NP-MRD: Showing NP-Card for (1s,4e,7s,9r)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one (NP0272184)

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Record Information

Version

2.0

Created at

2022-09-08 18:43:27 UTC

Updated at

2022-09-08 18:43:27 UTC

NP-MRD ID

NP0272184

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4e,7s,9r)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one

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. (1s,4e,7s,9r)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one is found in Huperzia serrata, Penicillium chrysogenum, Penicillium farinosum, Penicillium roqueforti, Penicillium simplicissimum and Penicillium solitum. (1s,4e,7s,9r)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one was first documented in 2021 (PMID: 34509930). Based on a literature review a small amount of articles have been published on Roquefortine C (PMID: 36008047) (PMID: 35202094) (PMID: 34425737) (PMID: 33917988).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082220432D          

 29 33  0  0  1  0            999 V2000
    0.7890    2.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    2.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2150    1.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085    1.8833    0.0000 C   0  0  0  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369    0.9521    0.0000 C   0  0  1  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
    4.5715    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5091   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3538   -1.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9181   -2.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5200   -2.8014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7098   -2.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6071   -1.8276    0.0000 N   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
    3.9504   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.0391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0612   -0.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385   -0.1271    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
   -0.0649    0.1418    0.0000 C   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
    0.8697    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.6832    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  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  1  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  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  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
 14 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  8 21  1  1  0  0  0
 22 21  1  6  0  0  0
  6 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
  6 29  1  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -1.2475   -2.5866   -2.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7986   -1.5819   -1.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5781   -1.3203   -0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2735   -2.0124   -0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7040   -1.9725    0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500    0.1485   -0.1300 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1423    0.4893    1.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1128    1.3293    1.2615 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8998    1.3828    2.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3555    1.9420    3.6367 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0993    0.9362    2.5594 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072    0.3281    1.4792 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0305   -0.1145    1.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7829   -0.7847    0.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5492   -1.9249   -0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5408   -2.1171   -0.9608 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4174   -1.1286   -0.8218 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9755   -0.3156    0.1417 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1004    0.2074    0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6304   -0.2894   -0.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7836    0.6727    0.1320 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2713    0.6768   -0.8843 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6588    2.0081   -1.2668 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0816    2.0468   -1.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9070    3.0152   -1.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2583    2.8965   -1.6925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7828    1.8127   -1.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9462    0.8431   -0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5793    0.9516   -0.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5923   -3.2831   -1.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285   -2.7496   -3.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4469   -0.9102   -2.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5190   -3.1143    0.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0936   -1.7327    0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4339   -1.9307   -0.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9926   -1.4193    1.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5744   -2.1923   -0.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3529   -2.9647    0.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405    1.1433    1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0591   -0.3740    1.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1429    2.3491    0.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8880    2.5064    4.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4900    0.0304    2.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6666   -2.5625    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3189   -1.0287   -1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4468    0.5604    0.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043    0.0915   -1.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0123    2.7667   -1.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5164    3.8757   -2.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9042    3.6708   -2.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8609    1.7090   -0.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4299    0.0204    0.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  5  1  0
  3  2  1  0
  2  1  2  3
  6  3  1  1
  6  7  1  0
  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 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 12 11  1  0
 11  9  2  0
  9 10  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  6
 22 47  1  6
 23 48  1  0
 25 49  1  0
 26 50  1  0
 27 51  1  0
 28 52  1  0
 13 43  1  0
 15 44  1  0
 17 45  1  0
 18 46  1  0
 10 42  1  0
M  END


  Mrv1652309082220432D          

 29 33  0  0  1  0            999 V2000
    0.7890    2.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    2.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2150    1.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085    1.8833    0.0000 C   0  0  0  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369    0.9521    0.0000 C   0  0  1  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
    4.5715    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5091   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3538   -1.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9181   -2.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5200   -2.8014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7098   -2.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6071   -1.8276    0.0000 N   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
    3.9504   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.0391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0612   -0.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385   -0.1271    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
   -0.0649    0.1418    0.0000 C   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
    0.8697    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.6832    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  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  1  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  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  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
 14 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  8 21  1  1  0  0  0
 22 21  1  6  0  0  0
  6 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
  6 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272184

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C=C)[C@@]12C[C@@H]3N([C@@H]1NC1=CC=CC=C21)C(=O)\C(=C/C1=CN=CN1)N=C3O

> <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-JJUKSXGLSA-N

> <FORMULA>
C22H23N5O2

> <MOLECULAR_WEIGHT>
389.459

> <EXACT_MASS>
389.185175001

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.37218012856633

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4E,7S,9R)-6-hydroxy-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-5,10,12,14-tetraen-3-one

> <JCHEM_LOGP>
1.2380437080619542

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.563903259448114

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3214599568369207

> <JCHEM_PKA_STRONGEST_BASIC>
7.5736177236606474

> <JCHEM_POLAR_SURFACE_AREA>
93.61000000000001

> <JCHEM_REFRACTIVITY>
112.02229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4E,7S,9R)-6-hydroxy-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-5,10,12,14-tetraen-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       1.473   4.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.007   4.255   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.662   2.861   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.268   2.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.056   3.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.316   1.467   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.440   2.520   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.789   1.777   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.244   2.282   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.533   3.795   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       9.409   1.275   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.119  -0.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.284  -1.244   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.994  -2.757   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.047  -3.880   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      10.304  -5.229   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       8.792  -4.940   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       8.600  -3.411   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       7.664  -0.742   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.374  -2.255   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0       6.499   0.265   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       4.971   0.073   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       3.848  -0.980   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       2.499  -0.237   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.044  -0.742   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.121   0.265   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.169   1.777   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.624   2.282   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.788   1.275   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   22   29                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14                                                       
CONECT   19   12   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    8   22                                                  
CONECT   22   21    6   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24    6                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
Roquefortin	MeSH
Roquefortine	MeSH
Isoroquefortine C	MeSH

Chemical Formula

C₂₂H₂₃N₅O₂

Average Mass

389.4590 Da

Monoisotopic Mass

389.18518 Da

IUPAC Name

(1S,4E,7S,9R)-6-hydroxy-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-5,10,12,14-tetraen-3-one

Traditional Name

(1S,4E,7S,9R)-6-hydroxy-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-5,10,12,14-tetraen-3-one

CAS Registry Number

Not Available

SMILES

CC(C)(C=C)[C@@]12C[C@@H]3N([C@@H]1NC1=CC=CC=C21)C(=O)\C(=C/C1=CN=CN1)N=C3O

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-JJUKSXGLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Huperzia serrata	LOTUS Database	35616633
Penicillium chrysogenum	LOTUS Database	35616633
Penicillium farinosum	LOTUS Database	35616633
Penicillium roqueforti	LOTUS Database	35616633
Penicillium simplicissimum	LOTUS Database	35616633
Penicillium solitum	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
N-alkylpiperazine
1,4-diazinane
Piperazine
Benzenoid
Heteroaromatic compound
Pyrrolidine
Pyrrole
Tertiary carboxylic acid amide
Azole
Imidazole
Secondary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Carboxylic acid derivative
Amine
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Organooxygen compound
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	1.24	ChemAxon
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	7.57	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	93.61 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	112.02 m³·mol⁻¹	ChemAxon
Polarizability	41.37 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

10246629

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Roquefortine C

METLIN ID

Not Available

PubChem Compound

21608802

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Maldonado ML, Patriarca A, Mc Cargo P, Iannone L, Sanchis V, Nielsen KF, Fernandez Pinto V: Diversity and metabolomic characterization of Penicillium expansum isolated from apples grown in Argentina and Spain. Fungal Biol. 2022 Sep;126(9):547-555. doi: 10.1016/j.funbio.2022.06.002. Epub 2022 Jun 25. [PubMed:36008047 ]
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 ]
LOTUS database [Link]

Showing NP-Card for (1s,4e,7s,9r)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one (NP0272184)

MOL for NP0272184 ((1s,4e,7s,9r)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D MOL for NP0272184 ((1s,4e,7s,9r)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D SDF for NP0272184 ((1s,4e,7s,9r)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D-SDF for NP0272184 ((1s,4e,7s,9r)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

PDB for NP0272184 ((1s,4e,7s,9r)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D PDB for NP0272184 ((1s,4e,7s,9r)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

SMILES for NP0272184 ((1s,4e,7s,9r)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

INCHI for NP0272184 ((1s,4e,7s,9r)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

Structure for NP0272184 ((1s,4e,7s,9r)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D Structure for NP0272184 ((1s,4e,7s,9r)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)