NP-MRD: Showing NP-Card for 5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol (NP0321158)

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Record Information

Version

2.0

Created at

2022-09-11 23:13:32 UTC

Updated at

2022-09-11 23:13:32 UTC

NP-MRD ID

NP0321158

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol

Description

Lyngbyatoxin A belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. The ornithine decarboxylation reaction catalyzed by ornithine decarboxylase (ODC) is the first and committed step in the synthesis of polyamines, particularly putrescine, spermidine and spermine. Lyngbyatoxin A is a very strong basic compound (based on its pKa). Lyngbyatoxin A is a potentially toxic compound. Lyngbyatoxin A is a potent irritant and vesicant, as well as a carcinogen. Lyngbyatoxin A is a cyanotoxin produced by certain cyanobacteria species, notably Moorea producens (formerly classified as Lyngbya majuscula). Gap junction genes are involved in communication between carcinogenic cells and tight junction genes act as tumor suppressors. Lyngbyatoxin A is a tumor promoter. The toxin is highly inflammatory and vesicatory. Low concentrations more commonly encountered cause milder symptoms, known as seaweed dermatitis.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 08291401052D          

 32 34  0  0  0  0            999 V2000
    0.2492    1.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9924    3.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4760   -0.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7896    0.2881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  8  1  2  0  0  0  0
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 32 26  1  0  0  0  0
M  END

     RDKit          3D

 71 73  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv0541 08291401052D          

 32 34  0  0  0  0            999 V2000
    0.2492    1.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8626   -0.9129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0321158

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1N(C)C2=C3C(CC(CO)N=C1O)=CNC3=C(C=C2)C(C)(CCC=C(C)C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C27H39N3O2/c1-8-27(6,13-9-10-17(2)3)21-11-12-22-23-19(15-28-24(21)23)14-20(16-31)29-26(32)25(18(4)5)30(22)7/h8,10-12,15,18,20,25,28,31H,1,9,13-14,16H2,2-7H3,(H,29,32)

> <INCHI_KEY>
KISDGNGREAJPQR-UHFFFAOYSA-N

> <FORMULA>
C27H39N3O2

> <MOLECULAR_WEIGHT>
437.6175

> <EXACT_MASS>
437.304227507

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.82882114273466

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(hydroxymethyl)-9-methyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol

> <ALOGPS_LOGP>
5.22

> <JCHEM_LOGP>
5.718160800069639

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.081800095121668

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.149220750010379

> <JCHEM_PKA_STRONGEST_BASIC>
5.203897585381636

> <JCHEM_POLAR_SURFACE_AREA>
71.85000000000001

> <JCHEM_REFRACTIVITY>
134.7735

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
teleocidin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0       0.465   3.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.344  -1.704   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.816   0.483   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.586   6.901   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.234   6.579   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.889  -0.489   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.291   5.389   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.417   2.301   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.291  -1.281   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.686  -1.933   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.763   3.093   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.158   3.746   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.159   0.254   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.869   0.019   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.595  -1.143   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.390  -0.066   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.949  -1.051   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.817   5.976   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.340   0.205   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.159   0.860   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.631   1.559   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.206   2.868   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.288   1.330   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.893   0.677   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.631   4.447   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.004   3.750   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.236   0.906   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       3.083  -0.851   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0       8.608   2.333   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0       5.131   4.099   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0      10.807   0.538   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.129   4.801   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   17                                                            
CONECT    3   17                                                            
CONECT    4   18                                                            
CONECT    5   18                                                            
CONECT    6   27                                                            
CONECT    7   30                                                            
CONECT    8    1   27                                                       
CONECT    9   10   13                                                       
CONECT   10    9   17                                                       
CONECT   11   12   21                                                       
CONECT   12   11   22                                                       
CONECT   13    9   27                                                       
CONECT   14   19   20                                                       
CONECT   15   19   28                                                       
CONECT   16   20   31                                                       
CONECT   17    2    3   10                                                  
CONECT   18    4    5   25                                                  
CONECT   19   14   15   23                                                  
CONECT   20   14   16   29                                                  
CONECT   21   11   24   27                                                  
CONECT   22   12   23   30                                                  
CONECT   23   19   22   24                                                  
CONECT   24   21   23   28                                                  
CONECT   25   18   26   30                                                  
CONECT   26   25   29   32                                                  
CONECT   27    6    8   13   21                                             
CONECT   28   15   24                                                       
CONECT   29   20   26                                                       
CONECT   30    7   22   25                                                  
CONECT   31   16                                                            
CONECT   32   26                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₉N₃O₂

Average Mass

437.6175 Da

Monoisotopic Mass

437.30423 Da

IUPAC Name

5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(hydroxymethyl)-9-methyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol

Traditional Name

teleocidin

CAS Registry Number

Not Available

SMILES

CC(C)C1N(C)C2=C3C(CC(CO)N=C1O)=CNC3=C(C=C2)C(C)(CCC=C(C)C)C=C

InChI Identifier

InChI=1S/C27H39N3O2/c1-8-27(6,13-9-10-17(2)3)21-11-12-22-23-19(15-28-24(21)23)14-20(16-31)29-26(32)25(18(4)5)30(22)7/h8,10-12,15,18,20,25,28,31H,1,9,13-14,16H2,2-7H3,(H,29,32)

InChI Key

KISDGNGREAJPQR-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, 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 alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid amides

Alternative Parents

Substituents

Alpha-amino acid amide
Aromatic monoterpenoid
Monoterpenoid
3-alkylindole
Indole
Indole or derivatives
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Tertiary amine
Secondary carboxylic acid amide
Carboxamide group
Lactam
Organoheterocyclic compound
Azacycle
Alcohol
Organonitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organopnictogen compound
Primary alcohol
Carbonyl group
Organic oxygen compound
Amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monoterpenoid (CHEBI:80050 )
Alkaloids (C15720 )

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	5.22	ALOGPS
logP	5.72	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	3.15	ChemAxon
pKa (Strongest Basic)	5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	71.85 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	134.77 m³·mol⁻¹	ChemAxon
Polarizability	51.83 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

C15720

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lyngbyatoxin-a

METLIN ID

Not Available

PubChem Compound

3979

PDB ID

Not Available

ChEBI ID

80050

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol (NP0321158)

MOL for NP0321158 (5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D MOL for NP0321158 (5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D SDF for NP0321158 (5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D-SDF for NP0321158 (5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

PDB for NP0321158 (5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D PDB for NP0321158 (5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

SMILES for NP0321158 (5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

INCHI for NP0321158 (5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

Structure for NP0321158 (5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D Structure for NP0321158 (5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)