   -1.6455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8598   -0.9815   -0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590   -0.0126   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1562    0.1004   -0.3017 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0471   -0.4351    0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785   -0.1217    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3755   -0.7121    1.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8378   -0.4494    1.0693 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2676   -1.0046   -0.1748 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1728    0.9822    1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8685    1.6389    2.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8142    1.5942    0.0788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1153    0.9187    0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980    1.2459   -0.1921 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0641    2.1265   -1.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2866    2.0090    0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4477    2.4457    0.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1375    0.0507   -0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3061   -1.1429   -0.9056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8410   -2.2575   -1.0777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9737   -3.6579   -1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2820   -3.8039   -1.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5882   -3.2314   -0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5447    0.6178   -1.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8419   -0.0496    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9137   -1.5428    0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7007   -0.4903   -0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6347    0.9820    0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1659   -0.2582    2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2458   -1.7961    1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4054   -0.9897    1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7991   -1.8924   -0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2874   -0.3107   -0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5879    2.5662   -0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4062    0.4207    1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495    1.8338    0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9389    3.0150   -0.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7309    2.8964    1.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5679    1.3143    1.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7238    3.3364    0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9475   -0.2611    0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7084    0.3402   -1.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  4 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 15 19  1  0
 19 20  1  0
 20 21  2  0
 20  3  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  1
 10 33  1  0
 10 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2-Amino-5-{[5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}pentanoate	Generator

Chemical Formula

C₁₃H₂₂N₂O₆

Average Mass

302.3270 Da

Monoisotopic Mass

302.14779 Da

IUPAC Name

(2R)-2-amino-5-{[(5R)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}pentanoic acid

Traditional Name

(2R)-2-amino-5-{[(5R)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}pentanoic acid

CAS Registry Number

Not Available

SMILES

COC1=C(CC(O)(CO)CC1=O)NCCCC(N)C(O)=O

InChI Identifier

InChI=1S/C13H22N2O6/c1-21-11-9(5-13(20,7-16)6-10(11)17)15-4-2-3-8(14)12(18)19/h8,15-16,20H,2-7,14H2,1H3,(H,18,19)

InChI Key

AERJYLRVJRRKIZ-UHFFFAOYSA-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
Nodularia spumigena	NPAtlas	19691450

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.8	ALOGPS
logP	-4.8	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.71	ChemAxon
pKa (Strongest Basic)	9.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	142.11 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	75.48 m³·mol⁻¹	ChemAxon
Polarizability	30.77 Å³	ChemAxon
Number of Rings	1	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

NPA028839

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

146684857

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Katoch M, Mazmouz R, Chau R, Pearson LA, Pickford R, Neilan BA: Heterologous Production of Cyanobacterial Mycosporine-Like Amino Acids Mycosporine-Ornithine and Mycosporine-Lysine in Escherichia coli. Appl Environ Microbiol. 2016 Sep 30;82(20):6167-6173. doi: 10.1128/AEM.01632-16. Print 2016 Oct 15. [PubMed:27520810 ]

Showing NP-Card for Mycosporine-ornithine (NP0008681)

MOL for NP0008681 (Mycosporine-ornithine)

3D MOL for NP0008681 (Mycosporine-ornithine)

3D SDF for NP0008681 (Mycosporine-ornithine)

3D-SDF for NP0008681 (Mycosporine-ornithine)

PDB for NP0008681 (Mycosporine-ornithine)

3D PDB for NP0008681 (Mycosporine-ornithine)

SMILES for NP0008681 (Mycosporine-ornithine)

INCHI for NP0008681 (Mycosporine-ornithine)

Structure for NP0008681 (Mycosporine-ornithine)

3D Structure for NP0008681 (Mycosporine-ornithine)