NP-MRD: Showing NP-Card for Psammaplysene D (NP0077023)

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Record Information

Version

2.0

Created at

2022-04-28 22:11:50 UTC

Updated at

2022-04-28 22:11:50 UTC

NP-MRD ID

NP0077023

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Psammaplysene D

Description

PSAMMAPLYSENE D belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid. Psammaplysene D is found in Psammoclemma sp. Psammaplysene D was first documented in 2018 (PMID: 29702602). Based on a literature review very few articles have been published on PSAMMAPLYSENE D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200112D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292200112D          

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  5  8  1  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 21 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 19 31  1  0  0  0  0
 12 32  1  0  0  0  0
  4 33  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077023

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(C)CCCOC1=C(Br)C=C(\C=C\C(=O)N(C)CCCOC2=C(Br)C=C(CCN(C)C)C=C2Br)C=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C28H37Br4N3O3/c1-33(2)11-6-14-37-27-22(29)16-20(17-23(27)30)8-9-26(36)35(5)12-7-15-38-28-24(31)18-21(19-25(28)32)10-13-34(3)4/h8-9,16-19H,6-7,10-15H2,1-5H3/b9-8+

> <INCHI_KEY>
YAKDQOSJNFRMRB-CMDGGOBGSA-N

> <FORMULA>
C28H37Br4N3O3

> <MOLECULAR_WEIGHT>
783.238

> <EXACT_MASS>
778.956844

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
69.32044512374313

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-N-(3-{2,6-dibromo-4-[2-(dimethylamino)ethyl]phenoxy}propyl)-3-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}-N-methylprop-2-enamide

> <ALOGPS_LOGP>
6.42

> <JCHEM_LOGP>
6.706506592666667

> <ALOGPS_LOGS>
-6.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
9.468082804171717

> <JCHEM_POLAR_SURFACE_AREA>
45.25

> <JCHEM_REFRACTIVITY>
173.22969999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.55e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-N-(3-{2,6-dibromo-4-[2-(dimethylamino)ethyl]phenoxy}propyl)-3-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}-N-methylprop-2-enamide

> <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      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335 -10.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667 -10.780   0.000  0.00  0.00           C+0
HETATM    7 Br   UNK     0      -1.334 -11.550   0.000  0.00  0.00          Br+0
HETATM    8  O   UNK     0      -1.334  -8.470   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.001  -8.470   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335 -10.780   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   23 Br   UNK     0      12.003  -6.930   0.000  0.00  0.00          Br+0
HETATM   24  O   UNK     0      12.003  -3.850   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.670  -3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      17.338  -3.850   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      18.672  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.338  -2.310   0.000  0.00  0.00           C+0
HETATM   31 Br   UNK     0       9.336  -2.310   0.000  0.00  0.00          Br+0
HETATM   32  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   33 Br   UNK     0      -4.001  -6.930   0.000  0.00  0.00          Br+0
HETATM   34  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -6.668 -13.090   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      -8.002 -13.860   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0      -8.002 -15.400   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -9.336 -13.090   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   33                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   32                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   31                                                  
CONECT   20   19   21   24                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   17                                                       
CONECT   23   21                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   19                                                            
CONECT   32   12                                                            
CONECT   33    4                                                            
CONECT   34    2   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₇Br₄N₃O₃

Average Mass

783.2380 Da

Monoisotopic Mass

778.95684 Da

IUPAC Name

(2E)-N-(3-{2,6-dibromo-4-[2-(dimethylamino)ethyl]phenoxy}propyl)-3-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}-N-methylprop-2-enamide

Traditional Name

(2E)-N-(3-{2,6-dibromo-4-[2-(dimethylamino)ethyl]phenoxy}propyl)-3-{3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl}-N-methylprop-2-enamide

CAS Registry Number

Not Available

SMILES

CN(C)CCCOC1=C(Br)C=C(\C=C\C(=O)N(C)CCCOC2=C(Br)C=C(CCN(C)C)C=C2Br)C=C1Br

InChI Identifier

InChI=1S/C28H37Br4N3O3/c1-33(2)11-6-14-37-27-22(29)16-20(17-23(27)30)8-9-26(36)35(5)12-7-15-38-28-24(31)18-21(19-25(28)32)10-13-34(3)4/h8-9,16-19H,6-7,10-15H2,1-5H3/b9-8+

InChI Key

YAKDQOSJNFRMRB-CMDGGOBGSA-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
Psammoclemma sp.	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Not Available

Direct Parent

Cinnamic acids and derivatives

Alternative Parents

Substituents

Cinnamic acid or derivatives
Phenethylamine
Phenoxy compound
Styrene
Phenol ether
Alkyl aryl ether
Aralkylamine
Bromobenzene
Halobenzene
Aryl bromide
Aryl halide
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Amino acid or derivatives
Tertiary aliphatic amine
Carboxamide group
Tertiary amine
Ether
Carboxylic acid derivative
Organooxygen compound
Organic nitrogen compound
Organohalogen compound
Carbonyl group
Organobromide
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	6.42	ALOGPS
logP	6.71	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Basic)	9.47	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	45.25 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	173.23 m³·mol⁻¹	ChemAxon
Polarizability	69.32 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

C00040089

Chemspider ID

23076745

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24179853

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

El-Demerdash A, Moriou C, Toullec J, Besson M, Soulet S, Schmitt N, Petek S, Lecchini D, Debitus C, Al-Mourabit A: Bioactive Bromotyrosine-Derived Alkaloids from the Polynesian Sponge Suberea ianthelliformis. Mar Drugs. 2018 Apr 27;16(5):146. doi: 10.3390/md16050146. [PubMed:29702602 ]

Showing NP-Card for Psammaplysene D (NP0077023)

MOL for NP0077023 (Psammaplysene D)

3D MOL for NP0077023 (Psammaplysene D)

3D SDF for NP0077023 (Psammaplysene D)

3D-SDF for NP0077023 (Psammaplysene D)

PDB for NP0077023 (Psammaplysene D)

3D PDB for NP0077023 (Psammaplysene D)

SMILES for NP0077023 (Psammaplysene D)

INCHI for NP0077023 (Psammaplysene D)

Structure for NP0077023 (Psammaplysene D)

3D Structure for NP0077023 (Psammaplysene D)