NP-MRD: Showing NP-Card for Tryptoquivaline E (NP0066212)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-04-28 10:22:47 UTC

Updated at

2022-04-28 10:22:47 UTC

NP-MRD ID

NP0066212

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tryptoquivaline E

Description

Fumitremorgin E belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. Tryptoquivaline E is found in Aspergillus clavatus and Aspergillus fumigatus. It was first documented in 2015 (PMID: 26640821). Based on a literature review a significant number of articles have been published on Fumitremorgin E (PMID: 27865702) (PMID: 34180322) (PMID: 31915017) (PMID: 27280693).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212222D          

 31 36  0  0  1  0            999 V2000
   -1.8708   -6.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9570   -6.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7107   -7.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3781   -6.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2919   -5.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5382   -5.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2033   -7.2245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6513   -6.6114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0638   -5.8969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4763   -5.1824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9243   -4.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0958   -3.7624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1706   -4.9049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2568   -5.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5439   -4.4924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2584   -4.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2584   -5.7299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9728   -4.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9728   -3.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2584   -3.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5439   -3.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6873   -3.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4018   -3.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4018   -4.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6873   -4.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1024   -6.9469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0161   -7.7674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6292   -8.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7908   -7.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1264   -8.6926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8169   -6.5344    0.0000 O   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
  2  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 13 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 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
 15 21  1  0  0  0  0
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 18 25  2  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
  7 29  1  0  0  0  0
 29 30  2  0  0  0  0
 26 31  1  0  0  0  0
M  END

     RDKit          3D

 49 54  0  0  0  0  0  0  0  0999 V2000
   -4.2901   -2.8455   -1.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8561   -1.4025   -1.0778 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4719   -0.6431    0.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6342   -0.6919    0.5117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4587    0.2272    0.5409 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1017    1.4300    1.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8603    2.2242    2.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2741    3.3634    2.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9759    3.7235    2.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2271    2.9318    1.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975    1.7828    0.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2722    0.7441   -0.0218 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1450    0.4081    0.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9780    1.0800   -0.6989 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2765    0.5328   -0.8907 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9536    0.7876   -2.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2039    0.2863   -2.2449 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8066   -0.4914   -1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0697   -1.0211   -1.5225 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6619   -1.8156   -0.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0039   -2.1105    0.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7436   -1.5825    0.8020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1458   -0.7776   -0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8731   -0.2466    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3299   -0.5506    1.1258 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0642    0.9923   -1.8557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3651    0.8413   -3.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2243    1.1123   -1.3575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950   -0.4402    0.2213 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4409   -1.2374   -0.9322 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8362   -2.4417   -0.7447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0614   -3.2851   -0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3876   -2.8535   -1.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8077   -3.3421   -1.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1616   -0.8965   -2.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8766    1.9348    2.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8640    3.9769    3.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5630    4.6366    2.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2199    3.2400    1.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2069   -0.7046    0.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3497    0.7993    1.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1274    2.1402   -0.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653    1.4076   -2.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5653   -0.7820   -2.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6531   -2.2395   -0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4594   -2.7346    1.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2056   -1.8005    1.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8981   -0.9963    1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9976   -2.6702    0.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 30  1  0
 30 31  1  0
 30 29  1  0
 29  5  1  0
  5  3  1  0
  3  4  2  0
  5  6  1  0
  6 11  2  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  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
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 14 26  1  0
 26 27  2  0
 26 28  1  0
  3  2  1  0
  7  6  1  0
 12 28  1  6
 12 29  1  0
 24 15  1  0
 23 18  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  6
 31 49  1  0
 29 48  1  1
 10 39  1  0
  9 38  1  0
  8 37  1  0
  7 36  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  1
 16 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
M  END


  Mrv1652304282212222D          

 31 36  0  0  1  0            999 V2000
   -1.8708   -6.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9570   -6.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7107   -7.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3781   -6.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2919   -5.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5382   -5.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2033   -7.2245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6513   -6.6114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0638   -5.8969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4763   -5.1824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9243   -4.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0958   -3.7624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1706   -4.9049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2568   -5.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5439   -4.4924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2584   -4.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2584   -5.7299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9728   -4.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9728   -3.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2584   -3.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5439   -3.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6873   -3.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4018   -3.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4018   -4.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6873   -4.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1024   -6.9469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0161   -7.7674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6292   -8.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7908   -7.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1264   -8.6926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8169   -6.5344    0.0000 O   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
  2  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 13 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 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
 15 21  1  0  0  0  0
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 18 25  2  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
  7 29  1  0  0  0  0
 29 30  2  0  0  0  0
 26 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066212

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1N(O)[C@@H]2N(C1=O)C1=C(C=CC=C1)[C@@]21C[C@@H](N2C=NC3=CC=CC=C3C2=O)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C22H18N4O5/c1-12-18(27)25-16-9-5-3-7-14(16)22(21(25)26(12)30)10-17(20(29)31-22)24-11-23-15-8-4-2-6-13(15)19(24)28/h2-9,11-12,17,21,30H,10H2,1H3/t12-,17+,21-,22-/m0/s1

> <INCHI_KEY>
LSEZQEFBFFRCNW-TYTLQBBQSA-N

> <FORMULA>
C22H18N4O5

> <MOLECULAR_WEIGHT>
418.409

> <EXACT_MASS>
418.127719696

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
41.554251059065365

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4'R,9S,9aS)-1-hydroxy-2-methyl-4'-(4-oxo-3,4-dihydroquinazolin-3-yl)-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-3,5'-dione

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
1.1606668626666672

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.60568359782272

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.922229993990126

> <JCHEM_PKA_STRONGEST_BASIC>
2.687589276386899

> <JCHEM_POLAR_SURFACE_AREA>
102.75

> <JCHEM_REFRACTIVITY>
108.63519999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4'R,9S,9aS)-1-hydroxy-2-methyl-4'-(4-oxoquinazolin-3-yl)-2,9a-dihydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-3,5'-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      -3.492 -11.328   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.653 -12.859   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.060 -13.486   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.306 -12.581   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.145 -11.049   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.738 -10.423   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -2.246 -13.486   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.216 -12.341   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.986 -11.008   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.756  -9.674   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.725  -8.529   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.045  -7.023   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.318  -9.156   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.479 -10.687   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       1.015  -8.386   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.349  -9.156   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.349 -10.696   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.683  -8.386   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.683  -6.846   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.349  -6.076   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       1.015  -6.846   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.016  -6.076   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.350  -6.846   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.350  -8.386   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.016  -9.156   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       0.191 -12.968   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       0.030 -14.499   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.175 -15.530   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.476 -14.819   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.103 -16.226   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.525 -12.198   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2    8   29                                                  
CONECT    8    7    9   26                                                  
CONECT    9    8    1   10   14                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   25                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   15                                                       
CONECT   22   19   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   18                                                       
CONECT   26    8   27   31                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27    7   30                                                  
CONECT   30   29                                                            
CONECT   31   26                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₁₈N₄O₅

Average Mass

418.4090 Da

Monoisotopic Mass

418.12772 Da

IUPAC Name

(2S,4'R,9S,9aS)-1-hydroxy-2-methyl-4'-(4-oxo-3,4-dihydroquinazolin-3-yl)-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-3,5'-dione

Traditional Name

(2S,4'R,9S,9aS)-1-hydroxy-2-methyl-4'-(4-oxoquinazolin-3-yl)-2,9a-dihydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-3,5'-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1N(O)[C@@H]2N(C1=O)C1=C(C=CC=C1)[C@@]21C[C@@H](N2C=NC3=CC=CC=C3C2=O)C(=O)O1

InChI Identifier

InChI=1S/C22H18N4O5/c1-12-18(27)25-16-9-5-3-7-14(16)22(21(25)26(12)30)10-17(20(29)31-22)24-11-23-15-8-4-2-6-13(15)19(24)28/h2-9,11-12,17,21,30H,10H2,1H3/t12-,17+,21-,22-/m0/s1

InChI Key

LSEZQEFBFFRCNW-TYTLQBBQSA-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 clavatus	Fungi	KNApSAcK
Aspergillus fumigatus	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Diazanaphthalene
Quinazoline
Indole or derivatives
Pyrimidone
Gamma butyrolactone
Imidazolidinone
Pyrimidine
Benzenoid
Tetrahydrofuran
Tertiary carboxylic acid amide
Heteroaromatic compound
Imidazolidine
Carboxamide group
Carboxylic acid ester
Lactone
Lactam
N-organohydroxylamine
Organoheterocyclic compound
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Carbonyl group
Organopnictogen compound
Organic oxide
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	1.13	ALOGPS
logP	1.16	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	14.92	ChemAxon
pKa (Strongest Basic)	2.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	102.75 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	108.64 m³·mol⁻¹	ChemAxon
Polarizability	41.55 Å³	ChemAxon
Number of Rings	6	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

158572

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

182322

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Motoyama T, Osada H: Biosynthetic approaches to creating bioactive fungal metabolites: Pathway engineering and activation of secondary metabolism. Bioorg Med Chem Lett. 2016 Dec 15;26(24):5843-5850. doi: 10.1016/j.bmcl.2016.11.013. Epub 2016 Nov 9. [PubMed:27865702 ]
Zou R, Wei C, Zhang X, Zhou D, Xu J: Alkaloids from endophytic fungus Aspergillus fumigatus HQD24 isolated from the Chinese mangrove plant Rhizophora mucronata. Nat Prod Res. 2021 Jun 28:1-5. doi: 10.1080/14786419.2021.1916017. [PubMed:34180322 ]
Thiele Nee Schrewe L, Guse K, Tietz S, Remlinger J, Demir S, Pedreiturria X, Hoepner R, Salmen A, Pistor M, Turner T, Engelhardt B, Hermann DM, Luhder F, Wiese S, Chan A: Functional relevance of the multi-drug transporter abcg2 on teriflunomide therapy in an animal model of multiple sclerosis. J Neuroinflammation. 2020 Jan 8;17(1):9. doi: 10.1186/s12974-019-1677-z. [PubMed:31915017 ]
Spindler A, Stefan K, Wiese M: Synthesis and Investigation of Tetrahydro-beta-carboline Derivatives as Inhibitors of the Breast Cancer Resistance Protein (ABCG2). J Med Chem. 2016 Jul 14;59(13):6121-35. doi: 10.1021/acs.jmedchem.6b00035. Epub 2016 Jun 17. [PubMed:27280693 ]
Shah GR, Wesener SR, Cheng YQ: Engineered Production of Tryprostatins in E. coli through Reconstitution of a Partial ftm Biosynthetic Gene Cluster from Aspergillus sp. Jacobs J Biotechnol Bioeng. 2015 Apr;2(1). Epub 2014 Dec 18. [PubMed:26640821 ]

Showing NP-Card for Tryptoquivaline E (NP0066212)

MOL for NP0066212 (Tryptoquivaline E)

3D MOL for NP0066212 (Tryptoquivaline E)

3D SDF for NP0066212 (Tryptoquivaline E)

3D-SDF for NP0066212 (Tryptoquivaline E)

PDB for NP0066212 (Tryptoquivaline E)

3D PDB for NP0066212 (Tryptoquivaline E)

SMILES for NP0066212 (Tryptoquivaline E)

INCHI for NP0066212 (Tryptoquivaline E)

Structure for NP0066212 (Tryptoquivaline E)

3D Structure for NP0066212 (Tryptoquivaline E)