NP-MRD: Showing NP-Card for Lagriamide B (NP0332828)

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Record Information

Version

2.0

Created at

2024-04-22 20:44:17 UTC

Updated at

2025-12-20 21:41:05 UTC

NP-MRD ID

NP0332828

Natural Product DOI

https://doi.org/10.57994/2102

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lagriamide B

Description

Lagriamide B belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain. Lagriamide B was first documented in 2024 (PMID: 38817573). Based on a literature review very few articles have been published on Lagriamide B.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01042323212D          

 50 52  0  0  1  0            999 V2000
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  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
   -0.0000    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  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4315    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8605    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1460   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  0  0  0  0
 11 12  1  6  0  0  0
  7 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 31 30  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 33  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  6  0  0  0
 31 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 37 41  2  0  0  0  0
 27 42  2  0  0  0  0
 24 43  1  6  0  0  0
 23 44  1  1  0  0  0
 22 45  2  0  0  0  0
 15 46  1  6  0  0  0
  4 47  1  6  0  0  0
  2 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  2  0  0  0  0
M  END


  Mrv2104 01042323212D          

 50 52  0  0  1  0            999 V2000
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  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
   -0.0000    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  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4315    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8605    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1460   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  0  0  0  0
 11 12  1  6  0  0  0
  7 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 31 30  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 33  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  6  0  0  0
 31 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 37 41  2  0  0  0  0
 27 42  2  0  0  0  0
 24 43  1  6  0  0  0
 23 44  1  1  0  0  0
 22 45  2  0  0  0  0
 15 46  1  6  0  0  0
  4 47  1  6  0  0  0
  2 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332828

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\C(=O)C[C@H]1CC[C@H](C)[C@H](CC(=O)NC[C@H](O)[C@H](C)C(=O)NCCC[C@H]2O[C@@]3(CCC[C@@H](CC[C@H](C)C[C@H](C)C(O)=O)O3)CC[C@@H]2C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C39H66N2O9/c1-7-10-30(42)22-32-16-14-26(3)35(48-32)23-36(44)41-24-33(43)29(6)37(45)40-20-9-12-34-27(4)17-19-39(50-34)18-8-11-31(49-39)15-13-25(2)21-28(5)38(46)47/h7,10,25-29,31-35,43H,8-9,11-24H2,1-6H3,(H,40,45)(H,41,44)(H,46,47)/b10-7+/t25-,26-,27-,28-,29-,31-,32+,33-,34+,35-,39-/m0/s1

> <INCHI_KEY>
DWTZELUXJCFHIK-ZGLZGSKZSA-N

> <FORMULA>
C39H66N2O9

> <MOLECULAR_WEIGHT>
706.962

> <EXACT_MASS>
706.476831713

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
116

> <JCHEM_AVERAGE_POLARIZABILITY>
79.8554995717263

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4S)-6-[(2S,6S,8R,9S)-8-{3-[(2S,3R)-3-hydroxy-2-methyl-4-{2-[(2S,3S,6R)-3-methyl-6-[(3E)-2-oxopent-3-en-1-yl]oxan-2-yl]acetamido}butanamido]propyl}-9-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]-2,4-dimethylhexanoic acid

> <JCHEM_LOGP>
5.761843782333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.30282787317716

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.377044322691312

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0248320677626526

> <JCHEM_POLAR_SURFACE_AREA>
160.48999999999998

> <JCHEM_REFRACTIVITY>
192.38970000000012

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S)-6-[(2S,6S,8R,9S)-8-{3-[(2S,3R)-3-hydroxy-2-methyl-4-{2-[(2S,3S,6R)-3-methyl-6-[(3E)-2-oxopent-3-en-1-yl]oxan-2-yl]acetamido}butanamido]propyl}-9-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]-2,4-dimethylhexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JAN-23         0                                  
HETATM    1  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      10.669   1.540   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.670   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      17.338   0.770   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.005   0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.339   1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      21.339   3.080   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      22.673   3.850   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      24.006   3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      24.006   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      22.673   0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      22.673  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      22.673   5.390   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      24.006   6.160   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      24.006   7.700   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      25.340   8.470   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      25.340  10.010   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      25.340   5.390   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      18.672   3.080   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      14.670  -0.770   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      13.337   3.080   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   48                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   47                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   17                                             
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   46                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   11                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   45                                                  
CONECT   23   22   24   44                                                  
CONECT   24   23   25   43                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   42                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29   35                                                  
CONECT   35   34                                                            
CONECT   36   31   37                                                       
CONECT   37   36   38   41                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   37                                                            
CONECT   42   27                                                            
CONECT   43   24                                                            
CONECT   44   23                                                            
CONECT   45   22                                                            
CONECT   46   15                                                            
CONECT   47    4                                                            
CONECT   48    2   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  104    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₉H₆₆N₂O₉

Average Mass

706.9620 Da

Monoisotopic Mass

706.47683 Da

IUPAC Name

(2S,4S)-6-[(2S,6S,8R,9S)-8-{3-[(2S,3R)-3-hydroxy-2-methyl-4-{2-[(2S,3S,6R)-3-methyl-6-[(3E)-2-oxopent-3-en-1-yl]oxan-2-yl]acetamido}butanamido]propyl}-9-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]-2,4-dimethylhexanoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

C\C=C\C(=O)C[C@H]1CC[C@H](C)[C@H](CC(=O)NC[C@H](O)[C@H](C)C(=O)NCCC[C@H]2O[C@@]3(CCC[C@@H](CC[C@H](C)C[C@H](C)C(O)=O)O3)CC[C@@H]2C)O1

InChI Identifier

InChI=1S/C39H66N2O9/c1-7-10-30(42)22-32-16-14-26(3)35(48-32)23-36(44)41-24-33(43)29(6)37(45)40-20-9-12-34-27(4)17-19-39(50-34)18-8-11-31(49-39)15-13-25(2)21-28(5)38(46)47/h7,10,25-29,31-35,43H,8-9,11-24H2,1-6H3,(H,40,45)(H,41,44)(H,46,47)/b10-7+/t25-,26-,27-,28-,29-,31-,32+,33-,34+,35-,39-/m0/s1

InChI Key

DWTZELUXJCFHIK-ZGLZGSKZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 601 MHz, C2D6OS, experimental)	jsaulog@sfu.ca	Simon Fraser University	Julia Saulog	2024-04-22	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 601 MHz, D2O, experimental)	jsaulog@sfu.ca	Simon Fraser University	Julia Saulog	2024-04-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 601 MHz, C2D6OS, experimental)	jsaulog@sfu.ca	Simon Fraser University	Julia Saulog	2024-04-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 601 MHz, C2D6OS, experimental)	jsaulog@sfu.ca	Simon Fraser University	Julia Saulog	2024-04-22	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 601 MHz, C2D6OS, experimental)	jsaulog@sfu.ca	Simon Fraser University	Julia Saulog	2024-04-22	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 601 MHz, C2D6OS, experimental)	jsaulog@sfu.ca	Simon Fraser University	Julia Saulog	2024-04-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 601 MHz, C2D6OS, experimental)	jsaulog@sfu.ca	Simon Fraser University	Julia Saulog	2024-04-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 601 MHz, C2D6OS, experimental)	jsaulog@sfu.ca	Simon Fraser University	Julia Saulog	2024-04-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 601 MHz, C2D6OS, experimental)	jsaulog@sfu.ca	Simon Fraser University	Julia Saulog	2024-04-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 601 MHz, C2D6OS, experimental)	jsaulog@sfu.ca	Simon Fraser University	Julia Saulog	2024-04-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 601 MHz, C2D6OS, experimental)	jsaulog@sfu.ca	Simon Fraser University	Julia Saulog	2024-04-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 601 MHz, C2D6OS, experimental)	jsaulog@sfu.ca	Simon Fraser University	Julia Saulog	2024-04-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	jsaulog@sfu.ca	Simon Fraser University	Julia Saulog	2024-04-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, C2D6OS, simulated)	jsaulog@sfu.ca	Simon Fraser University	Julia Saulog	2024-04-22	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Paraburkholderia acidicola		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Heterocyclic fatty acids

Alternative Parents

Substituents

Ketal
Methyl-branched fatty acid
Hydroxy fatty acid
Heterocyclic fatty acid
Branched fatty acid
Oxane
N-acyl-amine
Fatty amide
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Secondary alcohol
Ketone
Carboxamide group
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
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	5.76	ChemAxon
pKa (Strongest Acidic)	4.38	ChemAxon
pKa (Strongest Basic)	-1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	160.49 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	192.39 m³·mol⁻¹	ChemAxon
Polarizability	79.86 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fergusson CH, Saulog J, Paulo BS, Wilson DM, Liu DY, Morehouse NJ, Waterworth S, Barkei J, Gray CA, Kwan JC, Eustaquio AS, Linington RG: Discovery of a lagriamide polyketide by integrated genome mining, isotopic labeling, and untargeted metabolomics. Chem Sci. 2024 May 7;15(21):8089-8096. doi: 10.1039/d4sc00825a. eCollection 2024 May 29. [PubMed:38817573 ]
DOI: 10.1039/d4sc00825a

Showing NP-Card for Lagriamide B (NP0332828)

MOL for NP0332828 (Lagriamide B)

3D MOL for NP0332828 (Lagriamide B)

3D SDF for NP0332828 (Lagriamide B)

3D-SDF for NP0332828 (Lagriamide B)

PDB for NP0332828 (Lagriamide B)

3D PDB for NP0332828 (Lagriamide B)

SMILES for NP0332828 (Lagriamide B)

INCHI for NP0332828 (Lagriamide B)

Structure for NP0332828 (Lagriamide B)

3D Structure for NP0332828 (Lagriamide B)