NP-MRD: Showing NP-Card for Oscillatoxin A (NP0081128)

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Record Information

Version

2.0

Created at

2022-04-29 02:05:43 UTC

Updated at

2022-04-29 02:05:44 UTC

NP-MRD ID

NP0081128

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oscillatoxin A

Description

(1S,3S,4S,5R,9R,13R,14S)-13-hydroxy-9-(hydroxymethyl)-3-[(2S,5S)-5-(3-hydroxyphenyl)-5-methoxypentan-2-yl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1¹,⁵]Octadecane-7,11-dione belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Oscillatoxin A is found in Lyngbya majuscula. Based on a literature review very few articles have been published on (1S,3S,4S,5R,9R,13R,14S)-13-hydroxy-9-(hydroxymethyl)-3-[(2S,5S)-5-(3-hydroxyphenyl)-5-methoxypentan-2-yl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1¹,⁵]Octadecane-7,11-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204052D          

 41 44  0  0  1  0            999 V2000
    1.9940   -3.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5392   -2.5493    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304292204052D          

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    4.9552    0.9027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1192    1.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5010    2.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6650    3.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4473    3.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0655    2.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9014    1.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0468    3.6124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6211    0.3142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4571   -0.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221   -0.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9458    0.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7509    0.5102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4974    0.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7287    1.5835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3575    1.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1147    0.6419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5816   -0.0505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5507   -0.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4049   -1.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9076   -1.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5845    1.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3997    2.4717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0473   -2.2973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0009   -3.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 12 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 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
 18 23  1  0  0  0  0
 20 24  1  0  0  0  0
 17 25  1  1  0  0  0
 25 26  1  0  0  0  0
 14 27  1  6  0  0  0
 11 28  1  6  0  0  0
 10 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
  3 37  1  0  0  0  0
 33 38  1  6  0  0  0
 38 39  1  0  0  0  0
  3 40  1  1  0  0  0
  2 41  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0081128

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H](CC[C@H](C)[C@@H]1O[C@@]23C[C@@H](OC(=O)C[C@H](CO)OC(=O)C[C@@](O)(O2)[C@@H](C)CC3(C)C)[C@@H]1C)C1=CC(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H46O10/c1-18(10-11-24(37-6)21-8-7-9-22(33)12-21)28-20(3)25-15-31(40-28)29(4,5)14-19(2)30(36,41-31)16-27(35)38-23(17-32)13-26(34)39-25/h7-9,12,18-20,23-25,28,32-33,36H,10-11,13-17H2,1-6H3/t18-,19-,20-,23+,24-,25+,28-,30+,31-/m0/s1

> <INCHI_KEY>
GKTXURNRIDXUNG-NOTKKQJRSA-N

> <FORMULA>
C31H46O10

> <MOLECULAR_WEIGHT>
578.699

> <EXACT_MASS>
578.309097681

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
61.530829119815884

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,4S,5R,9R,13R,14S)-13-hydroxy-9-(hydroxymethyl)-3-[(2S,5S)-5-(3-hydroxyphenyl)-5-methoxypentan-2-yl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1^{1,5}]octadecane-7,11-dione

> <ALOGPS_LOGP>
3.06

> <JCHEM_LOGP>
4.849883087333332

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.520489877298804

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.361697284095289

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9597089139064368

> <JCHEM_POLAR_SURFACE_AREA>
140.98000000000002

> <JCHEM_REFRACTIVITY>
147.67170000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,4S,5R,9R,13R,14S)-13-hydroxy-9-(hydroxymethyl)-3-[(2S,5S)-5-(3-hydroxyphenyl)-5-methoxypentan-2-yl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1^{1,5}]octadecane-7,11-dione

> <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       3.722  -5.895   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.740  -4.759   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.882  -3.438   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.928  -4.092   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.477  -3.088   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.217  -5.149   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.604  -5.666   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.888  -6.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.150  -2.215   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.207  -0.641   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.620  -0.024   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.940  -0.740   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.750  -2.196   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.845   0.587   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.659   2.205   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.563   2.257   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.250   1.685   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.556   3.194   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.402   4.214   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.708   5.723   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.168   6.213   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.322   5.193   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.016   3.684   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.554   6.743   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.493   0.587   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.187  -0.923   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.828  -0.717   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.765   1.418   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.402   0.952   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.795   1.837   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.360   2.956   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.401   1.944   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.814   1.198   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.686  -0.094   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.628  -1.661   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.222  -2.315   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.428  -2.774   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.691   2.953   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.346   4.614   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       5.688  -4.288   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       5.602  -6.244   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   41                                                  
CONECT    3    2    4   37   40                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    9   13                                             
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   29                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    5                                                       
CONECT   14   12   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   20                                                            
CONECT   25   17   26                                                       
CONECT   26   25                                                            
CONECT   27   14                                                            
CONECT   28   11                                                            
CONECT   29   10   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    3                                                       
CONECT   38   33   39                                                       
CONECT   39   38                                                            
CONECT   40    3                                                            
CONECT   41    2                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₆O₁₀

Average Mass

578.6990 Da

Monoisotopic Mass

578.30910 Da

IUPAC Name

(1S,3S,4S,5R,9R,13R,14S)-13-hydroxy-9-(hydroxymethyl)-3-[(2S,5S)-5-(3-hydroxyphenyl)-5-methoxypentan-2-yl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1^{1,5}]octadecane-7,11-dione

Traditional Name

(1S,3S,4S,5R,9R,13R,14S)-13-hydroxy-9-(hydroxymethyl)-3-[(2S,5S)-5-(3-hydroxyphenyl)-5-methoxypentan-2-yl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1^{1,5}]octadecane-7,11-dione

CAS Registry Number

Not Available

SMILES

CO[C@@H](CC[C@H](C)[C@@H]1O[C@@]23C[C@@H](OC(=O)C[C@H](CO)OC(=O)C[C@@](O)(O2)[C@@H](C)CC3(C)C)[C@@H]1C)C1=CC(O)=CC=C1

InChI Identifier

InChI=1S/C31H46O10/c1-18(10-11-24(37-6)21-8-7-9-22(33)12-21)28-20(3)25-15-31(40-28)29(4,5)14-19(2)30(36,41-31)16-27(35)38-23(17-32)13-26(34)39-25/h7-9,12,18-20,23-25,28,32-33,36H,10-11,13-17H2,1-6H3/t18-,19-,20-,23+,24-,25+,28-,30+,31-/m0/s1

InChI Key

GKTXURNRIDXUNG-NOTKKQJRSA-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
Lyngbya majuscula	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Benzylether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
Phenol
Benzenoid
Oxane
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	3.06	ALOGPS
logP	4.85	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	9.36	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	140.98 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	147.67 m³·mol⁻¹	ChemAxon
Polarizability	61.53 Å³	ChemAxon
Number of Rings	4	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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162861727

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Oscillatoxin A (NP0081128)

MOL for NP0081128 (Oscillatoxin A)

3D MOL for NP0081128 (Oscillatoxin A)

3D SDF for NP0081128 (Oscillatoxin A)

3D-SDF for NP0081128 (Oscillatoxin A)

PDB for NP0081128 (Oscillatoxin A)

3D PDB for NP0081128 (Oscillatoxin A)

SMILES for NP0081128 (Oscillatoxin A)

INCHI for NP0081128 (Oscillatoxin A)

Structure for NP0081128 (Oscillatoxin A)

3D Structure for NP0081128 (Oscillatoxin A)