NP-MRD: Showing NP-Card for butyl (3e,5r)-5-[(1s,5s,6e,9z,11r,13s,15s)-5-(acetyloxy)-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate (NP0159960)

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Record Information

Version

2.0

Created at

2022-09-02 17:48:29 UTC

Updated at

2022-09-02 17:48:29 UTC

NP-MRD ID

NP0159960

Secondary Accession Numbers

None

Natural Product Identification

Common Name

butyl (3e,5r)-5-[(1s,5s,6e,9z,11r,13s,15s)-5-(acetyloxy)-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate

Description

Haterumalide NC 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 Haterumalide NC.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022219482D          

 37 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022219482D          

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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 14 12  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 18 17  1  1  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 16 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0159960

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCOC(=O)C\C(C)=C\[C@@H](O)[C@@H]1O[C@@H]2C[C@@H]1OC(=O)C[C@H](OC(C)=O)\C(C)=C\C\C=C(Cl)\[C@H](O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C27H39ClO9/c1-5-6-10-34-25(32)12-16(2)11-22(31)27-24-14-19(36-27)13-21(30)20(28)9-7-8-17(3)23(35-18(4)29)15-26(33)37-24/h8-9,11,19,21-24,27,30-31H,5-7,10,12-15H2,1-4H3/b16-11+,17-8+,20-9-/t19-,21+,22+,23-,24-,27-/m0/s1

> <INCHI_KEY>
ZLWFEQFAHDURAA-OQIWQVAGSA-N

> <FORMULA>
C27H39ClO9

> <MOLECULAR_WEIGHT>
543.05

> <EXACT_MASS>
542.2282605

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.798658862256275

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
butyl (3E,5R)-5-[(1S,5S,6E,9Z,11R,13S,15S)-5-(acetyloxy)-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
2.426221363999998

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.000285190141781

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.395279515974984

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3527475299202543

> <JCHEM_POLAR_SURFACE_AREA>
128.59

> <JCHEM_REFRACTIVITY>
138.6717

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butyl (3E,5R)-5-[(1S,5S,6E,9Z,11R,13S,15S)-5-(acetyloxy)-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate

> <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       1.008 -15.415   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.342 -14.645   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.675 -15.415   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.009 -14.645   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.343 -15.415   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.676 -14.645   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.676 -13.105   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.010 -15.415   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.344 -14.645   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.344 -13.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.677 -15.415   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.011 -14.645   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.011 -13.105   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      14.345 -15.415   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      14.478 -16.949   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      15.978 -17.297   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.772 -15.977   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.027 -14.630   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.821 -13.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      18.360 -13.338   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      19.106 -14.685   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      19.154 -12.018   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.694 -12.046   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      21.488 -10.726   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      23.028 -10.754   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      23.822  -9.435   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      23.773 -12.102   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      21.440 -13.393   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.980 -13.421   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.646 -14.713   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      21.392 -16.060   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      20.598 -17.380   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      19.058 -17.352   0.000  0.00  0.00           C+0
HETATM   34 Cl   UNK     0      18.312 -16.005   0.000  0.00  0.00          Cl+0
HETATM   35  C   UNK     0      18.264 -18.672   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      19.010 -20.019   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      16.724 -18.644   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   37                                                  
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   16                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₉ClO₉

Average Mass

543.0500 Da

Monoisotopic Mass

542.22826 Da

IUPAC Name

butyl (3E,5R)-5-[(1S,5S,6E,9Z,11R,13S,15S)-5-(acetyloxy)-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate

Traditional Name

butyl (3E,5R)-5-[(1S,5S,6E,9Z,11R,13S,15S)-5-(acetyloxy)-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate

CAS Registry Number

Not Available

SMILES

CCCCOC(=O)C\C(C)=C\[C@@H](O)[C@@H]1O[C@@H]2C[C@@H]1OC(=O)C[C@H](OC(C)=O)\C(C)=C\C\C=C(Cl)\[C@H](O)C2

InChI Identifier

InChI=1S/C27H39ClO9/c1-5-6-10-34-25(32)12-16(2)11-22(31)27-24-14-19(36-27)13-21(30)20(28)9-7-8-17(3)23(35-18(4)29)15-26(33)37-24/h8-9,11,19,21-24,27,30-31H,5-7,10,12-15H2,1-4H3/b16-11+,17-8+,20-9-/t19-,21+,22+,23-,24-,27-/m0/s1

InChI Key

ZLWFEQFAHDURAA-OQIWQVAGSA-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
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Monosaccharide
Tetrahydrofuran
Secondary alcohol
Lactone
Halohydrin
Chlorohydrin
Carboxylic acid ester
Oxacycle
Chloroalkene
Haloalkene
Organoheterocyclic compound
Vinyl halide
Vinyl chloride
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Alcohol
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	2.83	ALOGPS
logP	2.43	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	13.4	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.59 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	138.67 m³·mol⁻¹	ChemAxon
Polarizability	55.8 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

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

100936921

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for butyl (3e,5r)-5-[(1s,5s,6e,9z,11r,13s,15s)-5-(acetyloxy)-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate (NP0159960)

MOL for NP0159960 (butyl (3e,5r)-5-[(1s,5s,6e,9z,11r,13s,15s)-5-(acetyloxy)-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

3D MOL for NP0159960 (butyl (3e,5r)-5-[(1s,5s,6e,9z,11r,13s,15s)-5-(acetyloxy)-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

3D SDF for NP0159960 (butyl (3e,5r)-5-[(1s,5s,6e,9z,11r,13s,15s)-5-(acetyloxy)-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

3D-SDF for NP0159960 (butyl (3e,5r)-5-[(1s,5s,6e,9z,11r,13s,15s)-5-(acetyloxy)-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

PDB for NP0159960 (butyl (3e,5r)-5-[(1s,5s,6e,9z,11r,13s,15s)-5-(acetyloxy)-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

3D PDB for NP0159960 (butyl (3e,5r)-5-[(1s,5s,6e,9z,11r,13s,15s)-5-(acetyloxy)-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

SMILES for NP0159960 (butyl (3e,5r)-5-[(1s,5s,6e,9z,11r,13s,15s)-5-(acetyloxy)-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

INCHI for NP0159960 (butyl (3e,5r)-5-[(1s,5s,6e,9z,11r,13s,15s)-5-(acetyloxy)-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

Structure for NP0159960 (butyl (3e,5r)-5-[(1s,5s,6e,9z,11r,13s,15s)-5-(acetyloxy)-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

3D Structure for NP0159960 (butyl (3e,5r)-5-[(1s,5s,6e,9z,11r,13s,15s)-5-(acetyloxy)-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)