NP-MRD: Showing NP-Card for Makaluvamine A (NP0003600)

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Record Information

Version

1.0

Created at

2020-12-09 00:48:18 UTC

Updated at

2021-07-15 16:46:51 UTC

NP-MRD ID

NP0003600

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Makaluvamine A

Provided By

NPAtlas

Description

Makaluvamine A is found in Didymium bahiense, Zyzzya fuliginosa and Zyzzya sp.. It was first documented in 2001 (PMID: 11170681). Based on a literature review very few articles have been published on 10-amino-2-methyl-2,7-diazatricyclo[6.3.1.0⁴,¹²]Dodeca-1(12),3,7,9-tetraen-11-one (PMID: 25607930) (PMID: 22310802).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117483D          

 26 28  0  0  0  0            999 V2000
   -0.6052    3.1769    0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7595    1.7812    0.4357 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9423    1.1334    0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6403   -0.2128    0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2813   -0.2966   -0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2647    0.9305    0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7275    0.9901    0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2715    2.0974    0.3910 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4950   -0.2285   -0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149   -0.1404   -0.1669 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8971   -1.4094   -0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417   -1.5131   -0.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2434   -2.5754   -0.5563 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6808   -2.6499   -0.5249 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4381   -1.4144   -0.2061 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4784    3.7373   -0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3225    3.3711    1.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4864    3.5851    1.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9519    1.4965    0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3928    0.7433   -0.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4753   -0.9779    0.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4803   -2.2653   -0.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9202   -3.4376    0.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0650   -3.0595   -1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9735   -1.5979    0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2171   -1.2642   -0.9968 H   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  2  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
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 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
  6  2  1  0  0  0  0
 15  4  1  0  0  0  0
 12  5  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  3 19  1  0  0  0  0
 10 20  1  0  0  0  0
 10 21  1  0  0  0  0
 11 22  1  0  0  0  0
 14 23  1  0  0  0  0
 14 24  1  0  0  0  0
 15 25  1  0  0  0  0
 15 26  1  0  0  0  0
M  END


  Mrv1652306242117483D          

 26 28  0  0  0  0            999 V2000
   -0.6052    3.1769    0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7595    1.7812    0.4357 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9423    1.1334    0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6403   -0.2128    0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2813   -0.2966   -0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2647    0.9305    0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7275    0.9901    0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2715    2.0974    0.3910 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4950   -0.2285   -0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149   -0.1404   -0.1669 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8971   -1.4094   -0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417   -1.5131   -0.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2434   -2.5754   -0.5563 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6808   -2.6499   -0.5249 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4381   -1.4144   -0.2061 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4784    3.7373   -0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3225    3.3711    1.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4864    3.5851    1.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9519    1.4965    0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3928    0.7433   -0.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4753   -0.9779    0.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4803   -2.2653   -0.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9202   -3.4376    0.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0650   -3.0595   -1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9735   -1.5979    0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2171   -1.2642   -0.9968 H   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  2  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
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 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
  6  2  1  0  0  0  0
 15  4  1  0  0  0  0
 12  5  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  3 19  1  0  0  0  0
 10 20  1  0  0  0  0
 10 21  1  0  0  0  0
 11 22  1  0  0  0  0
 14 23  1  0  0  0  0
 14 24  1  0  0  0  0
 15 25  1  0  0  0  0
 15 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003600

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N([H])C1=C([H])C2=NC([H])([H])C([H])([H])C3=C([H])N(C(=C23)C1=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C11H11N3O/c1-14-5-6-2-3-13-8-4-7(12)11(15)10(14)9(6)8/h4-5H,2-3,12H2,1H3

> <INCHI_KEY>
RUIRYCQUTHWLMZ-UHFFFAOYSA-N

> <FORMULA>
C11H11N3O

> <MOLECULAR_WEIGHT>
201.229

> <EXACT_MASS>
201.090211986

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.413278923646235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-amino-2-methyl-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(12),3,7,9-tetraen-11-one

> <ALOGPS_LOGP>
0.58

> <JCHEM_LOGP>
-0.16173325433333283

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.912375947115777

> <JCHEM_PKA_STRONGEST_BASIC>
8.506874038698239

> <JCHEM_POLAR_SURFACE_AREA>
60.379999999999995

> <JCHEM_REFRACTIVITY>
59.60450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-amino-2-methyl-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(12),3,7,9-tetraen-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.605   3.177   0.740  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.760   1.781   0.436  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.942   1.133   0.337  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.640  -0.213   0.027  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.281  -0.297  -0.044  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.265   0.931   0.208  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.728   0.990   0.166  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.272   2.097   0.391  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.495  -0.229  -0.133  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.915  -0.140  -0.167  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.897  -1.409  -0.373  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.442  -1.513  -0.341  0.00  0.00           C+0
HETATM   13  N   UNK     0      -0.243  -2.575  -0.556  0.00  0.00           N+0
HETATM   14  C   UNK     0      -1.681  -2.650  -0.525  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.438  -1.414  -0.206  0.00  0.00           C+0
HETATM   16  H   UNK     0      -0.478   3.737  -0.223  0.00  0.00           H+0
HETATM   17  H   UNK     0       0.323   3.371   1.325  0.00  0.00           H+0
HETATM   18  H   UNK     0      -1.486   3.585   1.292  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.952   1.496   0.457  0.00  0.00           H+0
HETATM   20  H   UNK     0       4.393   0.743  -0.417  0.00  0.00           H+0
HETATM   21  H   UNK     0       4.475  -0.978   0.064  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.480  -2.265  -0.585  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.920  -3.438   0.267  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.065  -3.059  -1.520  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.974  -1.598   0.786  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.217  -1.264  -0.997  0.00  0.00           H+0
CONECT    1    2   16   17   18                                             
CONECT    2    1    3    6                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    7    2                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9   20   21                                                  
CONECT   11    9   12   22                                                  
CONECT   12   11   13    5                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23   24                                             
CONECT   15   14    4   25   26                                             
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    3                                                            
CONECT   20   10                                                            
CONECT   21   10                                                            
CONECT   22   11                                                            
CONECT   23   14                                                            
CONECT   24   14                                                            
CONECT   25   15                                                            
CONECT   26   15                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₁H₁₁N₃O

Average Mass

201.2290 Da

Monoisotopic Mass

201.09021 Da

IUPAC Name

10-amino-2-methyl-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(12),3,7,9-tetraen-11-one

Traditional Name

10-amino-2-methyl-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(12),3,7,9-tetraen-11-one

CAS Registry Number

Not Available

SMILES

CN1C=C2CCN=C3C=C(N)C(=O)C1=C23

InChI Identifier

InChI=1S/C11H11N3O/c1-14-5-6-2-3-13-8-4-7(12)11(15)10(14)9(6)8/h4-5H,2-3,12H2,1H3

InChI Key

RUIRYCQUTHWLMZ-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
Didymium bahiense	NPAtlas	11170681
Zyzzya fuliginosa	-	KNApSAcK
Zyzzya sp.	-	KNApSAcK

Chemical Taxonomy

Description

This compound 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
N-methylpyrrole
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Ketimine
Ketone
Propargyl-type 1,3-dipolar organic compound
Enamine
Organic 1,3-dipolar compound
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Primary aliphatic amine
Amine
Organic nitrogen compound
Imine
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	0.58	ALOGPS
logP	-0.16	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	19.91	ChemAxon
pKa (Strongest Basic)	8.51	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.38 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	59.6 m³·mol⁻¹	ChemAxon
Polarizability	21.41 Å³	ChemAxon
Number of Rings	3	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

NPAtlas ID

NPA002777

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00033155

Chemspider ID

3862

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ishibashi M, Iwasaki T, Imai S, Sakamoto S, Yamaguchi K, Ito A: Laboratory culture of the myxomycetes: formation of fruiting bodies of Didymium bahiense and its plasmodial production of Makaluvamine A. J Nat Prod. 2001 Jan;64(1):108-10. doi: 10.1021/np000382m. [PubMed:11170681 ]
Boucle S, Melin C, Clastre M, Guillard J: Design, synthesis and evaluation of new marine alkaloid-derived pentacyclic structures with anti-tumoral potency. Mar Drugs. 2015 Jan 19;13(1):655-65. doi: 10.3390/md13010655. [PubMed:25607930 ]
Walmsley TA, Matcher GF, Zhang F, Hill RT, Davies-Coleman MT, Dorrington RA: Diversity of bacterial communities associated with the Indian Ocean sponge Tsitsikamma favus that contains the bioactive pyrroloiminoquinones, tsitsikammamine A and B. Mar Biotechnol (NY). 2012 Dec;14(6):681-91. doi: 10.1007/s10126-012-9430-y. Epub 2012 Feb 5. [PubMed:22310802 ]

Showing NP-Card for Makaluvamine A (NP0003600)

MOL for NP0003600 (Makaluvamine A)

3D MOL for NP0003600 (Makaluvamine A)

3D SDF for NP0003600 (Makaluvamine A)

3D-SDF for NP0003600 (Makaluvamine A)

PDB for NP0003600 (Makaluvamine A)

3D PDB for NP0003600 (Makaluvamine A)

SMILES for NP0003600 (Makaluvamine A)

INCHI for NP0003600 (Makaluvamine A)

Structure for NP0003600 (Makaluvamine A)

3D Structure for NP0003600 (Makaluvamine A)