NP-MRD: Showing NP-Card for Fumiquinazoline B (NP0069894)

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Record Information

Version

2.0

Created at

2022-04-28 15:12:14 UTC

Updated at

2022-04-28 15:12:14 UTC

NP-MRD ID

NP0069894

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fumiquinazoline B

Description

Fumiquinazoline B belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring. Fumiquinazoline B is found in Aspergillus fumigatus. Fumiquinazoline B was first documented in 2020 (PMID: 33332106). Based on a literature review very few articles have been published on Fumiquinazoline B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282217122D          

 33 38  0  0  1  0            999 V2000
    2.2780    4.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0386    3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    3.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6712    4.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106    5.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7140    5.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466    5.7299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568    5.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6963    4.7530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1323    4.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3717    3.3614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4997    4.5656    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0637    5.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671    4.9802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8243    5.9571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0209    6.1445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7814    6.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7391    3.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751    3.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4982    2.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7377    1.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5625    1.8965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8329    2.6760    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6577    2.6597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8971    1.8702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2203    1.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2040    0.5737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6766    1.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1737    1.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6298    1.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8692    2.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3052    2.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6353    3.7978    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
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  6  0  0  0
 12 18  1  6  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  2  0  0  0  0
 25 28  1  6  0  0  0
 21 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 20 32  1  0  0  0  0
 19 33  1  1  0  0  0
M  END

     RDKit          3D

 56 61  0  0  0  0  0  0  0  0999 V2000
   -4.5233    0.0120    3.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8193   -0.7482    2.3890 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6557    0.0363    1.8485 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5382   -0.5828    0.5372 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9505   -0.1703    0.1400 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7203   -0.7929    1.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8580   -1.2335    1.0197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8824    0.6544   -0.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9002    1.2978   -1.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5907    2.1408   -2.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2887    2.3665   -3.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2847    1.7339   -2.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5915    0.8963   -1.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7451    0.0159   -0.5015 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6467   -1.1642   -1.4695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3266    0.4255   -0.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6357   -0.6487   -0.2181 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5542   -1.7003    0.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1571   -1.7146    1.7648 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4204   -2.8484    0.5420 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5170   -2.6689   -0.3747 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6666   -3.5746   -0.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9394   -1.2284   -0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2523   -0.9124   -0.1483 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7116    0.3446   -0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0570    0.6428    0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5253    1.9279    0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5778    2.9353    0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2112    2.6712    0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872    1.3719    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4220    1.0509   -0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6568    2.0387    0.0509 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0578   -0.2165   -0.1427 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8415    0.8161    3.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4403    0.5382    3.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8813   -0.6255    4.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4990   -1.7279    2.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8886   -0.0930    2.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666   -1.6936    0.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9287    1.1408   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3574    2.6609   -3.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0297    3.0256   -3.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2616    1.9288   -2.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2158   -0.7848   -2.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0850    0.9796   -1.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2597    1.2021    0.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6806   -1.2349   -1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2724   -3.7572    1.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1366   -2.7482   -1.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5956   -2.9838    0.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8930   -4.1300   -1.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4554   -4.3016    0.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7691   -0.1626   -0.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5855    2.1771    0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8887    3.9670    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4649    3.4488    0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  5  8  1  0
  8 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
 13 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  0
 17 33  1  0
 33 31  1  0
 31 32  2  0
 31 30  1  0
 30 29  2  0
 29 28  1  0
 28 27  2  0
 27 26  1  0
 26 25  2  0
 25 24  1  0
 24 23  2  0
 23 21  1  0
 21 22  1  0
 21 20  1  0
 20 18  1  0
 18 19  2  0
  6  2  1  0
  9  8  1  0
 18 17  1  0
 14  4  1  0
 23 33  1  0
 25 30  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  1
  3 38  1  0
  4 39  1  1
 12 43  1  0
 11 42  1  0
 10 41  1  0
  9 40  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  6
 29 56  1  0
 28 55  1  0
 27 54  1  0
 26 53  1  0
 21 49  1  6
 22 50  1  0
 22 51  1  0
 22 52  1  0
 20 48  1  0
M  END


  Mrv1652304282217122D          

 33 38  0  0  1  0            999 V2000
    2.2780    4.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0386    3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    3.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6712    4.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106    5.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7140    5.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466    5.7299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568    5.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6963    4.7530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1323    4.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3717    3.3614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4997    4.5656    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0637    5.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671    4.9802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8243    5.9571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0209    6.1445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7814    6.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7391    3.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751    3.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4982    2.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7377    1.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5625    1.8965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8329    2.6760    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6577    2.6597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8971    1.8702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2203    1.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2040    0.5737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6766    1.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1737    1.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6298    1.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8692    2.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3052    2.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6353    3.7978    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
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  6  0  0  0
 12 18  1  6  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  2  0  0  0  0
 25 28  1  6  0  0  0
 21 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 20 32  1  0  0  0  0
 19 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0069894

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1N[C@H]2N(C1=O)C1=C(C=CC=C1)[C@@]2(O)C[C@H]1N2C(=O)C3=CC=CC=C3N=C2[C@@H](C)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H23N5O4/c1-12-19-27-16-9-5-3-7-14(16)22(32)28(19)18(20(30)25-12)11-24(33)15-8-4-6-10-17(15)29-21(31)13(2)26-23(24)29/h3-10,12-13,18,23,26,33H,11H2,1-2H3,(H,25,30)/t12-,13+,18-,23+,24+/m1/s1

> <INCHI_KEY>
DQQCCKFZJNINST-ZRCGILORSA-N

> <FORMULA>
C24H23N5O4

> <MOLECULAR_WEIGHT>
445.479

> <EXACT_MASS>
445.175004241

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
45.709183447384376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4R)-4-{[(2S,9S,9aS)-9-hydroxy-2-methyl-3-oxo-1H,2H,3H,9H,9aH-imidazo[1,2-a]indol-9-yl]methyl}-1-methyl-1H,2H,3H,4H,6H-pyrazino[2,1-b]quinazoline-3,6-dione

> <ALOGPS_LOGP>
0.45

> <JCHEM_LOGP>
0.6135689210000002

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.939703635617395

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.21022030873247

> <JCHEM_PKA_STRONGEST_BASIC>
4.021145684896284

> <JCHEM_POLAR_SURFACE_AREA>
114.34000000000002

> <JCHEM_REFRACTIVITY>
119.50699999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R)-4-{[(2S,9S,9aS)-9-hydroxy-2-methyl-3-oxo-1H,2H,9aH-imidazo[1,2-a]indol-9-yl]methyl}-1-methyl-1H,2H,4H-pyrazino[2,1-b]quinazoline-3,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.252   8.798   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.805   7.324   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   6.974   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.253   8.098   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.700   9.572   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.200   9.922   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.647  10.696   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.853  10.346   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.300   8.872   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.247   7.748   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.694   6.275   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.799   8.522   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.852   9.646   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.352   9.296   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      -3.405  11.120   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -1.906  11.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.459  12.944   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.246   7.049   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.194   5.925   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.930   5.044   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.377   3.571   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -2.917   3.540   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      -3.421   4.995   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      -4.961   4.965   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      -5.408   3.491   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.144   2.611   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.114   1.071   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -6.863   2.986   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.324   2.447   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.176   2.796   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.623   4.270   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.570   5.394   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.186   7.089   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    8   17                                                  
CONECT   17   16                                                            
CONECT   18   12   19                                                       
CONECT   19   18   20   23   33                                             
CONECT   20   19   21   32                                                  
CONECT   21   20   22   29                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   19   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   22   27                                                  
CONECT   27   26                                                            
CONECT   28   25                                                            
CONECT   29   21   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   20                                                       
CONECT   33   19                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₃N₅O₄

Average Mass

445.4790 Da

Monoisotopic Mass

445.17500 Da

IUPAC Name

(1R,4R)-4-{[(2S,9S,9aS)-9-hydroxy-2-methyl-3-oxo-1H,2H,3H,9H,9aH-imidazo[1,2-a]indol-9-yl]methyl}-1-methyl-1H,2H,3H,4H,6H-pyrazino[2,1-b]quinazoline-3,6-dione

Traditional Name

(1R,4R)-4-{[(2S,9S,9aS)-9-hydroxy-2-methyl-3-oxo-1H,2H,9aH-imidazo[1,2-a]indol-9-yl]methyl}-1-methyl-1H,2H,4H-pyrazino[2,1-b]quinazoline-3,6-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1N[C@H]2N(C1=O)C1=C(C=CC=C1)[C@@]2(O)C[C@H]1N2C(=O)C3=CC=CC=C3N=C2[C@@H](C)NC1=O

InChI Identifier

InChI=1S/C24H23N5O4/c1-12-19-27-16-9-5-3-7-14(16)22(32)28(19)18(20(30)25-12)11-24(33)15-8-4-6-10-17(15)29-21(31)13(2)26-23(24)29/h3-10,12-13,18,23,26,33H,11H2,1-2H3,(H,25,30)/t12-,13+,18-,23+,24+/m1/s1

InChI Key

DQQCCKFZJNINST-ZRCGILORSA-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 fumigatus	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinazolines

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Quinazoline
Indole or derivatives
Pyrimidone
Imidazolidinone
Pyrimidine
Benzenoid
Tertiary carboxylic acid amide
Tertiary alcohol
Heteroaromatic compound
Imidazolidine
Secondary carboxylic acid amide
Carboxamide group
Lactam
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Carbonyl group
Amine
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	0.45	ALOGPS
logP	0.61	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.21	ChemAxon
pKa (Strongest Basic)	4.02	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.34 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	119.51 m³·mol⁻¹	ChemAxon
Polarizability	45.71 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

C00028285

Chemspider ID

10216892

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15224332

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Matsushita T, Kishimoto S, Hara K, Hashimoto H, Watanabe K: Structural and Functional Analyses of a Spiro-Carbon-Forming, Highly Promiscuous Epoxidase from Fungal Natural Product Biosynthesis. Biochemistry. 2020 Dec 29;59(51):4787-4792. doi: 10.1021/acs.biochem.0c00896. Epub 2020 Dec 17. [PubMed:33332106 ]

Showing NP-Card for Fumiquinazoline B (NP0069894)

MOL for NP0069894 (Fumiquinazoline B)

3D MOL for NP0069894 (Fumiquinazoline B)

3D SDF for NP0069894 (Fumiquinazoline B)

3D-SDF for NP0069894 (Fumiquinazoline B)

PDB for NP0069894 (Fumiquinazoline B)

3D PDB for NP0069894 (Fumiquinazoline B)

SMILES for NP0069894 (Fumiquinazoline B)

INCHI for NP0069894 (Fumiquinazoline B)

Structure for NP0069894 (Fumiquinazoline B)

3D Structure for NP0069894 (Fumiquinazoline B)