NP-MRD: Showing NP-Card for (1'r,2s,9s,9as,12's)-16'-hydroxy-2,12'-dimethyl-2,9a-dihydro-1h-13'-oxa-2',10',17'-triazaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[10.3.2.0²,¹¹.0⁴,⁹]heptadecane]-4',6',8',10',16'-pentaene-3,3'-dione (NP0186735)

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Record Information

Version

2.0

Created at

2022-09-04 02:41:58 UTC

Updated at

2022-09-04 02:41:58 UTC

NP-MRD ID

NP0186735

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,2s,9s,9as,12's)-16'-hydroxy-2,12'-dimethyl-2,9a-dihydro-1h-13'-oxa-2',10',17'-triazaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[10.3.2.0²,¹¹.0⁴,⁹]heptadecane]-4',6',8',10',16'-pentaene-3,3'-dione

Description

Fumiquinazoline C 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. (1'r,2s,9s,9as,12's)-16'-hydroxy-2,12'-dimethyl-2,9a-dihydro-1h-13'-oxa-2',10',17'-triazaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[10.3.2.0²,¹¹.0⁴,⁹]heptadecane]-4',6',8',10',16'-pentaene-3,3'-dione is found in Aspergillus fumigatus and Streptomyces piomogenus. (1'r,2s,9s,9as,12's)-16'-hydroxy-2,12'-dimethyl-2,9a-dihydro-1h-13'-oxa-2',10',17'-triazaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[10.3.2.0²,¹¹.0⁴,⁹]heptadecane]-4',6',8',10',16'-pentaene-3,3'-dione was first documented in 2014 (PMID: 24612080). Based on a literature review a small amount of articles have been published on fumiquinazoline C (PMID: 28453536) (PMID: 28213885) (PMID: 29902496) (PMID: 33705521).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042204412D          

 33 39  0  0  1  0            999 V2000
    8.2871    5.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2235    4.6383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5207    4.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7144    3.4044    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5369    3.3408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8516    4.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6535    4.2971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7306    2.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4562    2.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4789    1.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7761    0.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0505    1.2821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0278    2.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3997    2.6417    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2263    1.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4876    1.4679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1923    2.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4200    1.7420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0472    2.6329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0523    3.2698    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6850    4.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8772    3.2802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5461    2.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547    2.8516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1571    2.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658    2.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7681    1.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9618    1.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7532    0.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3508    1.4809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1422    1.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3359    0.4458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7398    1.8164    0.0000 N   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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
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  4 14  1  0  0  0  0
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 17 18  1  0  0  0  0
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 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 23 33  1  0  0  0  0
 16 33  1  1  0  0  0
M  END

     RDKit          2D

 54 60  0  0  0  0  0  0  0  0999 V2000
    5.6918   -0.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0008    1.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5762    1.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6018    2.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4993    5.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7526    4.9657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6629    3.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6787    2.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0777    1.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0777   -1.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3846   -1.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7184   -3.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5574   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5574    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9088    1.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2289    1.0028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950    1.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1286    2.5670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    3.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484    4.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1447    5.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3175    4.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0939    2.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6817   -1.1496    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4096    7.2893    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0941    5.6367    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0061    2.8008    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2031    0.2750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7786   -1.0712    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0130   -2.5242    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1518   -3.5898    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2603    2.0517    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5597    0.0494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4276    2.8215    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3842    5.2220    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5474    6.5912    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7138    4.7591    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4581    2.1041    0.0000 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  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 14 13  1  6
 14 15  1  0
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 33 31  1  0
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 23 20  1  0
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 20 22  1  0
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  6  2  1  0
 13  8  1  0
 22 14  1  0
 14  4  1  0
 17 16  1  0
 23 33  1  0
 25 30  1  0
  1 34  1  0
  1 35  1  0
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  2 37  1  1
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  4 39  1  1
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 29 54  1  0
 28 53  1  0
 27 52  1  0
 26 51  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 18 47  1  0
M  END


  Mrv1652309042204412D          

 33 39  0  0  1  0            999 V2000
    8.2871    5.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2235    4.6383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5207    4.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7144    3.4044    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5369    3.3408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8516    4.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6535    4.2971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7306    2.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4562    2.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4789    1.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7761    0.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0505    1.2821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0278    2.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3997    2.6417    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2263    1.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4876    1.4679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1923    2.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4200    1.7420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0472    2.6329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0523    3.2698    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6850    4.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8772    3.2802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5461    2.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547    2.8516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1571    2.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658    2.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7681    1.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9618    1.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7532    0.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3508    1.4809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1422    1.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3359    0.4458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7398    1.8164    0.0000 N   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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 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
  8 13  1  0  0  0  0
 14 13  1  6  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
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 27 28  2  0  0  0  0
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 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
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 16 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0186735

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1N[C@H]2N(C1=O)C1=CC=CC=C1[C@@]21C[C@H]2N3C(=O)C4=CC=CC=C4N=C3[C@](C)(O1)N=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C24H21N5O4/c1-12-19(31)28-16-10-6-4-8-14(16)24(22(28)25-12)11-17-18(30)27-23(2,33-24)21-26-15-9-5-3-7-13(15)20(32)29(17)21/h3-10,12,17,22,25H,11H2,1-2H3,(H,27,30)/t12-,17+,22-,23-,24-/m0/s1

> <INCHI_KEY>
POEYRUBMWIOMTB-LTQSKDJASA-N

> <FORMULA>
C24H21N5O4

> <MOLECULAR_WEIGHT>
443.463

> <EXACT_MASS>
443.159354176

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.67051577046233

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'R,2S,9S,9aS,12'S)-16'-hydroxy-2,12'-dimethyl-1,2,3,9a-tetrahydro-13'-oxa-2',10',17'-triazaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[10.3.2.0^{2,11}.0^{4,9}]heptadecane]-4',6',8',10',16'-pentaene-3,3'-dione

> <JCHEM_LOGP>
0.7712595454121002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.45809684459416

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6325334147327033

> <JCHEM_PKA_STRONGEST_BASIC>
5.102201500749111

> <JCHEM_POLAR_SURFACE_AREA>
106.83

> <JCHEM_REFRACTIVITY>
118.22660000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2S,9S,9aS,12'S)-16'-hydroxy-2,12'-dimethyl-2,9a-dihydro-1H-13'-oxa-2',10',17'-triazaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[10.3.2.0^{2,11}.0^{4,9}]heptadecane]-4',6',8',10',16'-pentaene-3,3'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      15.469  10.194   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.351   8.658   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      14.039   7.852   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      14.400   6.355   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      15.936   6.236   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      16.523   7.660   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      18.020   8.021   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      16.297   4.739   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.652   4.006   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.694   2.467   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.382   1.660   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.028   2.393   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.985   3.933   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.813   4.931   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.489   3.426   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.110   2.740   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.559   3.794   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.117   3.252   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0      11.288   4.915   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      11.298   6.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.612   7.483   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.838   6.123   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.353   4.888   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       8.876   5.323   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       7.760   4.261   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.283   4.697   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.167   3.635   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.529   2.138   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.006   1.703   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.121   2.764   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.599   2.329   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.960   0.832   0.000  0.00  0.00           O+0
HETATM   33  N   UNK     0      10.714   3.391   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13    4   15   22                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   33                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20   14                                                       
CONECT   23   20   24   33                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25   31                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   23   16                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₁N₅O₄

Average Mass

443.4630 Da

Monoisotopic Mass

443.15935 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1N[C@H]2N(C1=O)C1=CC=CC=C1[C@@]21C[C@H]2N3C(=O)C4=CC=CC=C4N=C3[C@](C)(O1)N=C2O

InChI Identifier

InChI=1S/C24H21N5O4/c1-12-19(31)28-16-10-6-4-8-14(16)24(22(28)25-12)11-17-18(30)27-23(2,33-24)21-26-15-9-5-3-7-13(15)20(32)29(17)21/h3-10,12,17,22,25H,11H2,1-2H3,(H,27,30)/t12-,17+,22-,23-,24-/m0/s1

InChI Key

POEYRUBMWIOMTB-LTQSKDJASA-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
Streptomyces piomogenus	LOTUS Database	35616633

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
Meta-oxazepine
Pyrimidone
Imidazolidinone
Benzenoid
Pyrimidine
Imidazolidine
Heteroaromatic compound
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Lactam
Carboxylic acid derivative
Secondary aliphatic amine
Oxacycle
Azacycle
Secondary amine
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Amine
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heteroheptacyclic compound (CHEBI:64551 )
azaspiro compound (CHEBI:64551 )
oxaspiro compound (CHEBI:64551 )
fumiquinazoline (CHEBI:64551 )
imidazoindole (CHEBI:64551 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00026833

Chemspider ID

9514662

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11339719

PDB ID

Not Available

ChEBI ID

64551

Good Scents ID

Not Available

References

General References

Myers RR, Smith TD, Elsawa SF, Puel O, Tadrist S, Calvo AM: rtfA controls development, secondary metabolism, and virulence in Aspergillus fumigatus. PLoS One. 2017 Apr 28;12(4):e0176702. doi: 10.1371/journal.pone.0176702. eCollection 2017. [PubMed:28453536 ]
Magotra A, Kumar M, Kushwaha M, Awasthi P, Raina C, Gupta AP, Shah BA, Gandhi SG, Chaubey A: Epigenetic modifier induced enhancement of fumiquinazoline C production in Aspergillus fumigatus (GA-L7): an endophytic fungus from Grewia asiatica L. AMB Express. 2017 Dec;7(1):43. doi: 10.1186/s13568-017-0343-z. Epub 2017 Feb 17. [PubMed:28213885 ]
Abdel-Razek AS, Hamed A, Frese M, Sewald N, Shaaban M: Penicisteroid C: New polyoxygenated steroid produced by co-culturing of Streptomyces piomogenus with Aspergillus niger. Steroids. 2018 Oct;138:21-25. doi: 10.1016/j.steroids.2018.06.005. Epub 2018 Jun 15. [PubMed:29902496 ]
Rocha MC, Fabri JHTM, Silva LP, Angolini CFF, Bertolini MC, da Cunha AF, Valiante V, Goldman GH, Fill TP, Malavazi I: Transcriptional Control of the Production of Aspergillus fumigatus Conidia-Borne Secondary Metabolite Fumiquinazoline C Important for Phagocytosis Protection. Genetics. 2021 May 17;218(1):iyab036. doi: 10.1093/genetics/iyab036. [PubMed:33705521 ]
Lim FY, Ames B, Walsh CT, Keller NP: Co-ordination between BrlA regulation and secretion of the oxidoreductase FmqD directs selective accumulation of fumiquinazoline C to conidial tissues in Aspergillus fumigatus. Cell Microbiol. 2014 Aug;16(8):1267-83. doi: 10.1111/cmi.12284. Epub 2014 Apr 15. [PubMed:24612080 ]
LOTUS database [Link]

Showing NP-Card for (1'r,2s,9s,9as,12's)-16'-hydroxy-2,12'-dimethyl-2,9a-dihydro-1h-13'-oxa-2',10',17'-triazaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[10.3.2.0²,¹¹.0⁴,⁹]heptadecane]-4',6',8',10',16'-pentaene-3,3'-dione (NP0186735)

MOL for NP0186735 ((1'r,2s,9s,9as,12's)-16'-hydroxy-2,12'-dimethyl-2,9a-dihydro-1h-13'-oxa-2',10',17'-triazaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[10.3.2.0²,¹¹.0⁴,⁹]heptadecane]-4',6',8',10',16'-pentaene-3,3'-dione)

3D MOL for NP0186735 ((1'r,2s,9s,9as,12's)-16'-hydroxy-2,12'-dimethyl-2,9a-dihydro-1h-13'-oxa-2',10',17'-triazaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[10.3.2.0²,¹¹.0⁴,⁹]heptadecane]-4',6',8',10',16'-pentaene-3,3'-dione)

3D SDF for NP0186735 ((1'r,2s,9s,9as,12's)-16'-hydroxy-2,12'-dimethyl-2,9a-dihydro-1h-13'-oxa-2',10',17'-triazaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[10.3.2.0²,¹¹.0⁴,⁹]heptadecane]-4',6',8',10',16'-pentaene-3,3'-dione)

3D-SDF for NP0186735 ((1'r,2s,9s,9as,12's)-16'-hydroxy-2,12'-dimethyl-2,9a-dihydro-1h-13'-oxa-2',10',17'-triazaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[10.3.2.0²,¹¹.0⁴,⁹]heptadecane]-4',6',8',10',16'-pentaene-3,3'-dione)

PDB for NP0186735 ((1'r,2s,9s,9as,12's)-16'-hydroxy-2,12'-dimethyl-2,9a-dihydro-1h-13'-oxa-2',10',17'-triazaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[10.3.2.0²,¹¹.0⁴,⁹]heptadecane]-4',6',8',10',16'-pentaene-3,3'-dione)

3D PDB for NP0186735 ((1'r,2s,9s,9as,12's)-16'-hydroxy-2,12'-dimethyl-2,9a-dihydro-1h-13'-oxa-2',10',17'-triazaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[10.3.2.0²,¹¹.0⁴,⁹]heptadecane]-4',6',8',10',16'-pentaene-3,3'-dione)

SMILES for NP0186735 ((1'r,2s,9s,9as,12's)-16'-hydroxy-2,12'-dimethyl-2,9a-dihydro-1h-13'-oxa-2',10',17'-triazaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[10.3.2.0²,¹¹.0⁴,⁹]heptadecane]-4',6',8',10',16'-pentaene-3,3'-dione)

INCHI for NP0186735 ((1'r,2s,9s,9as,12's)-16'-hydroxy-2,12'-dimethyl-2,9a-dihydro-1h-13'-oxa-2',10',17'-triazaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[10.3.2.0²,¹¹.0⁴,⁹]heptadecane]-4',6',8',10',16'-pentaene-3,3'-dione)

Structure for NP0186735 ((1'r,2s,9s,9as,12's)-16'-hydroxy-2,12'-dimethyl-2,9a-dihydro-1h-13'-oxa-2',10',17'-triazaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[10.3.2.0²,¹¹.0⁴,⁹]heptadecane]-4',6',8',10',16'-pentaene-3,3'-dione)

3D Structure for NP0186735 ((1'r,2s,9s,9as,12's)-16'-hydroxy-2,12'-dimethyl-2,9a-dihydro-1h-13'-oxa-2',10',17'-triazaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[10.3.2.0²,¹¹.0⁴,⁹]heptadecane]-4',6',8',10',16'-pentaene-3,3'-dione)