NP-MRD: Showing NP-Card for Avermectin B1a (NP0137196)

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Record Information

Version

2.0

Created at

2022-05-30 16:44:44 UTC

Updated at

2022-05-30 16:44:44 UTC

NP-MRD ID

NP0137196

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Avermectin B1a

Description

Avermectin B1a 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. They show activity against a broad range of nematodes and arthropod parasites of domestic animals at dose rates of 300 microgram/kg or less. The avermectins are a series of macrocyclic lactone derivatives with potent anthelmintic properties. Avermectin B1a is an extremely weak basic (essentially neutral) compound (based on its pKa). Avermectin B1a is a potentially toxic compound. It has low solubility in water and extensive non-specific binding. It opens GABA-insensitive chloride channels, reducing membrane resistance and increasing conductance inward. A commonly used therapy in recent times has been based on oral or parenteral administration of avermectins, which are macrocyclic lactones produced by fermentation of various, carefully prepared laboratory broths using the soil micro-organism Streptomyces avermitilis. Unlike the macrolide or polyene antibiotics, they lack significant antibacterial or antifungal activity. Avermectin B1a is found in Streptomyces avermitilis. Avermectins cause irritation of skin and eyes, central nervous system depression (incoordination, tremors, lethargy, excitation, pupil dilation, coma), vomiting, convulsions and/or tremors, and respiratory failure at high doses.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241204332D          

 62 68  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 02241204332D          

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M  END
> <DATABASE_ID>
NP0137196

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C1OC2(CC3CC(CC=C(C)C(OC4CC(OC)C(OC5CC(OC)C(O)C(C)O5)C(C)O4)C(C)C=CC=C4COC5C(O)C(C)=CC(C(=O)O3)C45O)O2)C=CC1C

> <INCHI_IDENTIFIER>
InChI=1S/C48H72O14/c1-11-25(2)43-28(5)17-18-47(62-43)23-34-20-33(61-47)16-15-27(4)42(26(3)13-12-14-32-24-55-45-40(49)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-10)44(31(8)57-39)60-38-21-36(53-9)41(50)30(7)56-38/h12-15,17-19,25-26,28,30-31,33-45,49-50,52H,11,16,20-24H2,1-10H3

> <INCHI_KEY>
RRZXIRBKKLTSOM-UHFFFAOYSA-N

> <FORMULA>
C48H72O14

> <MOLECULAR_WEIGHT>
873.0769

> <EXACT_MASS>
872.492207012

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
97.33800970315559

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(butan-2-yl)-21',24'-dihydroxy-12'-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,11',13',22'-tetramethyl-5,6-dihydro-3',7',19'-trioxaspiro[pyran-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
5.848432925000001

> <ALOGPS_LOGS>
-5.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.169097735979488

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.467904935832085

> <JCHEM_PKA_STRONGEST_BASIC>
-3.449075134180017

> <JCHEM_POLAR_SURFACE_AREA>
170.06

> <JCHEM_REFRACTIVITY>
231.17980000000009

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
21',24'-dihydroxy-12'-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,11',13',22'-tetramethyl-6-(sec-butyl)-5,6-dihydro-3',7',19'-trioxaspiro[pyran-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      23.445   0.485   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.230   1.430   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.803   0.851   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.592  -0.675   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.587   1.796   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      18.161   1.216   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      16.945   2.162   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.730   3.108   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.303   2.528   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.092   1.002   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.307   0.057   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.096  -1.469   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.670  -2.048   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.458  -3.574   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.674  -4.520   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.032  -4.154   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.820  -5.679   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.394  -6.259   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.183  -7.785   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.756  -8.364   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.545  -9.890   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.118 -10.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.540  -7.419   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.114  -7.998   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.898  -7.053   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.472  -7.633   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.256  -6.687   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.830  -7.267   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.618  -8.792   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.467  -5.162   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.252  -4.216   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.894  -4.582   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.105  -3.056   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.109  -5.527   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.752  -5.893   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.536  -4.948   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.178  -5.313   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.816  -3.208   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.390  -3.788   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.027  -1.683   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.812  -0.737   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.023   0.788   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.808   1.734   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       7.272   1.623   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       6.692   3.050   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       7.869   4.042   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       7.920   5.582   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       6.612   6.395   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       9.278   6.307   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       9.329   7.847   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      10.586   5.494   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      10.445   3.839   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      11.661   2.894   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      11.450   1.368   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      13.088   3.473   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       9.019   3.259   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       9.182   4.791   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      16.734   0.637   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      17.157   3.687   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      18.583   4.267   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      19.799   3.322   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      21.225   3.902   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   61                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   58   59                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   55                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   58                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   38                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   37                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   35                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   25                                                       
CONECT   35   23   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   18                                                       
CONECT   38   16   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   56                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   56                                                  
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52                                                       
CONECT   52   51   53   56                                                  
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53    9                                                       
CONECT   56   52   43   46   57                                             
CONECT   57   56                                                            
CONECT   58   11    7                                                       
CONECT   59    7   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60    5   62                                                  
CONECT   62   61                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  136    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₈H₇₂O₁₄

Average Mass

873.0769 Da

Monoisotopic Mass

872.49221 Da

IUPAC Name

6-(butan-2-yl)-21',24'-dihydroxy-12'-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,11',13',22'-tetramethyl-5,6-dihydro-3',7',19'-trioxaspiro[pyran-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one

Traditional Name

21',24'-dihydroxy-12'-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,11',13',22'-tetramethyl-6-(sec-butyl)-5,6-dihydro-3',7',19'-trioxaspiro[pyran-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one

CAS Registry Number

Not Available

SMILES

CCC(C)C1OC2(CC3CC(CC=C(C)C(OC4CC(OC)C(OC5CC(OC)C(O)C(C)O5)C(C)O4)C(C)C=CC=C4COC5C(O)C(C)=CC(C(=O)O3)C45O)O2)C=CC1C

InChI Identifier

InChI=1S/C48H72O14/c1-11-25(2)43-28(5)17-18-47(62-43)23-34-20-33(61-47)16-15-27(4)42(26(3)13-12-14-32-24-55-45-40(49)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-10)44(31(8)57-39)60-38-21-36(53-9)41(50)30(7)56-38/h12-15,17-19,25-26,28,30-31,33-45,49-50,52H,11,16,20-24H2,1-10H3

InChI Key

RRZXIRBKKLTSOM-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

Species Name	Source	Reference
Streptomyces avermitilis	LOTUS Database	35616633

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
Disaccharide
Glycosyl compound
O-glycosyl compound
Ketal
Oxane
Pyran
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Lactone
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organic oxygen compound
Alcohol
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

an avermectin (CPD-12963 )

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	4.22	ALOGPS
logP	5.85	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	12.47	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	170.06 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	231.18 m³·mol⁻¹	ChemAxon
Polarizability	97.34 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	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

2262

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Avermectin B1a (NP0137196)

MOL for NP0137196 (Avermectin B1a)

3D MOL for NP0137196 (Avermectin B1a)

3D SDF for NP0137196 (Avermectin B1a)

3D-SDF for NP0137196 (Avermectin B1a)

PDB for NP0137196 (Avermectin B1a)

3D PDB for NP0137196 (Avermectin B1a)

SMILES for NP0137196 (Avermectin B1a)

INCHI for NP0137196 (Avermectin B1a)

Structure for NP0137196 (Avermectin B1a)

3D Structure for NP0137196 (Avermectin B1a)