NP-MRD: Showing NP-Card for 22-epoxyberkeleydione (NP0007522)

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Record Information

Version

2.0

Created at

2020-12-09 04:22:57 UTC

Updated at

2024-09-03 04:15:51 UTC

NP-MRD ID

NP0007522

Natural Product DOI

https://doi.org/10.57994/0430

Secondary Accession Numbers

None

Natural Product Identification

Common Name

22-epoxyberkeleydione

Provided By

NPAtlas

Description

22-epoxyberkeleydione is found in Penicillium and Talaromyces minioluteus. 22-epoxyberkeleydione was first documented in 2023 (PMID: 36526742). Based on a literature review very few articles have been published on 22-epoxyberkeleydione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118413D          

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M  END

     RDKit          3D

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M  END


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   -2.3604   -3.1898    1.4148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2189   -1.6964   -0.4232 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1740   -2.5722   -1.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8494   -1.8514   -0.9768 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1526   -0.8887   -0.4252 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4821   -1.1627   -0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6833   -2.1401   -2.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6133   -0.5715   -0.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8380   -1.0271   -1.3402 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0553   -0.7021   -0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1611   -0.7034   -1.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9320   -0.4226    0.7860 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0209    0.5370    1.2688 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7252    0.1659    2.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6450    1.8941    1.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7671    0.4424    0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8419    1.3382    0.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5246    1.5837    0.1433 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2704    0.5324   -0.4729 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4187    0.8720   -1.9628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6354   -0.2594   -0.7071 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3691    0.0391   -1.8578 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0048    0.0243   -0.6445 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2322   -1.4302    3.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8153   -2.6758   -2.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2012   -2.1290   -1.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1967   -3.5855   -0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4936   -2.8773   -0.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9794   -1.7874   -2.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2099   -1.1484    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4194   -1.6934   -2.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8226   -2.3910   -2.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1119   -3.1114   -1.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9653   -0.4775   -2.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8703   -2.1329   -1.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6886    1.1080    3.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8190   -0.4417    2.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5698   -0.4197    3.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6114    1.8902    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7984    2.2919    2.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9677    2.5688    0.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1721    1.9945    1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6990    2.4464   -0.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0414    2.1712    0.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470    0.7547   -2.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0698    0.2050   -2.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6038    1.9451   -2.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4122    1.0249   -2.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5870   -0.7949   -2.5901 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
  5  3  1  1  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  0  0  0  0
  8 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 13 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30  5  1  0  0  0  0
 32 34  1  1  0  0  0
 32  5  1  0  0  0  0
 30 16  1  0  0  0  0
 27 19  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  9 38  1  0  0  0  0
  9 39  1  0  0  0  0
  9 40  1  0  0  0  0
 10 41  1  0  0  0  0
 14 42  1  0  0  0  0
 14 43  1  0  0  0  0
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 15 46  1  0  0  0  0
 16 47  1  1  0  0  0
 18 48  1  0  0  0  0
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 20 51  1  0  0  0  0
 20 52  1  0  0  0  0
 25 53  1  0  0  0  0
 25 54  1  0  0  0  0
 25 55  1  0  0  0  0
 26 56  1  0  0  0  0
 26 57  1  0  0  0  0
 26 58  1  0  0  0  0
 28 59  1  0  0  0  0
 29 60  1  0  0  0  0
 29 61  1  0  0  0  0
 31 62  1  0  0  0  0
 31 63  1  0  0  0  0
 31 64  1  0  0  0  0
 33 65  1  0  0  0  0
 33 66  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0007522

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1(C(=O)[C@]2(C([H])([H])[H])C([H])([H])[C@@]3([H])C(=C4C(=C([H])C([H])([H])[C@]3(C([H])([H])[H])[C@](C(=O)OC([H])([H])[H])(C1=O)[C@]21OC1([H])[H])C(OC(=O)C4([H])[H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O8/c1-13-14-10-17(27)34-21(2,3)15(14)8-9-22(4)16(13)11-23(5)18(28)24(6,31)19(29)26(22,20(30)32-7)25(23)12-33-25/h8,16,31H,9-12H2,1-7H3/t16-,22-,23-,24-,25+,26+/m0/s1

> <INCHI_KEY>
DRMIYYPESWIXHQ-PSNFPAJSSA-N

> <FORMULA>
C26H32O8

> <MOLECULAR_WEIGHT>
472.534

> <EXACT_MASS>
472.20971799

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.563386178731356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1'R,2R,2'S,12'S,14'R,16'S)-16'-hydroxy-2',6',6',11',14',16'-hexamethyl-8',15',17'-trioxo-7'-oxaspiro[oxirane-2,18'-tetracyclo[12.3.1.0^{2,12}.0^{5,10}]octadecane]-4',10'-diene-1'-carboxylate

> <ALOGPS_LOGP>
2.59

> <JCHEM_LOGP>
2.330900041333334

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.493394151558357

> <JCHEM_PKA_STRONGEST_BASIC>
-4.220250654629465

> <JCHEM_POLAR_SURFACE_AREA>
119.5

> <JCHEM_REFRACTIVITY>
120.71969999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1'R,2R,2'S,12'S,14'R,16'S)-16'-hydroxy-2',6',6',11',14',16'-hexamethyl-8',15',17'-trioxo-7'-oxaspiro[oxirane-2,18'-tetracyclo[12.3.1.0^{2,12}.0^{5,10}]octadecane]-4',10'-diene-1'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 66 70  0  0  0  0  0  0  0  0999 V2000
   -3.0148    4.0461   -1.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5111    2.7313   -1.0688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2359    1.9983    0.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4878    2.6422    1.1486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7069    0.6168    0.1025 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6651    0.1381    1.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9220    0.5839    2.3593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838   -0.9408    1.9545 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3055   -1.3849    3.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9181   -0.5354    1.9288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3805   -2.0556    0.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3604   -3.1898    1.4148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2189   -1.6964   -0.4232 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1740   -2.5722   -1.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8494   -1.8514   -0.9768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -0.8887   -0.4252 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4821   -1.1627   -0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6833   -2.1401   -2.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6133   -0.5715   -0.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8380   -1.0271   -1.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0553   -0.7021   -0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1611   -0.7034   -1.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9320   -0.4226    0.7860 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0209    0.5370    1.2688 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7252    0.1659    2.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6450    1.8941    1.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7671    0.4424    0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8419    1.3382    0.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5246    1.5837    0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2704    0.5324   -0.4729 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4187    0.8720   -1.9628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6354   -0.2594   -0.7071 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3691    0.0391   -1.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0048    0.0243   -0.6445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2730    4.3212   -2.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9908    4.0038   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3380    4.7691   -0.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7087   -0.5644    4.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8455   -2.3304    3.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2322   -1.4302    3.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9938    0.4142    2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8153   -2.6758   -2.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2012   -2.1290   -1.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1967   -3.5855   -0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4936   -2.8773   -0.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9794   -1.7874   -2.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2099   -1.1484    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4194   -1.6934   -2.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9653   -0.4775   -2.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8703   -2.1329   -1.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6886    1.1080    3.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8190   -0.4417    2.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7984    2.2919    2.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9677    2.5688    0.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1721    1.9945    1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6990    2.4464   -0.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0414    2.1712    0.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470    0.7547   -2.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0698    0.2050   -2.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6038    1.9451   -2.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4122    1.0249   -2.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5870   -0.7949   -2.5901 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
  5  3  1  1
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  1
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  1
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 27 28  2  0
 28 29  1  0
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 30 31  1  6
 13 32  1  0
 32 33  1  0
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 30  5  1  0
 32 34  1  1
 32  5  1  0
 30 16  1  0
 27 19  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  9 38  1  0
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 29 60  1  0
 29 61  1  0
 31 62  1  0
 31 63  1  0
 31 64  1  0
 33 65  1  0
 33 66  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      -3.015   4.046  -1.058  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.511   2.731  -1.069  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.236   1.998   0.070  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.488   2.642   1.149  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.707   0.617   0.103  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.665   0.138   1.531  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.922   0.584   2.359  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.584  -0.941   1.954  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.305  -1.385   3.375  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.918  -0.535   1.929  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.381  -2.056   0.986  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.360  -3.190   1.415  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.219  -1.696  -0.423  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.174  -2.572  -1.232  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.849  -1.851  -0.977  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.153  -0.889  -0.425  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.482  -1.163  -0.995  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.683  -2.140  -2.071  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.613  -0.572  -0.602  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.838  -1.027  -1.340  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.055  -0.702  -0.544  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.161  -0.703  -1.156  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.932  -0.423   0.786  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.021   0.537   1.269  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.725   0.166   2.714  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.645   1.894   1.156  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.767   0.442   0.442  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.842   1.338   0.719  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.525   1.584   0.143  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.270   0.532  -0.473  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.419   0.872  -1.963  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.635  -0.259  -0.707  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.369   0.039  -1.858  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.005   0.024  -0.645  0.00  0.00           O+0
HETATM   35  H   UNK     0      -3.273   4.321  -2.104  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.991   4.004  -0.508  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.338   4.769  -0.580  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.709  -0.564   4.031  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.845  -2.330   3.544  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.232  -1.430   3.558  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.994   0.414   2.191  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.815  -2.676  -2.259  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.201  -2.129  -1.171  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.197  -3.586  -0.755  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.494  -2.877  -0.770  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.979  -1.787  -2.088  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.210  -1.148   0.679  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.419  -1.693  -2.805  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.823  -2.391  -2.684  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.112  -3.111  -1.723  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.965  -0.478  -2.302  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.870  -2.133  -1.460  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.689   1.108   3.313  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.819  -0.442   2.819  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.570  -0.420   3.133  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.611   1.890   0.592  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.798   2.292   2.183  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.968   2.569   0.600  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.172   1.994   1.540  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.699   2.446  -0.597  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.041   2.171   0.946  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.647   0.755  -2.353  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.070   0.205  -2.508  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.604   1.945  -2.028  0.00  0.00           H+0
HETATM   65  H   UNK     0      -3.412   1.025  -2.404  0.00  0.00           H+0
HETATM   66  H   UNK     0      -3.587  -0.795  -2.590  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   30   32                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   11                                             
CONECT    9    8   38   39   40                                             
CONECT   10    8   41                                                       
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   32                                             
CONECT   14   13   42   43   44                                             
CONECT   15   13   16   45   46                                             
CONECT   16   15   17   30   47                                             
CONECT   17   16   18   19                                                  
CONECT   18   17   48   49   50                                             
CONECT   19   17   20   27                                                  
CONECT   20   19   21   51   52                                             
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24   53   54   55                                             
CONECT   26   24   56   57   58                                             
CONECT   27   24   28   19                                                  
CONECT   28   27   29   59                                                  
CONECT   29   28   30   60   61                                             
CONECT   30   29   31    5   16                                             
CONECT   31   30   62   63   64                                             
CONECT   32   13   33   34    5                                             
CONECT   33   32   34   65   66                                             
CONECT   34   33   32                                                       
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    9                                                            
CONECT   39    9                                                            
CONECT   40    9                                                            
CONECT   41   10                                                            
CONECT   42   14                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   18                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   20                                                            
CONECT   52   20                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   26                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
CONECT   59   28                                                            
CONECT   60   29                                                            
CONECT   61   29                                                            
CONECT   62   31                                                            
CONECT   63   31                                                            
CONECT   64   31                                                            
CONECT   65   33                                                            
CONECT   66   33                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  140    0
END

RDKit          3D

66 70  0  0  0  0  0  0  0  0999 V2000
   -3.0148    4.0461   -1.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5111    2.7313   -1.0688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2359    1.9983    0.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4878    2.6422    1.1486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7069    0.6168    0.1025 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6651    0.1381    1.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9220    0.5839    2.3593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838   -0.9408    1.9545 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3055   -1.3849    3.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9181   -0.5354    1.9288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3805   -2.0556    0.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3604   -3.1898    1.4148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2189   -1.6964   -0.4232 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1740   -2.5722   -1.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8494   -1.8514   -0.9768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -0.8887   -0.4252 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4821   -1.1627   -0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6833   -2.1401   -2.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6133   -0.5715   -0.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8380   -1.0271   -1.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0553   -0.7021   -0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1611   -0.7034   -1.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9320   -0.4226    0.7860 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0209    0.5370    1.2688 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7252    0.1659    2.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6450    1.8941    1.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7671    0.4424    0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8419    1.3382    0.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5246    1.5837    0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2704    0.5324   -0.4729 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4187    0.8720   -1.9628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6354   -0.2594   -0.7071 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3691    0.0391   -1.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0048    0.0243   -0.6445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2730    4.3212   -2.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9908    4.0038   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3380    4.7691   -0.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7087   -0.5644    4.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8455   -2.3304    3.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2322   -1.4302    3.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9938    0.4142    2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8153   -2.6758   -2.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2012   -2.1290   -1.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1967   -3.5855   -0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4936   -2.8773   -0.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9794   -1.7874   -2.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2099   -1.1484    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4194   -1.6934   -2.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8226   -2.3910   -2.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1119   -3.1114   -1.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9653   -0.4775   -2.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8703   -2.1329   -1.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6886    1.1080    3.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8190   -0.4417    2.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5698   -0.4197    3.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6114    1.8902    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7984    2.2919    2.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9677    2.5688    0.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1721    1.9945    1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6990    2.4464   -0.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0414    2.1712    0.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470    0.7547   -2.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0698    0.2050   -2.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6038    1.9451   -2.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4122    1.0249   -2.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5870   -0.7949   -2.5901 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
  5  3  1  1
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  1
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  1
 24 26  1  0
 24 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  1  6
 13 32  1  0
 32 33  1  0
 33 34  1  0
 30  5  1  0
 32 34  1  1
 32  5  1  0
 30 16  1  0
 27 19  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  9 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  1
 18 48  1  0
 18 49  1  0
 18 50  1  0
 20 51  1  0
 20 52  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 26 58  1  0
 28 59  1  0
 29 60  1  0
 29 61  1  0
 31 62  1  0
 31 63  1  0
 31 64  1  0
 33 65  1  0
 33 66  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl (1'r,2R,2's,12's,14'r,16's)-16'-hydroxy-2',6',6',11',14',16'-hexamethyl-8',15',17'-trioxo-7'-oxaspiro[oxirane-2,18'-tetracyclo[12.3.1.0,.0,]octadecane]-4',10'-diene-1'-carboxylic acid	Generator

Chemical Formula

C₂₆H₃₂O₈

Average Mass

472.5340 Da

Monoisotopic Mass

472.20972 Da

IUPAC Name

methyl (1'R,2R,2'S,12'S,14'R,16'S)-16'-hydroxy-2',6',6',11',14',16'-hexamethyl-8',15',17'-trioxo-7'-oxaspiro[oxirane-2,18'-tetracyclo[12.3.1.0^{2,12}.0^{5,10}]octadecane]-4',10'-diene-1'-carboxylate

Traditional Name

methyl (1'R,2R,2'S,12'S,14'R,16'S)-16'-hydroxy-2',6',6',11',14',16'-hexamethyl-8',15',17'-trioxo-7'-oxaspiro[oxirane-2,18'-tetracyclo[12.3.1.0^{2,12}.0^{5,10}]octadecane]-4',10'-diene-1'-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]12C(=O)[C@@](C)(O)C(=O)[C@](C)(C[C@H]3C(C)=C4CC(=O)OC(C)(C)C4=CC[C@]13C)[C@]21CO1

InChI Identifier

InChI=1S/C26H32O8/c1-13-14-10-17(27)34-21(2,3)15(14)8-9-22(4)16(13)11-23(5)18(28)24(6,31)19(29)26(22,20(30)32-7)25(23)12-33-25/h8,16,31H,9-12H2,1-7H3/t16-,22-,23-,24-,25+,26+/m0/s1

InChI Key

DRMIYYPESWIXHQ-PSNFPAJSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C6D6, experimental)	hyeriku@gmail.com	Not Available	Not Available	2024-05-11	View Spectrum

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
Penicillium	NPAtlas	18237180
sp. SSW03M2 GY		Not Available
Talaromyces minioluteus	LOTUS Database	35616633

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	2.59	ALOGPS
logP	2.33	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	11.49	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	119.5 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	120.72 m³·mol⁻¹	ChemAxon
Polarizability	48.56 Å³	ChemAxon
Number of Rings	5	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

NPA018251

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

76772438

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24809133

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ku H, Lee Y, Lee S, Lee JW, Kang HS, Joo HS, Shim SH: New meroterpenoids from a soil-derived fungus Penicillium sp. SSW03M2 GY and their anti-virulence activity. J Antibiot (Tokyo). 2023 Feb;76(2):57-64. doi: 10.1038/s41429-022-00587-7. Epub 2022 Dec 16. [PubMed:36526742 ]

Showing NP-Card for 22-epoxyberkeleydione (NP0007522)

MOL for NP0007522 (22-epoxyberkeleydione)

3D MOL for NP0007522 (22-epoxyberkeleydione)

3D SDF for NP0007522 (22-epoxyberkeleydione)

3D-SDF for NP0007522 (22-epoxyberkeleydione)

PDB for NP0007522 (22-epoxyberkeleydione)

3D PDB for NP0007522 (22-epoxyberkeleydione)

SMILES for NP0007522 (22-epoxyberkeleydione)

INCHI for NP0007522 (22-epoxyberkeleydione)

Structure for NP0007522 (22-epoxyberkeleydione)

3D Structure for NP0007522 (22-epoxyberkeleydione)