NP-MRD: Showing NP-Card for Roquefortine C (NP0137607)

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Record Information

Version

2.0

Created at

2022-05-30 16:57:35 UTC

Updated at

2022-05-30 16:57:35 UTC

NP-MRD ID

NP0137607

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Roquefortine C

Description

Roquefortine 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. They cause a neurological disease of cattle known as "staggers syndrome". They are thought to inhibit gamma-aminobutyric acid (GABA) receptors, both pre- and postsynaptic, as well as inhibit transmitter breakdown at the GABA-T receptors. Roquefortine is a very strong basic compound (based on its pKa). Roquefortine is a potentially toxic compound. Tremorgenic mycotoxins exert their toxic effects by interfering with neurotransmitter release, possibly by causing degeneration of nerve terminals. Roquefortine C also interacts with different forms of the cytochromes. Prostration, seizures, and death can also follow after absorption. Generalized seizures may be treated with diazepam followed by methocarbamol or a barbiturate such as pentobarbital sodium. Gastric lavage should be performed and activated charcoal administered to limit further absorption of toxins. To control severe tremors caused by tremorgenic mycotoxins, methocarbamol should be administered. Roquefortine C is found in Penicillium roqueforti and Penicillium solitum. They cause a neurological disease of cattle known as "staggers syndrome", which is characterized by muscle tremors, hyperexcitability, convulsions and ataxia.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 09061400402D          

 30 34  0  0  0  0            999 V2000
    4.1864    2.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2669    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7605    1.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643    2.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4162   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5337   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612    1.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9901   -0.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3770    0.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3130   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816    0.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0137    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6476   -0.3692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5521    0.3936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9143   -0.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4039    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3784   -1.4769    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  2  0  0  0  0
 14  7  2  0  0  0  0
 15  8  2  0  0  0  0
 15 14  1  0  0  0  0
 16  9  2  0  0  0  0
 17 10  1  0  0  0  0
 18 17  1  0  0  0  0
 19 16  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21  4  1  0  0  0  0
 22 10  1  0  0  0  0
 22 14  1  0  0  0  0
 22 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 11  1  0  0  0  0
 23 12  2  0  0  0  0
 24 12  1  0  0  0  0
 24 13  1  0  0  0  0
 25 16  1  0  0  0  0
 25 18  2  0  0  0  0
 26 15  1  0  0  0  0
 26 20  1  0  0  0  0
 27 17  1  0  0  0  0
 27 19  1  0  0  0  0
 27 20  1  0  0  0  0
 28 18  1  0  0  0  0
 29 19  2  0  0  0  0
 30  9  1  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -4.8248   -1.3305    0.6471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5732   -0.9269    0.7376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7215   -0.8700   -0.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4195   -2.2868   -0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5681   -0.2723   -1.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5137   -0.0400   -0.1550 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5367    0.0724   -1.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5876   -0.8269   -0.9421 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8568   -0.6538   -1.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8507   -0.6594   -3.0438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9974   -0.5103   -1.0097 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1365   -0.4715    0.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2797   -0.3666    1.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5096   -0.2833    0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7616    0.3731   -0.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0619    0.1513   -1.2010 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6185   -0.6212   -0.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6637   -0.8853    0.6505 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8710   -0.5791    1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9502   -0.5615    2.4136 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417   -0.6950    0.5046 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7488   -0.6595    0.9748 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8931    0.2419    2.0909 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5046    1.4313    1.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605    2.6461    2.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3811    3.6991    1.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7539    3.5638    0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5049    2.3799   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8729    1.2972    0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2193   -1.6206   -0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4865   -1.3863    1.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2053   -0.6447    1.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3663   -2.9044   -0.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6715   -2.7831   -0.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0807   -2.3482   -1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9875    0.1964   -2.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1839   -1.0854   -2.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2851    0.4170   -1.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1978    1.1171   -1.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9955   -0.1687   -2.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2729   -1.9042   -1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463    0.1705   -3.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2714   -0.3459    2.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0733    0.9548   -1.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6337   -0.9834   -0.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7755   -1.4667    1.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0314   -1.6740    1.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022    0.0682    3.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4560    2.7277    3.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5719    4.6170    2.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2429    4.3976   -0.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7988    2.2929   -1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 12  2  0
 12 11  1  0
 11  9  2  0
  9 10  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6 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
 22 21  1  0
 21 19  1  0
 19 20  2  0
  6  3  1  6
  3  4  1  0
  3  5  1  0
  3  2  1  0
  2  1  2  3
 18 14  1  0
 19 12  1  0
 21  8  1  0
 29  6  1  0
 29 24  1  0
 13 43  1  0
 15 44  1  0
 17 45  1  0
 18 46  1  0
 10 42  1  0
  8 41  1  1
  7 39  1  0
  7 40  1  0
 22 47  1  1
 23 48  1  0
 25 49  1  0
 26 50  1  0
 27 51  1  0
 28 52  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
M  END


  Mrv0541 09061400402D          

 30 34  0  0  0  0            999 V2000
    4.1864    2.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2669    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7605    1.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643    2.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4162   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5337   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612    1.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9901   -0.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3770    0.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3130   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816    0.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0137    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6476   -0.3692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5521    0.3936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9143   -0.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4039    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3784   -1.4769    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  2  0  0  0  0
 14  7  2  0  0  0  0
 15  8  2  0  0  0  0
 15 14  1  0  0  0  0
 16  9  2  0  0  0  0
 17 10  1  0  0  0  0
 18 17  1  0  0  0  0
 19 16  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21  4  1  0  0  0  0
 22 10  1  0  0  0  0
 22 14  1  0  0  0  0
 22 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 11  1  0  0  0  0
 23 12  2  0  0  0  0
 24 12  1  0  0  0  0
 24 13  1  0  0  0  0
 25 16  1  0  0  0  0
 25 18  2  0  0  0  0
 26 15  1  0  0  0  0
 26 20  1  0  0  0  0
 27 17  1  0  0  0  0
 27 19  1  0  0  0  0
 27 20  1  0  0  0  0
 28 18  1  0  0  0  0
 29 19  2  0  0  0  0
 30  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137607

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(C1=CN=CN1)=C1\N=C(O)C2CC3(C(NC4=CC=CC=C34)N2C1=O)C(C)(C)C=C

> <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-

> <INCHI_KEY>
SPWSUFUPTSJWNG-SXGWCWSVSA-N

> <FORMULA>
C22H23N5O2

> <MOLECULAR_WEIGHT>
389.4503

> <EXACT_MASS>
389.185175005

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.500861730773536

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4Z)-6-hydroxy-4-(1H-imidazol-5-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

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
1.2380437080619542

> <ALOGPS_LOGS>
-3.52

> <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

> <ALOGPS_SOLUBILITY>
1.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4Z)-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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-14         0                                  
HETATM    1  C   UNK     0       7.815   4.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.232   3.516   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.020   2.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.280   4.255   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.119   1.777   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.409   0.265   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.664   2.282   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.244  -0.742   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.996  -1.244   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.848   2.520   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.715  -1.619   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.437   0.766   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.451  -0.739   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.499   1.275   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.789  -0.237   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.169  -0.237   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.499   1.777   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.044   2.282   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.624  -0.742   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.316   0.073   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.626   2.861   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.971   1.467   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      -4.942  -0.689   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0      -2.897   0.735   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0      -0.121   1.275   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0       5.440  -0.980   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0       2.788   0.265   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0       0.754   3.795   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.913  -2.255   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      -0.706  -2.757   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   21                                                            
CONECT    3   21                                                            
CONECT    4    1   21                                                       
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5   14                                                       
CONECT    8    6   15                                                       
CONECT    9   13   16   30                                                  
CONECT   10   17   22                                                       
CONECT   11   13   23                                                       
CONECT   12   23   24                                                       
CONECT   13    9   11   24                                                  
CONECT   14    7   15   22                                                  
CONECT   15    8   14   26                                                  
CONECT   16    9   19   25                                                  
CONECT   17   10   18   27                                                  
CONECT   18   17   25   28                                                  
CONECT   19   16   27   29                                                  
CONECT   20   22   26   27                                                  
CONECT   21    2    3    4   22                                             
CONECT   22   10   14   20   21                                             
CONECT   23   11   12                                                       
CONECT   24   12   13                                                       
CONECT   25   16   18                                                       
CONECT   26   15   20                                                       
CONECT   27   17   19   20                                                  
CONECT   28   18                                                            
CONECT   29   19                                                            
CONECT   30    9                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
Isoroquefortine C	MeSH
Roquefortin	MeSH
Roquefortine C	MeSH

Chemical Formula

C₂₂H₂₃N₅O₂

Average Mass

389.4503 Da

Monoisotopic Mass

389.18518 Da

IUPAC Name

(4Z)-6-hydroxy-4-(1H-imidazol-5-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

Traditional Name

(4Z)-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

CAS Registry Number

Not Available

SMILES

[H]\C(C1=CN=CN1)=C1\N=C(O)C2CC3(C(NC4=CC=CC=C34)N2C1=O)C(C)(C)C=C

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-

InChI Key

SPWSUFUPTSJWNG-SXGWCWSVSA-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
Penicillium roqueforti	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
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	2.48	ALOGPS
logP	1.24	ChemAxon
logS	-3.5	ALOGPS
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	41.5 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Roquefortine C

METLIN ID

Not Available

PubChem Compound

5358951

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Roquefortine C (NP0137607)

MOL for NP0137607 (Roquefortine C)

3D MOL for NP0137607 (Roquefortine C)

3D SDF for NP0137607 (Roquefortine C)

3D-SDF for NP0137607 (Roquefortine C)

PDB for NP0137607 (Roquefortine C)

3D PDB for NP0137607 (Roquefortine C)

SMILES for NP0137607 (Roquefortine C)

INCHI for NP0137607 (Roquefortine C)

Structure for NP0137607 (Roquefortine C)

3D Structure for NP0137607 (Roquefortine C)