NP-MRD: Showing NP-Card for Roquefortine A (NP0021817)

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Record Information

Version

2.0

Created at

2021-01-06 07:04:45 UTC

Updated at

2021-07-15 17:37:22 UTC

NP-MRD ID

NP0021817

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Roquefortine A

Provided By

NPAtlas

Description

Roquefortine A is found in Aspergillus fumigatus, Aspergillus tamarii, Aspergullus fumigatus, Neosartarya fumigata Af293, Penicillium commune, Penicillium roquefortii and Unknown-fungus sp.. Roquefortine A was first documented in 1977 (PMID: 613945). Based on a literature review very few articles have been published on (2R,3R,4S,7R)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadeca-1(16),9,12,14-tetraen-3-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105193D          

 44 47  0  0  0  0            999 V2000
    3.4130    2.9138   -0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6804    1.7496    0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678    1.5373    1.4741 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0511    0.7865   -0.5308 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3767   -0.2832   -0.0753 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9345   -1.6543   -0.3700 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1016   -1.9292    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8248   -2.6296    0.0689 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0179   -2.1014    1.1229 N   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7351   -3.1488    1.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651   -0.9504    0.7603 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2101   -1.1751    0.6205 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8080    0.1460    0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0506    0.7292    0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0566    1.9446   -0.2551 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8292    2.1301   -0.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1970    3.1363   -1.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8826    2.9920   -1.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1171    1.8558   -1.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7348    0.8647   -0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474    1.0415   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0713   -0.3543   -0.4843 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6657    2.7699   -1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189    3.8513   -0.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3664    2.9834    0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4246   -0.2268    1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0840   -1.8687   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7429   -2.2011    1.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7886   -1.0704    0.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7202   -2.7864    0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406   -2.9975   -0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3146   -3.5572    0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0657   -4.0559    1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6326   -3.4538    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9551   -2.8945    2.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6020   -0.1870    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4975   -1.9734   -0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6439   -1.3866    1.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8924    0.2982    0.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8313    2.6179   -0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7998    4.0041   -1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4140    3.7725   -2.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8820    1.8405   -1.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1773   -1.0796   -1.3362 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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 16 17  2  0  0  0  0
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 22  5  1  0  0  0  0
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  1 23  1  0  0  0  0
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  5 26  1  1  0  0  0
  6 27  1  6  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
  7 30  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
 10 33  1  0  0  0  0
 10 34  1  0  0  0  0
 10 35  1  0  0  0  0
 11 36  1  1  0  0  0
 12 37  1  0  0  0  0
 12 38  1  0  0  0  0
 14 39  1  0  0  0  0
 15 40  1  0  0  0  0
 17 41  1  0  0  0  0
 18 42  1  0  0  0  0
 19 43  1  0  0  0  0
 22 44  1  6  0  0  0
M  END

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
    3.4130    2.9138   -0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6804    1.7496    0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678    1.5373    1.4741 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0511    0.7865   -0.5308 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3767   -0.2832   -0.0753 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9345   -1.6543   -0.3700 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1016   -1.9292    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8248   -2.6296    0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0179   -2.1014    1.1229 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7351   -3.1488    1.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651   -0.9504    0.7603 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2101   -1.1751    0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8080    0.1460    0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0506    0.7292    0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0566    1.9446   -0.2551 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8292    2.1301   -0.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1970    3.1363   -1.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8826    2.9920   -1.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1171    1.8558   -1.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7348    0.8647   -0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474    1.0415   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0713   -0.3543   -0.4843 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6657    2.7699   -1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189    3.8513   -0.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3664    2.9834    0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4246   -0.2268    1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0840   -1.8687   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7429   -2.2011    1.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7886   -1.0704    0.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7202   -2.7864    0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406   -2.9975   -0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3146   -3.5572    0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0657   -4.0559    1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6326   -3.4538    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9551   -2.8945    2.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6020   -0.1870    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4975   -1.9734   -0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6439   -1.3866    1.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8924    0.2982    0.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7998    4.0041   -1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4140    3.7725   -2.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8820    1.8405   -1.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1773   -1.0796   -1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
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  5  6  1  0
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  6  8  1  0
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  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
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 14 39  1  0
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 22 44  1  6
M  END


  Mrv1652306242105193D          

 44 47  0  0  0  0            999 V2000
    3.4130    2.9138   -0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6804    1.7496    0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678    1.5373    1.4741 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0511    0.7865   -0.5308 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3767   -0.2832   -0.0753 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9345   -1.6543   -0.3700 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1016   -1.9292    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8248   -2.6296    0.0689 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0179   -2.1014    1.1229 N   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7351   -3.1488    1.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651   -0.9504    0.7603 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2101   -1.1751    0.6205 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8080    0.1460    0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0506    0.7292    0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0566    1.9446   -0.2551 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8292    2.1301   -0.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1970    3.1363   -1.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8826    2.9920   -1.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1171    1.8558   -1.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7348    0.8647   -0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474    1.0415   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0713   -0.3543   -0.4843 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6657    2.7699   -1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189    3.8513   -0.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3664    2.9834    0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4246   -0.2268    1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0840   -1.8687   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7429   -2.2011    1.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7886   -1.0704    0.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7202   -2.7864    0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406   -2.9975   -0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3146   -3.5572    0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0657   -4.0559    1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6326   -3.4538    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9551   -2.8945    2.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6020   -0.1870    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4975   -1.9734   -0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8924    0.2982    0.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8313    2.6179   -0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7998    4.0041   -1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4140    3.7725   -2.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8820    1.8405   -1.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1773   -1.0796   -1.3362 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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
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 18 19  2  0  0  0  0
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 22  5  1  0  0  0  0
 22 11  1  0  0  0  0
 21 13  1  0  0  0  0
 21 16  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  5 26  1  1  0  0  0
  6 27  1  6  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
  7 30  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
 10 33  1  0  0  0  0
 10 34  1  0  0  0  0
 10 35  1  0  0  0  0
 11 36  1  1  0  0  0
 12 37  1  0  0  0  0
 12 38  1  0  0  0  0
 14 39  1  0  0  0  0
 15 40  1  0  0  0  0
 17 41  1  0  0  0  0
 18 42  1  0  0  0  0
 19 43  1  0  0  0  0
 22 44  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0021817

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C([H])=C2C3=C(C([H])=C([H])C([H])=C13)[C@@]1([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])N(C([H])([H])[H])[C@]1([H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H22N2O2/c1-10-9-20(3)15-7-12-8-19-14-6-4-5-13(16(12)14)17(15)18(10)22-11(2)21/h4-6,8,10,15,17-19H,7,9H2,1-3H3/t10-,15+,17+,18+/m0/s1

> <INCHI_KEY>
GJSSYQDXZLZOLR-QMHBMSAFSA-N

> <FORMULA>
C18H22N2O2

> <MOLECULAR_WEIGHT>
298.386

> <EXACT_MASS>
298.168127956

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
33.53602015782534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4S,7R)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-3-yl acetate

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
2.2402231293333337

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.053048852645148

> <JCHEM_PKA_STRONGEST_BASIC>
8.495710975765837

> <JCHEM_POLAR_SURFACE_AREA>
45.33

> <JCHEM_REFRACTIVITY>
85.858

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,7R)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
    3.4130    2.9138   -0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6804    1.7496    0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678    1.5373    1.4741 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0511    0.7865   -0.5308 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3767   -0.2832   -0.0753 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9345   -1.6543   -0.3700 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1016   -1.9292    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8248   -2.6296    0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0179   -2.1014    1.1229 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7351   -3.1488    1.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651   -0.9504    0.7603 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2101   -1.1751    0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8080    0.1460    0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0506    0.7292    0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0566    1.9446   -0.2551 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8292    2.1301   -0.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1970    3.1363   -1.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8826    2.9920   -1.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1171    1.8558   -1.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7348    0.8647   -0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474    1.0415   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0713   -0.3543   -0.4843 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6657    2.7699   -1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189    3.8513   -0.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3664    2.9834    0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4246   -0.2268    1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0840   -1.8687   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7429   -2.2011    1.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7886   -1.0704    0.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7202   -2.7864    0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406   -2.9975   -0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3146   -3.5572    0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0657   -4.0559    1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6326   -3.4538    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9551   -2.8945    2.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6020   -0.1870    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4975   -1.9734   -0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6439   -1.3866    1.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8924    0.2982    0.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8313    2.6179   -0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7998    4.0041   -1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4140    3.7725   -2.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8820    1.8405   -1.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1773   -1.0796   -1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22  5  1  0
 22 11  1  0
 21 13  1  0
 21 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  1
  6 27  1  6
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  1
 12 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 22 44  1  6
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       3.413   2.914  -0.314  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.680   1.750   0.245  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.568   1.537   1.474  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.051   0.787  -0.531  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.377  -0.283  -0.075  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.935  -1.654  -0.370  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.102  -1.929   0.520  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.825  -2.630   0.069  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.018  -2.101   1.123  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.735  -3.149   1.736  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.765  -0.950   0.760  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.210  -1.175   0.621  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.808   0.146   0.202  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.051   0.729   0.345  0.00  0.00           C+0
HETATM   15  N   UNK     0      -4.057   1.945  -0.255  0.00  0.00           N+0
HETATM   16  C   UNK     0      -2.829   2.130  -0.774  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.197   3.136  -1.514  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.883   2.992  -1.918  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.117   1.856  -1.618  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.735   0.865  -0.889  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.047   1.042  -0.505  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.071  -0.354  -0.484  0.00  0.00           C+0
HETATM   23  H   UNK     0       3.666   2.770  -1.382  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.819   3.851  -0.201  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.366   2.983   0.276  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.425  -0.227   1.066  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.084  -1.869  -1.426  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.743  -2.201   1.546  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.789  -1.070   0.637  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.720  -2.786   0.182  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.241  -2.998  -0.796  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.315  -3.557   0.489  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.066  -4.056   1.766  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.633  -3.454   1.157  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.955  -2.894   2.785  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.602  -0.187   1.556  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.498  -1.973  -0.085  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.644  -1.387   1.607  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.892   0.298   0.852  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.831   2.618  -0.320  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.800   4.004  -1.736  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.414   3.773  -2.486  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.882   1.841  -1.999  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.177  -1.080  -1.336  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   22   26                                             
CONECT    6    5    7    8   27                                             
CONECT    7    6   28   29   30                                             
CONECT    8    6    9   31   32                                             
CONECT    9    8   10   11                                                  
CONECT   10    9   33   34   35                                             
CONECT   11    9   12   22   36                                             
CONECT   12   11   13   37   38                                             
CONECT   13   12   14   21                                                  
CONECT   14   13   15   39                                                  
CONECT   15   14   16   40                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18   41                                                  
CONECT   18   17   19   42                                                  
CONECT   19   18   20   43                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   13   16                                                  
CONECT   22   20    5   11   44                                             
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    5                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
CONECT   29    7                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32    8                                                            
CONECT   33   10                                                            
CONECT   34   10                                                            
CONECT   35   10                                                            
CONECT   36   11                                                            
CONECT   37   12                                                            
CONECT   38   12                                                            
CONECT   39   14                                                            
CONECT   40   15                                                            
CONECT   41   17                                                            
CONECT   42   18                                                            
CONECT   43   19                                                            
CONECT   44   22                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   94    0
END

RDKit          3D

44 47  0  0  0  0  0  0  0  0999 V2000
    3.4130    2.9138   -0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6804    1.7496    0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678    1.5373    1.4741 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0511    0.7865   -0.5308 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3767   -0.2832   -0.0753 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9345   -1.6543   -0.3700 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1016   -1.9292    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8248   -2.6296    0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0179   -2.1014    1.1229 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7351   -3.1488    1.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651   -0.9504    0.7603 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2101   -1.1751    0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8080    0.1460    0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0506    0.7292    0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0566    1.9446   -0.2551 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8292    2.1301   -0.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1970    3.1363   -1.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8826    2.9920   -1.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1171    1.8558   -1.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7348    0.8647   -0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474    1.0415   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0713   -0.3543   -0.4843 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6657    2.7699   -1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189    3.8513   -0.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3664    2.9834    0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4246   -0.2268    1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0840   -1.8687   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7429   -2.2011    1.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7886   -1.0704    0.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7202   -2.7864    0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406   -2.9975   -0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3146   -3.5572    0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0657   -4.0559    1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6326   -3.4538    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9551   -2.8945    2.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6020   -0.1870    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4975   -1.9734   -0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6439   -1.3866    1.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8924    0.2982    0.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8313    2.6179   -0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7998    4.0041   -1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4140    3.7725   -2.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8820    1.8405   -1.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1773   -1.0796   -1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22  5  1  0
 22 11  1  0
 21 13  1  0
 21 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  1
  6 27  1  6
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  1
 12 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 22 44  1  6
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2R,3R,4S,7R)-4,6-Dimethyl-6,11-diazatetracyclo[7.6.1.0,.0,]hexadeca-1(16),9,12,14-tetraen-3-yl acetic acid	Generator
9-Acetoxy-6,8-dimethylergoline	MeSH
Isofumigaclavine a	MeSH
Isofumigaclavine a, (8alpha,9beta)-isomer	MeSH

Chemical Formula

C₁₈H₂₂N₂O₂

Average Mass

298.3860 Da

Monoisotopic Mass

298.16813 Da

IUPAC Name

(2R,3R,4S,7R)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-3-yl acetate

Traditional Name

(2R,3R,4S,7R)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-3-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1CN(C)[C@@H]2CC3=CNC4=CC=CC([C@H]2[C@@H]1OC(C)=O)=C34

InChI Identifier

InChI=1S/C18H22N2O2/c1-10-9-20(3)15-7-12-8-19-14-6-4-5-13(16(12)14)17(15)18(10)22-11(2)21/h4-6,8,10,15,17-19H,7,9H2,1-3H3/t10-,15+,17+,18+/m0/s1

InChI Key

GJSSYQDXZLZOLR-QMHBMSAFSA-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 fumigatus	Fungi	KNApSAcK
Aspergillus tamarii	Fungi	KNApSAcK
Aspergullus fumigatus	-	KNApSAcK
Neosartarya fumigata Af293	-	KNApSAcK
Penicillium commune	Fungi	KNApSAcK
Penicillium roqueforti	Fungi	KNApSAcK
Unknown-fungus sp.	NPAtlas	613945

Species Where Detected

Species Name	Source	Reference
Penicillium roquefortii	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	ALOGPS
logP	2.24	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	17.05	ChemAxon
pKa (Strongest Basic)	8.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.33 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.86 m³·mol⁻¹	ChemAxon
Polarizability	33.54 Å³	ChemAxon
Number of Rings	4	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

NPA017298

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58828645

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101286186

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Polonsky J, Merrien MA, Scott PM: Roquefortine and isofumigaclavine A, alkaloids from Penicillium roqueforti. Ann Nutr Aliment. 1977;31(4-6):963-8. [PubMed:613945 ]

Showing NP-Card for Roquefortine A (NP0021817)

MOL for NP0021817 (Roquefortine A)

3D MOL for NP0021817 (Roquefortine A)

3D SDF for NP0021817 (Roquefortine A)

3D-SDF for NP0021817 (Roquefortine A)

PDB for NP0021817 (Roquefortine A)

3D PDB for NP0021817 (Roquefortine A)

SMILES for NP0021817 (Roquefortine A)

INCHI for NP0021817 (Roquefortine A)

Structure for NP0021817 (Roquefortine A)

3D Structure for NP0021817 (Roquefortine A)