NP-MRD: Showing NP-Card for (9s,12s,15s)-9-amino-12-[(1r,2s)-3-carbamimidamido-1,2-dihydroxypropyl]-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid (NP0282205)

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Record Information

Version

2.0

Created at

2022-09-09 08:57:08 UTC

Updated at

2022-09-09 08:57:09 UTC

NP-MRD ID

NP0282205

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9s,12s,15s)-9-amino-12-[(1r,2s)-3-carbamimidamido-1,2-dihydroxypropyl]-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid

Description

Eurypamide A belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Based on a literature review very few articles have been published on Eurypamide A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092210572D          

 38 40  0  0  1  0            999 V2000
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   -1.9657    1.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309092210572D          

 38 40  0  0  1  0            999 V2000
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 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 32 36  1  0  0  0  0
 36 37  2  0  0  0  0
 10 37  1  0  0  0  0
 37 38  1  4  0  0  0
M  END
> <DATABASE_ID>
NP0282205

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@H]1CC2=CC=C(O)C(OC3=CC=C(C[C@H](N=C(O)[C@@H](N=C1O)[C@@H](O)[C@@H](O)CNC(N)=N)C(O)=O)C=C3)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C24H30N6O8/c25-14-7-12-3-6-16(31)18(9-12)38-13-4-1-11(2-5-13)8-15(23(36)37)29-22(35)19(30-21(14)34)20(33)17(32)10-28-24(26)27/h1-6,9,14-15,17,19-20,31-33H,7-8,10,25H2,(H,29,35)(H,30,34)(H,36,37)(H4,26,27,28)/t14-,15-,17-,19-,20-/m0/s1

> <INCHI_KEY>
WGXANKDMVJQLAR-UHBFJLORSA-N

> <FORMULA>
C24H30N6O8

> <MOLECULAR_WEIGHT>
530.538

> <EXACT_MASS>
530.21251195

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
51.762689889402544

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9S,12S,15S)-9-amino-12-[(1R,2S)-3-carbamimidamido-1,2-dihydroxypropyl]-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1^{3,7}]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid

> <JCHEM_LOGP>
-6.782382755085792

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
1.4916807963824104

> <JCHEM_PKA_STRONGEST_ACIDIC>
-9.71263892234327

> <JCHEM_PKA_STRONGEST_BASIC>
14.475075863368549

> <JCHEM_POLAR_SURFACE_AREA>
260.32

> <JCHEM_REFRACTIVITY>
143.37800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(9S,12S,15S)-9-amino-12-[(1R,2S)-3-carbamimidamido-1,2-dihydroxypropyl]-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1^{3,7}]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  N   UNK     0      -5.003   1.341   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -3.669   2.111   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -3.669   3.651   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      -2.336   1.341   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -1.002   2.111   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.332   1.341   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.332  -0.199   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.665   2.111   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.999   1.341   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.665   3.651   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.109   3.969   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -1.189   4.817   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.252   3.702   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.102   6.075   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -3.499   5.428   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -2.473   7.590   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.244   9.147   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.451  10.141   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.225  11.675   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.781  12.239   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.582  13.766   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.511  11.308   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.802   9.750   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.987  11.956   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.621  11.810   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.318  10.295   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.368   9.167   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.892   9.486   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.277  11.021   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.172  12.119   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.327   7.925   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.339   6.343   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.834   5.976   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.264   4.497   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       7.900   7.087   0.000  0.00  0.00           O+0
HETATM   36  N   UNK     0       4.582   4.921   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0       3.272   3.979   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.889   2.568   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   37                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22   17                                                       
CONECT   24   22   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   28   32                                                       
CONECT   32   31   33   36                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   32   37                                                       
CONECT   37   36   10   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₀N₆O₈

Average Mass

530.5380 Da

Monoisotopic Mass

530.21251 Da

IUPAC Name

(9S,12S,15S)-9-amino-12-[(1R,2S)-3-carbamimidamido-1,2-dihydroxypropyl]-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1^{3,7}]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid

Traditional Name

(9S,12S,15S)-9-amino-12-[(1R,2S)-3-carbamimidamido-1,2-dihydroxypropyl]-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1^{3,7}]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid

CAS Registry Number

Not Available

SMILES

N[C@H]1CC2=CC=C(O)C(OC3=CC=C(C[C@H](N=C(O)[C@@H](N=C1O)[C@@H](O)[C@@H](O)CNC(N)=N)C(O)=O)C=C3)=C2

InChI Identifier

InChI=1S/C24H30N6O8/c25-14-7-12-3-6-16(31)18(9-12)38-13-4-1-11(2-5-13)8-15(23(36)37)29-22(35)19(30-21(14)34)20(33)17(32)10-28-24(26)27/h1-6,9,14-15,17,19-20,31-33H,7-8,10,25H2,(H,29,35)(H,30,34)(H,36,37)(H4,26,27,28)/t14-,15-,17-,19-,20-/m0/s1

InChI Key

WGXANKDMVJQLAR-UHBFJLORSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Cyclic alpha peptide
Oxyneolignan skeleton
Macrolactam
Alpha-amino acid amide
Diaryl ether
Alpha-amino acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Benzenoid
Guanidine
Lactam
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Amino acid or derivatives
1,2-diol
Azacycle
Oxacycle
Monocarboxylic acid or derivatives
Carboximidamide
Carboxylic acid
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Ether
Primary amine
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Primary aliphatic amine
Carbonyl group
Organonitrogen compound
Amine
Organooxygen compound
Organic nitrogen compound
Alcohol
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	-6.8	ChemAxon
pKa (Strongest Acidic)	-9.7	ChemAxon
pKa (Strongest Basic)	14.48	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	260.32 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	143.38 m³·mol⁻¹	ChemAxon
Polarizability	51.76 Å³	ChemAxon
Number of Rings	3	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

Not Available

Chemspider ID

9516497

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11341555

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (9s,12s,15s)-9-amino-12-[(1r,2s)-3-carbamimidamido-1,2-dihydroxypropyl]-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid (NP0282205)

MOL for NP0282205 ((9s,12s,15s)-9-amino-12-[(1r,2s)-3-carbamimidamido-1,2-dihydroxypropyl]-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

3D MOL for NP0282205 ((9s,12s,15s)-9-amino-12-[(1r,2s)-3-carbamimidamido-1,2-dihydroxypropyl]-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

3D SDF for NP0282205 ((9s,12s,15s)-9-amino-12-[(1r,2s)-3-carbamimidamido-1,2-dihydroxypropyl]-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

3D-SDF for NP0282205 ((9s,12s,15s)-9-amino-12-[(1r,2s)-3-carbamimidamido-1,2-dihydroxypropyl]-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

PDB for NP0282205 ((9s,12s,15s)-9-amino-12-[(1r,2s)-3-carbamimidamido-1,2-dihydroxypropyl]-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

3D PDB for NP0282205 ((9s,12s,15s)-9-amino-12-[(1r,2s)-3-carbamimidamido-1,2-dihydroxypropyl]-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

SMILES for NP0282205 ((9s,12s,15s)-9-amino-12-[(1r,2s)-3-carbamimidamido-1,2-dihydroxypropyl]-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

INCHI for NP0282205 ((9s,12s,15s)-9-amino-12-[(1r,2s)-3-carbamimidamido-1,2-dihydroxypropyl]-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

Structure for NP0282205 ((9s,12s,15s)-9-amino-12-[(1r,2s)-3-carbamimidamido-1,2-dihydroxypropyl]-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

3D Structure for NP0282205 ((9s,12s,15s)-9-amino-12-[(1r,2s)-3-carbamimidamido-1,2-dihydroxypropyl]-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)