NP-MRD: Showing NP-Card for (2s)-6-amino-2-{[(2s)-2-{[(2s)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-n-[(1s)-1-(c-hydroxycarbonimidoyl)ethyl]hexanimidic acid (NP0213001)

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Record Information

Version

2.0

Created at

2022-09-05 11:50:35 UTC

Updated at

2022-09-05 11:50:35 UTC

NP-MRD ID

NP0213001

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-6-amino-2-{[(2s)-2-{[(2s)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-n-[(1s)-1-(c-hydroxycarbonimidoyl)ethyl]hexanimidic acid

Description

3-Phenyllactyl-phenylalanyl-lysyl-alaninamide, also known as antho-kaamide or L-3-phenyllactyl-phe-lys-ala-NH2, 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. (2s)-6-amino-2-{[(2s)-2-{[(2s)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-n-[(1s)-1-(c-hydroxycarbonimidoyl)ethyl]hexanimidic acid is found in Anthopleura elegantissima. Based on a literature review very few articles have been published on 3-Phenyllactyl-phenylalanyl-lysyl-alaninamide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052213502D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309052213502D          

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  6  7  1  0  0  0  0
  7  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
  6 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  4  0  0  0
 13 15  1  0  0  0  0
 15 16  1  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
 15 23  1  1  0  0  0
 23 24  2  0  0  0  0
 24 25  1  4  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213001

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](N=C(O)[C@H](CCCCN)N=C(O)[C@H](CC1=CC=CC=C1)N=C(O)[C@@H](O)CC1=CC=CC=C1)C(O)=N

> <INCHI_IDENTIFIER>
InChI=1S/C27H37N5O5/c1-18(24(29)34)30-25(35)21(14-8-9-15-28)31-26(36)22(16-19-10-4-2-5-11-19)32-27(37)23(33)17-20-12-6-3-7-13-20/h2-7,10-13,18,21-23,33H,8-9,14-17,28H2,1H3,(H2,29,34)(H,30,35)(H,31,36)(H,32,37)/t18-,21-,22-,23-/m0/s1

> <INCHI_KEY>
XPSMGYNORQJNOF-QGQQZZQASA-N

> <FORMULA>
C27H37N5O5

> <MOLECULAR_WEIGHT>
511.623

> <EXACT_MASS>
511.279469311

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
55.146355025717845

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-6-amino-2-{[(2S)-2-{[(2S)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-N-[(1S)-1-(C-hydroxycarbonimidoyl)ethyl]hexanimidic acid

> <JCHEM_LOGP>
-1.6845778662332933

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
3.5090966245559496

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.9517343592749787

> <JCHEM_PKA_STRONGEST_BASIC>
12.81246666318477

> <JCHEM_POLAR_SURFACE_AREA>
188.1

> <JCHEM_REFRACTIVITY>
151.60610000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-6-amino-2-{[(2S)-2-{[(2S)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-N-[(1S)-1-(C-hydroxycarbonimidoyl)ethyl]hexanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.000  -7.700   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       8.002 -10.780   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       0.000 -10.780   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334 -13.090   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.334 -13.090   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001 -13.090   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335 -15.400   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.668 -13.090   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      -1.334 -14.630   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       0.000 -15.400   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.000 -16.940   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334 -17.710   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.334 -17.710   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667 -20.020   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667 -21.560   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334 -22.330   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000 -21.560   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000 -20.020   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       1.334  -3.850   0.000  0.00  0.00           N+0
HETATM   37  O   UNK     0       2.667  -6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    6   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   15   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35    2   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Value	Source
Antho-kaamide	MeSH
L-3-Phenyllactyl-phe-lys-ala-NH2	MeSH

Chemical Formula

C₂₇H₃₇N₅O₅

Average Mass

511.6230 Da

Monoisotopic Mass

511.27947 Da

IUPAC Name

(2S)-6-amino-2-{[(2S)-2-{[(2S)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-N-[(1S)-1-(C-hydroxycarbonimidoyl)ethyl]hexanimidic acid

Traditional Name

(2S)-6-amino-2-{[(2S)-2-{[(2S)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-N-[(1S)-1-(C-hydroxycarbonimidoyl)ethyl]hexanimidic acid

CAS Registry Number

Not Available

SMILES

C[C@H](N=C(O)[C@H](CCCCN)N=C(O)[C@H](CC1=CC=CC=C1)N=C(O)[C@@H](O)CC1=CC=CC=C1)C(O)=N

InChI Identifier

InChI=1S/C27H37N5O5/c1-18(24(29)34)30-25(35)21(14-8-9-15-28)31-26(36)22(16-19-10-4-2-5-11-19)32-27(37)23(33)17-20-12-6-3-7-13-20/h2-7,10-13,18,21-23,33H,8-9,14-17,28H2,1H3,(H2,29,34)(H,30,35)(H,31,36)(H,32,37)/t18-,21-,22-,23-/m0/s1

InChI Key

XPSMGYNORQJNOF-QGQQZZQASA-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

Species Name	Source	Reference
Anthopleura elegantissima	LOTUS Database	35616633

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
Phenylalanine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alanine or derivatives
Amphetamine or derivatives
Alpha-amino acid or derivatives
N-substituted-alpha-amino acid
Fatty acyl
Benzenoid
N-acyl-amine
Fatty amide
Monocyclic benzene moiety
Secondary carboxylic acid amide
Secondary alcohol
Primary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Alcohol
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	-1.7	ChemAxon
pKa (Strongest Acidic)	-3	ChemAxon
pKa (Strongest Basic)	12.81	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	188.1 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	151.61 m³·mol⁻¹	ChemAxon
Polarizability	55.15 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

Not Available

Chemspider ID

116651

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132052

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-6-amino-2-{[(2s)-2-{[(2s)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-n-[(1s)-1-(c-hydroxycarbonimidoyl)ethyl]hexanimidic acid (NP0213001)

MOL for NP0213001 ((2s)-6-amino-2-{[(2s)-2-{[(2s)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-n-[(1s)-1-(c-hydroxycarbonimidoyl)ethyl]hexanimidic acid)

3D MOL for NP0213001 ((2s)-6-amino-2-{[(2s)-2-{[(2s)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-n-[(1s)-1-(c-hydroxycarbonimidoyl)ethyl]hexanimidic acid)

3D SDF for NP0213001 ((2s)-6-amino-2-{[(2s)-2-{[(2s)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-n-[(1s)-1-(c-hydroxycarbonimidoyl)ethyl]hexanimidic acid)

3D-SDF for NP0213001 ((2s)-6-amino-2-{[(2s)-2-{[(2s)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-n-[(1s)-1-(c-hydroxycarbonimidoyl)ethyl]hexanimidic acid)

PDB for NP0213001 ((2s)-6-amino-2-{[(2s)-2-{[(2s)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-n-[(1s)-1-(c-hydroxycarbonimidoyl)ethyl]hexanimidic acid)

3D PDB for NP0213001 ((2s)-6-amino-2-{[(2s)-2-{[(2s)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-n-[(1s)-1-(c-hydroxycarbonimidoyl)ethyl]hexanimidic acid)

SMILES for NP0213001 ((2s)-6-amino-2-{[(2s)-2-{[(2s)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-n-[(1s)-1-(c-hydroxycarbonimidoyl)ethyl]hexanimidic acid)

INCHI for NP0213001 ((2s)-6-amino-2-{[(2s)-2-{[(2s)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-n-[(1s)-1-(c-hydroxycarbonimidoyl)ethyl]hexanimidic acid)

Structure for NP0213001 ((2s)-6-amino-2-{[(2s)-2-{[(2s)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-n-[(1s)-1-(c-hydroxycarbonimidoyl)ethyl]hexanimidic acid)

3D Structure for NP0213001 ((2s)-6-amino-2-{[(2s)-2-{[(2s)-1,2-dihydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-n-[(1s)-1-(c-hydroxycarbonimidoyl)ethyl]hexanimidic acid)