NP-MRD: Showing NP-Card for Madangamine B (NP0070079)

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Record Information

Version

2.0

Created at

2022-04-28 15:20:53 UTC

Updated at

2022-04-28 15:20:53 UTC

NP-MRD ID

NP0070079

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Madangamine B

Description

(1R,2R,4S,10Z,16S,21Z,24Z,28Z)-5,18-diazapentacyclo[16.12.1.1¹,⁵.0²,¹⁶.0⁴,¹⁴]Dotriaconta-10,13,21,24,28-pentaene belongs to the class of organic compounds known as naphthyridines. Naphthyridines are compounds containing a naphthyridine moiety, a naphthalene in which a carbon atom has been replaced by a nitrogen in each of the two rings. The naphthyridine skeleton can also be described as an assembly two fused pyridine rings, which do not share their nitrogen atom. Madangamine B is found in Xestospongia ingens. Based on a literature review very few articles have been published on (1R,2R,4S,10Z,16S,21Z,24Z,28Z)-5,18-diazapentacyclo[16.12.1.1¹,⁵.0²,¹⁶.0⁴,¹⁴]Dotriaconta-10,13,21,24,28-pentaene.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282217202D          

 32 36  0  0  1  0            999 V2000
   10.4476    1.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6889    2.7447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1884    3.0737    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    9.6336    1.6141    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282217202D          

 32 36  0  0  1  0            999 V2000
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  4 31  1  0  0  0  0
 21 32  1  1  0  0  0
  5 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0070079

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1[C@@H]2N3C[C@@]45CN(C[C@@H](C\C2=C\C\C=C/CCCC3)[C@@H]14)CC\C=C/C\C=C/CC\C=C\C5

> <INCHI_IDENTIFIER>
InChI=1S/C30H44N2/c1-2-4-7-11-15-19-31-23-27-21-26-17-13-9-5-8-12-16-20-32-25-30(24-31,18-14-10-6-3-1)28(27)22-29(26)32/h1-2,5,7,9-11,14,17,27-29H,3-4,6,8,12-13,15-16,18-25H2/b2-1-,9-5-,11-7-,14-10+,26-17-/t27-,28-,29+,30-/m1/s1

> <INCHI_KEY>
KUMBPXIFTSDSMO-SPTSMKJNSA-N

> <FORMULA>
C30H44N2

> <MOLECULAR_WEIGHT>
432.696

> <EXACT_MASS>
432.350449425

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
53.4188404611148

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,10Z,16S,21Z,24Z,28E)-5,18-diazapentacyclo[16.12.1.1^{1,5}.0^{2,16}.0^{4,14}]dotriaconta-10,13,21,24,28-pentaene

> <ALOGPS_LOGP>
7.07

> <JCHEM_LOGP>
6.176439865333334

> <ALOGPS_LOGS>
-6.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
10.685033541918356

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
144.19329999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.86e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,10Z,16S,21Z,24Z,28E)-5,18-diazapentacyclo[16.12.1.1^{1,5}.0^{2,16}.0^{4,14}]dotriaconta-10,13,21,24,28-pentaene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      19.502   3.625   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      19.953   5.123   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      18.722   6.161   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.152   5.738   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.108   4.233   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.983   3.013   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.875   1.680   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.655   0.318   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.203   0.275   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.325  -0.805   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.799  -0.332   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.338  -0.551   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.252   0.719   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.199   2.291   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.957   3.851   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.778   4.915   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.189   5.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.595   5.288   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.006   1.733   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      15.361   1.848   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      14.599   3.378   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.344   5.071   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.861   5.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.405   4.917   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.837   3.459   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.983   1.901   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.586   0.462   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.755  -0.565   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.252  -0.929   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.254   0.259   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.594   6.194   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.674   3.765   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   31                                                  
CONECT    5    4    6   32                                                  
CONECT    6    5    1    7   19                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    2                                                       
CONECT   19    6   20                                                       
CONECT   20   19   21   30                                                  
CONECT   21   20   22   32                                                  
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   20                                                       
CONECT   31   22    4                                                       
CONECT   32   21    5                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄N₂

Average Mass

432.6960 Da

Monoisotopic Mass

432.35045 Da

IUPAC Name

(1R,2R,4S,10Z,16S,21Z,24Z,28E)-5,18-diazapentacyclo[16.12.1.1^{1,5}.0^{2,16}.0^{4,14}]dotriaconta-10,13,21,24,28-pentaene

Traditional Name

(1R,2R,4S,10Z,16S,21Z,24Z,28E)-5,18-diazapentacyclo[16.12.1.1^{1,5}.0^{2,16}.0^{4,14}]dotriaconta-10,13,21,24,28-pentaene

CAS Registry Number

Not Available

SMILES

C1[C@@H]2N3C[C@@]45CN(C[C@@H](C\C2=C\C\C=C/CCCC3)[C@@H]14)CC\C=C/C\C=C/CC\C=C\C5

InChI Identifier

InChI=1S/C30H44N2/c1-2-4-7-11-15-19-31-23-27-21-26-17-13-9-5-8-12-16-20-32-25-30(24-31,18-14-10-6-3-1)28(27)22-29(26)32/h1-2,5,7,9-11,14,17,27-29H,3-4,6,8,12-13,15-16,18-25H2/b2-1-,9-5-,11-7-,14-10+,26-17-/t27-,28-,29+,30-/m1/s1

InChI Key

KUMBPXIFTSDSMO-SPTSMKJNSA-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
Xestospongia ingens	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthyridines. Naphthyridines are compounds containing a naphthyridine moiety, a naphthalene in which a carbon atom has been replaced by a nitrogen in each of the two rings. The naphthyridine skeleton can also be described as an assembly two fused pyridine rings, which do not share their nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Naphthyridines

Direct Parent

Naphthyridines

Alternative Parents

Substituents

Naphthyridine
Piperidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organic nitrogen compound
Organopnictogen 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	7.07	ALOGPS
logP	6.18	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	10.69	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	144.19 m³·mol⁻¹	ChemAxon
Polarizability	53.42 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

10237030

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21604140

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Madangamine B (NP0070079)

MOL for NP0070079 (Madangamine B)

3D MOL for NP0070079 (Madangamine B)

3D SDF for NP0070079 (Madangamine B)

3D-SDF for NP0070079 (Madangamine B)

PDB for NP0070079 (Madangamine B)

3D PDB for NP0070079 (Madangamine B)

SMILES for NP0070079 (Madangamine B)

INCHI for NP0070079 (Madangamine B)

Structure for NP0070079 (Madangamine B)

3D Structure for NP0070079 (Madangamine B)