NP-MRD: Showing NP-Card for (11e)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone (NP0272126)

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Record Information

Version

2.0

Created at

2022-09-08 18:38:26 UTC

Updated at

2022-09-08 18:38:27 UTC

NP-MRD ID

NP0272126

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(11e)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone

Description

Vermiculine belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (11e)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone is found in Talaromyces flavus. (11e)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone was first documented in 2019 (PMID: 30672028). Based on a literature review very few articles have been published on Vermiculine (PMID: 34124819).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082220382D          

 28 28  0  0  0  0            999 V2000
    0.8936    3.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1186    2.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5437    1.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9184    2.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7183    2.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5182    1.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7432    1.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5430    0.8161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1683    0.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3932   -0.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8183   -0.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0184   -0.7569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0433   -1.7527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4684   -2.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933   -3.1381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1184   -3.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3434   -4.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3185   -3.5278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6685   -2.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4435   -1.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6436   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0687   -1.7382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4187   -0.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9936    0.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7686    1.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313    1.2346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3435    1.6243    0.0000 O   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
  2  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  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 22  1  4  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  5 28  1  0  0  0  0
M  END

     RDKit          3D

 52 52  0  0  0  0  0  0  0  0999 V2000
   -6.2315    1.7119    0.9944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9293    1.0265    0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7917    0.6795   -0.4759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9913    0.8580    1.7752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6686    0.2092    1.4099 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9688    0.0407    2.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160   -0.8079    2.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1754   -0.6557    1.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3910    0.5002    1.1334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -1.5616    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6207   -2.4210   -0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9799   -2.7313    0.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2587   -3.9022    0.3569 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8994   -1.6966    0.0369 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0040   -0.6029   -0.8214 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4782   -0.3100   -1.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2892   -0.2859    0.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7466   -0.0204   -0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8177   -0.4741    1.1916 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2249   -0.6208   -2.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2425    0.5224   -2.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0870    0.0816   -2.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1006   -1.1449   -3.1590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3298    0.7757   -2.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0795    1.4147   -1.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9606    1.7052   -0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7780    2.9896   -0.3201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0020    0.9297    0.5068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0901    1.2104    0.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1623    2.7236    0.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4179    1.7864    2.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5089    0.2623    2.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8298    1.8587    2.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9094   -0.8209    1.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6685   -0.2984    3.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6438    1.0661    3.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059   -1.8111    2.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0307   -0.3820    3.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753   -1.4931   -0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2216   -3.0412   -1.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7028    0.3063   -0.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5194    0.6181   -1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8047   -1.1849   -1.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2458   -0.8776   -0.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9486    0.9282   -0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1921    0.0949    0.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9609   -0.5068   -2.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7384   -1.5976   -2.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1271    1.0603   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6749    1.2924   -2.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7529    0.7272   -3.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246    1.8689   -2.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 19  2  0
 17 16  1  0
 16 15  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 16 42  1  0
 16 43  1  0
 15 41  1  1
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 24 51  1  0
 25 52  1  0
  5 34  1  6
  4 32  1  0
  4 33  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  7 38  1  0
 10 39  1  0
 11 40  1  0
M  END


  Mrv1652309082220382D          

 28 28  0  0  0  0            999 V2000
    0.8936    3.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1186    2.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5437    1.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9184    2.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7183    2.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5182    1.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7432    1.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5430    0.8161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1683    0.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3932   -0.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8183   -0.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0184   -0.7569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0433   -1.7527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4684   -2.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933   -3.1381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1184   -3.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3434   -4.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3185   -3.5278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6685   -2.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4435   -1.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6436   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0687   -1.7382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4187   -0.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9936    0.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7686    1.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313    1.2346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3435    1.6243    0.0000 O   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
  2  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  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 22  1  4  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  5 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272126

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)CC1CCC(=O)\C=C\C(=O)OC(CC(C)=O)CCC(=O)C=CC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O8/c1-13(21)11-17-7-3-15(23)6-10-20(26)28-18(12-14(2)22)8-4-16(24)5-9-19(25)27-17/h5-6,9-10,17-18H,3-4,7-8,11-12H2,1-2H3/b9-5+,10-6?

> <INCHI_KEY>
CFDVIOQSLRJWSU-IIWBTEQSSA-N

> <FORMULA>
C20H24O8

> <MOLECULAR_WEIGHT>
392.404

> <EXACT_MASS>
392.147117733

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.76517463708031

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(11E)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone

> <JCHEM_LOGP>
1.9986603639999991

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.58506347772258

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.174161965264837

> <JCHEM_PKA_STRONGEST_BASIC>
-6.530661030857388

> <JCHEM_POLAR_SURFACE_AREA>
120.88

> <JCHEM_REFRACTIVITY>
99.65559999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(11E)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       1.668   5.995   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.088   4.514   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.015   3.409   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.581   4.137   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.655   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.074   3.759   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.567   3.382   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.987   1.901   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.480   1.523   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.914   0.796   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.334  -0.686   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.261  -1.790   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.768  -1.413   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.681  -3.272   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.608  -4.376   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.028  -5.858   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.954  -6.962   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.374  -8.444   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.461  -6.585   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.115  -3.999   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.695  -2.517   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.201  -2.140   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.128  -3.245   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.782  -0.659   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.855   0.446   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.435   1.928   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.058   2.305   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.508   3.032   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    5                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   56    0
END

View in JSmol

Synonyms

Value	Source
Vermiculin	MeSH

Chemical Formula

C₂₀H₂₄O₈

Average Mass

392.4040 Da

Monoisotopic Mass

392.14712 Da

IUPAC Name

(11E)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone

Traditional Name

(11E)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone

CAS Registry Number

Not Available

SMILES

CC(=O)CC1CCC(=O)\C=C\C(=O)OC(CC(C)=O)CCC(=O)C=CC(=O)O1

InChI Identifier

InChI=1S/C20H24O8/c1-13(21)11-17-7-3-15(23)6-10-20(26)28-18(12-14(2)22)8-4-16(24)5-9-19(25)27-17/h5-6,9-10,17-18H,3-4,7-8,11-12H2,1-2H3/b9-5+,10-6?

InChI Key

CFDVIOQSLRJWSU-IIWBTEQSSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Talaromyces flavus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2	ChemAxon
pKa (Strongest Acidic)	18.17	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	120.88 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.66 m³·mol⁻¹	ChemAxon
Polarizability	38.77 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018839

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vermiculine

METLIN ID

Not Available

PubChem Compound

139589197

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu H, Ottosen RN, Jennet KM, Svenningsen EB, Kristensen TF, Biltoft M, Jakobsen MR, Poulsen TB: Macrodiolide Diversification Reveals Broad Immunosuppressive Activity That Impairs the cGAS-STING Pathway. Angew Chem Int Ed Engl. 2021 Aug 16;60(34):18734-18741. doi: 10.1002/anie.202105793. Epub 2021 Jul 16. [PubMed:34124819 ]
Steib P, Breit B: Concise Total Synthesis of (-)-Vermiculine through a Rhodium-Catalyzed C(2) -Symmetric Dimerization Strategy. Chemistry. 2019 Mar 7;25(14):3532-3535. doi: 10.1002/chem.201900216. Epub 2019 Feb 12. [PubMed:30672028 ]
LOTUS database [Link]

Showing NP-Card for (11e)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone (NP0272126)

MOL for NP0272126 ((11e)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone)

3D MOL for NP0272126 ((11e)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone)

3D SDF for NP0272126 ((11e)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone)

3D-SDF for NP0272126 ((11e)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone)

PDB for NP0272126 ((11e)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone)

3D PDB for NP0272126 ((11e)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone)

SMILES for NP0272126 ((11e)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone)

INCHI for NP0272126 ((11e)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone)

Structure for NP0272126 ((11e)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone)

3D Structure for NP0272126 ((11e)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone)