NP-MRD: Showing NP-Card for Microcystin-[Leu1]-Leu-Phe (NP0333532)

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Record Information

Version

2.0

Created at

2024-06-27 00:49:05 UTC

Updated at

2025-07-30 21:53:24 UTC

NP-MRD ID

NP0333532

Natural Product DOI

https://doi.org/10.57994/2988

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Microcystin-[Leu1]-Leu-Phe

Description

Microcystin-[Leu1]-Leu-Phe belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues. Based on a literature review very few articles have been published on Microcystin-[Leu1]-Leu-Phe.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03112303232D          

 72 73  0  0  1  0            999 V2000
   -9.3288   10.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5275    9.8652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -7.7267    7.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2978    5.3322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 30 71  2  0  0  0  0
 22 72  2  0  0  0  0
M  END


  Mrv2104 03112303232D          

 72 73  0  0  1  0            999 V2000
   -9.3288   10.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5275    9.8652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 59 58  1  0  0  0  0
 59 60  1  1  0  0  0
 60 61  1  0  0  0  0
 60 62  2  0  0  0  0
 59 63  1  6  0  0  0
 63 64  1  0  0  0  0
  2 64  1  0  0  0  0
 64 65  2  0  0  0  0
 56 66  2  0  0  0  0
 53 67  2  0  0  0  0
 52 68  2  0  0  0  0
 45 69  2  0  0  0  0
 38 70  2  0  0  0  0
 30 71  2  0  0  0  0
 22 72  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333532

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H](CC1=CC=CC=C1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C\C(C)=C\C)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C53H79N7O12/c1-14-31(6)27-42-50(66)54-38(21-20-32(7)26-33(8)43(72-13)28-37-18-16-15-17-19-37)34(9)46(62)55-39(52(68)69)22-23-44(61)60(12)36(11)48(64)57-40(24-29(2)3)49(65)58-41(25-30(4)5)51(67)59-45(53(70)71)35(10)47(63)56-42/h14-21,26,29-30,33-35,38-43,45H,11,22-25,27-28H2,1-10,12-13H3,(H,54,66)(H,55,62)(H,56,63)(H,57,64)(H,58,65)(H,59,67)(H,68,69)(H,70,71)/b21-20+,31-14+,32-26+/t33-,34-,35-,38-,39?,40+,41-,42-,43-,45+/m0/s1

> <INCHI_KEY>
CQLOBUSFHIQNPL-XXPCRBDKSA-N

> <FORMULA>
C53H79N7O12

> <MOLECULAR_WEIGHT>
1006.252

> <EXACT_MASS>
1005.578671012

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
151

> <JCHEM_AVERAGE_POLARIZABILITY>
107.5706101605156

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,8S,11R,12S,15S,18S,19S,22R)-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,12,19-trimethyl-15-[(2E)-2-methylbut-2-en-1-yl]-2-methylidene-5,8-bis(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid

> <JCHEM_LOGP>
4.021560791333337

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.019844278095707

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.401654395896846

> <JCHEM_POLAR_SURFACE_AREA>
278.73999999999995

> <JCHEM_REFRACTIVITY>
272.9469000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5R,8S,11R,12S,15S,18S,19S,22R)-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,12,19-trimethyl-15-[(2E)-2-methylbut-2-en-1-yl]-2-methylidene-5,8-bis(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-MAR-23         0                                  
HETATM    1  C   UNK     0     -17.414  18.781   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -15.918  18.415   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -15.757  16.884   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -14.423  16.114   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -14.423  14.574   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -13.090  13.804   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -11.756  14.574   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -13.090  12.264   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -11.756  11.494   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -11.756   9.954   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -13.090   9.184   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0     -13.090   7.644   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.422   9.184   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -10.422   7.644   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.089   6.874   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.089   5.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -10.422   4.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -11.756   5.334   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -11.756   6.874   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -10.422  12.264   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0     -17.164  16.257   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0     -18.194  17.402   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -19.861  17.650   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -20.793  16.424   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -20.197  15.004   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -21.129  13.778   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -18.670  14.810   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -18.074  13.390   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0     -20.487  19.057   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0     -22.019  19.218   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -22.645  20.625   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -21.740  21.871   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -24.177  20.786   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -25.082  19.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -26.614  19.701   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0     -24.456  18.133   0.000  0.00  0.00           O+0
HETATM   37  N   UNK     0     -24.803  22.193   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0     -26.335  22.354   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -26.961  23.761   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -28.493  23.922   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -29.398  22.676   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -28.772  21.269   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -30.929  22.837   0.000  0.00  0.00           C+0
HETATM   44  N   UNK     0     -26.056  25.007   0.000  0.00  0.00           N+0
HETATM   45  C   UNK     0     -26.682  26.414   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -25.777  27.659   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -26.403  29.066   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -25.498  30.312   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -26.125  31.719   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -23.967  30.151   0.000  0.00  0.00           C+0
HETATM   51  N   UNK     0     -24.246  27.498   0.000  0.00  0.00           N+0
HETATM   52  C   UNK     0     -23.619  26.092   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0     -22.088  25.931   0.000  0.00  0.00           C+0
HETATM   54  N   UNK     0     -21.461  24.524   0.000  0.00  0.00           N+0
HETATM   55  C   UNK     0     -22.366  23.278   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0     -19.930  24.363   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0     -19.303  22.956   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0     -17.772  22.795   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0     -17.145  21.388   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0     -16.240  22.634   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0     -14.709  22.473   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0     -16.867  24.041   0.000  0.00  0.00           O+0
HETATM   63  N   UNK     0     -15.614  21.227   0.000  0.00  0.00           N+0
HETATM   64  C   UNK     0     -14.987  19.820   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0     -13.453  19.692   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0     -19.024  25.609   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0     -21.182  27.176   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0     -24.524  24.846   0.000  0.00  0.00           O+0
HETATM   69  O   UNK     0     -28.214  26.575   0.000  0.00  0.00           O+0
HETATM   70  O   UNK     0     -27.240  21.108   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0     -22.924  17.972   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0     -17.920  18.917   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   64                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    9                                                            
CONECT   21    3   22                                                       
CONECT   22   21   23   72                                                  
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   23   30                                                       
CONECT   30   29   31   71                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   37                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   33   38                                                       
CONECT   38   37   39   70                                                  
CONECT   39   38   40   44                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   39   45                                                       
CONECT   45   44   46   69                                                  
CONECT   46   45   47   51                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51   46   52                                                       
CONECT   52   51   53   68                                                  
CONECT   53   52   54   67                                                  
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57   66                                                  
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60   63                                                  
CONECT   60   59   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60                                                            
CONECT   63   59   64                                                       
CONECT   64   63    2   65                                                  
CONECT   65   64                                                            
CONECT   66   56                                                            
CONECT   67   53                                                            
CONECT   68   52                                                            
CONECT   69   45                                                            
CONECT   70   38                                                            
CONECT   71   30                                                            
CONECT   72   22                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  146    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₃H₇₉N₇O₁₂

Average Mass

1006.2520 Da

Monoisotopic Mass

1005.57867 Da

IUPAC Name

(5R,8S,11R,12S,15S,18S,19S,22R)-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,12,19-trimethyl-15-[(2E)-2-methylbut-2-en-1-yl]-2-methylidene-5,8-bis(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@@H](CC1=CC=CC=C1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C\C(C)=C\C)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C53H79N7O12/c1-14-31(6)27-42-50(66)54-38(21-20-32(7)26-33(8)43(72-13)28-37-18-16-15-17-19-37)34(9)46(62)55-39(52(68)69)22-23-44(61)60(12)36(11)48(64)57-40(24-29(2)3)49(65)58-41(25-30(4)5)51(67)59-45(53(70)71)35(10)47(63)56-42/h14-21,26,29-30,33-35,38-43,45H,11,22-25,27-28H2,1-10,12-13H3,(H,54,66)(H,55,62)(H,56,63)(H,57,64)(H,58,65)(H,59,67)(H,68,69)(H,70,71)/b21-20+,31-14+,32-26+/t33-,34-,35-,38-,39?,40+,41-,42-,43-,45+/m0/s1

InChI Key

CQLOBUSFHIQNPL-XXPCRBDKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
MLEV NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mbertin@uri.edu	Case Western Reserve University	Matt Bertin	2024-06-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	mbertin@uri.edu	Case Western Reserve University	Matt Bertin	2024-06-27	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Moorena sp.		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.

Kingdom

Organic compounds

Super Class

Organic Polymers

Class

Polypeptides

Sub Class

Not Available

Direct Parent

Polypeptides

Alternative Parents

Substituents

Polypeptide
Cyclic alpha peptide
Glutamine or derivatives
Leucine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-substituted-alpha-amino acid
Fatty acyl
Benzenoid
N-acyl-amine
Fatty amide
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Tertiary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	4.02	ChemAxon
pKa (Strongest Acidic)	3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	278.74 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	272.95 m³·mol⁻¹	ChemAxon
Polarizability	107.57 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Microcystin-[Leu1]-Leu-Phe (NP0333532)

MOL for NP0333532 (Microcystin-[Leu1]-Leu-Phe)

3D MOL for NP0333532 (Microcystin-[Leu1]-Leu-Phe)

3D SDF for NP0333532 (Microcystin-[Leu1]-Leu-Phe)

3D-SDF for NP0333532 (Microcystin-[Leu1]-Leu-Phe)

PDB for NP0333532 (Microcystin-[Leu1]-Leu-Phe)

3D PDB for NP0333532 (Microcystin-[Leu1]-Leu-Phe)

SMILES for NP0333532 (Microcystin-[Leu1]-Leu-Phe)

INCHI for NP0333532 (Microcystin-[Leu1]-Leu-Phe)

Structure for NP0333532 (Microcystin-[Leu1]-Leu-Phe)

3D Structure for NP0333532 (Microcystin-[Leu1]-Leu-Phe)