NP-MRD: Showing NP-Card for n-(2-bromoethyl)-1-{[(1r,4z,8e,10z,12s,15r,17s)-17-[(4r)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid (NP0149115)

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Record Information

Version

2.0

Created at

2022-09-02 04:57:36 UTC

Updated at

2022-09-02 04:57:36 UTC

NP-MRD ID

NP0149115

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-(2-bromoethyl)-1-{[(1r,4z,8e,10z,12s,15r,17s)-17-[(4r)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid

Description

CHEMBL255678 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. n-(2-bromoethyl)-1-{[(1r,4z,8e,10z,12s,15r,17s)-17-[(4r)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid is found in Negombata magnifica. Based on a literature review very few articles have been published on CHEMBL255678.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022206572D          

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  Mrv1652309022206572D          

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 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 21 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 29 34  1  6  0  0  0
 21 35  1  0  0  0  0
  7 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0149115

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@@H]2C[C@H](C[C@@](OC(O)=NCCBr)(O2)[C@@H]2CSC(O)=N2)OC(=O)\C=C(C)/CC\C=C\C=C/1

> <INCHI_IDENTIFIER>
InChI=1S/C25H35BrN2O6S/c1-17-7-5-3-4-6-8-18(2)13-22(29)32-20-14-19(10-9-17)33-25(15-20,21-16-35-24(31)28-21)34-23(30)27-12-11-26/h3-5,7,13,17,19-21H,6,8-12,14-16H2,1-2H3,(H,27,30)(H,28,31)/b4-3+,7-5-,18-13-/t17-,19-,20-,21+,25+/m1/s1

> <INCHI_KEY>
ZPHSMQHQJGJQEQ-ODVPECJOSA-N

> <FORMULA>
C25H35BrN2O6S

> <MOLECULAR_WEIGHT>
571.53

> <EXACT_MASS>
570.139921

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
55.41633764287879

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(2-bromoethyl)-1-{[(1R,4Z,8E,10Z,12S,15R,17S)-17-[(4R)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid

> <ALOGPS_LOGP>
4.37

> <JCHEM_LOGP>
5.517498080016479

> <ALOGPS_LOGS>
-5.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.0420801739425536

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.3116007635606932

> <JCHEM_PKA_STRONGEST_BASIC>
2.718295569653231

> <JCHEM_POLAR_SURFACE_AREA>
109.94000000000001

> <JCHEM_REFRACTIVITY>
142.3251

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.30e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(2-bromoethyl)-1-{[(1R,4Z,8E,10Z,12S,15R,17S)-17-[(4R)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      10.161  -9.185   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.391  -7.851   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.851  -7.851   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.081  -6.517   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.851  -5.184   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.541  -6.517   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.771  -5.184   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.541  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.771  -2.516   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.541  -1.183   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -1.183   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.851   0.151   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081   1.485   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.391   0.151   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.161  -1.183   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.391  -2.516   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.161  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.391  -5.184   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.161  -6.517   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.231  -2.516   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.461  -3.850   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.281  -2.860   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.549  -1.344   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.996  -0.817   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       0.369  -0.354   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      -1.078  -0.880   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.258   0.110   0.000  0.00  0.00           C+0
HETATM   28 Br   UNK     0      -3.705  -0.417   0.000  0.00  0.00          Br+0
HETATM   29  C   UNK     0       1.281  -4.840   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.389  -6.376   0.000  0.00  0.00           C+0
HETATM   31  S   UNK     0      -0.039  -6.953   0.000  0.00  0.00           S+0
HETATM   32  C   UNK     0      -1.029  -5.773   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.565  -5.881   0.000  0.00  0.00           O+0
HETATM   34  N   UNK     0      -0.213  -4.467   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       3.231  -5.184   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   35                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    2                                                       
CONECT   20    9   21                                                       
CONECT   21   20   22   29   35                                             
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   21   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   29                                                       
CONECT   35   21    7                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₅BrN₂O₆S

Average Mass

571.5300 Da

Monoisotopic Mass

570.13992 Da

IUPAC Name

N-(2-bromoethyl)-1-{[(1R,4Z,8E,10Z,12S,15R,17S)-17-[(4R)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid

Traditional Name

N-(2-bromoethyl)-1-{[(1R,4Z,8E,10Z,12S,15R,17S)-17-[(4R)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@@H]2C[C@H](C[C@@](OC(O)=NCCBr)(O2)[C@@H]2CSC(O)=N2)OC(=O)\C=C(C)/CC\C=C\C=C/1

InChI Identifier

InChI=1S/C25H35BrN2O6S/c1-17-7-5-3-4-6-8-18(2)13-22(29)32-20-14-19(10-9-17)33-25(15-20,21-16-35-24(31)28-21)34-23(30)27-12-11-26/h3-5,7,13,17,19-21H,6,8-12,14-16H2,1-2H3,(H,27,30)(H,28,31)/b4-3+,7-5-,18-13-/t17-,19-,20-,21+,25+/m1/s1

InChI Key

ZPHSMQHQJGJQEQ-ODVPECJOSA-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
Negombata magnifica	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
Ketal
Oxane
Thiazolidine
Carbamic acid ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Thiocarbamic acid derivative
Azacycle
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organobromide
Organohalogen compound
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Alkyl halide
Alkyl bromide
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	4.37	ALOGPS
logP	5.52	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	0.31	ChemAxon
pKa (Strongest Basic)	2.72	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.94 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	142.33 m³·mol⁻¹	ChemAxon
Polarizability	55.42 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

23314411

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24853809

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-(2-bromoethyl)-1-{[(1r,4z,8e,10z,12s,15r,17s)-17-[(4r)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid (NP0149115)

MOL for NP0149115 (n-(2-bromoethyl)-1-{[(1r,4z,8e,10z,12s,15r,17s)-17-[(4r)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid)

3D MOL for NP0149115 (n-(2-bromoethyl)-1-{[(1r,4z,8e,10z,12s,15r,17s)-17-[(4r)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid)

3D SDF for NP0149115 (n-(2-bromoethyl)-1-{[(1r,4z,8e,10z,12s,15r,17s)-17-[(4r)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid)

3D-SDF for NP0149115 (n-(2-bromoethyl)-1-{[(1r,4z,8e,10z,12s,15r,17s)-17-[(4r)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid)

PDB for NP0149115 (n-(2-bromoethyl)-1-{[(1r,4z,8e,10z,12s,15r,17s)-17-[(4r)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid)

3D PDB for NP0149115 (n-(2-bromoethyl)-1-{[(1r,4z,8e,10z,12s,15r,17s)-17-[(4r)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid)

SMILES for NP0149115 (n-(2-bromoethyl)-1-{[(1r,4z,8e,10z,12s,15r,17s)-17-[(4r)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid)

INCHI for NP0149115 (n-(2-bromoethyl)-1-{[(1r,4z,8e,10z,12s,15r,17s)-17-[(4r)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid)

Structure for NP0149115 (n-(2-bromoethyl)-1-{[(1r,4z,8e,10z,12s,15r,17s)-17-[(4r)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid)

3D Structure for NP0149115 (n-(2-bromoethyl)-1-{[(1r,4z,8e,10z,12s,15r,17s)-17-[(4r)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]oxy}methanimidic acid)