NP-MRD: Showing NP-Card for Isogranulatimide (NP0068564)

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Record Information

Version

2.0

Created at

2022-04-28 13:49:35 UTC

Updated at

2022-04-28 13:49:35 UTC

NP-MRD ID

NP0068564

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isogranulatimide

Description

8-Hydroxy-2,4,9,19-tetraazapentacyclo[10.7.0.0²,⁶.0⁷,¹¹.0¹³,¹⁸]Nonadeca-1(12),3,5,7(11),8,13,15,17-octaen-10-one belongs to the class of organic compounds known as alpha carbolines. These are organic compounds containing a pyrido[2,3-b]indole core (which is a pyridine fused to an indole). Isogranulatimide is found in Didemnum conchyliatum and Didemnum granulatum. 8-Hydroxy-2,4,9,19-tetraazapentacyclo[10.7.0.0²,⁶.0⁷,¹¹.0¹³,¹⁸]Nonadeca-1(12),3,5,7(11),8,13,15,17-octaen-10-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 33  0  0  0  0  0  0  0  0999 V2000
    0.6292    3.2970   -0.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4309    2.6817   -0.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7277    3.3045    0.1411 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7162    2.3253    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9532    2.4756    0.4575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0268    1.0282    0.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6569    1.2540    0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1630    0.1229   -0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5296    0.0136   -0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5708    0.8734   -0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8747    0.3674   -0.5224 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1382   -0.9812   -0.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0953   -1.8624   -0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8178   -1.3461   -0.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6647   -2.0037   -0.0349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583   -1.1579    0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6822   -1.3256    0.2577 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4028   -2.4486    0.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7072   -2.0763    0.5455 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7846   -0.7378    0.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4928   -0.2657    0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8565    4.3424    0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4299    1.9231   -0.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6555    1.1200   -0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414   -1.3512   -0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2895   -2.9264   -0.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5452   -3.0546    0.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1060   -3.4852    0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6425   -0.1064    0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2  7  1  0
  7  6  2  0
  6 21  1  0
 21 20  2  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  1  0
 16  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
  6  4  1  0
 17 21  1  0
 15 16  1  0
  8  7  1  0
 14  9  1  0
  3 22  1  0
 20 29  1  0
 18 28  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
 15 27  1  0
M  END


  Mrv1533004191514352D          

 21 25  0  0  0  0            999 V2000
    4.9113   -0.4316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1175   -0.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4691   -0.1462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7836   -0.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0093   -0.3203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0083   -1.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8327   -1.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2175   -2.1603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0173   -2.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7028   -1.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4431   -2.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4978   -3.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8123   -3.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0720   -3.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3061   -3.4923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7779   -2.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9535   -2.8269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3784   -3.4184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381   -3.0542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7557   -2.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5687   -2.0971    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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  6 21  1  0  0  0  0
 17 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068564

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1NC(=O)C2=C1C1=CN=CN1C1=C2C2=CC=CC=C2N1

> <INCHI_IDENTIFIER>
InChI=1S/C15H8N4O2/c20-14-11-9-5-16-6-19(9)13-10(12(11)15(21)18-14)7-3-1-2-4-8(7)17-13/h1-6,17H,(H,18,20,21)

> <INCHI_KEY>
WXUJAQBSBZLVEV-UHFFFAOYSA-N

> <FORMULA>
C15H8N4O2

> <MOLECULAR_WEIGHT>
276.255

> <EXACT_MASS>
276.064725514

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
27.2549942048633

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4,9,19-tetraazapentacyclo[10.7.0.0²,⁶.0⁷,¹¹.0¹³,¹⁸]nonadeca-1(12),3,5,7(11),13,15,17-heptaene-8,10-dione

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
0.3637874414275931

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.479878757536184

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.796386312968881

> <JCHEM_PKA_STRONGEST_BASIC>
6.480678118665572

> <JCHEM_POLAR_SURFACE_AREA>
79.26

> <JCHEM_REFRACTIVITY>
76.0256

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,9,19-tetraazapentacyclo[10.7.0.0²,⁶.0⁷,¹¹.0¹³,¹⁸]nonadeca-1(12),3,5,7(11),13,15,17-heptaene-8,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  O   UNK     0       9.168  -0.806   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.686  -1.225   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       6.476  -0.273   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.196  -1.130   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.751  -0.598   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.615  -2.611   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.154  -2.670   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.873  -4.033   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.366  -4.410   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.645  -3.553   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.027  -4.233   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.129  -5.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.850  -6.627   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.468  -5.947   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       8.038  -6.519   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       7.052  -5.336   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.513  -5.277   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       4.440  -6.381   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.058  -5.701   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       3.277  -4.177   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.795  -3.915   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   21                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    8   17                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    6   17                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₈N₄O₂

Average Mass

276.2550 Da

Monoisotopic Mass

276.06473 Da

IUPAC Name

2,4,9,19-tetraazapentacyclo[10.7.0.0²,⁶.0⁷,¹¹.0¹³,¹⁸]nonadeca-1(12),3,5,7(11),13,15,17-heptaene-8,10-dione

Traditional Name

2,4,9,19-tetraazapentacyclo[10.7.0.0²,⁶.0⁷,¹¹.0¹³,¹⁸]nonadeca-1(12),3,5,7(11),13,15,17-heptaene-8,10-dione

CAS Registry Number

Not Available

SMILES

O=C1NC(=O)C2=C1C1=CN=CN1C1=C2C2=CC=CC=C2N1

InChI Identifier

InChI=1S/C15H8N4O2/c20-14-11-9-5-16-6-19(9)13-10(12(11)15(21)18-14)7-3-1-2-4-8(7)17-13/h1-6,17H,(H,18,20,21)

InChI Key

WXUJAQBSBZLVEV-UHFFFAOYSA-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
Didemnum conchyliatum	Animalia	KNApSAcK
Didemnum granulatum	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha carbolines. These are organic compounds containing a pyrido[2,3-b]indole core (which is a pyridine fused to an indole).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Alpha carbolines

Alternative Parents

Substituents

Alpha-carboline
Indole
Pyridine carboxylic acid or derivatives
Pyrrolopyridine
N-substituted imidazole
Pyridine
Benzenoid
Azole
Carboxylic acid imide
Imidazole
Carboxylic acid imide, n-unsubstituted
Heteroaromatic compound
Pyrrole
Vinylogous amide
Carboxylic acid derivative
Azacycle
Organic oxide
Organonitrogen compound
Organooxygen compound
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	1.51	ALOGPS
logP	0.36	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
pKa (Strongest Basic)	6.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.26 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	76.03 m³·mol⁻¹	ChemAxon
Polarizability	27.25 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

6419741

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isogranulatimide (NP0068564)

MOL for NP0068564 (Isogranulatimide)

3D MOL for NP0068564 (Isogranulatimide)

3D SDF for NP0068564 (Isogranulatimide)

3D-SDF for NP0068564 (Isogranulatimide)

PDB for NP0068564 (Isogranulatimide)

3D PDB for NP0068564 (Isogranulatimide)

SMILES for NP0068564 (Isogranulatimide)

INCHI for NP0068564 (Isogranulatimide)

Structure for NP0068564 (Isogranulatimide)

3D Structure for NP0068564 (Isogranulatimide)