NP-MRD: Showing NP-Card for Akunolide B acyclic derivative (NP0332583)

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Record Information

Version

2.0

Created at

2024-02-27 00:00:41 UTC

Updated at

2024-09-03 04:19:41 UTC

NP-MRD ID

NP0332583

Natural Product DOI

https://doi.org/10.57994/1843

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Akunolide B acyclic derivative

Description

Akunolide B acyclic derivative (6) belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain. Based on a literature review very few articles have been published on Akunolide B acyclic derivative (6).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 10242304012D          

 51 52  0  0  1  0            999 V2000
   -5.0013   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -9.4875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1283   -9.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3033  -10.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4302  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592  -10.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8592  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881  -10.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.2881  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171  -10.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.7171   -9.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315  -11.5500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.4315  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460  -11.9625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4282  -11.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9585  -10.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460  -10.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.8605   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5749  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -13.5749   -9.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5749  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2894  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0039  -11.1375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -15.7184  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7184  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0039  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -15.7184   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7184   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2894   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -14.2894   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -9.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -9.9000    0.0000 C   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
  3  4  1  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
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 15 12  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 21 20  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 27 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  6  0  0  0
 27 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 36 33  1  0  0  0  0
 36 37  1  0  0  0  0
 38 37  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 42 41  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 45 42  1  0  0  0  0
 45 46  1  6  0  0  0
 46 47  1  0  0  0  0
 45 48  1  0  0  0  0
 48 38  1  0  0  0  0
 48 49  1  1  0  0  0
 36 50  1  6  0  0  0
 36 51  1  0  0  0  0
 24 51  1  0  0  0  0
M  END


  Mrv2104 10242304012D          

 51 52  0  0  1  0            999 V2000
   -5.0013   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -9.4875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1283   -9.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3033  -10.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4302  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592  -10.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8592  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881  -10.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.2881  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171  -10.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.7171   -9.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315  -11.5500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.4315  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460  -11.9625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4282  -11.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9585  -10.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460  -10.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.8605   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5749  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -13.5749   -9.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5749  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2894  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0039  -11.1375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -15.7184  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7184  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0039  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -15.7184   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7184   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2894   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -14.2894   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -9.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -9.9000    0.0000 C   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
  3  4  1  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
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 15 12  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 21 20  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 27 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  6  0  0  0
 27 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 36 33  1  0  0  0  0
 36 37  1  0  0  0  0
 38 37  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 42 41  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 45 42  1  0  0  0  0
 45 46  1  6  0  0  0
 46 47  1  0  0  0  0
 45 48  1  0  0  0  0
 48 38  1  0  0  0  0
 48 49  1  1  0  0  0
 36 50  1  6  0  0  0
 36 51  1  0  0  0  0
 24 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332583

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(C[C@H](O)C[C@H](C)C[C@@H](O)C(C)(C)[C@H](O)CCCCCCCCC)C[C@]([H])(O[C@]2([H])OC[C@@H](OC)[C@H](OC)[C@H]2O)C(C)(C)[C@]([H])(CC(O)=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C36H68O11/c1-9-10-11-12-13-14-15-16-27(38)35(3,4)28(39)18-23(2)17-24(37)19-25-20-29(36(5,6)30(46-25)21-31(40)41)47-34-32(42)33(44-8)26(43-7)22-45-34/h23-30,32-34,37-39,42H,9-22H2,1-8H3,(H,40,41)/t23-,24+,25+,26+,27+,28+,29-,30-,32+,33-,34-/m0/s1

> <INCHI_KEY>
KGLHZMOOXWBKCG-FBWVBYSTSA-N

> <FORMULA>
C36H68O11

> <MOLECULAR_WEIGHT>
676.929

> <EXACT_MASS>
676.47616301

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
115

> <JCHEM_AVERAGE_POLARIZABILITY>
77.94995037577847

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2S,4S,6R)-4-{[(2S,3R,4R,5R)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-3,3-dimethyl-6-[(2R,4S,6R,8R)-2,6,8-trihydroxy-4,7,7-trimethylheptadecyl]oxan-2-yl]acetic acid

> <JCHEM_LOGP>
4.895377628666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.360439267150182

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.087951339675763

> <JCHEM_PKA_STRONGEST_BASIC>
-2.724915808126612

> <JCHEM_POLAR_SURFACE_AREA>
164.36999999999998

> <JCHEM_REFRACTIVITY>
178.09049999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,4S,6R)-4-{[(2S,3R,4R,5R)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-3,3-dimethyl-6-[(2R,4S,6R,8R)-2,6,8-trihydroxy-4,7,7-trimethylheptadecyl]oxan-2-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-OCT-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-OCT-23         0                                  
HETATM    1  O   UNK     0      -9.336 -16.170   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -9.336 -17.710   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002 -18.480   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668 -17.710   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335 -18.480   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001 -17.710   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667 -18.480   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334 -17.710   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000 -18.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334 -17.710   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.669 -18.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -11.439 -17.146   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.899 -19.814   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -12.003 -19.250   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0     -12.003 -20.790   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0     -13.337 -18.480   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -14.670 -19.250   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -14.670 -20.790   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -16.004 -18.480   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -17.338 -19.250   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -17.338 -20.790   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0     -18.672 -18.480   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -20.005 -19.250   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0     -20.005 -17.710   0.000  0.00  0.00           H+0
HETATM   26  O   UNK     0     -20.005 -20.790   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0     -21.339 -21.560   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -21.339 -23.100   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -20.005 -23.870   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -18.672 -23.100   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -20.005 -25.410   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0     -22.673 -22.330   0.000  0.00  0.00           H+0
HETATM   33  C   UNK     0     -22.673 -20.790   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -23.199 -22.237   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -24.189 -20.523   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -22.673 -19.250   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0     -24.006 -18.480   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0     -25.340 -19.250   0.000  0.00  0.00           C+0
HETATM   39  H   UNK     0     -25.340 -17.710   0.000  0.00  0.00           H+0
HETATM   40  O   UNK     0     -25.340 -20.790   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0     -26.674 -21.560   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -28.007 -20.790   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0     -29.341 -21.560   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0     -29.341 -23.100   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -28.007 -19.250   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0     -29.341 -18.480   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0     -29.341 -16.940   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -26.674 -18.480   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0     -26.674 -16.940   0.000  0.00  0.00           O+0
HETATM   50  H   UNK     0     -22.673 -17.710   0.000  0.00  0.00           H+0
HETATM   51  C   UNK     0     -21.339 -18.480   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    2   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26   51                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   32   33                                             
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27                                                            
CONECT   33   27   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33   37   50   51                                             
CONECT   37   36   38                                                       
CONECT   38   37   39   40   48                                             
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   45                                                  
CONECT   43   42   44                                                       
CONECT   44   43                                                            
CONECT   45   42   46   48                                                  
CONECT   46   45   47                                                       
CONECT   47   46                                                            
CONECT   48   45   38   49                                                  
CONECT   49   48                                                            
CONECT   50   36                                                            
CONECT   51   36   24                                                       
MASTER        0    0    0    0    0    0    0    0   51    0  104    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₆₈O₁₁

Average Mass

676.9290 Da

Monoisotopic Mass

676.47616 Da

IUPAC Name

2-[(2S,4S,6R)-4-{[(2S,3R,4R,5R)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-3,3-dimethyl-6-[(2R,4S,6R,8R)-2,6,8-trihydroxy-4,7,7-trimethylheptadecyl]oxan-2-yl]acetic acid

Traditional Name

[(2S,4S,6R)-4-{[(2S,3R,4R,5R)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-3,3-dimethyl-6-[(2R,4S,6R,8R)-2,6,8-trihydroxy-4,7,7-trimethylheptadecyl]oxan-2-yl]acetic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(C[C@H](O)C[C@H](C)C[C@@H](O)C(C)(C)[C@H](O)CCCCCCCCC)C[C@]([H])(O[C@]2([H])OC[C@@H](OC)[C@H](OC)[C@H]2O)C(C)(C)[C@]([H])(CC(O)=O)O1

InChI Identifier

InChI=1S/C36H68O11/c1-9-10-11-12-13-14-15-16-27(38)35(3,4)28(39)18-23(2)17-24(37)19-25-20-29(36(5,6)30(46-25)21-31(40)41)47-34-32(42)33(44-8)26(43-7)22-45-34/h23-30,32-34,37-39,42H,9-22H2,1-8H3,(H,40,41)/t23-,24+,25+,26+,27+,28+,29-,30-,32+,33-,34-/m0/s1

InChI Key

KGLHZMOOXWBKCG-FBWVBYSTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 396 MHz, CD3OD, experimental)	[email protected]	Not Available	Not Available	2024-02-27	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

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

Hydroxy fatty acid
Heterocyclic fatty acid
Branched fatty acid
Oxane
Monosaccharide
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	4.9	ChemAxon
pKa (Strongest Acidic)	4.09	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	164.37 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	178.09 m³·mol⁻¹	ChemAxon
Polarizability	77.95 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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

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

DOI: 10.1021/acs.jnatprod.3c00742

Showing NP-Card for Akunolide B acyclic derivative (NP0332583)

MOL for NP0332583 (Akunolide B acyclic derivative)

3D MOL for NP0332583 (Akunolide B acyclic derivative)

3D SDF for NP0332583 (Akunolide B acyclic derivative)

3D-SDF for NP0332583 (Akunolide B acyclic derivative)

PDB for NP0332583 (Akunolide B acyclic derivative)

3D PDB for NP0332583 (Akunolide B acyclic derivative)

SMILES for NP0332583 (Akunolide B acyclic derivative)

INCHI for NP0332583 (Akunolide B acyclic derivative)

Structure for NP0332583 (Akunolide B acyclic derivative)

3D Structure for NP0332583 (Akunolide B acyclic derivative)