NP-MRD: Showing NP-Card for Citreoviridin (NP0015253)

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Record Information

Version

2.0

Created at

2021-01-06 00:25:43 UTC

Updated at

2021-07-15 17:19:27 UTC

NP-MRD ID

NP0015253

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Citreoviridin

Provided By

NPAtlas

Description

Citreoviridin is found in Aspergillus, Aspergillus aureoterreus and Penicillium miczynskii. Citreoviridin was first documented in 2016 (PMID: 26954888). Based on a literature review very few articles have been published on 6-[(1E,3E,5E,7E)-8-[(2S,3R,4R,5R)-3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl]-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methyl-2H-pyran-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117173D          

 59 60  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242117173D          

 59 60  0  0  0  0            999 V2000
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   10.1359   -2.2821   -3.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4217   -2.2582   -1.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4835   -0.7315   -2.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1458    0.0765   -0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8348    1.8108    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9603   -0.7423   -0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5585    1.6083    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5649   -0.9091   -0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1606    1.4561    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8172   -1.1226   -0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0266    1.5179    2.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3307    2.0621    1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6542    2.2394    1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0689   -1.3722   -0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.2486   -0.8806    1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1219   -1.3221   -1.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8614   -2.6555   -0.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6005   -2.3594   -1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.6236    0.8154   -0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7182    2.2907   -0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3021    0.3599   -1.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9275    1.7197   -0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4660    1.7325    2.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5249   -2.0460   -1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4905   -1.5553   -2.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1106   -0.5464   -2.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  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  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  6  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
  8 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28  3  1  0  0  0  0
 26 18  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  4 33  1  0  0  0  0
  9 34  1  0  0  0  0
 10 35  1  0  0  0  0
 11 36  1  0  0  0  0
 12 37  1  0  0  0  0
 13 38  1  0  0  0  0
 14 39  1  0  0  0  0
 16 40  1  0  0  0  0
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 16 42  1  0  0  0  0
 17 43  1  0  0  0  0
 19 44  1  0  0  0  0
 19 45  1  0  0  0  0
 19 46  1  0  0  0  0
 21 47  1  1  0  0  0
 22 48  1  0  0  0  0
 22 49  1  0  0  0  0
 22 50  1  0  0  0  0
 24 51  1  0  0  0  0
 24 52  1  0  0  0  0
 24 53  1  0  0  0  0
 25 54  1  0  0  0  0
 26 55  1  6  0  0  0
 27 56  1  0  0  0  0
 29 57  1  0  0  0  0
 29 58  1  0  0  0  0
 29 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0015253

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])[C@@](O[C@]([H])(C([H])([H])[H])[C@@]1(O[H])C([H])([H])[H])(C(\[H])=C(\C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])C1=C(C(OC([H])([H])[H])=C([H])C(=O)O1)C([H])([H])[H])/C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O6/c1-15(14-22(4)21(25)23(5,26)17(3)29-22)11-9-7-8-10-12-18-16(2)19(27-6)13-20(24)28-18/h7-14,17,21,25-26H,1-6H3/b8-7+,11-9+,12-10+,15-14+/t17-,21+,22+,23+/m1/s1

> <INCHI_KEY>
JLSVDPQAIKFBTO-OMCRQDLASA-N

> <FORMULA>
C23H30O6

> <MOLECULAR_WEIGHT>
402.487

> <EXACT_MASS>
402.204238686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
46.13047467750626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(1E,3E,5E,7E)-8-[(2S,3R,4R,5R)-3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl]-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methyl-2H-pyran-2-one

> <ALOGPS_LOGP>
3.89

> <JCHEM_LOGP>
2.4590114166666655

> <ALOGPS_LOGS>
-4.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.027781536676848

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.600983692839542

> <JCHEM_PKA_STRONGEST_BASIC>
-3.662280515270547

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
118.01280000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(1E,3E,5E,7E)-8-[(2S,3R,4R,5R)-3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl]-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 60  0  0  0  0  0  0  0  0999 V2000
    9.9599   -1.6837   -2.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5725   -1.4978   -2.0246 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1684   -0.5544   -1.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0738    0.1974   -0.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6145    1.1085    0.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3943    1.8408    1.2062 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4011    0.5484    0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0302    0.8529    0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9545    0.1881    0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6255    0.6793    0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5155    0.0218    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2165    0.5170    0.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617   -0.1979    0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2166    0.2655    0.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3902    1.5202    1.5447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2785   -0.4325    0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6303   -0.1444    0.8663 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7991   -0.3290    2.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3791   -1.2610    0.3884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6896   -0.9223    0.2933 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3675   -1.8507   -0.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5564    0.4402   -0.3617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8004    1.2095   -0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2783    0.2868   -1.6883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3610    1.0094    0.4460 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0104    1.6379    1.5143 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7868   -0.3749   -0.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8962   -1.1670   -1.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1359   -2.2821   -3.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4217   -2.2582   -1.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4835   -0.7315   -2.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1458    0.0765   -0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8348    1.8108    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9603   -0.7423   -0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5585    1.6083    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5649   -0.9091   -0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1606    1.4561    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8172   -1.1226   -0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0266    1.5179    2.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3307    2.0621    1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6542    2.2394    1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0689   -1.3722   -0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0883    0.3560    2.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8485   -0.2207    2.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4765   -1.3619    2.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2486   -0.8806    1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1219   -1.3221   -1.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8614   -2.6555   -0.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6005   -2.3594   -1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1508    1.1677    0.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6236    0.8154   -0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7182    2.2907   -0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3021    0.3599   -1.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9275    1.7197   -0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4660    1.7325    2.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5249   -2.0460   -1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4905   -1.5553   -2.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1106   -0.5464   -2.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 18 17  1  1
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  6
 23 26  1  0
 26 27  1  0
  8 28  2  0
 28 29  1  0
 28  3  1  0
 26 18  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 21 47  1  1
 22 48  1  0
 22 49  1  0
 22 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 26 55  1  6
 27 56  1  0
 29 57  1  0
 29 58  1  0
 29 59  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       9.960  -1.684  -2.241  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.572  -1.498  -2.025  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.168  -0.554  -1.095  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.074   0.197  -0.386  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.614   1.109   0.514  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.394   1.841   1.206  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.349   1.245   0.681  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.401   0.548   0.029  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.030   0.853   0.361  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.954   0.188   0.100  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.626   0.679   0.528  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.516   0.022   0.275  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.217   0.517   0.701  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.862  -0.198   0.413  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.217   0.266   0.826  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.390   1.520   1.545  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.279  -0.433   0.551  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.630  -0.144   0.866  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.799  -0.329   2.394  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.379  -1.261   0.388  0.00  0.00           O+0
HETATM   21  C   UNK     0      -6.690  -0.922   0.293  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.367  -1.851  -0.690  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.556   0.440  -0.362  0.00  0.00           C+0
HETATM   24  C   UNK     0      -7.800   1.210  -0.145  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.278   0.287  -1.688  0.00  0.00           O+0
HETATM   26  C   UNK     0      -5.361   1.009   0.446  0.00  0.00           C+0
HETATM   27  O   UNK     0      -6.010   1.638   1.514  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.787  -0.375  -0.885  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.896  -1.167  -1.736  0.00  0.00           C+0
HETATM   30  H   UNK     0      10.136  -2.282  -3.179  0.00  0.00           H+0
HETATM   31  H   UNK     0      10.422  -2.258  -1.411  0.00  0.00           H+0
HETATM   32  H   UNK     0      10.483  -0.732  -2.377  0.00  0.00           H+0
HETATM   33  H   UNK     0      10.146   0.077  -0.531  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.835   1.811   0.921  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.960  -0.742  -0.381  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.559   1.608   1.065  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.565  -0.909  -0.262  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.161   1.456   1.248  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.817  -1.123  -0.119  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.027   1.518   2.587  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.331   2.062   1.396  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.654   2.239   1.042  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.069  -1.372  -0.005  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.088   0.356   2.871  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.848  -0.221   2.681  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.476  -1.362   2.654  0.00  0.00           H+0
HETATM   47  H   UNK     0      -7.249  -0.881   1.244  0.00  0.00           H+0
HETATM   48  H   UNK     0      -8.122  -1.322  -1.308  0.00  0.00           H+0
HETATM   49  H   UNK     0      -7.861  -2.656  -0.074  0.00  0.00           H+0
HETATM   50  H   UNK     0      -6.601  -2.359  -1.297  0.00  0.00           H+0
HETATM   51  H   UNK     0      -8.151   1.168   0.919  0.00  0.00           H+0
HETATM   52  H   UNK     0      -8.624   0.815  -0.758  0.00  0.00           H+0
HETATM   53  H   UNK     0      -7.718   2.291  -0.382  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.302   0.360  -1.837  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.928   1.720  -0.283  0.00  0.00           H+0
HETATM   56  H   UNK     0      -5.466   1.732   2.326  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.525  -2.046  -1.201  0.00  0.00           H+0
HETATM   58  H   UNK     0       6.490  -1.555  -2.632  0.00  0.00           H+0
HETATM   59  H   UNK     0       5.111  -0.546  -2.171  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5   33                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   28                                                  
CONECT    9    8   10   34                                                  
CONECT   10    9   11   35                                                  
CONECT   11   10   12   36                                                  
CONECT   12   11   13   37                                                  
CONECT   13   12   14   38                                                  
CONECT   14   13   15   39                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   40   41   42                                             
CONECT   17   15   18   43                                                  
CONECT   18   17   19   20   26                                             
CONECT   19   18   44   45   46                                             
CONECT   20   18   21                                                       
CONECT   21   20   22   23   47                                             
CONECT   22   21   48   49   50                                             
CONECT   23   21   24   25   26                                             
CONECT   24   23   51   52   53                                             
CONECT   25   23   54                                                       
CONECT   26   23   27   18   55                                             
CONECT   27   26   56                                                       
CONECT   28    8   29    3                                                  
CONECT   29   28   57   58   59                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    4                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   11                                                            
CONECT   37   12                                                            
CONECT   38   13                                                            
CONECT   39   14                                                            
CONECT   40   16                                                            
CONECT   41   16                                                            
CONECT   42   16                                                            
CONECT   43   17                                                            
CONECT   44   19                                                            
CONECT   45   19                                                            
CONECT   46   19                                                            
CONECT   47   21                                                            
CONECT   48   22                                                            
CONECT   49   22                                                            
CONECT   50   22                                                            
CONECT   51   24                                                            
CONECT   52   24                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   26                                                            
CONECT   56   27                                                            
CONECT   57   29                                                            
CONECT   58   29                                                            
CONECT   59   29                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  120    0
END

RDKit          3D

59 60  0  0  0  0  0  0  0  0999 V2000
    9.9599   -1.6837   -2.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5725   -1.4978   -2.0246 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1684   -0.5544   -1.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0738    0.1974   -0.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6145    1.1085    0.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3943    1.8408    1.2062 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3487    1.2449    0.6812 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4011    0.5484    0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0302    0.8529    0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9545    0.1881    0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6255    0.6793    0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5155    0.0218    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2165    0.5170    0.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617   -0.1979    0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2166    0.2655    0.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3902    1.5202    1.5447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2785   -0.4325    0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6303   -0.1444    0.8663 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7991   -0.3290    2.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3791   -1.2610    0.3884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6896   -0.9223    0.2933 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3675   -1.8507   -0.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5564    0.4402   -0.3617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8004    1.2095   -0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2783    0.2868   -1.6883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3610    1.0094    0.4460 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0104    1.6379    1.5143 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7868   -0.3749   -0.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8962   -1.1670   -1.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1359   -2.2821   -3.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4217   -2.2582   -1.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4835   -0.7315   -2.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1458    0.0765   -0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8348    1.8108    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9603   -0.7423   -0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5585    1.6083    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5649   -0.9091   -0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1606    1.4561    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8172   -1.1226   -0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0266    1.5179    2.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3307    2.0621    1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6542    2.2394    1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0689   -1.3722   -0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0883    0.3560    2.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8485   -0.2207    2.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4765   -1.3619    2.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2486   -0.8806    1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1219   -1.3221   -1.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8614   -2.6555   -0.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6005   -2.3594   -1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1508    1.1677    0.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6236    0.8154   -0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7182    2.2907   -0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3021    0.3599   -1.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9275    1.7197   -0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4660    1.7325    2.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5249   -2.0460   -1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4905   -1.5553   -2.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1106   -0.5464   -2.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 18 17  1  1
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  6
 23 26  1  0
 26 27  1  0
  8 28  2  0
 28 29  1  0
 28  3  1  0
 26 18  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 21 47  1  1
 22 48  1  0
 22 49  1  0
 22 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 26 55  1  6
 27 56  1  0
 29 57  1  0
 29 58  1  0
 29 59  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀O₆

Average Mass

402.4870 Da

Monoisotopic Mass

402.20424 Da

IUPAC Name

6-[(1E,3E,5E,7E)-8-[(2S,3R,4R,5R)-3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl]-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methyl-2H-pyran-2-one

Traditional Name

6-[(1E,3E,5E,7E)-8-[(2S,3R,4R,5R)-3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl]-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC(\C=C\C=C\C=C\C(\C)=C\[C@]2(C)O[C@H](C)[C@](C)(O)[C@H]2O)=C1C

InChI Identifier

InChI=1S/C23H30O6/c1-15(14-22(4)21(25)23(5,26)17(3)29-22)11-9-7-8-10-12-18-16(2)19(27-6)13-20(24)28-18/h7-14,17,21,25-26H,1-6H3/b8-7+,11-9+,12-10+,15-14+/t17-,21+,22+,23+/m1/s1

InChI Key

JLSVDPQAIKFBTO-OMCRQDLASA-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
Aspergillus	NPAtlas	26954888
Aspergillus aureoterreus	LOTUS Database	35616633
Penicillium miczynskii	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Aspergillus terreus	KNApSAcK Database	22123792
Penicillium citreo-viride	KNApSAcK Database	22123792
Penicillium ochrosalmoneum	KNApSAcK Database	22123792
Penicillium toxicarium	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

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	3.89	ALOGPS
logP	2.46	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	12.6	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	118.01 m³·mol⁻¹	ChemAxon
Polarizability	46.13 Å³	ChemAxon
Number of Rings	2	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

NPA023799

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00055193

Chemspider ID

4940705

KEGG Compound ID

C16766

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6436023

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lin TS, Chiang YM, Wang CC: Biosynthetic Pathway of the Reduced Polyketide Product Citreoviridin in Aspergillus terreus var. aureus Revealed by Heterologous Expression in Aspergillus nidulans. Org Lett. 2016 Mar 18;18(6):1366-9. doi: 10.1021/acs.orglett.6b00299. Epub 2016 Mar 8. [PubMed:26954888 ]

Showing NP-Card for Citreoviridin (NP0015253)

MOL for NP0015253 (Citreoviridin)

3D MOL for NP0015253 (Citreoviridin)

3D SDF for NP0015253 (Citreoviridin)

3D-SDF for NP0015253 (Citreoviridin)

PDB for NP0015253 (Citreoviridin)

3D PDB for NP0015253 (Citreoviridin)

SMILES for NP0015253 (Citreoviridin)

INCHI for NP0015253 (Citreoviridin)

Structure for NP0015253 (Citreoviridin)

3D Structure for NP0015253 (Citreoviridin)