NP-MRD: Showing NP-Card for (2s)-2-{[(1e,5s)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid (NP0300753)

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Record Information

Version

2.0

Created at

2022-09-10 13:19:32 UTC

Updated at

2022-09-10 13:19:32 UTC

NP-MRD ID

NP0300753

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(1e,5s)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid

Description

Shinorine belongs to the class of organic compounds known as serine and derivatives. Serine and derivatives are compounds containing serine or a derivative thereof resulting from reaction of serine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. (2s)-2-{[(1e,5s)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid is found in Patiria pectinifera. (2s)-2-{[(1e,5s)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid was first documented in 2004 (PMID: 15291302). Based on a literature review a small amount of articles have been published on shinorine (PMID: 21890703) (PMID: 15480487) (PMID: 18557824).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 43  0  0  0  0  0  0  0  0999 V2000
    0.4711    2.7430    1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6658    2.1989    0.0680 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4511    0.8236   -0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4924    0.0403    0.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7847    0.6081    0.1725 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672    0.1484    1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9890    0.9829    0.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0369    1.9426    0.1404 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0957    0.7590    1.7524 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2811   -1.4368   -0.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2012   -1.6546   -1.1278 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5848   -1.0238   -2.3102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0158   -3.1331   -1.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823   -3.6806   -1.7814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1167   -1.0252   -0.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9267    0.3128   -0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9469    1.0241    0.0917 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2404    0.4931   -0.0820 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0896    0.8777    1.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4513    0.3195    2.2628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9194    1.1430   -1.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3480    2.0285   -1.9406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2091    0.7886   -1.6351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5696    2.5679    1.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1127    2.1584    2.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7955    3.7840    1.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9987    1.4197   -0.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4048    0.2267    2.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0502   -0.9083    0.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0286    1.0303    1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9230   -1.8661    0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1888   -1.9412   -0.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5582   -0.9611   -2.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8563   -3.2981   -2.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2922   -3.5480   -0.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1393   -3.7443   -2.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855   -1.1438   -1.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5307   -1.6951    0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3396   -0.5790   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0766    0.3964    1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1559    1.9677    1.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4248   -0.6685    2.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9078    1.5226   -1.6132 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 10  1  0
 10 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 23  1  0
 21 22  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  7  8  2  0
 16  3  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 18 39  1  6
 19 40  1  0
 19 41  1  0
 20 42  1  0
 23 43  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  9 30  1  0
M  END


  Mrv1652309102215192D          

 23 23  0  0  1  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   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  2  0  0  0  0
  7  9  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  1  0  0  0
 13 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  2  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0300753

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C[C@@](O)(CO)C\C1=N/[C@@H](CO)C(O)=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H20N2O8/c1-23-11-7(14-4-10(18)19)2-13(22,6-17)3-8(11)15-9(5-16)12(20)21/h9,14,16-17,22H,2-6H2,1H3,(H,18,19)(H,20,21)/b15-8+/t9-,13-/m0/s1

> <INCHI_KEY>
WXEQFJUHQIGKNG-MZNRBSSJSA-N

> <FORMULA>
C13H20N2O8

> <MOLECULAR_WEIGHT>
332.309

> <EXACT_MASS>
332.121965612

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.92278809908877

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(1E,5S)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid

> <JCHEM_LOGP>
-4.13850423847851

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.2599210986180776

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8959580677248367

> <JCHEM_PKA_STRONGEST_BASIC>
3.6986309841550193

> <JCHEM_POLAR_SURFACE_AREA>
168.90999999999997

> <JCHEM_REFRACTIVITY>
77.3521

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(1E,5S)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.344   3.490   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.840   3.222   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4   11                                                       
CONECT   11   10   12   13   15                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   11   16                                                       
CONECT   16   15    3   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₂₀N₂O₈

Average Mass

332.3090 Da

Monoisotopic Mass

332.12197 Da

IUPAC Name

(2S)-2-{[(1E,5S)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid

Traditional Name

(2S)-2-{[(1E,5S)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid

CAS Registry Number

Not Available

SMILES

COC1=C(C[C@@](O)(CO)C\C1=N/[C@@H](CO)C(O)=O)NCC(O)=O

InChI Identifier

InChI=1S/C13H20N2O8/c1-23-11-7(14-4-10(18)19)2-13(22,6-17)3-8(11)15-9(5-16)12(20)21/h9,14,16-17,22H,2-6H2,1H3,(H,18,19)(H,20,21)/b15-8+/t9-,13-/m0/s1

InChI Key

WXEQFJUHQIGKNG-MZNRBSSJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Asterina pectinifera	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Serine and derivatives

Alternative Parents

Substituents

Serine or derivatives
Alpha-amino acid
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Azomethine
Secondary ketimine
Tertiary alcohol
Amino acid
Ketimine
Carboxylic acid
Secondary aliphatic amine
Enamine
Organic 1,3-dipolar compound
Secondary amine
Propargyl-type 1,3-dipolar organic compound
Imine
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Alcohol
Carbonyl group
Amine
Organonitrogen compound
Organooxygen compound
Primary alcohol
Organic oxygen compound
Organopnictogen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	-4.1	ChemAxon
pKa (Strongest Acidic)	2.9	ChemAxon
pKa (Strongest Basic)	3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	168.91 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	77.35 m³·mol⁻¹	ChemAxon
Polarizability	31.92 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00054306

Chemspider ID

29420737

KEGG Compound ID

Not Available

BioCyc ID

CPD-18778

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

131712

Good Scents ID

Not Available

References

General References

Gao Q, Garcia-Pichel F: An ATP-grasp ligase involved in the last biosynthetic step of the iminomycosporine shinorine in Nostoc punctiforme ATCC 29133. J Bacteriol. 2011 Nov;193(21):5923-8. doi: 10.1128/JB.05730-11. Epub 2011 Sep 2. [PubMed:21890703 ]
Krabs G, Watanabe M, Wiencke C: A monochromatic action spectrum for the photoinduction of the UV-absorbing mycosporine-like amino acid shinorine in the red alga Chondrus crispus. Photochem Photobiol. 2004 Jun;79(6):515-9. doi: 10.1562/2003-12-14-ra.1. [PubMed:15291302 ]
Conde FR, Churio MS, Previtali CM: The deactivation pathways of the excited-states of the mycosporine-like amino acids shinorine and porphyra-334 in aqueous solution. Photochem Photobiol Sci. 2004 Oct;3(10):960-7. doi: 10.1039/b405782a. Epub 2004 Sep 6. [PubMed:15480487 ]
Singh SP, Klisch M, Sinha RP, Hader DP: Effects of abiotic stressors on synthesis of the mycosporine-like amino acid shinorine in the Cyanobacterium Anabaena variabilis PCC 7937. Photochem Photobiol. 2008 Nov-Dec;84(6):1500-5. doi: 10.1111/j.1751-1097.2008.00376.x. Epub 2008 Jun 13. [PubMed:18557824 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(1e,5s)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid (NP0300753)

MOL for NP0300753 ((2s)-2-{[(1e,5s)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid)

3D MOL for NP0300753 ((2s)-2-{[(1e,5s)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid)

3D SDF for NP0300753 ((2s)-2-{[(1e,5s)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid)

3D-SDF for NP0300753 ((2s)-2-{[(1e,5s)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid)

PDB for NP0300753 ((2s)-2-{[(1e,5s)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid)

3D PDB for NP0300753 ((2s)-2-{[(1e,5s)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid)

SMILES for NP0300753 ((2s)-2-{[(1e,5s)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid)

INCHI for NP0300753 ((2s)-2-{[(1e,5s)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid)

Structure for NP0300753 ((2s)-2-{[(1e,5s)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid)

3D Structure for NP0300753 ((2s)-2-{[(1e,5s)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxypropanoic acid)