NP-MRD: Showing NP-Card for Oxoglyantrypine (NP0043940)

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Record Information

Version

1.0

Created at

2021-06-22 17:41:53 UTC

Updated at

2021-06-22 17:41:53 UTC

NP-MRD ID

NP0043940

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oxoglyantrypine

Description

3-Hydroxy-4-[(1H-indol-3-yl)methyl]-1H,4H,6H-pyrazino[2,1-b]quinazoline-1,6-dione 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. Oxoglyantrypine is found in Cladosporium sp. PJX41. It was first documented in 2013 (PMID: 23758051). Based on a literature review very few articles have been published on 3-hydroxy-4-[(1H-indol-3-yl)methyl]-1H,4H,6H-pyrazino[2,1-b]quinazoline-1,6-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306222119412D          

 27 31  0  0  0  0            999 V2000
    3.3187   -1.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0638   -0.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2568   -0.8189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0019   -0.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1949    0.1373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5539    0.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2990    1.3635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8510    1.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5961    2.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1481    3.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9551    3.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2100    2.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6580    1.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9129    1.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7199    0.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3609    0.4073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6158   -0.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4228   -0.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6777   -1.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1928   -2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6777   -2.6683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623   -2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1768   -2.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8913   -2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8913   -1.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1768   -1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623   -1.5884    0.0000 C   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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  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
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
 22 27  1  0  0  0  0
M  END

NP0043940
     RDKit          3D

 41 45  0  0  0  0  0  0  0  0999 V2000
    2.0730    3.0556   -2.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4700    2.2939   -1.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957    2.4752   -1.5872 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5491    1.5689   -0.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5713    2.0512   -0.0335 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0219    0.2593   -0.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6884   -0.6869    0.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0740   -0.9409   -0.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4194   -1.7681   -1.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7447   -1.7083   -1.3289 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3040   -0.8730   -0.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6002   -0.5100   -0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8846    0.3368    0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8822    0.8258    1.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6008    0.4401    1.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2464   -0.4066    0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4633    0.3730   -0.2907 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1363    1.1925   -1.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096    1.2157   -1.1626 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2111    0.4064   -0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5836    0.3682   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3187   -0.4570    0.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6155   -1.2826    1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2121   -1.2656    1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5158   -0.4223    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1136   -0.4414    0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6149   -1.2348    1.3477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130    3.2108   -2.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0381   -0.1833   -1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7568   -0.3825    1.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1793   -1.7056    0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6996   -2.3344   -1.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3333   -2.2003   -2.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3929   -0.9061   -0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9230    0.6261    1.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1120    1.4903    2.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7750    0.8093    2.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1058    1.0222   -1.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4095   -0.4447    0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1386   -1.9549    2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6793   -1.9115    1.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  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
 25 26  1  0
 26 27  2  0
 18  2  1  0
 25 20  1  0
 16  8  1  0
 26 17  1  0
 16 11  1  0
  3 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 21 38  1  0
 22 39  1  0
 23 40  1  0
 24 41  1  0
M  END


  Mrv1652306222119412D          

 27 31  0  0  0  0            999 V2000
    3.3187   -1.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0638   -0.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2568   -0.8189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0019   -0.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1949    0.1373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5539    0.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2990    1.3635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8510    1.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5961    2.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1481    3.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9551    3.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2100    2.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6580    1.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9129    1.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7199    0.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3609    0.4073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6158   -0.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4228   -0.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6777   -1.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1928   -2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6777   -2.6683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623   -2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1768   -2.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8913   -2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8913   -1.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1768   -1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623   -1.5884    0.0000 C   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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  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
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
 22 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043940

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1NC(=O)C2=NC3=CC=CC=C3C(=O)N2C1CC1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H14N4O3/c25-18-16(9-11-10-21-14-7-3-1-5-12(11)14)24-17(19(26)23-18)22-15-8-4-2-6-13(15)20(24)27/h1-8,10,16,21H,9H2,(H,23,25,26)

> <INCHI_KEY>
PRYGKAJEGXTQNF-UHFFFAOYSA-N

> <FORMULA>
C20H14N4O3

> <MOLECULAR_WEIGHT>
358.357

> <EXACT_MASS>
358.106590327

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
36.2196123314928

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1H-indol-3-yl)methyl]-1H,2H,3H,4H,6H-pyrazino[2,1-b]quinazoline-1,3,6-trione

> <ALOGPS_LOGP>
2.33

> <JCHEM_LOGP>
2.163558029666666

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.954819476735942

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.397983308684895

> <JCHEM_PKA_STRONGEST_BASIC>
-0.616626436379686

> <JCHEM_POLAR_SURFACE_AREA>
94.63

> <JCHEM_REFRACTIVITY>
99.10990000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(1H-indol-3-ylmethyl)-2H,4H-pyrazino[2,1-b]quinazoline-1,3,6-trione

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043940
     RDKit          3D

 41 45  0  0  0  0  0  0  0  0999 V2000
    2.0730    3.0556   -2.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4700    2.2939   -1.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957    2.4752   -1.5872 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5491    1.5689   -0.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5713    2.0512   -0.0335 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0219    0.2593   -0.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6884   -0.6869    0.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0740   -0.9409   -0.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4194   -1.7681   -1.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7447   -1.7083   -1.3289 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3040   -0.8730   -0.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6002   -0.5100   -0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8846    0.3368    0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8822    0.8258    1.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6008    0.4401    1.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2464   -0.4066    0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4633    0.3730   -0.2907 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1363    1.1925   -1.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096    1.2157   -1.1626 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2111    0.4064   -0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5836    0.3682   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3187   -0.4570    0.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6155   -1.2826    1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2121   -1.2656    1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5158   -0.4223    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1136   -0.4414    0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6149   -1.2348    1.3477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130    3.2108   -2.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0381   -0.1833   -1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7568   -0.3825    1.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1793   -1.7056    0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6996   -2.3344   -1.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3333   -2.2003   -2.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3929   -0.9061   -0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9230    0.6261    1.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1120    1.4903    2.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7750    0.8093    2.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1058    1.0222   -1.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4095   -0.4447    0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1386   -1.9549    2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6793   -1.9115    1.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  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
 25 26  1  0
 26 27  2  0
 18  2  1  0
 25 20  1  0
 16  8  1  0
 26 17  1  0
 16 11  1  0
  3 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 21 38  1  0
 22 39  1  0
 23 40  1  0
 24 41  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  O   UNK     0       6.195  -3.313   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.719  -1.849   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.213  -1.529   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.737  -0.064   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.230   0.256   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.767   1.081   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       4.291   2.545   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.322   3.690   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.846   5.154   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.876   6.299   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.383   5.978   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.859   4.514   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.828   3.369   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.304   1.905   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.810   1.585   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       6.274   0.760   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       6.750  -0.704   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.256  -1.024   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.732  -2.489   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.827  -3.735   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       8.732  -4.981   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      10.196  -4.505   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.530  -5.275   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.864  -4.505   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.864  -2.965   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.530  -2.195   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.196  -2.965   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    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   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    6   17                                                  
CONECT   17   16    2   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   19   22                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

COMPND    NP0043940
HETATM    1  O1  UNL     1       2.073   3.056  -2.628  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.470   2.294  -1.831  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.096   2.475  -1.587  1.00  0.00           N  
HETATM    4  C2  UNL     1      -0.549   1.569  -0.636  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.571   2.051  -0.033  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.022   0.259  -0.480  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.688  -0.687   0.381  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.074  -0.941  -0.068  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.419  -1.768  -1.150  1.00  0.00           C  
HETATM   10  N2  UNL     1      -3.745  -1.708  -1.329  1.00  0.00           N  
HETATM   11  C7  UNL     1      -4.304  -0.873  -0.407  1.00  0.00           C  
HETATM   12  C8  UNL     1      -5.600  -0.510  -0.158  1.00  0.00           C  
HETATM   13  C9  UNL     1      -5.885   0.337   0.887  1.00  0.00           C  
HETATM   14  C10 UNL     1      -4.882   0.826   1.688  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.601   0.440   1.405  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.246  -0.407   0.369  1.00  0.00           C  
HETATM   17  N3  UNL     1       1.463   0.373  -0.291  1.00  0.00           N  
HETATM   18  C13 UNL     1       2.136   1.192  -1.117  1.00  0.00           C  
HETATM   19  N4  UNL     1       3.510   1.216  -1.163  1.00  0.00           N  
HETATM   20  C14 UNL     1       4.211   0.406  -0.356  1.00  0.00           C  
HETATM   21  C15 UNL     1       5.584   0.368  -0.337  1.00  0.00           C  
HETATM   22  C16 UNL     1       6.319  -0.457   0.488  1.00  0.00           C  
HETATM   23  C17 UNL     1       5.616  -1.283   1.334  1.00  0.00           C  
HETATM   24  C18 UNL     1       4.212  -1.266   1.337  1.00  0.00           C  
HETATM   25  C19 UNL     1       3.516  -0.422   0.493  1.00  0.00           C  
HETATM   26  C20 UNL     1       2.114  -0.441   0.530  1.00  0.00           C  
HETATM   27  O3  UNL     1       1.615  -1.235   1.348  1.00  0.00           O  
HETATM   28  H1  UNL     1      -0.513   3.211  -2.022  1.00  0.00           H  
HETATM   29  H2  UNL     1      -0.038  -0.183  -1.588  1.00  0.00           H  
HETATM   30  H3  UNL     1      -0.757  -0.383   1.447  1.00  0.00           H  
HETATM   31  H4  UNL     1      -0.179  -1.706   0.431  1.00  0.00           H  
HETATM   32  H5  UNL     1      -1.700  -2.334  -1.708  1.00  0.00           H  
HETATM   33  H6  UNL     1      -4.333  -2.200  -2.047  1.00  0.00           H  
HETATM   34  H7  UNL     1      -6.393  -0.906  -0.803  1.00  0.00           H  
HETATM   35  H8  UNL     1      -6.923   0.626   1.084  1.00  0.00           H  
HETATM   36  H9  UNL     1      -5.112   1.490   2.509  1.00  0.00           H  
HETATM   37  H10 UNL     1      -2.775   0.809   2.039  1.00  0.00           H  
HETATM   38  H11 UNL     1       6.106   1.022  -1.007  1.00  0.00           H  
HETATM   39  H12 UNL     1       7.409  -0.445   0.459  1.00  0.00           H  
HETATM   40  H13 UNL     1       6.139  -1.955   2.008  1.00  0.00           H  
HETATM   41  H14 UNL     1       3.679  -1.911   1.999  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   18
CONECT    3    4   28
CONECT    4    5    5    6
CONECT    6    7   17   29
CONECT    7    8   30   31
CONECT    8    9    9   16
CONECT    9   10   32
CONECT   10   11   33
CONECT   11   12   12   16
CONECT   12   13   34
CONECT   13   14   14   35
CONECT   14   15   36
CONECT   15   16   16   37
CONECT   17   18   26
CONECT   18   19   19
CONECT   19   20
CONECT   20   21   21   25
CONECT   21   22   38
CONECT   22   23   23   39
CONECT   23   24   40
CONECT   24   25   25   41
CONECT   25   26
CONECT   26   27   27
END

NP0043940
     RDKit          3D

41 45  0  0  0  0  0  0  0  0999 V2000
    2.0730    3.0556   -2.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4700    2.2939   -1.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957    2.4752   -1.5872 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5491    1.5689   -0.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5713    2.0512   -0.0335 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0219    0.2593   -0.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6884   -0.6869    0.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0740   -0.9409   -0.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4194   -1.7681   -1.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7447   -1.7083   -1.3289 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3040   -0.8730   -0.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6002   -0.5100   -0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8846    0.3368    0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8822    0.8258    1.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6008    0.4401    1.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2464   -0.4066    0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4633    0.3730   -0.2907 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1363    1.1925   -1.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096    1.2157   -1.1626 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2111    0.4064   -0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5836    0.3682   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3187   -0.4570    0.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6155   -1.2826    1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2121   -1.2656    1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5158   -0.4223    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1136   -0.4414    0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6149   -1.2348    1.3477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130    3.2108   -2.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0381   -0.1833   -1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7568   -0.3825    1.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1793   -1.7056    0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6996   -2.3344   -1.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3333   -2.2003   -2.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3929   -0.9061   -0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9230    0.6261    1.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1120    1.4903    2.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7750    0.8093    2.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1058    1.0222   -1.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4095   -0.4447    0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1386   -1.9549    2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6793   -1.9115    1.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  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
 25 26  1  0
 26 27  2  0
 18  2  1  0
 25 20  1  0
 16  8  1  0
 26 17  1  0
 16 11  1  0
  3 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 21 38  1  0
 22 39  1  0
 23 40  1  0
 24 41  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₀H₁₄N₄O₃

Average Mass

358.3570 Da

Monoisotopic Mass

358.10659 Da

IUPAC Name

4-[(1H-indol-3-yl)methyl]-1H,2H,3H,4H,6H-pyrazino[2,1-b]quinazoline-1,3,6-trione

Traditional Name

4-(1H-indol-3-ylmethyl)-2H,4H-pyrazino[2,1-b]quinazoline-1,3,6-trione

CAS Registry Number

Not Available

SMILES

O=C1NC(=O)C2=NC3=CC=CC=C3C(=O)N2C1CC1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C20H14N4O3/c25-18-16(9-11-10-21-14-7-3-1-5-12(11)14)24-17(19(26)23-18)22-15-8-4-2-6-13(15)20(24)27/h1-8,10,16,21H,9H2,(H,23,25,26)

InChI Key

PRYGKAJEGXTQNF-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, dmso, 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
Cladosporium sp. PJX41	Linigton's dataset	23758051

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

Quinazoline
3-alkylindole
Indole
Indole or derivatives
Pyrimidone
Pyrimidine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Lactam
Carboxylic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.33	ALOGPS
logP	2.16	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.4	ChemAxon
pKa (Strongest Basic)	-0.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.63 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	99.11 m³·mol⁻¹	ChemAxon
Polarizability	36.22 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78159861

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Peng J, Lin T, Wang W, Xin Z, Zhu T, Gu Q, Li D: Antiviral alkaloids produced by the mangrove-derived fungus Cladosporium sp. PJX-41. J Nat Prod. 2013 Jun 28;76(6):1133-40. doi: 10.1021/np400200k. Epub 2013 Jun 12. [PubMed:23758051 ]

Showing NP-Card for Oxoglyantrypine (NP0043940)

MOL for NP0043940 (Oxoglyantrypine)

3D MOL for NP0043940 (Oxoglyantrypine)

3D SDF for NP0043940 (Oxoglyantrypine)

3D-SDF for NP0043940 (Oxoglyantrypine)

PDB for NP0043940 (Oxoglyantrypine)

3D PDB for NP0043940 (Oxoglyantrypine)

SMILES for NP0043940 (Oxoglyantrypine)

INCHI for NP0043940 (Oxoglyantrypine)

Structure for NP0043940 (Oxoglyantrypine)

3D Structure for NP0043940 (Oxoglyantrypine)