NP-MRD: Showing NP-Card for Aurafuron B (NP0005921)

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Record Information

Version

2.0

Created at

2020-12-09 03:02:13 UTC

Updated at

2021-07-15 16:53:21 UTC

NP-MRD ID

NP0005921

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aurafuron B

Provided By

NPAtlas

Description

Aurafuron B belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Aurafuron B is found in Stigmatella aurantiaca. Aurafuron B was first documented in 2005 (PMID: 15981410). Based on a literature review very few articles have been published on Aurafuron B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118233D          

 58 58  0  0  0  0            999 V2000
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    6.2325   -1.6702    0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0359   -1.0898    0.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7976   -1.7808    0.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6476   -1.1155    0.5599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4298   -1.8047    0.9360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2656   -1.2008    0.9802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0912    0.2105    0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1186    0.7242    0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3484    2.1445    0.4152 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.8023    1.5546   -1.8288 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
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 17 18  1  0  0  0  0
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 18 20  1  0  0  0  0
  3 21  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306242118233D          

 58 58  0  0  0  0            999 V2000
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   -0.6006   -1.8182    1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587    0.7735    0.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9361    0.0573    1.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7294    2.7162    1.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7322    2.7504    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2264    3.7819   -0.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3317    2.1696   -0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4329    3.2825   -1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3072    0.7270   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7806    3.2312    1.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3640    2.8414    0.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6665    1.7415    1.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7766    0.1818   -1.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3063    0.3386   -1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0711    0.9151    0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0890   -1.3121    0.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0873   -1.8995   -1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3935   -3.1482   -0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7094   -1.7532   -2.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6544   -0.7892    0.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5704   -1.5957   -0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2182   -2.5828    0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6764    2.3922   -1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9917    1.7140   -0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3879    2.2644    0.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8540   -0.1453   -2.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  6  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25  2  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  4 30  1  0  0  0  0
  5 31  1  0  0  0  0
  6 32  1  0  0  0  0
  7 33  1  0  0  0  0
  8 34  1  0  0  0  0
  9 35  1  0  0  0  0
 10 36  1  1  0  0  0
 11 37  1  0  0  0  0
 11 38  1  0  0  0  0
 11 39  1  0  0  0  0
 12 40  1  6  0  0  0
 13 41  1  0  0  0  0
 15 42  1  0  0  0  0
 15 43  1  0  0  0  0
 15 44  1  0  0  0  0
 16 45  1  0  0  0  0
 17 46  1  0  0  0  0
 17 47  1  0  0  0  0
 18 48  1  1  0  0  0
 19 49  1  0  0  0  0
 19 50  1  0  0  0  0
 19 51  1  0  0  0  0
 20 52  1  0  0  0  0
 20 53  1  0  0  0  0
 20 54  1  0  0  0  0
 23 55  1  0  0  0  0
 23 56  1  0  0  0  0
 23 57  1  0  0  0  0
 24 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005921

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]([H])(C(=C(/[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])\C([H])([H])[H])[C@@]([H])(C(\[H])=C(/[H])\C(\[H])=C(\[H])/C(/[H])=C(\[H])C1=C(C(=O)[C@@](O[H])(O1)C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O4/c1-15(2)13-14-17(4)20(23)16(3)11-9-7-8-10-12-19-18(5)21(24)22(6,25)26-19/h7-12,14-16,20,23,25H,13H2,1-6H3/b8-7-,11-9+,12-10+,17-14+/t16-,20-,22+/m1/s1

> <INCHI_KEY>
CEFLFJSAQJIEGR-HCPLIJRZSA-N

> <FORMULA>
C22H32O4

> <MOLECULAR_WEIGHT>
360.494

> <EXACT_MASS>
360.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.643596943961406

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-hydroxy-5-[(1E,3Z,5E,7R,8R,9E)-8-hydroxy-7,9,12-trimethyltrideca-1,3,5,9-tetraen-1-yl]-2,4-dimethyl-2,3-dihydrofuran-3-one

> <ALOGPS_LOGP>
4.53

> <JCHEM_LOGP>
4.527964512333336

> <ALOGPS_LOGS>
-4.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.862917532102376

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.461872171602984

> <JCHEM_PKA_STRONGEST_BASIC>
-1.109106814131673

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
111.6555

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-hydroxy-5-[(1E,3Z,5E,7R,8R,9E)-8-hydroxy-7,9,12-trimethyltrideca-1,3,5,9-tetraen-1-yl]-2,4-dimethylfuran-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 58  0  0  0  0  0  0  0  0999 V2000
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    3.7976   -1.7808    0.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6476   -1.1155    0.5599 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0912    0.2105    0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0618    2.7524   -0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3307    2.2034   -0.7460 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8023    1.5546   -1.8288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6805    1.7257   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4120    2.4313    0.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2926    0.6967   -0.9275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6499    0.2397   -0.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6418   -1.1947   -0.0247 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1459   -2.0820   -1.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1075   -1.5740    0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1248    0.2452   -0.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3357    0.4242   -0.8981 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8990    1.8065   -0.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0544    0.2011   -2.2474 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1739   -0.6384   -0.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4157   -0.7379   -0.1747 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2795   -3.7567   -0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5085   -3.2553    0.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7946   -3.4168    1.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8034   -2.8281    0.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7059   -0.0816    0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5070   -2.8725    1.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7322    2.7504    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2264    3.7819   -0.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3317    2.1696   -0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4329    3.2825   -1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3072    0.7270   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7806    3.2312    1.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3640    2.8414    0.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6665    1.7415    1.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7766    0.1818   -1.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3063    0.3386   -1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0711    0.9151    0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0890   -1.3121    0.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0873   -1.8995   -1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3935   -3.1482   -0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7094   -1.7532   -2.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6544   -0.7892    0.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5704   -1.5957   -0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2182   -2.5828    0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6764    2.3922   -1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9917    1.7140   -0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3879    2.2644    0.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8540   -0.1453   -2.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
  3 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  6
 22 25  1  0
 25 26  2  0
 25  2  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  1
 11 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  6
 13 41  1  0
 15 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  1
 19 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       6.476  -3.095   0.413  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.232  -1.670   0.098  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.036  -1.090   0.154  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.798  -1.781   0.534  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.648  -1.115   0.560  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.430  -1.805   0.936  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.266  -1.201   0.980  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.091   0.211   0.657  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.119   0.724   0.731  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.348   2.144   0.415  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.062   2.752  -0.087  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.331   2.203  -0.746  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.802   1.555  -1.829  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.680   1.726  -0.360  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.412   2.431   0.729  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.293   0.697  -0.928  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.650   0.240  -0.519  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.642  -1.195  -0.025  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.146  -2.082  -1.147  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.107  -1.574   0.199  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.125   0.245  -0.194  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.336   0.424  -0.898  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.899   1.807  -0.685  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.054   0.201  -2.247  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.174  -0.638  -0.322  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.416  -0.738  -0.175  0.00  0.00           O+0
HETATM   27  H   UNK     0       6.279  -3.757  -0.455  0.00  0.00           H+0
HETATM   28  H   UNK     0       7.508  -3.255   0.767  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.795  -3.417   1.248  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.803  -2.828   0.794  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.706  -0.082   0.292  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.507  -2.873   1.190  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.601  -1.818   1.280  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.959   0.774   0.372  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.936   0.057   1.035  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.729   2.716   1.292  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.732   2.750   0.696  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.226   3.782  -0.488  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.332   2.170  -0.941  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.433   3.283  -1.010  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.307   0.727  -1.617  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.781   3.231   1.185  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.364   2.841   0.333  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.667   1.742   1.560  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.777   0.182  -1.712  0.00  0.00           H+0
HETATM   46  H   UNK     0      -6.306   0.339  -1.407  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.071   0.915   0.261  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.089  -1.312   0.909  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.087  -1.900  -1.343  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.394  -3.148  -0.976  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.709  -1.753  -2.066  0.00  0.00           H+0
HETATM   52  H   UNK     0      -7.654  -0.789   0.752  0.00  0.00           H+0
HETATM   53  H   UNK     0      -7.570  -1.596  -0.824  0.00  0.00           H+0
HETATM   54  H   UNK     0      -7.218  -2.583   0.613  0.00  0.00           H+0
HETATM   55  H   UNK     0       6.676   2.392  -1.612  0.00  0.00           H+0
HETATM   56  H   UNK     0       7.992   1.714  -0.552  0.00  0.00           H+0
HETATM   57  H   UNK     0       6.388   2.264   0.192  0.00  0.00           H+0
HETATM   58  H   UNK     0       6.854  -0.145  -2.732  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    1    3   25                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5   30                                                  
CONECT    5    4    6   31                                                  
CONECT    6    5    7   32                                                  
CONECT    7    6    8   33                                                  
CONECT    8    7    9   34                                                  
CONECT    9    8   10   35                                                  
CONECT   10    9   11   12   36                                             
CONECT   11   10   37   38   39                                             
CONECT   12   10   13   14   40                                             
CONECT   13   12   41                                                       
CONECT   14   12   15   16                                                  
CONECT   15   14   42   43   44                                             
CONECT   16   14   17   45                                                  
CONECT   17   16   18   46   47                                             
CONECT   18   17   19   20   48                                             
CONECT   19   18   49   50   51                                             
CONECT   20   18   52   53   54                                             
CONECT   21    3   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22   55   56   57                                             
CONECT   24   22   58                                                       
CONECT   25   22   26    2                                                  
CONECT   26   25                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    4                                                            
CONECT   31    5                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34    8                                                            
CONECT   35    9                                                            
CONECT   36   10                                                            
CONECT   37   11                                                            
CONECT   38   11                                                            
CONECT   39   11                                                            
CONECT   40   12                                                            
CONECT   41   13                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   15                                                            
CONECT   45   16                                                            
CONECT   46   17                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   19                                                            
CONECT   51   19                                                            
CONECT   52   20                                                            
CONECT   53   20                                                            
CONECT   54   20                                                            
CONECT   55   23                                                            
CONECT   56   23                                                            
CONECT   57   23                                                            
CONECT   58   24                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  116    0
END

RDKit          3D

58 58  0  0  0  0  0  0  0  0999 V2000
    6.4765   -3.0946    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2325   -1.6702    0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0359   -1.0898    0.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7976   -1.7808    0.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6476   -1.1155    0.5599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4298   -1.8047    0.9360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2656   -1.2008    0.9802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0912    0.2105    0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1186    0.7242    0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3484    2.1445    0.4152 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0618    2.7524   -0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3307    2.2034   -0.7460 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8023    1.5546   -1.8288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6805    1.7257   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4120    2.4313    0.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2926    0.6967   -0.9275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6499    0.2397   -0.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6418   -1.1947   -0.0247 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1459   -2.0820   -1.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1075   -1.5740    0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1248    0.2452   -0.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3357    0.4242   -0.8981 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8990    1.8065   -0.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0544    0.2011   -2.2474 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1739   -0.6384   -0.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4157   -0.7379   -0.1747 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2795   -3.7567   -0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5085   -3.2553    0.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7946   -3.4168    1.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8034   -2.8281    0.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7059   -0.0816    0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5070   -2.8725    1.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6006   -1.8182    1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587    0.7735    0.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9361    0.0573    1.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7294    2.7162    1.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7322    2.7504    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2264    3.7819   -0.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3317    2.1696   -0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4329    3.2825   -1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3072    0.7270   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7806    3.2312    1.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3640    2.8414    0.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6665    1.7415    1.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7766    0.1818   -1.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3063    0.3386   -1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0711    0.9151    0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0890   -1.3121    0.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0873   -1.8995   -1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3935   -3.1482   -0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7094   -1.7532   -2.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6544   -0.7892    0.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5704   -1.5957   -0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2182   -2.5828    0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6764    2.3922   -1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9917    1.7140   -0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3879    2.2644    0.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8540   -0.1453   -2.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
  3 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  6
 22 25  1  0
 25 26  2  0
 25  2  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  1
 11 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  6
 13 41  1  0
 15 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  1
 19 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₂H₃₂O₄

Average Mass

360.4940 Da

Monoisotopic Mass

360.23006 Da

IUPAC Name

(2S)-2-hydroxy-5-[(1E,3Z,5E,7R,8R,9E)-8-hydroxy-7,9,12-trimethyltrideca-1,3,5,9-tetraen-1-yl]-2,4-dimethyl-2,3-dihydrofuran-3-one

Traditional Name

(2S)-2-hydroxy-5-[(1E,3Z,5E,7R,8R,9E)-8-hydroxy-7,9,12-trimethyltrideca-1,3,5,9-tetraen-1-yl]-2,4-dimethylfuran-3-one

CAS Registry Number

Not Available

SMILES

CC(C)C\C=C(/C)[C@H](O)[C@H](C)\C=C\C=C/C=C/C1=C(C)C(=O)C(C)(O)O1

InChI Identifier

InChI=1S/C22H32O4/c1-15(2)13-14-17(4)20(23)16(3)11-9-7-8-10-12-19-18(5)21(24)22(6,25)26-19/h7-12,14-16,20,23,25H,13H2,1-6H3/b8-7-,11-9+,12-10+,17-14+/t16-,20-,22?/m1/s1

InChI Key

CEFLFJSAQJIEGR-HCPLIJRZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stigmatella aurantiaca	NPAtlas	15981410

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Acyloin
3-furanone
Dihydrofuran
Vinylogous ester
Hemiacetal
Ketone
Secondary alcohol
Cyclic ketone
Oxacycle
Organoheterocyclic compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Aldehyde
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	4.53	ALOGPS
logP	4.53	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	10.46	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	111.66 m³·mol⁻¹	ChemAxon
Polarizability	42.64 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA004117

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9454878

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11279879

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kunze B, Reichenbach H, Muller R, Hofle G: Aurafuron A and B, new bioactive polyketides from Stigmatella aurantiaca and Archangium gephyra (Myxobacteria). Fermentation, isolation, physico-chemical properties, structure and biological activity. J Antibiot (Tokyo). 2005 Apr;58(4):244-51. doi: 10.1038/ja.2005.28. [PubMed:15981410 ]

Showing NP-Card for Aurafuron B (NP0005921)

MOL for NP0005921 (Aurafuron B)

3D MOL for NP0005921 (Aurafuron B)

3D SDF for NP0005921 (Aurafuron B)

3D-SDF for NP0005921 (Aurafuron B)

PDB for NP0005921 (Aurafuron B)

3D PDB for NP0005921 (Aurafuron B)

SMILES for NP0005921 (Aurafuron B)

INCHI for NP0005921 (Aurafuron B)

Structure for NP0005921 (Aurafuron B)

3D Structure for NP0005921 (Aurafuron B)