NP-MRD: Showing NP-Card for Isoroquefortine C (NP0069999)

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Record Information

Version

2.0

Created at

2022-04-28 15:16:59 UTC

Updated at

2022-04-28 15:17:00 UTC

NP-MRD ID

NP0069999

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isoroquefortine C

Description

Roquefortine C belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Isoroquefortine C is found in Hordeum vulgare, Penicillium hirsutum, Penicillium roqueforti and Penicillium verrucosum. Isoroquefortine C was first documented in 2021 (PMID: 34509930). Based on a literature review a small amount of articles have been published on Roquefortine C (PMID: 35202094) (PMID: 34425737) (PMID: 33917988) (PMID: 33893697).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282217172D          

 29 33  0  0  1  0            999 V2000
    4.8850   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4162    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.0391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3124    0.7859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9143    1.3501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385   -0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0612   -0.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4039   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5337    1.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3130    1.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5521    0.4314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3770    0.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6476    1.1942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9901    1.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0137   -0.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643   -1.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8929   -2.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7605   -0.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2669   -1.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  4  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 18 22  2  0  0  0  0
 16 23  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  2  0  0  0  0
  7 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 25 28  1  0  0  0  0
 25 29  1  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -1.5597   -2.6992   -1.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2109   -1.4340   -0.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1963   -0.4251   -0.4501 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1985   -1.0651    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9162    0.0296   -1.6948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5168    0.6879    0.2841 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8694    0.0666    1.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6249    0.1715    1.3388 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3122   -1.1116    1.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8488   -2.0725    2.1732 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5661   -1.3621    0.8682 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9554   -0.5446   -0.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0812   -0.7164   -0.8825 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0434   -1.7219   -0.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5530   -2.0011    0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4132   -3.0453    0.5486 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4439   -3.4113   -0.7399 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5910   -2.5832   -1.3921 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0414    0.4912   -0.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3255    1.2620   -1.6351 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8090    0.6771    0.0158 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3826    1.3407   -0.3871 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3194    2.6614    0.2765 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6631    2.9494    0.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2045    4.2119    0.8761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5417    4.3542    1.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3263    3.2201    1.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7640    1.9918    0.9009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4264    1.8084    0.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5839   -3.0455   -1.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8186   -3.4416   -1.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1533   -1.2436   -0.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1217   -0.6858    1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9685   -2.1692    0.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2359   -1.0702    0.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4446    0.8499   -2.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9808    0.3020   -1.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9678   -0.8440   -2.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1345   -1.0147    1.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1564    0.6111    2.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0375    0.9559    2.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2004   -2.1145    1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2559   -0.0302   -1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3826   -1.5334    1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0386   -4.2159   -1.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4187   -2.6469   -2.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4840    1.4698   -1.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393    3.2280    0.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5736    5.1098    0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9415    5.3368    1.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4012    3.3147    1.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4198    1.1472    0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  1
  3  5  1  0
  3  2  1  0
  2  1  2  3
  6  3  1  0
  6  7  1  1
  7  8  1  0
  8 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 21 19  1  0
 19 20  2  0
 19 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 22  6  1  0
 29 24  1  0
 18 14  1  0
 29  6  1  0
  9  8  1  0
  4 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  5 38  1  0
  2 32  1  0
  1 30  1  0
  1 31  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  1
 22 47  1  6
 23 48  1  0
 25 49  1  0
 26 50  1  0
 27 51  1  0
 28 52  1  0
 11 42  1  0
 13 43  1  0
 15 44  1  0
 17 45  1  0
 18 46  1  0
M  END


  Mrv1652304282217172D          

 29 33  0  0  1  0            999 V2000
    4.8850   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4162    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.0391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3124    0.7859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9143    1.3501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385   -0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0612   -0.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4039   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5337    1.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3130    1.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5521    0.4314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3770    0.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6476    1.1942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9901    1.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0137   -0.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643   -1.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8929   -2.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7605   -0.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2669   -1.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  4  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 18 22  2  0  0  0  0
 16 23  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  2  0  0  0  0
  7 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 25 28  1  0  0  0  0
 25 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069999

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C=C)[C@@]12C[C@@H]3N([C@@H]1NC1=CC=CC=C21)C(=O)\C(NC3=O)=C\C1=CN=CN1

> <INCHI_IDENTIFIER>
InChI=1S/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9-/t17-,20-,22+/m0/s1

> <INCHI_KEY>
SPWSUFUPTSJWNG-LIMLNZRCSA-N

> <FORMULA>
C22H23N5O2

> <MOLECULAR_WEIGHT>
389.459

> <EXACT_MASS>
389.185175001

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.503781063970486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4Z,7S,9R)-4-[(1H-imidazol-5-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-triene-3,6-dione

> <ALOGPS_LOGP>
2.84

> <JCHEM_LOGP>
1.2362421293333332

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.411515618343884

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.59434191175849

> <JCHEM_PKA_STRONGEST_BASIC>
6.56093755260911

> <JCHEM_POLAR_SURFACE_AREA>
90.12

> <JCHEM_REFRACTIVITY>
111.50059999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4Z,7S,9R)-4-(3H-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-triene-3,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.119  -0.237   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.409   1.275   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.244   2.282   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.789   1.777   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.499   0.265   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.664  -0.742   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.971   0.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.316   1.467   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       5.440   2.520   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       2.788   1.275   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.499  -0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.848  -0.980   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.044  -0.742   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.754  -2.255   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      -0.121   0.265   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       0.169   1.777   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.996   2.784   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.451   2.279   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -2.897   0.805   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      -4.437   0.774   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -4.942   2.229   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      -3.715   3.159   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.624   2.282   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.913   3.795   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.626  -1.321   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.280  -2.715   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.400  -3.979   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.020  -0.666   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.232  -1.976   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   12   25                                             
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8   11   23                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   18                                                       
CONECT   23   16   10   24                                                  
CONECT   24   23                                                            
CONECT   25    7   26   28   29                                             
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25                                                            
CONECT   29   25                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
Isoroquefortine C	MeSH
Roquefortin	MeSH
Roquefortine	MeSH

Chemical Formula

C₂₂H₂₃N₅O₂

Average Mass

389.4590 Da

Monoisotopic Mass

389.18518 Da

IUPAC Name

(1S,4Z,7S,9R)-4-[(1H-imidazol-5-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-triene-3,6-dione

Traditional Name

(1S,4Z,7S,9R)-4-(3H-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-triene-3,6-dione

CAS Registry Number

Not Available

SMILES

CC(C)(C=C)[C@@]12C[C@@H]3N([C@@H]1NC1=CC=CC=C21)C(=O)\C(NC3=O)=C\C1=CN=CN1

InChI Identifier

InChI=1S/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9-/t17-,20-,22+/m0/s1

InChI Key

SPWSUFUPTSJWNG-LIMLNZRCSA-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
Hordeum vulgare	LOTUS Database	35616633
Penicillium corymbiferum	LOTUS Database	35616633
Penicillium roqueforti	Fungi	KNApSAcK
Penicillium verrucosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Alpha-amino acid or derivatives
Indole
Dihydroindole
Dioxopiperazine
2,5-dioxopiperazine
Secondary aliphatic/aromatic amine
N-alkylpiperazine
1,4-diazinane
Piperazine
Benzenoid
Heteroaromatic compound
Pyrrolidine
Pyrrole
Tertiary carboxylic acid amide
Azole
Imidazole
Secondary carboxylic acid amide
Amino acid or derivatives
Lactam
Carboxamide group
Secondary amine
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.84	ALOGPS
logP	1.24	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	11.59	ChemAxon
pKa (Strongest Basic)	6.56	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	111.5 m³·mol⁻¹	ChemAxon
Polarizability	41.5 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00011251

Chemspider ID

4941441

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Roquefortine C

METLIN ID

Not Available

PubChem Compound

6436831

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Stranska M, Dzuman Z, Prusova N, Behner A, Kolouchova I, Lovecka P, Rezanka T, Kolarik M, Hajslova J: Fungal Endophytes of Vitis vinifera-Plant Growth Promoters or Potentially Toxinogenic Agents? Toxins (Basel). 2022 Jan 19;14(2). pii: toxins14020066. doi: 10.3390/toxins14020066. [PubMed:35202094 ]
Ertas Onmaz N, Gungor C, Al S, Dishan A, Hizlisoy H, Yildirim Y, Kasap Tekinsen F, Disli HB, Barel M, Karadal F: Mycotoxigenic and phylogenetic perspective to the yeasts and filamentous moulds in mould-matured Turkish cheese. Int J Food Microbiol. 2021 Nov 2;357:109385. doi: 10.1016/j.ijfoodmicro.2021.109385. Epub 2021 Sep 6. [PubMed:34509930 ]
Maragos CM: Roquefortine C in blue-veined and soft-ripened Cheeses in the USA. Food Addit Contam Part B Surveill. 2022 Mar;15(1):1-9. doi: 10.1080/19393210.2021.1967462. Epub 2021 Aug 23. [PubMed:34425737 ]
Al-Jaal B, Latiff A, Salama S, Hussain HM, Al-Thani NA, Al-Naimi N, Al-Qasmi N, Horvatovich P, Jaganjac M: Analysis of Multiple Mycotoxins in the Qatari Population and Their Relation to Markers of Oxidative Stress. Toxins (Basel). 2021 Apr 8;13(4). pii: toxins13040267. doi: 10.3390/toxins13040267. [PubMed:33917988 ]
Franciosa I, Coton M, Ferrocino I, Corvaglia MR, Poirier E, Jany JL, Rantsiou K, Cocolin L, Mounier J: Mycobiota dynamics and mycotoxin detection in PGI Salame Piemonte. J Appl Microbiol. 2021 Nov;131(5):2336-2350. doi: 10.1111/jam.15114. Epub 2021 May 8. [PubMed:33893697 ]

Showing NP-Card for Isoroquefortine C (NP0069999)

MOL for NP0069999 (Isoroquefortine C)

3D MOL for NP0069999 (Isoroquefortine C)

3D SDF for NP0069999 (Isoroquefortine C)

3D-SDF for NP0069999 (Isoroquefortine C)

PDB for NP0069999 (Isoroquefortine C)

3D PDB for NP0069999 (Isoroquefortine C)

SMILES for NP0069999 (Isoroquefortine C)

INCHI for NP0069999 (Isoroquefortine C)

Structure for NP0069999 (Isoroquefortine C)

3D Structure for NP0069999 (Isoroquefortine C)