NP-MRD: Showing NP-Card for (1s,2s,10s,13s,15r,18r,19r,21s)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0³,⁸.0¹⁰,²¹.0¹²,²⁰.0¹⁵,¹⁹]docosa-3,8,12(20)-triene-5,17-dione (NP0200492)

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Record Information

Version

2.0

Created at

2022-09-04 19:21:01 UTC

Updated at

2022-09-04 19:21:01 UTC

NP-MRD ID

NP0200492

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,10s,13s,15r,18r,19r,21s)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0³,⁸.0¹⁰,²¹.0¹²,²⁰.0¹⁵,¹⁹]docosa-3,8,12(20)-triene-5,17-dione

Description

Paraherquonin belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. (1s,2s,10s,13s,15r,18r,19r,21s)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0³,⁸.0¹⁰,²¹.0¹²,²⁰.0¹⁵,¹⁹]docosa-3,8,12(20)-triene-5,17-dione is found in Penicillium brasilianum and Penicillium paraherquei. (1s,2s,10s,13s,15r,18r,19r,21s)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0³,⁸.0¹⁰,²¹.0¹²,²⁰.0¹⁵,¹⁹]docosa-3,8,12(20)-triene-5,17-dione was first documented in 2016 (PMID: 27602587). Based on a literature review a small amount of articles have been published on Paraherquonin (PMID: 29881687) (PMID: 29317628).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042221212D          

 31 36  0  0  1  0            999 V2000
    1.4498   -3.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5862   -2.7646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9498   -2.2397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0862   -1.4260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6751   -0.5206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2637    0.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1420    0.8734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954   -0.3237    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0460    0.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7682   -0.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4047   -0.5599    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1258   -0.1592    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0777    0.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8887   -0.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4598    0.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2609   -0.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8320    0.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4911   -0.8668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9201   -1.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6056   -1.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5871   -2.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1189   -1.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6430   -1.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8194   -1.9875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3261   -2.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3591   -2.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4954   -1.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2683   -1.3735    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0605   -1.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8590   -1.1373    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7226   -1.9510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 11 10  1  1  0  0  0
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 12 13  1  6  0  0  0
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 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
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  4 30  1  0  0  0  0
  8 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END

     RDKit          3D

 59 64  0  0  0  0  0  0  0  0999 V2000
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   -4.4210   -0.0494    1.5213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6381   -1.1676    1.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2115   -1.2848   -0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0951   -2.2403   -0.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5066   -1.9301   -0.5058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3900   -2.8140   -0.6919 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8997   -0.6321   -0.3564 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1054    0.4073    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5126    1.6698   -0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4013    0.5684    1.6505 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6821    0.1009   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9131    1.1547   -0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5029    1.4176   -0.5231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1241    2.2778    0.4110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4780    2.0999    0.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6648    0.8836   -0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3990    0.2525   -0.6591 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4896   -0.1562   -2.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3585    0.1768   -1.5941 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1038   -3.1756   -0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3806   -1.8785    1.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410   -2.7351    0.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2612   -0.4450    1.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -2.2382   -1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8532   -4.0291    0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1729   -3.1183    1.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9188   -3.1260    1.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8118   -3.2758   -0.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9053    1.8515   -1.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4208    2.5517    0.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5659    1.6023   -0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7192   -0.0978    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2763    1.6368    1.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4639    0.2437    1.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4681    2.0951   -0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024    1.9997   -1.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9360    0.6763   -2.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5635   -0.2476   -2.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0742   -1.0638   -2.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2105    1.0466   -2.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  4  5  1  0
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 30 31  1  6
 26  2  1  0
 30  4  1  0
 30  8  1  0
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 28 24  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  6
  4 36  1  6
  9 37  1  0
  9 38  1  0
  9 39  1  0
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 10 41  1  0
 11 42  1  1
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 21 53  1  0
 23 54  1  0
 24 55  1  6
 29 56  1  0
 29 57  1  0
 29 58  1  0
 31 59  1  0
M  END


  Mrv1652309042221212D          

 31 36  0  0  1  0            999 V2000
    1.4498   -3.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5862   -2.7646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9498   -2.2397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0862   -1.4260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6751   -0.5206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2637    0.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1420    0.8734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954   -0.3237    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.7682   -0.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8887   -0.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0605   -1.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8590   -1.1373    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  2  3  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0200492

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H]2OC(=O)[C@]3(C)C[C@H]4[C@H](C)C5=CC(=O)OC(C)(C)C5=C[C@@H]5OC1=C([C@]45C)[C@]23O

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O7/c1-10-12-7-16(25)31-21(3,4)13(12)8-15-23(6)14(10)9-22(5)19(26)30-20-24(22,27)18(23)17(29-15)11(2)28-20/h7-8,10-11,14-15,20,27H,9H2,1-6H3/t10-,11+,14+,15+,20-,22+,23-,24+/m1/s1

> <INCHI_KEY>
DIPUOHVSHWSKHT-QUUCWOAOSA-N

> <FORMULA>
C24H28O7

> <MOLECULAR_WEIGHT>
428.481

> <EXACT_MASS>
428.183503242

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
44.191476690255094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,10S,13S,15R,18R,19R,21S)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0^{3,8}.0^{10,21}.0^{12,20}.0^{15,19}]docosa-3,8,12(20)-triene-5,17-dione

> <JCHEM_LOGP>
2.006571527333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.759636374523915

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.80895863861206

> <JCHEM_PKA_STRONGEST_BASIC>
-4.194561465639571

> <JCHEM_POLAR_SURFACE_AREA>
91.29000000000002

> <JCHEM_REFRACTIVITY>
110.35619999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,10S,13S,15R,18R,19R,21S)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0^{3,8}.0^{10,21}.0^{12,20}.0^{15,19}]docosa-3,8,12(20)-triene-5,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.706  -6.679   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.961  -5.161   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.773  -4.181   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.027  -2.662   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.260  -0.972   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.359   0.107   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.132   1.630   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.725  -0.604   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.819   0.933   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.167  -0.065   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.355  -1.045   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.702  -0.297   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.612   1.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.126  -0.883   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.192   0.228   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.687  -0.139   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.753   0.972   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.117  -1.618   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.051  -2.730   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.330  -3.586   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.429  -4.139   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.555  -2.362   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.667  -3.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.129  -3.710   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.209  -5.053   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.404  -4.622   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.658  -3.103   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.101  -2.564   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.580  -2.134   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.470  -2.123   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.216  -3.642   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   30                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   30                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   28                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   14   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25    2   27                                                  
CONECT   27   26   28   30                                                  
CONECT   28   27   24   11   29                                             
CONECT   29   28                                                            
CONECT   30   27    4    8   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₈O₇

Average Mass

428.4810 Da

Monoisotopic Mass

428.18350 Da

IUPAC Name

(1S,2S,10S,13S,15R,18R,19R,21S)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0^{3,8}.0^{10,21}.0^{12,20}.0^{15,19}]docosa-3,8,12(20)-triene-5,17-dione

Traditional Name

(1S,2S,10S,13S,15R,18R,19R,21S)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0^{3,8}.0^{10,21}.0^{12,20}.0^{15,19}]docosa-3,8,12(20)-triene-5,17-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H]2OC(=O)[C@]3(C)C[C@H]4[C@H](C)C5=CC(=O)OC(C)(C)C5=C[C@@H]5OC1=C([C@]45C)[C@]23O

InChI Identifier

InChI=1S/C24H28O7/c1-10-12-7-16(25)31-21(3,4)13(12)8-15-23(6)14(10)9-22(5)19(26)30-20-24(22,27)18(23)17(29-15)11(2)28-20/h7-8,10-11,14-15,20,27H,9H2,1-6H3/t10-,11+,14+,15+,20-,22+,23-,24+/m1/s1

InChI Key

DIPUOHVSHWSKHT-QUUCWOAOSA-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
Penicillium brasilianum	LOTUS Database	35616633
Penicillium paraherquei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Substituents

Furopyran
Dihydropyranone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Pyran
Cyclic alcohol
Dihydrofuran
Furan
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Acetal
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	2.01	ChemAxon
pKa (Strongest Acidic)	11.81	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	110.36 m³·mol⁻¹	ChemAxon
Polarizability	44.19 Å³	ChemAxon
Number of Rings	6	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

Not Available

Chemspider ID

58828706

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122394428

PDB ID

Not Available

ChEBI ID

156379

Good Scents ID

Not Available

References

General References

Matsuda Y, Iwabuchi T, Fujimoto T, Awakawa T, Nakashima Y, Mori T, Zhang H, Hayashi F, Abe I: Discovery of Key Dioxygenases that Diverged the Paraherquonin and Acetoxydehydroaustin Pathways in Penicillium brasilianum. J Am Chem Soc. 2016 Sep 28;138(38):12671-7. doi: 10.1021/jacs.6b08424. Epub 2016 Sep 16. [PubMed:27602587 ]
Zhang T, Wan J, Zhan Z, Bai J, Liu B, Hu Y: Activation of an unconventional meroterpenoid gene cluster in Neosartorya glabra leads to the production of new berkeleyacetals. Acta Pharm Sin B. 2018 May;8(3):478-487. doi: 10.1016/j.apsb.2017.12.005. Epub 2018 Feb 3. [PubMed:29881687 ]
Nakashima Y, Mori T, Nakamura H, Awakawa T, Hoshino S, Senda M, Senda T, Abe I: Structure function and engineering of multifunctional non-heme iron dependent oxygenases in fungal meroterpenoid biosynthesis. Nat Commun. 2018 Jan 9;9(1):104. doi: 10.1038/s41467-017-02371-w. [PubMed:29317628 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,10s,13s,15r,18r,19r,21s)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0³,⁸.0¹⁰,²¹.0¹²,²⁰.0¹⁵,¹⁹]docosa-3,8,12(20)-triene-5,17-dione (NP0200492)

MOL for NP0200492 ((1s,2s,10s,13s,15r,18r,19r,21s)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0³,⁸.0¹⁰,²¹.0¹²,²⁰.0¹⁵,¹⁹]docosa-3,8,12(20)-triene-5,17-dione)

3D MOL for NP0200492 ((1s,2s,10s,13s,15r,18r,19r,21s)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0³,⁸.0¹⁰,²¹.0¹²,²⁰.0¹⁵,¹⁹]docosa-3,8,12(20)-triene-5,17-dione)

3D SDF for NP0200492 ((1s,2s,10s,13s,15r,18r,19r,21s)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0³,⁸.0¹⁰,²¹.0¹²,²⁰.0¹⁵,¹⁹]docosa-3,8,12(20)-triene-5,17-dione)

3D-SDF for NP0200492 ((1s,2s,10s,13s,15r,18r,19r,21s)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0³,⁸.0¹⁰,²¹.0¹²,²⁰.0¹⁵,¹⁹]docosa-3,8,12(20)-triene-5,17-dione)

PDB for NP0200492 ((1s,2s,10s,13s,15r,18r,19r,21s)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0³,⁸.0¹⁰,²¹.0¹²,²⁰.0¹⁵,¹⁹]docosa-3,8,12(20)-triene-5,17-dione)

3D PDB for NP0200492 ((1s,2s,10s,13s,15r,18r,19r,21s)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0³,⁸.0¹⁰,²¹.0¹²,²⁰.0¹⁵,¹⁹]docosa-3,8,12(20)-triene-5,17-dione)

SMILES for NP0200492 ((1s,2s,10s,13s,15r,18r,19r,21s)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0³,⁸.0¹⁰,²¹.0¹²,²⁰.0¹⁵,¹⁹]docosa-3,8,12(20)-triene-5,17-dione)

INCHI for NP0200492 ((1s,2s,10s,13s,15r,18r,19r,21s)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0³,⁸.0¹⁰,²¹.0¹²,²⁰.0¹⁵,¹⁹]docosa-3,8,12(20)-triene-5,17-dione)

Structure for NP0200492 ((1s,2s,10s,13s,15r,18r,19r,21s)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0³,⁸.0¹⁰,²¹.0¹²,²⁰.0¹⁵,¹⁹]docosa-3,8,12(20)-triene-5,17-dione)

3D Structure for NP0200492 ((1s,2s,10s,13s,15r,18r,19r,21s)-19-hydroxy-2,7,7,13,18,21-hexamethyl-6,11,14,16-tetraoxahexacyclo[16.3.1.0³,⁸.0¹⁰,²¹.0¹²,²⁰.0¹⁵,¹⁹]docosa-3,8,12(20)-triene-5,17-dione)