NP-MRD: Showing NP-Card for Brevione E (NP0003592)

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Record Information

Version

1.0

Created at

2020-12-09 00:48:00 UTC

Updated at

2021-07-15 16:46:50 UTC

NP-MRD ID

NP0003592

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Brevione E

Provided By

NPAtlas

Description

Brevione E is found in Penicillium and Penicillium brevicompactum. It was first documented in 2000 (PMID: 11149849). Based on a literature review very few articles have been published on (1S,4R,10S,12R,13R,16R,21R,22R,23S)-3,6,7,17,22-pentamethyl-8,19-dioxo-5,11,24-trioxahexacyclo[19.2.1.0⁴,¹⁰.0⁴,¹³.0¹³,²³.0¹⁶,²²]Tetracosa-2,6,17-trien-12-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117483D          

 69 74  0  0  0  0            999 V2000
   -0.7620    4.5541    2.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4886    3.8274    0.9489 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 69 74  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242117483D          

 69 74  0  0  0  0            999 V2000
   -0.7620    4.5541    2.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4886    3.8274    0.9489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9195    4.2778   -0.1415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2362    2.6487    0.9055 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5149    1.9370   -0.2614 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9027    2.1421   -0.4726 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4838    0.8755   -0.4521 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9293    0.9986   -0.2281 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6207   -0.1556   -0.8751 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8234    0.0555   -1.1619 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0385   -1.4539   -1.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9390   -2.3267   -1.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8494   -1.9098   -0.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6247   -3.3058   -1.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8021   -1.3592   -0.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6513   -0.0182    0.3378 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7154   -0.0282    1.7970 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0296   -0.2913    2.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860    0.1682    2.6267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6934    0.4282    2.1731 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6266   -0.5110    2.6757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840   -0.5301    1.7266 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3463   -1.8625    1.7101 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6563   -1.7059    0.9963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7142   -2.0409    1.5840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7433   -1.1731   -0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7584   -0.7641   -1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1452   -0.2702   -2.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3362   -0.8035   -0.7957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4565   -0.2212   -1.8610 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.2655    0.4903   -0.1600 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6991   -0.0509    0.7529 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.7055    1.3713    0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0380    5.3311    2.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8713   -3.3869   -1.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1873   -4.0445   -0.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5342   -3.4799   -1.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -3.3040   -2.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7103   -0.8367    1.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4827    0.6096    2.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9255   -0.9825    3.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8853    0.1329    3.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1029    1.3989    2.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4355    0.1869    2.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7540   -2.6513    1.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116   -2.1912    2.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7504   -1.0980   -0.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2536   -0.2849   -2.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8086   -0.9747   -3.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8350    0.7664   -2.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403   -1.8745   -0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5453   -0.9124   -2.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7982    0.7627   -2.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3972   -1.1855   -1.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5099    0.3843   -2.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4742   -1.1673    0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7838    1.2221   -0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7396    2.0063    1.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2364    1.9133   -0.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
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 32  5  1  0  0  0  0
 16  7  1  0  0  0  0
 33 20  1  0  0  0  0
 32 16  1  0  0  0  0
 34 22  1  0  0  0  0
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  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  5 39  1  6  0  0  0
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 35 67  1  0  0  0  0
 35 68  1  0  0  0  0
 35 69  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003592

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C(C([H])([H])[H])[C@]23OC(=C(C(=O)C([H])([H])[C@]2([H])O[C@]([H])(OC(=O)C([H])([H])[H])[C@@]32C([H])([H])C([H])([H])[C@]3([H])C(=C([H])C(=O)C([H])([H])[C@@]4([H])O[C@]1([H])[C@@]2([H])[C@@]34C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O7/c1-13-9-18(30)11-22-26(6)19(13)7-8-27-24(26)21(33-22)10-14(2)28(27)23(34-25(27)32-17(5)29)12-20(31)15(3)16(4)35-28/h9-10,19,21-25H,7-8,11-12H2,1-6H3/t19-,21+,22-,23+,24+,25+,26+,27+,28+/m1/s1

> <INCHI_KEY>
MPBWVNYITUYHFY-VKIAQROPSA-N

> <FORMULA>
C28H34O7

> <MOLECULAR_WEIGHT>
482.573

> <EXACT_MASS>
482.230453435

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.63451598595812

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4R,10S,12R,13R,16R,21R,22R,23S)-3,6,7,17,22-pentamethyl-8,19-dioxo-5,11,24-trioxahexacyclo[19.2.1.0^{4,10}.0^{4,13}.0^{13,23}.0^{16,22}]tetracosa-2,6,17-trien-12-yl acetate

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
3.0744838906666674

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.373248110218373

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.00831626511186

> <JCHEM_PKA_STRONGEST_BASIC>
-3.852941668018191

> <JCHEM_POLAR_SURFACE_AREA>
88.13000000000001

> <JCHEM_REFRACTIVITY>
128.14259999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,10S,12R,13R,16R,21R,22R,23S)-3,6,7,17,22-pentamethyl-8,19-dioxo-5,11,24-trioxahexacyclo[19.2.1.0^{4,10}.0^{4,13}.0^{13,23}.0^{16,22}]tetracosa-2,6,17-trien-12-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 69 74  0  0  0  0  0  0  0  0999 V2000
   -0.7620    4.5541    2.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4886    3.8274    0.9489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9195    4.2778   -0.1415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2362    2.6487    0.9055 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5149    1.9370   -0.2614 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9027    2.1421   -0.4726 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4838    0.8755   -0.4521 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9293    0.9986   -0.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6207   -0.1556   -0.8751 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8234    0.0555   -1.1619 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0385   -1.4539   -1.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9390   -2.3267   -1.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8494   -1.9098   -0.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6247   -3.3058   -1.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8021   -1.3592   -0.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6513   -0.0182    0.3378 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7154   -0.0282    1.7970 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0296   -0.2913    2.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860    0.1682    2.6267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6934    0.4282    2.1731 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6266   -0.5110    2.6757 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3463   -1.8625    1.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6563   -1.7059    0.9963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7142   -2.0409    1.5840 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7584   -0.7641   -1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2655    0.4903   -0.1600 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6991   -0.0509    0.7529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1569   -0.0029    0.4499 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7055    1.3713    0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0380    5.3311    2.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3718    0.5384   -1.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2923    1.2471    0.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2665    1.8795   -0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7370   -2.1980   -3.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9951   -2.0225   -1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8713   -3.3869   -1.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1873   -4.0445   -0.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7103   -0.8367    1.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9255   -0.9825    3.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8853    0.1329    3.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1029    1.3989    2.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7504   -1.0980   -0.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2536   -0.2849   -2.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8086   -0.9747   -3.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8350    0.7664   -2.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403   -1.8745   -0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5453   -0.9124   -2.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7982    0.7627   -2.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3972   -1.1855   -1.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5099    0.3843   -2.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4742   -1.1673    0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  2  0
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 35 69  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      -0.762   4.554   2.221  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.489   3.827   0.949  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.920   4.278  -0.142  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.236   2.649   0.906  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.515   1.937  -0.261  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.903   2.142  -0.473  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.484   0.876  -0.452  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.929   0.999  -0.228  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.621  -0.156  -0.875  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.823   0.056  -1.162  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.038  -1.454  -1.188  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.939  -2.327  -1.988  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.849  -1.910  -0.850  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.625  -3.306  -1.370  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.802  -1.359  -0.128  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.651  -0.018   0.338  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.715  -0.028   1.797  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.030  -0.291   2.449  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.686   0.168   2.627  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.693   0.428   2.173  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.627  -0.511   2.676  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.684  -0.530   1.727  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.346  -1.863   1.710  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.656  -1.706   0.996  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.714  -2.041   1.584  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.743  -1.173  -0.369  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.758  -0.764  -1.195  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.145  -0.270  -2.525  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.336  -0.804  -0.796  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.456  -0.221  -1.861  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.013  -0.155  -1.529  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.266   0.490  -0.160  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.699  -0.051   0.753  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.157  -0.003   0.450  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.705   1.371   0.205  0.00  0.00           C+0
HETATM   36  H   UNK     0       0.038   5.331   2.309  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.719   5.083   2.220  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.616   3.867   3.078  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.063   2.431  -1.175  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.372   0.538  -1.536  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.292   1.247   0.761  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.266   1.880  -0.867  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.737  -2.198  -3.083  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.995  -2.022  -1.848  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.871  -3.387  -1.719  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.187  -4.045  -0.777  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.534  -3.480  -1.357  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.929  -3.304  -2.435  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.710  -0.837   1.769  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.483   0.610   2.896  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.926  -0.983   3.331  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.885   0.133   3.688  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.103   1.399   2.377  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.436   0.187   2.176  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.754  -2.651   1.204  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.512  -2.191   2.737  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.750  -1.098  -0.772  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.254  -0.285  -2.577  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.809  -0.975  -3.340  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.835   0.766  -2.732  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.040  -1.875  -0.676  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.545  -0.912  -2.749  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.798   0.763  -2.237  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.397  -1.186  -1.478  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.510   0.384  -2.341  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.474  -1.167   0.847  0.00  0.00           H+0
HETATM   67  H   UNK     0      -3.784   1.222  -0.103  0.00  0.00           H+0
HETATM   68  H   UNK     0      -2.740   2.006   1.093  0.00  0.00           H+0
HETATM   69  H   UNK     0      -2.236   1.913  -0.612  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   32   39                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   16   40                                             
CONECT    8    7    9   41   42                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11   43   44   45                                             
CONECT   13   11   14   15                                                  
CONECT   14   13   46   47   48                                             
CONECT   15   13   16                                                       
CONECT   16   15   17    7   32                                             
CONECT   17   16   18   19                                                  
CONECT   18   17   49   50   51                                             
CONECT   19   17   20   52                                                  
CONECT   20   19   21   33   53                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   34   54                                             
CONECT   23   22   24   55   56                                             
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   57                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   58   59   60                                             
CONECT   29   27   30   34   61                                             
CONECT   30   29   31   62   63                                             
CONECT   31   30   32   64   65                                             
CONECT   32   31   33    5   16                                             
CONECT   33   32   34   20   66                                             
CONECT   34   33   35   22   29                                             
CONECT   35   34   67   68   69                                             
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    5                                                            
CONECT   40    7                                                            
CONECT   41    8                                                            
CONECT   42    8                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   12                                                            
CONECT   46   14                                                            
CONECT   47   14                                                            
CONECT   48   14                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   18                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   22                                                            
CONECT   55   23                                                            
CONECT   56   23                                                            
CONECT   57   26                                                            
CONECT   58   28                                                            
CONECT   59   28                                                            
CONECT   60   28                                                            
CONECT   61   29                                                            
CONECT   62   30                                                            
CONECT   63   30                                                            
CONECT   64   31                                                            
CONECT   65   31                                                            
CONECT   66   33                                                            
CONECT   67   35                                                            
CONECT   68   35                                                            
CONECT   69   35                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  148    0
END

RDKit          3D

69 74  0  0  0  0  0  0  0  0999 V2000
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 18 50  1  0
 18 51  1  0
 19 52  1  0
 20 53  1  6
 22 54  1  1
 23 55  1  0
 23 56  1  0
 26 57  1  0
 28 58  1  0
 28 59  1  0
 28 60  1  0
 29 61  1  1
 30 62  1  0
 30 63  1  0
 31 64  1  0
 31 65  1  0
 33 66  1  1
 35 67  1  0
 35 68  1  0
 35 69  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(1S,4R,10S,12R,13R,16R,21R,22R,23S)-3,6,7,17,22-Pentamethyl-8,19-dioxo-5,11,24-trioxahexacyclo[19.2.1.0,.0,.0,.0,]tetracosa-2,6,17-trien-12-yl acetic acid	Generator

Chemical Formula

C₂₈H₃₄O₇

Average Mass

482.5730 Da

Monoisotopic Mass

482.23045 Da

IUPAC Name

(1S,4R,10S,12R,13R,16R,21R,22R,23S)-3,6,7,17,22-pentamethyl-8,19-dioxo-5,11,24-trioxahexacyclo[19.2.1.0^{4,10}.0^{4,13}.0^{13,23}.0^{16,22}]tetracosa-2,6,17-trien-12-yl acetate

Traditional Name

(1S,4R,10S,12R,13R,16R,21R,22R,23S)-3,6,7,17,22-pentamethyl-8,19-dioxo-5,11,24-trioxahexacyclo[19.2.1.0^{4,10}.0^{4,13}.0^{13,23}.0^{16,22}]tetracosa-2,6,17-trien-12-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1O[C@H]2CC(=O)C(C)=C(C)O[C@@]22C(C)=C[C@@H]3O[C@@H]4CC(=O)C=C(C)[C@H]5CC[C@]12[C@@H]3[C@]45C

InChI Identifier

InChI=1S/C28H34O7/c1-13-9-18(30)11-22-26(6)19(13)7-8-27-24(26)21(33-22)10-14(2)28(27)23(34-25(27)32-17(5)29)12-20(31)15(3)16(4)35-28/h9-10,19,21-25H,7-8,11-12H2,1-6H3/t19-,21+,22-,23+,24+,25+,26+,27+,28+/m1/s1

InChI Key

MPBWVNYITUYHFY-VKIAQROPSA-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
Penicillium	NPAtlas	11149849
Penicillium brevicompactum	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	2.79	ALOGPS
logP	3.07	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	16.01	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	88.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	128.14 m³·mol⁻¹	ChemAxon
Polarizability	51.63 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA019168

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78436213

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588445

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Macias FA, Varela RM, Simonet AM, Cutler HG, Cutler SJ, Dugan FM, Hill RA: Novel bioactive breviane spiroditerpenoids from Penicillium brevicompactum Dierckx. J Org Chem. 2000 Dec 29;65(26):9039-46. doi: 10.1021/jo0011078. [PubMed:11149849 ]

Showing NP-Card for Brevione E (NP0003592)

MOL for NP0003592 (Brevione E)

3D MOL for NP0003592 (Brevione E)

3D SDF for NP0003592 (Brevione E)

3D-SDF for NP0003592 (Brevione E)

PDB for NP0003592 (Brevione E)

3D PDB for NP0003592 (Brevione E)

SMILES for NP0003592 (Brevione E)

INCHI for NP0003592 (Brevione E)

Structure for NP0003592 (Brevione E)

3D Structure for NP0003592 (Brevione E)