NP-MRD: Showing NP-Card for Lyngbyatoxin A acetate (NP0081104)

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Record Information

Version

2.0

Created at

2022-04-29 02:04:40 UTC

Updated at

2022-04-29 02:04:40 UTC

NP-MRD ID

NP0081104

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lyngbyatoxin A acetate

Description

[(10S,13S)-5-[(3R)-3,7-dimethylocta-1,6-dien-3-yl]-11-hydroxy-9-methyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]Pentadeca-1,4,6,8(15),11-pentaen-13-yl]methyl acetate belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. Lyngbyatoxin A acetate is found in Stylocheilus longicauda. Based on a literature review very few articles have been published on [(10S,13S)-5-[(3R)-3,7-dimethylocta-1,6-dien-3-yl]-11-hydroxy-9-methyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]Pentadeca-1,4,6,8(15),11-pentaen-13-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204042D          

 35 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292204042D          

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 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  6 16  1  6  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  5 19  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  2 25  2  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  2  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  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
 32 34  1  0  0  0  0
 26 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0081104

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1N(C)C2=C3C(C[C@@H](COC(C)=O)NC1=O)=CNC3=C(C=C2)[C@](C)(CCC=C(C)C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C29H41N3O3/c1-9-29(7,14-10-11-18(2)3)23-12-13-24-25-21(16-30-26(23)25)15-22(17-35-20(6)33)31-28(34)27(19(4)5)32(24)8/h9,11-13,16,19,22,27,30H,1,10,14-15,17H2,2-8H3,(H,31,34)/t22-,27-,29-/m0/s1

> <INCHI_KEY>
WUGMGNWGTQDXDH-NVLPUFGLSA-N

> <FORMULA>
C29H41N3O3

> <MOLECULAR_WEIGHT>
479.665

> <EXACT_MASS>
479.314792192

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
54.946540476594784

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(10S,13S)-5-[(3R)-3,7-dimethylocta-1,6-dien-3-yl]-9-methyl-11-oxo-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0^{4,15}]pentadeca-1,4,6,8(15)-tetraen-13-yl]methyl acetate

> <ALOGPS_LOGP>
5.40

> <JCHEM_LOGP>
5.727058090666667

> <ALOGPS_LOGS>
-5.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.09777117842655

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.989180829359587

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6828700987876856

> <JCHEM_POLAR_SURFACE_AREA>
74.43

> <JCHEM_REFRACTIVITY>
143.40330000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.22e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(10S,13S)-5-[(3R)-3,7-dimethylocta-1,6-dien-3-yl]-10-isopropyl-9-methyl-11-oxo-3,9,12-triazatricyclo[6.6.1.0^{4,15}]pentadeca-1,4,6,8(15)-tetraen-13-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       2.529   2.995   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.001   2.809   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.051   1.684   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.134   0.147   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.792  -1.084   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.292  -1.433   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.665  -0.735   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.790  -1.787   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       4.268   0.682   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.820   2.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.051   3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.468   2.477   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.699   3.402   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.116   2.798   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.513   4.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.478  -2.961   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.894  -3.565   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.246  -3.887   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.049  -2.375   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.181  -0.732   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.576  -0.079   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.708   1.455   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.446   2.337   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      -1.256   3.865   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       0.256   4.157   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.103   2.108   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.451   3.503   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.332   4.765   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.498   2.761   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.631   4.295   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.025   4.947   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -7.158   6.482   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -8.553   7.134   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.895   7.363   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.756   0.713   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3   25                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    1   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    6   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    5                                                            
CONECT   20    4   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22    3   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24    2                                                       
CONECT   26   22   27   29   35                                             
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   26                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
[(10S,13S)-5-[(3R)-3,7-Dimethylocta-1,6-dien-3-yl]-11-hydroxy-9-methyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0,]pentadeca-1,4,6,8(15),11-pentaen-13-yl]methyl acetic acid	Generator

Chemical Formula

C₂₉H₄₁N₃O₃

Average Mass

479.6650 Da

Monoisotopic Mass

479.31479 Da

IUPAC Name

[(10S,13S)-5-[(3R)-3,7-dimethylocta-1,6-dien-3-yl]-9-methyl-11-oxo-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0^{4,15}]pentadeca-1,4,6,8(15)-tetraen-13-yl]methyl acetate

Traditional Name

[(10S,13S)-5-[(3R)-3,7-dimethylocta-1,6-dien-3-yl]-10-isopropyl-9-methyl-11-oxo-3,9,12-triazatricyclo[6.6.1.0^{4,15}]pentadeca-1,4,6,8(15)-tetraen-13-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1N(C)C2=C3C(C[C@@H](COC(C)=O)NC1=O)=CNC3=C(C=C2)[C@](C)(CCC=C(C)C)C=C

InChI Identifier

InChI=1S/C29H41N3O3/c1-9-29(7,14-10-11-18(2)3)23-12-13-24-25-21(16-30-26(23)25)15-22(17-35-20(6)33)31-28(34)27(19(4)5)32(24)8/h9,11-13,16,19,22,27,30H,1,10,14-15,17H2,2-8H3,(H,31,34)/t22-,27-,29-/m0/s1

InChI Key

WUGMGNWGTQDXDH-NVLPUFGLSA-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
Stylocheilus longicauda	Animalia	KNApSAcK

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
Pyrrole
Heteroaromatic compound
Carboxamide group
Carboxylic acid ester
Lactam
Secondary carboxylic acid amide
Tertiary amine
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
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	5.4	ALOGPS
logP	5.73	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	12.99	ChemAxon
pKa (Strongest Basic)	-0.68	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.43 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	143.4 m³·mol⁻¹	ChemAxon
Polarizability	54.95 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

8272201

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10096667

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lyngbyatoxin A acetate (NP0081104)

MOL for NP0081104 (Lyngbyatoxin A acetate)

3D MOL for NP0081104 (Lyngbyatoxin A acetate)

3D SDF for NP0081104 (Lyngbyatoxin A acetate)

3D-SDF for NP0081104 (Lyngbyatoxin A acetate)

PDB for NP0081104 (Lyngbyatoxin A acetate)

3D PDB for NP0081104 (Lyngbyatoxin A acetate)

SMILES for NP0081104 (Lyngbyatoxin A acetate)

INCHI for NP0081104 (Lyngbyatoxin A acetate)

Structure for NP0081104 (Lyngbyatoxin A acetate)

3D Structure for NP0081104 (Lyngbyatoxin A acetate)