NP-MRD: Showing NP-Card for (e,2e,4z)-n-[(1e)-3-[(8e,11z)-10,17-dihydroxy-7-(hydroxymethyl)-11-methyl-1,5-dioxo-4,7,10,13-tetrahydro-3h-2,6-benzodioxacyclopentadecin-3-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid (NP0233310)

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Record Information

Version

2.0

Created at

2022-09-06 14:52:03 UTC

Updated at

2022-09-06 14:52:03 UTC

NP-MRD ID

NP0233310

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(e,2e,4z)-n-[(1e)-3-[(8e,11z)-10,17-dihydroxy-7-(hydroxymethyl)-11-methyl-1,5-dioxo-4,7,10,13-tetrahydro-3h-2,6-benzodioxacyclopentadecin-3-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid

Description

Lobatamide F 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. Based on a literature review very few articles have been published on Lobatamide F.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062216522D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309062216522D          

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 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  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
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 29 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 13 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0233310

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO\N=C/C=C/C(/O)=N\C=C\CC1CC(=O)OC(CO)\C=C\C(O)\C(C)=C/CC2=CC=CC(O)=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C27H32N2O9/c1-18-10-11-19-6-3-8-23(32)26(19)27(35)38-20(7-4-14-28-24(33)9-5-15-29-36-2)16-25(34)37-21(17-30)12-13-22(18)31/h3-6,8-10,12-15,20-22,30-32H,7,11,16-17H2,1-2H3,(H,28,33)/b9-5+,13-12+,14-4+,18-10-,29-15-

> <INCHI_KEY>
JIRIKJKTSMGHQG-CFMTYHAKSA-N

> <FORMULA>
C27H32N2O9

> <MOLECULAR_WEIGHT>
528.558

> <EXACT_MASS>
528.210780618

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
54.61911731071008

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(E,2E,4Z)-N-[(1E)-3-[10,17-dihydroxy-7-(hydroxymethyl)-11-methyl-1,5-dioxo-3,4,5,7,10,13-hexahydro-1H-2,6-benzodioxacyclopentadecin-3-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid

> <JCHEM_LOGP>
0.47270512234388795

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.633050801395429

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.7206876073468083

> <JCHEM_PKA_STRONGEST_BASIC>
11.119811519370138

> <JCHEM_POLAR_SURFACE_AREA>
167.47

> <JCHEM_REFRACTIVITY>
142.14760000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(E,2E,4Z)-N-[(1E)-3-[10,17-dihydroxy-7-(hydroxymethyl)-11-methyl-1,5-dioxo-4,7,10,13-tetrahydro-3H-2,6-benzodioxacyclopentadecin-3-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      10.087  12.879   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.025  11.341   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      11.327  10.518   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      11.266   8.979   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.903   8.263   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.842   6.724   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.478   6.008   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.176   6.830   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       8.417   4.469   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       9.719   3.647   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.658   2.108   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.960   1.286   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.898  -0.253   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.342  -1.122   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.866  -0.895   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.577   0.471   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      14.552  -2.274   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.453  -3.352   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.840  -4.022   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      14.954  -5.558   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.277  -5.028   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.898  -5.715   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.804  -7.252   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.088  -8.103   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.425  -7.939   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.331  -9.476   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.141  -7.088   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.236  -5.551   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.952  -4.701   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.574  -5.387   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.290  -4.537   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.385  -2.999   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.763  -2.313   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.858  -0.776   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.047  -3.163   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.425  -2.477   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      10.709  -3.327   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       9.520  -0.940   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   38                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   29   36                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   13                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂N₂O₉

Average Mass

528.5580 Da

Monoisotopic Mass

528.21078 Da

IUPAC Name

(E,2E,4Z)-N-[(1E)-3-[10,17-dihydroxy-7-(hydroxymethyl)-11-methyl-1,5-dioxo-3,4,5,7,10,13-hexahydro-1H-2,6-benzodioxacyclopentadecin-3-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid

Traditional Name

(E,2E,4Z)-N-[(1E)-3-[10,17-dihydroxy-7-(hydroxymethyl)-11-methyl-1,5-dioxo-4,7,10,13-tetrahydro-3H-2,6-benzodioxacyclopentadecin-3-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid

CAS Registry Number

Not Available

SMILES

CO\N=C/C=C/C(/O)=N\C=C\CC1CC(=O)OC(CO)\C=C\C(O)\C(C)=C/CC2=CC=CC(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C27H32N2O9/c1-18-10-11-19-6-3-8-23(32)26(19)27(35)38-20(7-4-14-28-24(33)9-5-15-29-36-2)16-25(34)37-21(17-30)12-13-22(18)31/h3-6,8-10,12-15,20-22,30-32H,7,11,16-17H2,1-2H3,(H,28,33)/b9-5+,13-12+,14-4+,18-10-,29-15-

InChI Key

JIRIKJKTSMGHQG-CFMTYHAKSA-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 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
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Dicarboxylic acid or derivatives
Vinylogous acid
Secondary alcohol
Oxime ether
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen 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	0.47	ChemAxon
pKa (Strongest Acidic)	-0.72	ChemAxon
pKa (Strongest Basic)	11.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	167.47 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	142.15 m³·mol⁻¹	ChemAxon
Polarizability	54.62 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	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

32779150

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45027775

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (e,2e,4z)-n-[(1e)-3-[(8e,11z)-10,17-dihydroxy-7-(hydroxymethyl)-11-methyl-1,5-dioxo-4,7,10,13-tetrahydro-3h-2,6-benzodioxacyclopentadecin-3-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid (NP0233310)

MOL for NP0233310 ((e,2e,4z)-n-[(1e)-3-[(8e,11z)-10,17-dihydroxy-7-(hydroxymethyl)-11-methyl-1,5-dioxo-4,7,10,13-tetrahydro-3h-2,6-benzodioxacyclopentadecin-3-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid)

3D MOL for NP0233310 ((e,2e,4z)-n-[(1e)-3-[(8e,11z)-10,17-dihydroxy-7-(hydroxymethyl)-11-methyl-1,5-dioxo-4,7,10,13-tetrahydro-3h-2,6-benzodioxacyclopentadecin-3-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid)

3D SDF for NP0233310 ((e,2e,4z)-n-[(1e)-3-[(8e,11z)-10,17-dihydroxy-7-(hydroxymethyl)-11-methyl-1,5-dioxo-4,7,10,13-tetrahydro-3h-2,6-benzodioxacyclopentadecin-3-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid)

3D-SDF for NP0233310 ((e,2e,4z)-n-[(1e)-3-[(8e,11z)-10,17-dihydroxy-7-(hydroxymethyl)-11-methyl-1,5-dioxo-4,7,10,13-tetrahydro-3h-2,6-benzodioxacyclopentadecin-3-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid)

PDB for NP0233310 ((e,2e,4z)-n-[(1e)-3-[(8e,11z)-10,17-dihydroxy-7-(hydroxymethyl)-11-methyl-1,5-dioxo-4,7,10,13-tetrahydro-3h-2,6-benzodioxacyclopentadecin-3-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid)

3D PDB for NP0233310 ((e,2e,4z)-n-[(1e)-3-[(8e,11z)-10,17-dihydroxy-7-(hydroxymethyl)-11-methyl-1,5-dioxo-4,7,10,13-tetrahydro-3h-2,6-benzodioxacyclopentadecin-3-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid)

SMILES for NP0233310 ((e,2e,4z)-n-[(1e)-3-[(8e,11z)-10,17-dihydroxy-7-(hydroxymethyl)-11-methyl-1,5-dioxo-4,7,10,13-tetrahydro-3h-2,6-benzodioxacyclopentadecin-3-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid)

INCHI for NP0233310 ((e,2e,4z)-n-[(1e)-3-[(8e,11z)-10,17-dihydroxy-7-(hydroxymethyl)-11-methyl-1,5-dioxo-4,7,10,13-tetrahydro-3h-2,6-benzodioxacyclopentadecin-3-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid)

Structure for NP0233310 ((e,2e,4z)-n-[(1e)-3-[(8e,11z)-10,17-dihydroxy-7-(hydroxymethyl)-11-methyl-1,5-dioxo-4,7,10,13-tetrahydro-3h-2,6-benzodioxacyclopentadecin-3-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid)

3D Structure for NP0233310 ((e,2e,4z)-n-[(1e)-3-[(8e,11z)-10,17-dihydroxy-7-(hydroxymethyl)-11-methyl-1,5-dioxo-4,7,10,13-tetrahydro-3h-2,6-benzodioxacyclopentadecin-3-yl]prop-1-en-1-yl]-4-(methoxyimino)but-2-enimidic acid)