NP-MRD: Showing NP-Card for (1r,2r)-2-[(2s,8r,9s,11r,13s,14s,15r,16s)-7-cyano-8,14,16-trihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid (NP0178749)

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Record Information

Version

2.0

Created at

2022-09-03 16:48:01 UTC

Updated at

2022-09-03 16:48:01 UTC

NP-MRD ID

NP0178749

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r)-2-[(2s,8r,9s,11r,13s,14s,15r,16s)-7-cyano-8,14,16-trihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid

Description

Borrelidin L 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 a small amount of articles have been published on Borrelidin L.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032218482D          

 36 37  0  0  1  0            999 V2000
    5.6091    3.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    3.6509    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  2 35  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309032218482D          

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  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  3  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  4  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0178749

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H](C)[C@H](O)[C@H](C)[C@@H](O)CC(=O)O[C@@H](CC=CC=C(C#N)[C@H](O)[C@@H](C)C1)[C@@H]1CCC[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H43NO7/c1-16-12-17(2)26(32)19(4)23(30)14-25(31)36-24(21-9-7-10-22(21)28(34)35)11-6-5-8-20(15-29)27(33)18(3)13-16/h5-6,8,16-19,21-24,26-27,30,32-33H,7,9-14H2,1-4H3,(H,34,35)/t16-,17+,18+,19-,21-,22-,23+,24+,26+,27-/m1/s1

> <INCHI_KEY>
SIOKKMJNZJVHPS-VTKHTTOASA-N

> <FORMULA>
C28H43NO7

> <MOLECULAR_WEIGHT>
505.652

> <EXACT_MASS>
505.303952729

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
54.93225705120617

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R)-2-[(2S,8R,9S,11R,13S,14S,15R,16S)-7-cyano-8,14,16-trihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid

> <JCHEM_LOGP>
3.3921498693333323

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.642472543252502

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8741594427836277

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9602392158540924

> <JCHEM_POLAR_SURFACE_AREA>
148.07999999999998

> <JCHEM_REFRACTIVITY>
136.95200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R)-2-[(2S,8R,9S,11R,13S,14S,15R,16S)-7-cyano-8,14,16-trihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      10.470   6.045   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.137   6.815   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.137   8.355   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.470   9.125   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.470  10.665   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.804   8.355   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.804   6.815   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.178   5.408   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.138   6.045   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      14.471   6.815   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.138   4.505   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.471   5.275   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      15.805   6.045   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      14.471   3.735   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.471   2.195   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.138   1.425   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.138  -0.115   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.804  -0.885   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.804  -2.425   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.050  -3.330   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.574  -4.795   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.034  -4.795   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.558  -3.330   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.093  -2.854   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.949  -3.885   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.773  -1.348   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      10.470  -0.115   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.470   1.425   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.804   2.195   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.137   2.195   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.137   3.735   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.470   4.505   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.803   4.505   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.469   3.735   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.803   6.045   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.469   6.815   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   18   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    2   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₃NO₇

Average Mass

505.6520 Da

Monoisotopic Mass

505.30395 Da

IUPAC Name

(1R,2R)-2-[(2S,8R,9S,11R,13S,14S,15R,16S)-7-cyano-8,14,16-trihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid

Traditional Name

(1R,2R)-2-[(2S,8R,9S,11R,13S,14S,15R,16S)-7-cyano-8,14,16-trihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H](C)[C@H](O)[C@H](C)[C@@H](O)CC(=O)O[C@@H](CC=CC=C(C#N)[C@H](O)[C@@H](C)C1)[C@@H]1CCC[C@H]1C(O)=O

InChI Identifier

InChI=1S/C28H43NO7/c1-16-12-17(2)26(32)19(4)23(30)14-25(31)36-24(21-9-7-10-22(21)28(34)35)11-6-5-8-20(15-29)27(33)18(3)13-16/h5-6,8,16-19,21-24,26-27,30,32-33H,7,9-14H2,1-4H3,(H,34,35)/t16-,17+,18+,19-,21-,22-,23+,24+,26+,27-/m1/s1

InChI Key

SIOKKMJNZJVHPS-VTKHTTOASA-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
Dicarboxylic acid or derivatives
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Nitrile
Carbonitrile
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	3.39	ChemAxon
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	148.08 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	136.95 m³·mol⁻¹	ChemAxon
Polarizability	54.93 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

139591280

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r)-2-[(2s,8r,9s,11r,13s,14s,15r,16s)-7-cyano-8,14,16-trihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid (NP0178749)

MOL for NP0178749 ((1r,2r)-2-[(2s,8r,9s,11r,13s,14s,15r,16s)-7-cyano-8,14,16-trihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid)

3D MOL for NP0178749 ((1r,2r)-2-[(2s,8r,9s,11r,13s,14s,15r,16s)-7-cyano-8,14,16-trihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid)

3D SDF for NP0178749 ((1r,2r)-2-[(2s,8r,9s,11r,13s,14s,15r,16s)-7-cyano-8,14,16-trihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid)

3D-SDF for NP0178749 ((1r,2r)-2-[(2s,8r,9s,11r,13s,14s,15r,16s)-7-cyano-8,14,16-trihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid)

PDB for NP0178749 ((1r,2r)-2-[(2s,8r,9s,11r,13s,14s,15r,16s)-7-cyano-8,14,16-trihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid)

3D PDB for NP0178749 ((1r,2r)-2-[(2s,8r,9s,11r,13s,14s,15r,16s)-7-cyano-8,14,16-trihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid)

SMILES for NP0178749 ((1r,2r)-2-[(2s,8r,9s,11r,13s,14s,15r,16s)-7-cyano-8,14,16-trihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid)

INCHI for NP0178749 ((1r,2r)-2-[(2s,8r,9s,11r,13s,14s,15r,16s)-7-cyano-8,14,16-trihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid)

Structure for NP0178749 ((1r,2r)-2-[(2s,8r,9s,11r,13s,14s,15r,16s)-7-cyano-8,14,16-trihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid)

3D Structure for NP0178749 ((1r,2r)-2-[(2s,8r,9s,11r,13s,14s,15r,16s)-7-cyano-8,14,16-trihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid)