NP-MRD: Showing NP-Card for Mirabilin G (NP0080739)

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Record Information

Version

2.0

Created at

2022-04-29 01:44:05 UTC

Updated at

2022-04-29 01:44:06 UTC

NP-MRD ID

NP0080739

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mirabilin G

Description

Mirabilin G 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. Mirabilin G is found in Clathria sp. Mirabilin G was first documented in 2014 (PMID: 25196934). Based on a literature review very few articles have been published on Mirabilin G.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 47 49  0  0  0  0  0  0  0  0999 V2000
    5.6931    1.7893   -0.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2759    0.3397   -0.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7831    0.2289   -0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3877   -1.1868   -0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9575   -1.4753   -0.2486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0469   -0.5917    0.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3735   -0.8521    0.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1490    0.1674    0.5768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5740    1.4689    0.7093 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2676    2.5421    0.8071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5780    3.7827    0.9349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6736    2.4421    0.7834 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3965    1.2246    0.5136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8387    1.0843   -0.9038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8392   -0.3844   -1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130   -1.1024   -0.0239 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3212   -2.1682   -0.5234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9548   -2.1831    0.1200 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0158   -2.9443    1.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5818   -0.0267    0.7979 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2616    2.1465   -1.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7854    2.4565   -0.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2592    1.8936    0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4634    0.0572   -1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8596   -0.3413    0.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2940    0.9561   -0.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6159    0.5333    0.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6699   -1.5464   -1.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9541   -1.8073    0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6523   -2.5026   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4475    0.4233    0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8563    4.5487    0.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1801    3.9001    1.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2209    3.3033    0.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3057    1.2337    1.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1372    1.6485   -1.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8629    1.5128   -1.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2352   -0.5287   -2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8570   -0.7790   -1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0708   -1.5074    0.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7856   -3.1667   -0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2335   -2.1464   -1.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3187   -2.7831   -0.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8402   -2.2717    2.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3272   -3.8157    1.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0410   -3.3537    1.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7182   -0.2185    1.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 16 20  1  0
 18  7  1  0
 20  8  1  0
 20 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  1
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  1
 17 41  1  0
 17 42  1  0
 18 43  1  6
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  1
M  END


  Mrv1652304292203442D          

 20 22  0  0  1  0            999 V2000
   -0.5821   -0.4714    0.0000 C   0  0  1  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
    0.2578   -1.6275    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9252   -1.1425    0.0000 C   0  0  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6665    1.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5803    2.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2477    2.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1615    3.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8289    3.9297    0.0000 C   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 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -1.6275    0.0000 C   0  0  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1862   -0.1359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3358   -0.1359    0.0000 C   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
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  1  6  1  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
  3 18  1  1  0  0  0
 14 19  1  0  0  0  0
  1 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0080739

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC\C=C\C1=C2N=C(N)N[C@H]3CC[C@@H](C[C@@H]1C)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C17H27N3/c1-3-4-5-6-7-13-11(2)10-12-8-9-14-15(12)16(13)20-17(18)19-14/h6-7,11-12,14-15H,3-5,8-10H2,1-2H3,(H3,18,19,20)/b7-6+/t11-,12-,14-,15+/m0/s1

> <INCHI_KEY>
XPYZAFRSQMDKPJ-OFQNNGORSA-N

> <FORMULA>
C17H27N3

> <MOLECULAR_WEIGHT>
273.424

> <EXACT_MASS>
273.220497881

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
33.217092408803744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,10S,12R)-9-[(1E)-hex-1-en-1-yl]-10-methyl-5,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-6,8-dien-6-amine

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
2.929012368333334

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
11.425028149376669

> <JCHEM_POLAR_SURFACE_AREA>
50.41

> <JCHEM_REFRACTIVITY>
85.70339999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,10S,12R)-9-[(1E)-hex-1-en-1-yl]-10-methyl-5,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-6,8-dien-6-amine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -1.087  -0.880   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.926  -2.412   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.481  -3.038   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.727  -2.133   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.566  -0.601   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.159   0.025   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.002   1.557   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.244   2.462   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.083   3.994   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.329   4.899   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.168   6.430   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.414   7.335   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.295   0.025   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       4.541  -0.880   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.380  -2.412   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.973  -3.038   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.497  -4.503   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.957  -4.503   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       5.948  -0.254   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      -2.494  -0.254   0.000  0.00  0.00           C+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    5   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15    4   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    3                                                       
CONECT   19   14                                                            
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₇N₃

Average Mass

273.4240 Da

Monoisotopic Mass

273.22050 Da

IUPAC Name

(1S,4S,10S,12R)-9-[(1E)-hex-1-en-1-yl]-10-methyl-5,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-6,8-dien-6-amine

Traditional Name

(1S,4S,10S,12R)-9-[(1E)-hex-1-en-1-yl]-10-methyl-5,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-6,8-dien-6-amine

CAS Registry Number

Not Available

SMILES

CCCC\C=C\C1=C2N=C(N)N[C@H]3CC[C@@H](C[C@@H]1C)[C@@H]23

InChI Identifier

InChI=1S/C17H27N3/c1-3-4-5-6-7-13-11(2)10-12-8-9-14-15(12)16(13)20-17(18)19-14/h6-7,11-12,14-15H,3-5,8-10H2,1-2H3,(H3,18,19,20)/b7-6+/t11-,12-,14-,15+/m0/s1

InChI Key

XPYZAFRSQMDKPJ-OFQNNGORSA-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
Clathria sp.	Animalia	KNApSAcK

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
1,4,5,6-tetrahydropyrimidine
Hydropyrimidine
Guanidine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.99	ALOGPS
logP	2.93	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	11.43	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	50.41 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	85.7 m³·mol⁻¹	ChemAxon
Polarizability	33.22 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00046158

Chemspider ID

10007217

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11832570

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Grkovic T, Blees JS, Bayer MM, Colburn NH, Thomas CL, Henrich CJ, Peach ML, McMahon JB, Schmid T, Gustafson KR: Tricyclic guanidine alkaloids from the marine sponge Acanthella cavernosa that stabilize the tumor suppressor PDCD4. Mar Drugs. 2014 Aug 21;12(8):4593-601. doi: 10.3390/md12084593. [PubMed:25196934 ]

Showing NP-Card for Mirabilin G (NP0080739)

MOL for NP0080739 (Mirabilin G)

3D MOL for NP0080739 (Mirabilin G)

3D SDF for NP0080739 (Mirabilin G)

3D-SDF for NP0080739 (Mirabilin G)

PDB for NP0080739 (Mirabilin G)

3D PDB for NP0080739 (Mirabilin G)

SMILES for NP0080739 (Mirabilin G)

INCHI for NP0080739 (Mirabilin G)

Structure for NP0080739 (Mirabilin G)

3D Structure for NP0080739 (Mirabilin G)