NP-MRD: Showing NP-Card for Cyclic(3-phenyl-beta-alanyl-alpha-aminobutyrylserylseryl-3,4-dichloroprolyl) (NP0084872)

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Record Information

Version

2.0

Created at

2022-04-29 05:29:43 UTC

Updated at

2022-04-29 05:29:43 UTC

NP-MRD ID

NP0084872

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cyclic(3-phenyl-beta-alanyl-alpha-aminobutyrylserylseryl-3,4-dichloroprolyl)

Description

Islanditoxin belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. Cyclic(3-phenyl-beta-alanyl-alpha-aminobutyrylserylseryl-3,4-dichloroprolyl) is found in Penicillium islandicum. Islanditoxin is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061305142D          

 38 40  0  0  0  0            999 V2000
    9.1226   -1.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1047    1.2198    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


  Mrv0541 05061305142D          

 38 40  0  0  0  0            999 V2000
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 29 16  1  0  0  0  0
 29 21  2  0  0  0  0
 30 17  1  0  0  0  0
 30 22  2  0  0  0  0
 31  9  1  0  0  0  0
 31 20  1  0  0  0  0
 31 24  1  0  0  0  0
 32 10  1  0  0  0  0
 33 11  1  0  0  0  0
 34 18  1  0  0  0  0
 35 21  1  0  0  0  0
 36 22  1  0  0  0  0
 37 23  1  0  0  0  0
 38 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0084872

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1\N=C(O)/CC(\N=C(O)\C2C(Cl)C(Cl)CN2C(=O)C(CO)\N=C(O)/C(CO)\N=C1/O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H31Cl2N5O7/c1-2-14-21(35)29-16(10-32)22(36)30-17(11-33)24(38)31-9-13(25)19(26)20(31)23(37)28-15(8-18(34)27-14)12-6-4-3-5-7-12/h3-7,13-17,19-20,32-33H,2,8-11H2,1H3,(H,27,34)(H,28,37)(H,29,35)(H,30,36)

> <INCHI_KEY>
AIUAVRQIJPKJTG-UHFFFAOYSA-N

> <FORMULA>
C24H31Cl2N5O7

> <MOLECULAR_WEIGHT>
572.438

> <EXACT_MASS>
571.160053785

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
55.4373404590327

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
17,18-dichloro-7-ethyl-1,5,8,11-tetrahydroxy-10,13-bis(hydroxymethyl)-3-phenyl-3H,4H,7H,10H,13H,14H,16H,17H,18H,18aH-pyrrolo[2,1-c]1,4,7,10,13-pentaazacyclohexadecan-14-one

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
0.6404967448224195

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.655565019297956

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.863888277780098

> <JCHEM_PKA_STRONGEST_BASIC>
6.023093229143347

> <JCHEM_POLAR_SURFACE_AREA>
191.12999999999997

> <JCHEM_REFRACTIVITY>
136.87960000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17,18-dichloro-7-ethyl-1,5,8,11-tetrahydroxy-10,13-bis(hydroxymethyl)-3-phenyl-3H,4H,7H,10H,13H,16H,17H,18H,18aH-pyrrolo[2,1-c]1,4,7,10,13-pentaazacyclohexadecan-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      17.029  -3.120   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.625  -3.753   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.087   4.442   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.683   3.809   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.337   3.543   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.529   2.277   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.183   2.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.875  -1.054   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.004  -4.812   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.663  -6.551   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.201  -7.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.779   1.378   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.228  -3.482   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.375  -2.853   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.625  -0.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.413  -5.651   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.605  -6.917   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.279  -0.421   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.253  -2.333   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.663  -2.953   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.971  -3.486   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.259  -7.183   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.067  -2.320   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.759  -5.384   0.000  0.00  0.00           C+0
HETATM   25 Cl   UNK     0       3.696  -3.328   0.000  0.00  0.00          Cl+0
HETATM   26 Cl   UNK     0       5.926  -0.828   0.000  0.00  0.00          Cl+0
HETATM   27  N   UNK     0      14.529  -1.321   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0       9.221  -0.788   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0      12.817  -5.018   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0       9.855  -7.816   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0       7.509  -4.485   0.000  0.00  0.00           N+0
HETATM   32  O   UNK     0      14.067  -5.918   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       7.047  -9.082   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      13.433   1.111   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      11.721  -2.586   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      12.509  -8.083   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      10.317  -3.219   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      10.163  -4.752   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   14                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   12                                                       
CONECT    7    5   12                                                       
CONECT    8   15   18                                                       
CONECT    9   13   31                                                       
CONECT   10   16   32                                                       
CONECT   11   17   33                                                       
CONECT   12    6    7   15                                                  
CONECT   13    9   19   25                                                  
CONECT   14    2   21   27                                                  
CONECT   15    8   12   28                                                  
CONECT   16   10   22   29                                                  
CONECT   17   11   24   30                                                  
CONECT   18    8   27   34                                                  
CONECT   19   13   20   26                                                  
CONECT   20   19   23   31                                                  
CONECT   21   14   29   35                                                  
CONECT   22   16   30   36                                                  
CONECT   23   20   28   37                                                  
CONECT   24   17   31   38                                                  
CONECT   25   13                                                            
CONECT   26   19                                                            
CONECT   27   14   18                                                       
CONECT   28   15   23                                                       
CONECT   29   16   21                                                       
CONECT   30   17   22                                                       
CONECT   31    9   20   24                                                  
CONECT   32   10                                                            
CONECT   33   11                                                            
CONECT   34   18                                                            
CONECT   35   21                                                            
CONECT   36   22                                                            
CONECT   37   23                                                            
CONECT   38   24                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Value	Source
Cyclic(3-phenyl-b-alanyl-a-aminobutyrylserylseryl-3,4-dichloroprolyl), 9ci	HMDB

Chemical Formula

C₂₄H₃₁Cl₂N₅O₇

Average Mass

572.4380 Da

Monoisotopic Mass

571.16005 Da

IUPAC Name

17,18-dichloro-7-ethyl-1,5,8,11-tetrahydroxy-10,13-bis(hydroxymethyl)-3-phenyl-3H,4H,7H,10H,13H,14H,16H,17H,18H,18aH-pyrrolo[2,1-c]1,4,7,10,13-pentaazacyclohexadecan-14-one

Traditional Name

17,18-dichloro-7-ethyl-1,5,8,11-tetrahydroxy-10,13-bis(hydroxymethyl)-3-phenyl-3H,4H,7H,10H,13H,16H,17H,18H,18aH-pyrrolo[2,1-c]1,4,7,10,13-pentaazacyclohexadecan-14-one

CAS Registry Number

Not Available

SMILES

CCC1\N=C(O)/CC(\N=C(O)\C2C(Cl)C(Cl)CN2C(=O)C(CO)\N=C(O)/C(CO)\N=C1/O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C24H31Cl2N5O7/c1-2-14-21(35)29-16(10-32)22(36)30-17(11-33)24(38)31-9-13(25)19(26)20(31)23(37)28-15(8-18(34)27-14)12-6-4-3-5-7-12/h3-7,13-17,19-20,32-33H,2,8-11H2,1H3,(H,27,34)(H,28,37)(H,29,35)(H,30,36)

InChI Key

AIUAVRQIJPKJTG-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
Talaromyces islandicus	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid peptides

Alternative Parents

Substituents

Cyclic hybrid peptide
Alpha-oligopeptide
Macrolactam
Beta amino acid or derivatives
Alpha-amino acid or derivatives
Nitrogen mustard
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Pyrrolidine
Carboxamide group
Secondary carboxylic acid amide
Lactam
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Alcohol
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alkyl halide
Alkyl chloride
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	0.9	ALOGPS
logP	0.64	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	3.86	ChemAxon
pKa (Strongest Basic)	6.02	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	191.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	136.88 m³·mol⁻¹	ChemAxon
Polarizability	55.44 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

HMDB0030458

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002327

KNApSAcK ID

Not Available

Chemspider ID

102758

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

114782

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cyclic(3-phenyl-beta-alanyl-alpha-aminobutyrylserylseryl-3,4-dichloroprolyl) (NP0084872)

MOL for NP0084872 (Cyclic(3-phenyl-beta-alanyl-alpha-aminobutyrylserylseryl-3,4-dichloroprolyl))

3D MOL for NP0084872 (Cyclic(3-phenyl-beta-alanyl-alpha-aminobutyrylserylseryl-3,4-dichloroprolyl))

3D SDF for NP0084872 (Cyclic(3-phenyl-beta-alanyl-alpha-aminobutyrylserylseryl-3,4-dichloroprolyl))

3D-SDF for NP0084872 (Cyclic(3-phenyl-beta-alanyl-alpha-aminobutyrylserylseryl-3,4-dichloroprolyl))

PDB for NP0084872 (Cyclic(3-phenyl-beta-alanyl-alpha-aminobutyrylserylseryl-3,4-dichloroprolyl))

3D PDB for NP0084872 (Cyclic(3-phenyl-beta-alanyl-alpha-aminobutyrylserylseryl-3,4-dichloroprolyl))

SMILES for NP0084872 (Cyclic(3-phenyl-beta-alanyl-alpha-aminobutyrylserylseryl-3,4-dichloroprolyl))

INCHI for NP0084872 (Cyclic(3-phenyl-beta-alanyl-alpha-aminobutyrylserylseryl-3,4-dichloroprolyl))

Structure for NP0084872 (Cyclic(3-phenyl-beta-alanyl-alpha-aminobutyrylserylseryl-3,4-dichloroprolyl))

3D Structure for NP0084872 (Cyclic(3-phenyl-beta-alanyl-alpha-aminobutyrylserylseryl-3,4-dichloroprolyl))