NP-MRD: Showing NP-Card for (2s,9s,9as)-9-hydroxy-9-{[(1s,4s)-3-hydroxy-1-methyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2h,9ah-imidazo[1,2-a]indol-3-one (NP0323963)

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Record Information

Version

2.0

Created at

2022-09-12 03:43:35 UTC

Updated at

2022-09-12 03:43:35 UTC

NP-MRD ID

NP0323963

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,9s,9as)-9-hydroxy-9-{[(1s,4s)-3-hydroxy-1-methyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2h,9ah-imidazo[1,2-a]indol-3-one

Description

Fumigatoside D belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether). (2s,9s,9as)-9-hydroxy-9-{[(1s,4s)-3-hydroxy-1-methyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2h,9ah-imidazo[1,2-a]indol-3-one is found in Aspergillus fumigatus. Based on a literature review very few articles have been published on Fumigatoside D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122205432D          

 44 50  0  0  1  0            999 V2000
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6224    1.7213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8019    3.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9814    3.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6459    3.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1308    4.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513    4.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714    3.5549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8561    3.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1110    4.5945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3410    3.1424    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1660    3.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8561    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1110    1.6904    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5590    1.0773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8139    0.2927    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2619   -0.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5168   -1.1051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8758   -0.6635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1729    0.7342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9799    0.5627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9180    1.5189    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4700    2.1319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714    2.7299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  7  1  6  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 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
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 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
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 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  6  0  0  0
 33 21  1  6  0  0  0
 16 33  1  0  0  0  0
  8 33  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 37 42  1  0  0  0  0
 42 43  1  0  0  0  0
 34 43  1  0  0  0  0
 43 44  2  0  0  0  0
M  END

     RDKit          3D

 77 83  0  0  0  0  0  0  0  0999 V2000
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    3.6029   -1.5788   -2.8003 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6137   -0.0731   -2.8190 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7208    0.5401   -2.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643    1.8831   -2.0662 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7599   -0.3307   -1.3791 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6624    0.3184   -0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4261    1.0048   -1.3946 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -4.9864   -1.1196    0.9802 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.7376    0.3588   -0.9042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7628    0.9735    1.2219 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.6394   -1.1329    0.7767 C   0  0  0  0  0  0  0  0  0  0  0  0
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 30 70  1  0
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 32 72  1  0
M  END


  Mrv1652309122205432D          

 44 50  0  0  1  0            999 V2000
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6224    1.7213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8019    3.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9814    3.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6459    3.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9513    4.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714    3.5549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8561    3.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1110    4.5945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8561    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1110    1.6904    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5590    1.0773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8139    0.2927    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2619   -0.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5168   -1.1051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6209    0.1211    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8758   -0.6635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1729    0.7342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9799    0.5627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9180    1.5189    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4700    2.1319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714    2.7299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  7  1  6  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 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
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  6  0  0  0
 33 21  1  6  0  0  0
 16 33  1  0  0  0  0
  8 33  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 37 42  1  0  0  0  0
 42 43  1  0  0  0  0
 34 43  1  0  0  0  0
 43 44  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0323963

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1N([C@H]2N(C1=O)C1=CC=CC=C1[C@@]2(O)C[C@@H]1N2C(=O)C3=CC=CC=C3N=C2[C@H](C)N=C1O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H33N5O9/c1-13-24-32-17-9-5-3-7-15(17)27(42)34(24)19(25(40)31-13)11-30(43)16-8-4-6-10-18(16)35-26(41)14(2)33(29(30)35)28-23(39)22(38)21(37)20(12-36)44-28/h3-10,13-14,19-23,28-29,36-39,43H,11-12H2,1-2H3,(H,31,40)/t13-,14-,19-,20+,21+,22-,23+,28+,29-,30-/m0/s1

> <INCHI_KEY>
VCGAKVDKXANVTK-JZUNSPIXSA-N

> <FORMULA>
C30H33N5O9

> <MOLECULAR_WEIGHT>
607.62

> <EXACT_MASS>
607.227827663

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
59.93019151109732

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,9S,9aS)-9-hydroxy-9-{[(1S,4S)-3-hydroxy-1-methyl-6-oxo-1H,4H,6H-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H,2H,3H,9H,9aH-imidazo[1,2-a]indol-3-one

> <JCHEM_LOGP>
-0.7755950364604548

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.323386695189551

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9818356852597727

> <JCHEM_PKA_STRONGEST_BASIC>
2.331218622157094

> <JCHEM_POLAR_SURFACE_AREA>
199.18999999999997

> <JCHEM_REFRACTIVITY>
152.98550000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,9S,9aS)-9-hydroxy-9-{[(1S,4S)-3-hydroxy-1-methyl-6-oxo-1H,4H-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2H,9aH-imidazo[1,2-a]indol-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       8.002   0.000   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.628   3.213   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.097   5.866   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.565   6.027   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.939   7.434   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.844   8.680   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.376   8.519   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   7.112   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       9.467   6.636   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      10.931   7.112   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.407   8.576   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.837   5.866   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.377   5.866   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      10.931   4.620   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      11.407   3.155   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.377   2.011   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.853   0.546   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.822  -0.598   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.298  -2.063   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.359   0.226   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.835  -1.239   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      13.389   1.371   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.896   1.050   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.914   2.835   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      13.944   3.980   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.467   5.096   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   33                                             
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15   17   33                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   33                                                  
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31                                                            
CONECT   33   21   16    8                                                  
CONECT   34    6   35   43                                                  
CONECT   35   34    2   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   37   43                                                  
CONECT   43   42   34   44                                                  
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0  100    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₃N₅O₉

Average Mass

607.6200 Da

Monoisotopic Mass

607.22783 Da

IUPAC Name

(2S,9S,9aS)-9-hydroxy-9-{[(1S,4S)-3-hydroxy-1-methyl-6-oxo-1H,4H,6H-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H,2H,3H,9H,9aH-imidazo[1,2-a]indol-3-one

Traditional Name

(2S,9S,9aS)-9-hydroxy-9-{[(1S,4S)-3-hydroxy-1-methyl-6-oxo-1H,4H-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2H,9aH-imidazo[1,2-a]indol-3-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1N([C@H]2N(C1=O)C1=CC=CC=C1[C@@]2(O)C[C@@H]1N2C(=O)C3=CC=CC=C3N=C2[C@H](C)N=C1O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C30H33N5O9/c1-13-24-32-17-9-5-3-7-15(17)27(42)34(24)19(25(40)31-13)11-30(43)16-8-4-6-10-18(16)35-26(41)14(2)33(29(30)35)28-23(39)22(38)21(37)20(12-36)44-28/h3-10,13-14,19-23,28-29,36-39,43H,11-12H2,1-2H3,(H,31,40)/t13-,14-,19-,20+,21+,22-,23+,28+,29-,30-/m0/s1

InChI Key

VCGAKVDKXANVTK-JZUNSPIXSA-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
Aspergillus fumigatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glycosylamines

Alternative Parents

Substituents

Hexose monosaccharide
N-glycosyl compound
Diazanaphthalene
Quinazoline
Alpha-amino acid or derivatives
Indole or derivatives
Pyrimidone
Benzenoid
Pyrimidine
Oxane
Monosaccharide
Imidazolidinone
Heteroaromatic compound
Cyclic carboximidic acid
Tertiary carboxylic acid amide
Tertiary alcohol
Imidazolidine
Secondary alcohol
Lactam
Hemiaminal
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Carboxylic acid derivative
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organonitrogen compound
Carbonyl group
Alcohol
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	-0.78	ChemAxon
pKa (Strongest Acidic)	3.98	ChemAxon
pKa (Strongest Basic)	2.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	199.19 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	152.99 m³·mol⁻¹	ChemAxon
Polarizability	59.93 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

78438523

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122227489

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,9s,9as)-9-hydroxy-9-{[(1s,4s)-3-hydroxy-1-methyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2h,9ah-imidazo[1,2-a]indol-3-one (NP0323963)

MOL for NP0323963 ((2s,9s,9as)-9-hydroxy-9-{[(1s,4s)-3-hydroxy-1-methyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2h,9ah-imidazo[1,2-a]indol-3-one)

3D MOL for NP0323963 ((2s,9s,9as)-9-hydroxy-9-{[(1s,4s)-3-hydroxy-1-methyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2h,9ah-imidazo[1,2-a]indol-3-one)

3D SDF for NP0323963 ((2s,9s,9as)-9-hydroxy-9-{[(1s,4s)-3-hydroxy-1-methyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2h,9ah-imidazo[1,2-a]indol-3-one)

3D-SDF for NP0323963 ((2s,9s,9as)-9-hydroxy-9-{[(1s,4s)-3-hydroxy-1-methyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2h,9ah-imidazo[1,2-a]indol-3-one)

PDB for NP0323963 ((2s,9s,9as)-9-hydroxy-9-{[(1s,4s)-3-hydroxy-1-methyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2h,9ah-imidazo[1,2-a]indol-3-one)

3D PDB for NP0323963 ((2s,9s,9as)-9-hydroxy-9-{[(1s,4s)-3-hydroxy-1-methyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2h,9ah-imidazo[1,2-a]indol-3-one)

SMILES for NP0323963 ((2s,9s,9as)-9-hydroxy-9-{[(1s,4s)-3-hydroxy-1-methyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2h,9ah-imidazo[1,2-a]indol-3-one)

INCHI for NP0323963 ((2s,9s,9as)-9-hydroxy-9-{[(1s,4s)-3-hydroxy-1-methyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2h,9ah-imidazo[1,2-a]indol-3-one)

Structure for NP0323963 ((2s,9s,9as)-9-hydroxy-9-{[(1s,4s)-3-hydroxy-1-methyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2h,9ah-imidazo[1,2-a]indol-3-one)

3D Structure for NP0323963 ((2s,9s,9as)-9-hydroxy-9-{[(1s,4s)-3-hydroxy-1-methyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2h,9ah-imidazo[1,2-a]indol-3-one)