NP-MRD: Showing NP-Card for Veiutamine (NP0068860)

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Record Information

Version

2.0

Created at

2022-04-28 14:06:47 UTC

Updated at

2022-04-28 14:06:47 UTC

NP-MRD ID

NP0068860

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Veiutamine

Description

10-Amino-9-[(4-hydroxyphenyl)methyl]-2,7-diazatricyclo[6.3.1.0⁴,¹²]Dodeca-1(12),3,7,9-tetraen-11-one belongs to the class of organic compounds known as pyrrolo[4,3,2-de]quinolines. These are organic heterocyclic compounds with a structure based on the Pyrrolo[4,3,2-de]quinoline skeleton. Veiutamine is found in Zyzzya fuliginosa. 10-Amino-9-[(4-hydroxyphenyl)methyl]-2,7-diazatricyclo[6.3.1.0⁴,¹²]Dodeca-1(12),3,7,9-tetraen-11-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
   -0.4301    3.3148   -1.3023 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9819    2.1143   -0.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2852    1.3294    0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0815    1.6872    0.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1186    0.7304    0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6235    0.7197   -1.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6058   -0.1649   -1.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1132   -1.0657   -0.6812 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1166   -1.9784   -1.0272 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6143   -1.0697    0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6106   -0.1593    0.9687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9031    0.1139    0.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3561   -0.7269    1.3553 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9576   -1.9121    1.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3554   -2.2276    1.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9883   -1.2607    0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2169   -1.1200   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2413    0.0088   -0.8217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0309    0.6015   -0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658   -0.1689    0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3717    1.8145   -1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0165    2.5646   -1.9464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4383    3.4026   -2.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0471    4.0445   -0.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3424    2.6514   -0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1788    1.9320    1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620    1.4056   -1.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0233   -0.1910   -2.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4605   -2.6221   -0.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0207   -1.7828    1.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2842   -0.2250    1.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8857   -1.9448    2.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3094   -2.7767    1.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3968   -3.2208    0.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705   -2.3787    2.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0103   -1.8344    0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9970    0.3953   -1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  3 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 21  2  1  0
 11  5  1  0
 20 12  1  0
 20 16  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
M  END


  Mrv1533004251510552D          

 22 25  0  0  0  0            999 V2000
    0.0978    1.8373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514    1.5017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189    1.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326    2.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6790    3.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115    2.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422    2.9933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8284    3.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5821    4.1494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1610    4.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5927    3.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725    1.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987    1.9867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661    1.5017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713   -0.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9463   -0.4389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913    0.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    0.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2702    0.1963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588    0.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  2  0  0  0  0
 19 22  2  0  0  0  0
 12 22  1  0  0  0  0
 16 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068860

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=C(CC2=CC=C(O)C=C2)C2=NCCC3=CNC(=C23)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H15N3O2/c18-14-12(7-9-1-3-11(21)4-2-9)15-13-10(5-6-19-15)8-20-16(13)17(14)22/h1-4,8,20-21H,5-7,18H2

> <INCHI_KEY>
NMSJBBLQEXESEH-UHFFFAOYSA-N

> <FORMULA>
C17H15N3O2

> <MOLECULAR_WEIGHT>
293.326

> <EXACT_MASS>
293.116426735

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.656697121916928

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-amino-9-[(4-hydroxyphenyl)methyl]-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),3,7,9-tetraen-11-one

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.1029069042926873

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.327561247707347

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.522280011650857

> <JCHEM_PKA_STRONGEST_BASIC>
8.184323650101213

> <JCHEM_POLAR_SURFACE_AREA>
91.47

> <JCHEM_REFRACTIVITY>
85.74180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-amino-9-[(4-hydroxyphenyl)methyl]-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),3,7,9-tetraen-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  N   UNK     0       0.182   3.430   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.589   2.803   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.835   3.708   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.674   5.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.267   5.866   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.021   4.961   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.385   5.588   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.546   7.119   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.953   7.745   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.300   8.024   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.106   7.398   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.242   3.082   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       5.971   3.708   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       7.217   2.803   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.056   1.272   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.649   0.645   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.173  -0.819   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.633  -0.819   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.157   0.645   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.750   1.272   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.504   0.366   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.403   1.550   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    3   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19    2   21                                                  
CONECT   21   20                                                            
CONECT   22   19   12   16                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₅N₃O₂

Average Mass

293.3260 Da

Monoisotopic Mass

293.11643 Da

IUPAC Name

10-amino-9-[(4-hydroxyphenyl)methyl]-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),3,7,9-tetraen-11-one

Traditional Name

10-amino-9-[(4-hydroxyphenyl)methyl]-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),3,7,9-tetraen-11-one

CAS Registry Number

Not Available

SMILES

NC1=C(CC2=CC=C(O)C=C2)C2=NCCC3=CNC(=C23)C1=O

InChI Identifier

InChI=1S/C17H15N3O2/c18-14-12(7-9-1-3-11(21)4-2-9)15-13-10(5-6-19-15)8-20-16(13)17(14)22/h1-4,8,20-21H,5-7,18H2

InChI Key

NMSJBBLQEXESEH-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
Zyzzya fuliginosa	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolo[4,3,2-de]quinolines. These are organic heterocyclic compounds with a structure based on the Pyrrolo[4,3,2-de]quinoline skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Pyrroloquinolines

Direct Parent

Pyrrolo[4,3,2-de]quinolines

Alternative Parents

Substituents

Pyrrolo[4,3,2-de]quinoline
Indole or derivatives
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Pyrrole
Heteroaromatic compound
Ketimine
Ketone
Azacycle
Enamine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Primary amine
Organic oxide
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Organic oxygen compound
Imine
Organic nitrogen 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	1.87	ALOGPS
logP	1.1	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.52	ChemAxon
pKa (Strongest Basic)	8.18	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	91.47 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.74 m³·mol⁻¹	ChemAxon
Polarizability	30.66 Å³	ChemAxon
Number of Rings	4	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

10469638

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Veiutamine (NP0068860)

MOL for NP0068860 (Veiutamine)

3D MOL for NP0068860 (Veiutamine)

3D SDF for NP0068860 (Veiutamine)

3D-SDF for NP0068860 (Veiutamine)

PDB for NP0068860 (Veiutamine)

3D PDB for NP0068860 (Veiutamine)

SMILES for NP0068860 (Veiutamine)

INCHI for NP0068860 (Veiutamine)

Structure for NP0068860 (Veiutamine)

3D Structure for NP0068860 (Veiutamine)