NP-MRD: Showing NP-Card for 10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaen-11-ol (NP0222805)

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Record Information

Version

2.0

Created at

2022-09-06 00:44:03 UTC

Updated at

2022-09-06 00:44:04 UTC

NP-MRD ID

NP0222805

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaen-11-ol

Description

Makaluvamine N belongs to the class of organic compounds known as aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system. 10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaen-11-ol is found in Zyzzya fuliginosa. 10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaen-11-ol was first documented in 1997 (PMID: 9134749). Based on a literature review very few articles have been published on makaluvamine N.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062202442D          

 15 17  0  0  0  0            999 V2000
   -1.3358   -0.1359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5821   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4959   -1.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1634   -1.7768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2578   -1.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9252   -1.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -0.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0853    0.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0009    0.8340    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    0.0135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3463   -1.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -1.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3377   -2.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5127   -2.4121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  2  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  5 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222805

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=C(Br)C2=NCCC3=C2C(N=C3)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H8BrN3O/c11-6-7(12)10(15)9-5-4(3-14-9)1-2-13-8(5)6/h3,15H,1-2,12H2

> <INCHI_KEY>
UMVGTIHJQQYCQI-UHFFFAOYSA-N

> <FORMULA>
C10H8BrN3O

> <MOLECULAR_WEIGHT>
266.098

> <EXACT_MASS>
264.985075

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
22.424979686988358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(11),2,4(12),7,9-pentaen-11-ol

> <JCHEM_LOGP>
-1.3089937930714228

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.360807622864003

> <JCHEM_PKA_STRONGEST_BASIC>
6.871523765644435

> <JCHEM_POLAR_SURFACE_AREA>
70.97

> <JCHEM_REFRACTIVITY>
64.4409

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(11),2,4(12),7,9-pentaen-11-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  N   UNK     0      -2.494  -0.254   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.087  -0.880   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.926  -2.412   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.172  -3.317   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.481  -3.038   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.727  -2.133   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.566  -0.601   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.159   0.025   0.000  0.00  0.00           C+0
HETATM    9 Br   UNK     0      -0.002   1.557   0.000  0.00  0.00          Br+0
HETATM   10  N   UNK     0       3.295   0.025   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.541  -0.880   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.380  -2.412   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.973  -3.038   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.497  -4.503   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.957  -4.503   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   15                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14    5                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₈BrN₃O

Average Mass

266.0980 Da

Monoisotopic Mass

264.98508 Da

IUPAC Name

10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(11),2,4(12),7,9-pentaen-11-ol

Traditional Name

10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(11),2,4(12),7,9-pentaen-11-ol

CAS Registry Number

Not Available

SMILES

NC1=C(Br)C2=NCCC3=C2C(N=C3)=C1O

InChI Identifier

InChI=1S/C10H8BrN3O/c11-6-7(12)10(15)9-5-4(3-14-9)1-2-13-8(5)6/h3,15H,1-2,12H2

InChI Key

UMVGTIHJQQYCQI-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, 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
Zyzzya fuliginosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Aminoquinolines and derivatives

Direct Parent

Aminoquinolines and derivatives

Alternative Parents

Substituents

Aminoquinoline
Indole or derivatives
2-bromoaniline
3-bromophenol
Benzenoid
Aryl halide
Aryl bromide
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Imine
Amine
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	-1.3	ChemAxon
pKa (Strongest Acidic)	8.36	ChemAxon
pKa (Strongest Basic)	6.87	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.97 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	64.44 m³·mol⁻¹	ChemAxon
Polarizability	22.42 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

C00028556

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

135496970

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Venables DA, Concepcion GP, Matsumoto SS, Barrows LR, Ireland CM: Makaluvamine N: a new pyrroloiminoquinone from Zyzzya fuliginosa. J Nat Prod. 1997 Apr;60(4):408-10. doi: 10.1021/np9607262. [PubMed:9134749 ]
LOTUS database [Link]

Showing NP-Card for 10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaen-11-ol (NP0222805)

MOL for NP0222805 (10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaen-11-ol)

3D MOL for NP0222805 (10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaen-11-ol)

3D SDF for NP0222805 (10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaen-11-ol)

3D-SDF for NP0222805 (10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaen-11-ol)

PDB for NP0222805 (10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaen-11-ol)

3D PDB for NP0222805 (10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaen-11-ol)

SMILES for NP0222805 (10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaen-11-ol)

INCHI for NP0222805 (10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaen-11-ol)

Structure for NP0222805 (10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaen-11-ol)

3D Structure for NP0222805 (10-amino-9-bromo-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaen-11-ol)