NP-MRD: Showing NP-Card for (2s,3s)-n-[(s)-[(2s,6r)-6-[(2s,3r)-3-[(3r)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid (NP0249263)

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Record Information

Version

2.0

Created at

2022-09-07 11:46:02 UTC

Updated at

2022-09-07 11:46:02 UTC

NP-MRD ID

NP0249263

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s)-n-[(s)-[(2s,6r)-6-[(2s,3r)-3-[(3r)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid

Description

Irciniastatin B belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. (2s,3s)-n-[(s)-[(2s,6r)-6-[(2s,3r)-3-[(3r)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid is found in Ircinia ramosa. (2s,3s)-n-[(s)-[(2s,6r)-6-[(2s,3r)-3-[(3r)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid was first documented in 2012 (PMID: 22892009). Based on a literature review a small amount of articles have been published on Irciniastatin B (PMID: 26544018) (PMID: 23510264).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072213462D          

 43 45  0  0  1  0            999 V2000
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1868   -3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2474   -3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1460   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8605   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5749   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.0039   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -4.9500    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  4  0  0  0
 10 12  2  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 13  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 27  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 31 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 29 42  1  0  0  0  0
 23 43  1  0  0  0  0
 16 43  1  0  0  0  0
M  END


  Mrv1652309072213462D          

 43 45  0  0  1  0            999 V2000
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1868   -3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2474   -3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1460   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8605   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5749   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.0039   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -4.9500    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  4  0  0  0
 10 12  2  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 13  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 27  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 31 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 29 42  1  0  0  0  0
 23 43  1  0  0  0  0
 16 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249263

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H](CC(C)=C)[C@H](O)C(O)=N[C@@H](OC)[C@@H]1CC(=O)C(C)(C)[C@@H](C[C@H](O)[C@@H](C)[C@H]2CC3=C(C)C(O)=CC(O)=C3C(=O)O2)O1

> <INCHI_IDENTIFIER>
InChI=1S/C31H45NO11/c1-14(2)9-22(40-7)27(37)28(38)32-29(41-8)23-13-24(36)31(5,6)25(42-23)12-19(34)16(4)21-10-17-15(3)18(33)11-20(35)26(17)30(39)43-21/h11,16,19,21-23,25,27,29,33-35,37H,1,9-10,12-13H2,2-8H3,(H,32,38)/t16-,19+,21-,22+,23+,25-,27+,29+/m1/s1

> <INCHI_KEY>
MSZITYUGWBXQOC-BTSGJVQSSA-N

> <FORMULA>
C31H45NO11

> <MOLECULAR_WEIGHT>
607.697

> <EXACT_MASS>
607.299261273

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
62.53013331126779

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-N-[(S)-[(2S,6R)-6-[(2S,3R)-3-[(3R)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid

> <JCHEM_LOGP>
4.347241322666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.841724721470914

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3470472966318274

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3433027737502918

> <JCHEM_POLAR_SURFACE_AREA>
184.56999999999996

> <JCHEM_REFRACTIVITY>
156.1679

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-N-[(S)-[(2S,6R)-6-[(2S,3R)-3-[(3R)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      16.004 -13.860   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      17.338 -10.010   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      18.672 -12.320   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      20.005 -11.550   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      21.339 -12.320   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      22.673 -11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.005 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.672  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.672  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      17.338  -6.930   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      20.005  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.015  -5.750   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.995  -5.750   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.339  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      22.673  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      24.006  -7.700   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      24.006  -9.240   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      25.340  -6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      25.340  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      26.674  -7.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      28.007  -6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      29.341  -7.700   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      30.675  -6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      30.675  -5.390   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      32.008  -7.700   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      33.342  -6.930   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      32.008  -9.240   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      30.675 -10.010   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      30.675 -11.550   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      29.341  -9.240   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      28.007 -10.010   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      28.007 -11.550   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      26.674  -9.240   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      21.339  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   43                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24   43                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   42                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   39                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   31   40                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   29                                                       
CONECT   43   23   16                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₅NO₁₁

Average Mass

607.6970 Da

Monoisotopic Mass

607.29926 Da

IUPAC Name

(2S,3S)-N-[(S)-[(2S,6R)-6-[(2S,3R)-3-[(3R)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid

Traditional Name

(2S,3S)-N-[(S)-[(2S,6R)-6-[(2S,3R)-3-[(3R)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid

CAS Registry Number

Not Available

SMILES

CO[C@@H](CC(C)=C)[C@H](O)C(O)=N[C@@H](OC)[C@@H]1CC(=O)C(C)(C)[C@@H](C[C@H](O)[C@@H](C)[C@H]2CC3=C(C)C(O)=CC(O)=C3C(=O)O2)O1

InChI Identifier

InChI=1S/C31H45NO11/c1-14(2)9-22(40-7)27(37)28(38)32-29(41-8)23-13-24(36)31(5,6)25(42-23)12-19(34)16(4)21-10-17-15(3)18(33)11-20(35)26(17)30(39)43-21/h11,16,19,21-23,25,27,29,33-35,37H,1,9-10,12-13H2,2-8H3,(H,32,38)/t16-,19+,21-,22+,23+,25-,27+,29+/m1/s1

InChI Key

MSZITYUGWBXQOC-BTSGJVQSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ircinia ramosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic acid derivatives

Alternative Parents

Substituents

Dihydroxybenzoic acid
2-benzopyran
Isochromane
Benzopyran
1-hydroxy-2-unsubstituted benzenoid
Fatty acyl
Oxane
N-acyl-amine
Monosaccharide
Fatty amide
Vinylogous acid
Cyclic ketone
Secondary carboxylic acid amide
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Carboxamide group
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.35	ChemAxon
pKa (Strongest Acidic)	3.35	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	184.57 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	156.17 m³·mol⁻¹	ChemAxon
Polarizability	62.53 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28596819

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

66575256

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Uesugi S, Watanabe T, Imaizumi T, Ota Y, Yoshida K, Ebisu H, Chinen T, Nagumo Y, Shibuya M, Kanoh N, Usui T, Iwabuchi Y: Total Synthesis and Biological Evaluation of Irciniastatin A (a.k.a. Psymberin) and Irciniastatin B. J Org Chem. 2015 Dec 18;80(24):12333-50. doi: 10.1021/acs.joc.5b02256. Epub 2015 Nov 16. [PubMed:26544018 ]
An C, Jurica JA, Walsh SP, Hoye AT, Smith AB 3rd: Total synthesis of (+)-irciniastatin A (a.k.a. psymberin) and (-)-irciniastatin B. J Org Chem. 2013 May 3;78(9):4278-96. doi: 10.1021/jo400260m. Epub 2013 Apr 12. [PubMed:23510264 ]
An C, Hoye AT, Smith AB 3rd: Total synthesis of (-)-irciniastatin B and structural confirmation via chemical conversion to (+)-irciniastatin A (psymberin). Org Lett. 2012 Sep 7;14(17):4350-3. doi: 10.1021/ol301783p. Epub 2012 Aug 14. [PubMed:22892009 ]
LOTUS database [Link]

Showing NP-Card for (2s,3s)-n-[(s)-[(2s,6r)-6-[(2s,3r)-3-[(3r)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid (NP0249263)

MOL for NP0249263 ((2s,3s)-n-[(s)-[(2s,6r)-6-[(2s,3r)-3-[(3r)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid)

3D MOL for NP0249263 ((2s,3s)-n-[(s)-[(2s,6r)-6-[(2s,3r)-3-[(3r)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid)

3D SDF for NP0249263 ((2s,3s)-n-[(s)-[(2s,6r)-6-[(2s,3r)-3-[(3r)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid)

3D-SDF for NP0249263 ((2s,3s)-n-[(s)-[(2s,6r)-6-[(2s,3r)-3-[(3r)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid)

PDB for NP0249263 ((2s,3s)-n-[(s)-[(2s,6r)-6-[(2s,3r)-3-[(3r)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid)

3D PDB for NP0249263 ((2s,3s)-n-[(s)-[(2s,6r)-6-[(2s,3r)-3-[(3r)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid)

SMILES for NP0249263 ((2s,3s)-n-[(s)-[(2s,6r)-6-[(2s,3r)-3-[(3r)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid)

INCHI for NP0249263 ((2s,3s)-n-[(s)-[(2s,6r)-6-[(2s,3r)-3-[(3r)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid)

Structure for NP0249263 ((2s,3s)-n-[(s)-[(2s,6r)-6-[(2s,3r)-3-[(3r)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid)

3D Structure for NP0249263 ((2s,3s)-n-[(s)-[(2s,6r)-6-[(2s,3r)-3-[(3r)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-5,5-dimethyl-4-oxooxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid)