NP-MRD: Showing NP-Card for Aurafuron A (NP0005920)

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Record Information

Version

2.0

Created at

2020-12-09 03:02:11 UTC

Updated at

2021-07-15 16:53:21 UTC

NP-MRD ID

NP0005920

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aurafuron A

Provided By

NPAtlas

Description

Aurafuron A 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 A is found in Stigmatella aurantiaca. Aurafuron A was first documented in 2005 (PMID: 15981410). Based on a literature review a small amount of articles have been published on Aurafuron A (PMID: 17919655) (PMID: 22632656).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118233D          

 61 61  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242118233D          

 61 61  0  0  0  0            999 V2000
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   -3.4899   -1.5100   -0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3679    0.3546   -3.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0929   -0.3355   -3.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1325   -1.2762   -0.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4918   -1.2790   -1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3297   -2.0656    1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0436   -3.9574    1.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6200   -4.1098    0.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316   -3.6340   -0.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7599   -0.3028    1.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7490   -1.2444    2.9921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0865   -2.3067   -1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1264   -2.9850    0.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3835   -1.8984   -0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4906   -0.2276   -1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2808    0.8730    0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1787    3.5723    0.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8537    2.6583    1.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6986    3.0987   -0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0794    1.9880   -0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6514    0.7294   -1.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3606   -0.9360   -0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6512    0.2651   -0.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7468   -1.3426    0.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2151   -1.3165    2.3181 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  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  1  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26  2  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  5 33  1  6  0  0  0
  6 34  1  0  0  0  0
  7 35  1  0  0  0  0
  8 36  1  0  0  0  0
  9 37  1  0  0  0  0
 10 38  1  0  0  0  0
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 18 50  1  0  0  0  0
 19 51  1  1  0  0  0
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 21 56  1  0  0  0  0
 21 57  1  0  0  0  0
 24 58  1  0  0  0  0
 24 59  1  0  0  0  0
 24 60  1  0  0  0  0
 25 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005920

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O5/c1-14(2)11-12-16(4)20(24)15(3)9-7-8-10-18(23)13-19-17(5)21(25)22(6,26)27-19/h7-10,12,14-15,18,20,23-24,26H,11,13H2,1-6H3/b9-7+,10-8-,16-12+/t15-,18-,20-,22-/m1/s1

> <INCHI_KEY>
AQQYZHDRTDSOER-LYKBUVKOSA-N

> <FORMULA>
C22H34O5

> <MOLECULAR_WEIGHT>
378.509

> <EXACT_MASS>
378.240624195

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
43.59410809835402

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
3.4303736360000006

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.743087209786395

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.471998230900635

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1091041235386778

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
112.1648

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.28e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 61  0  0  0  0  0  0  0  0999 V2000
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   -0.4754   -1.0824   -1.1022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7969   -1.4542   -0.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2162   -2.0659    0.3723 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5738   -3.5251    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2694   -1.2586    1.0666 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6415   -1.8789    2.2606 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8414    0.2903   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4332    2.7619    0.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9058   -0.1478    1.0728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2947    0.0306    1.2730 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.4899   -1.5100   -0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3679    0.3546   -3.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0929   -0.3355   -3.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1325   -1.2762   -0.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0436   -3.9574    1.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7599   -0.3028    1.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7490   -1.2444    2.9921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0865   -2.3067   -1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1264   -2.9850    0.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3835   -1.8984   -0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792    1.0560    0.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6727    1.3068   -1.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4906   -0.2276   -1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2808    0.8730    0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1787    3.5723    0.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8537    2.6583    1.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6986    3.0987   -0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0794    1.9880   -0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2388    2.4963   -1.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6514    0.7294   -1.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3606   -0.9360   -0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6512    0.2651   -0.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7468   -1.3426    0.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2151   -1.3165    2.3181 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  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
  3 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  1
 23 26  1  0
 26 27  2  0
 26  2  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  6
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  1
 12 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  1
 14 44  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  1
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 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 21 57  1  0
 24 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  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      -5.072   3.161  -0.425  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.266   1.890   0.318  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.402   0.857   0.257  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.147   0.817  -0.539  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.147  -0.296  -1.575  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.268  -1.556  -1.059  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.099  -0.111  -2.586  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.866  -0.479  -2.356  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.475  -1.082  -1.102  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.797  -1.454  -0.885  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.216  -2.066   0.372  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.574  -3.525   0.207  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.269  -1.259   1.067  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.642  -1.879   2.261  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.466  -0.969   0.266  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.288  -2.096  -0.248  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.841   0.290  -0.016  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.038   0.627  -0.817  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.031   1.462  -0.032  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.433   2.762   0.426  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.306   1.672  -0.791  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.906  -0.148   1.073  0.00  0.00           O+0
HETATM   23  C   UNK     0      -6.295   0.031   1.273  0.00  0.00           C+0
HETATM   24  C   UNK     0      -7.065  -0.525   0.105  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.737  -0.452   2.488  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.370   1.531   1.207  0.00  0.00           C+0
HETATM   27  O   UNK     0      -7.163   2.314   1.760  0.00  0.00           O+0
HETATM   28  H   UNK     0      -4.752   2.910  -1.459  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.327   3.795   0.109  0.00  0.00           H+0
HETATM   30  H   UNK     0      -6.058   3.675  -0.500  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.048   1.810  -1.068  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.291   0.744   0.156  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.135  -0.123  -2.133  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.490  -1.510  -0.103  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.368   0.355  -3.564  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.093  -0.336  -3.118  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.133  -1.276  -0.277  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.492  -1.279  -1.684  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.330  -2.066   1.075  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.044  -3.957   1.087  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.620  -4.110   0.049  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.132  -3.634  -0.742  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.760  -0.303   1.392  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.749  -1.244   2.992  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.087  -2.307  -1.306  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.126  -2.985   0.417  0.00  0.00           H+0
HETATM   47  H   UNK     0       5.383  -1.898  -0.165  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.179   1.056   0.402  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.673   1.307  -1.643  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.491  -0.228  -1.315  0.00  0.00           H+0
HETATM   51  H   UNK     0       6.281   0.873   0.880  0.00  0.00           H+0
HETATM   52  H   UNK     0       6.179   3.572   0.540  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.854   2.658   1.379  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.699   3.099  -0.333  0.00  0.00           H+0
HETATM   55  H   UNK     0       8.079   1.988  -0.036  0.00  0.00           H+0
HETATM   56  H   UNK     0       7.239   2.496  -1.530  0.00  0.00           H+0
HETATM   57  H   UNK     0       7.651   0.729  -1.239  0.00  0.00           H+0
HETATM   58  H   UNK     0      -6.361  -0.936  -0.663  0.00  0.00           H+0
HETATM   59  H   UNK     0      -7.651   0.265  -0.407  0.00  0.00           H+0
HETATM   60  H   UNK     0      -7.747  -1.343   0.391  0.00  0.00           H+0
HETATM   61  H   UNK     0      -7.215  -1.317   2.318  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    1    3   26                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5   31   32                                             
CONECT    5    4    6    7   33                                             
CONECT    6    5   34                                                       
CONECT    7    5    8   35                                                  
CONECT    8    7    9   36                                                  
CONECT    9    8   10   37                                                  
CONECT   10    9   11   38                                                  
CONECT   11   10   12   13   39                                             
CONECT   12   11   40   41   42                                             
CONECT   13   11   14   15   43                                             
CONECT   14   13   44                                                       
CONECT   15   13   16   17                                                  
CONECT   16   15   45   46   47                                             
CONECT   17   15   18   48                                                  
CONECT   18   17   19   49   50                                             
CONECT   19   18   20   21   51                                             
CONECT   20   19   52   53   54                                             
CONECT   21   19   55   56   57                                             
CONECT   22    3   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23   58   59   60                                             
CONECT   25   23   61                                                       
CONECT   26   23   27    2                                                  
CONECT   27   26                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    6                                                            
CONECT   35    7                                                            
CONECT   36    8                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   12                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   20                                                            
CONECT   53   20                                                            
CONECT   54   20                                                            
CONECT   55   21                                                            
CONECT   56   21                                                            
CONECT   57   21                                                            
CONECT   58   24                                                            
CONECT   59   24                                                            
CONECT   60   24                                                            
CONECT   61   25                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  122    0
END

RDKit          3D

61 61  0  0  0  0  0  0  0  0999 V2000
   -5.0716    3.1609   -0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2665    1.8899    0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4022    0.8573    0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1473    0.8172   -0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1469   -0.2955   -1.5752 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2684   -1.5558   -1.0588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0986   -0.1106   -2.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8659   -0.4786   -2.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754   -1.0824   -1.1022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7969   -1.4542   -0.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2162   -2.0659    0.3723 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5738   -3.5251    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2694   -1.2586    1.0666 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6415   -1.8789    2.2606 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8414    0.2903   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0380    0.6269   -0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3057    1.6717   -0.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9058   -0.1478    1.0728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2947    0.0306    1.2730 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0654   -0.5246    0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7372   -0.4520    2.4878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3701    1.5308    1.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1631    2.3137    1.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7519    2.9103   -1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3269    3.7945    0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0579    3.6751   -0.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0477    1.8104   -1.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2914    0.7443    0.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1354   -0.1230   -2.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4899   -1.5100   -0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3679    0.3546   -3.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0929   -0.3355   -3.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1325   -1.2762   -0.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4918   -1.2790   -1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3297   -2.0656    1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0436   -3.9574    1.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6200   -4.1098    0.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316   -3.6340   -0.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7599   -0.3028    1.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7490   -1.2444    2.9921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0865   -2.3067   -1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1264   -2.9850    0.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3835   -1.8984   -0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792    1.0560    0.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6727    1.3068   -1.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4906   -0.2276   -1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2808    0.8730    0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1787    3.5723    0.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8537    2.6583    1.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6986    3.0987   -0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0794    1.9880   -0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2388    2.4963   -1.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6514    0.7294   -1.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3606   -0.9360   -0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6512    0.2651   -0.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7468   -1.3426    0.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2151   -1.3165    2.3181 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  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
  3 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  1
 23 26  1  0
 26 27  2  0
 26  2  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  6
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
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 11 39  1  1
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 14 44  1  0
 16 45  1  0
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 21 57  1  0
 24 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(-)-Aurafuron a	ChEBI

Chemical Formula

C₂₂H₃₄O₅

Average Mass

378.5090 Da

Monoisotopic Mass

378.24062 Da

IUPAC Name

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

Traditional Name

(2R)-5-[(2S,3Z,5E,7R,8R,9E)-2,8-dihydroxy-7,9,12-trimethyltrideca-3,5,9-trien-1-yl]-2-hydroxy-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@@H](O)CC1=C(C)C(=O)C(C)(O)O1

InChI Identifier

InChI=1S/C22H34O5/c1-14(2)11-12-16(4)20(24)15(3)9-7-8-10-18(23)13-19-17(5)21(25)22(6,26)27-19/h7-10,12,14-15,18,20,23-24,26H,11,13H2,1-6H3/b9-7+,10-8-,16-12+/t15-,18-,20-,22?/m1/s1

InChI Key

AQQYZHDRTDSOER-LYKBUVKOSA-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
Cyclic ketone
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Organooxygen compound
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	3.2	ALOGPS
logP	3.43	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	10.47	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	112.16 m³·mol⁻¹	ChemAxon
Polarizability	43.59 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

NPA001119

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9948038

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11773355

PDB ID

Not Available

ChEBI ID

156298

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 ]
Frank B, Wenzel SC, Bode HB, Scharfe M, Blocker H, Muller R: From genetic diversity to metabolic unity: studies on the biosynthesis of aurafurones and aurafuron-like structures in myxobacteria and streptomycetes. J Mol Biol. 2007 Nov 16;374(1):24-38. doi: 10.1016/j.jmb.2007.09.015. Epub 2007 Sep 11. [PubMed:17919655 ]
Hartmann O, Kalesse M: The total synthesis of (-)-aurafuron A. Org Lett. 2012 Jun 15;14(12):3064-7. doi: 10.1021/ol3011387. Epub 2012 May 25. [PubMed:22632656 ]

Showing NP-Card for Aurafuron A (NP0005920)

MOL for NP0005920 (Aurafuron A)

3D MOL for NP0005920 (Aurafuron A)

3D SDF for NP0005920 (Aurafuron A)

3D-SDF for NP0005920 (Aurafuron A)

PDB for NP0005920 (Aurafuron A)

3D PDB for NP0005920 (Aurafuron A)

SMILES for NP0005920 (Aurafuron A)

INCHI for NP0005920 (Aurafuron A)

Structure for NP0005920 (Aurafuron A)

3D Structure for NP0005920 (Aurafuron A)