NP-MRD: Showing NP-Card for (1r,2r)-2-[(2s,4e,6z,8r,9s,11r,13s,15s,16s)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclobutane-1-carboxylic acid (NP0150566)

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Record Information

Version

2.0

Created at

2022-09-02 06:42:19 UTC

Updated at

2022-09-02 06:42:19 UTC

NP-MRD ID

NP0150566

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

CHEMBL221697 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. (1r,2r)-2-[(2s,4e,6z,8r,9s,11r,13s,15s,16s)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclobutane-1-carboxylic acid is found in Streptomyces rochei. Based on a literature review very few articles have been published on CHEMBL221697.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022208422D          

 34 35  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022208422D          

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 24 25  1  0  0  0  0
 25 26  3  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
  2 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0150566

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H41NO6/c1-16-11-17(2)13-19(4)26(31)20(15-28)7-5-6-8-24(21-9-10-22(21)27(32)33)34-25(30)14-23(29)18(3)12-16/h5-7,16-19,21-24,26,29,31H,8-14H2,1-4H3,(H,32,33)/b6-5+,20-7-/t16-,17+,18-,19-,21+,22+,23-,24-,26+/m0/s1

> <INCHI_KEY>
AOKPUKQFVXDBSJ-GUNUBHQASA-N

> <FORMULA>
C27H41NO6

> <MOLECULAR_WEIGHT>
475.626

> <EXACT_MASS>
475.293388044

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.939266756551916

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
4.2147892743333335

> <ALOGPS_LOGS>
-4.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.698482800028899

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.809995234426774

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9329410031715746

> <JCHEM_POLAR_SURFACE_AREA>
127.85000000000001

> <JCHEM_REFRACTIVITY>
130.85729999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R)-2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclobutane-1-carboxylic 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      10.669   9.878   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  10.648   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337   9.878   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337   8.338   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.670   7.568   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003   7.568   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.003   6.028   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.669   8.338   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   7.568   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.336   6.028   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       8.002   8.338   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668   7.568   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   6.028   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.757   4.939   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.579   4.939   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.039   4.939   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.269   3.605   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.269   6.273   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.335   8.338   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   9.878   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  10.648   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  12.188   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  12.958   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  14.498   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       5.335  16.038   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       6.668  12.188   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.668  10.648   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.002  12.958   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002  14.498   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.336  12.188   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.669  12.958   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.669  14.498   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.003  12.188   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    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   20                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   13   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   12   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    2                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₁NO₆

Average Mass

475.6260 Da

Monoisotopic Mass

475.29339 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@@H](C)C[C@H](C)[C@@H](O)\C(=C/C=C/C[C@H](OC(=O)C[C@H](O)[C@@H](C)C1)[C@@H]1CC[C@H]1C(O)=O)C#N

InChI Identifier

InChI=1S/C27H41NO6/c1-16-11-17(2)13-19(4)26(31)20(15-28)7-5-6-8-24(21-9-10-22(21)27(32)33)34-25(30)14-23(29)18(3)12-16/h5-7,16-19,21-24,26,29,31H,8-14H2,1-4H3,(H,32,33)/b6-5+,20-7-/t16-,17+,18-,19-,21+,22+,23-,24-,26+/m0/s1

InChI Key

AOKPUKQFVXDBSJ-GUNUBHQASA-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 rochei	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
Dicarboxylic acid or derivatives
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Carbonitrile
Nitrile
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organic oxide
Cyanide
Organic oxygen compound
Alcohol
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
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	3.71	ALOGPS
logP	4.21	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	3.81	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	127.85 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	130.86 m³·mol⁻¹	ChemAxon
Polarizability	52.94 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

23279361

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44419577

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,4e,6z,8r,9s,11r,13s,15s,16s)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclobutane-1-carboxylic acid (NP0150566)

MOL for NP0150566 ((1r,2r)-2-[(2s,4e,6z,8r,9s,11r,13s,15s,16s)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclobutane-1-carboxylic acid)

3D MOL for NP0150566 ((1r,2r)-2-[(2s,4e,6z,8r,9s,11r,13s,15s,16s)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclobutane-1-carboxylic acid)

3D SDF for NP0150566 ((1r,2r)-2-[(2s,4e,6z,8r,9s,11r,13s,15s,16s)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclobutane-1-carboxylic acid)

3D-SDF for NP0150566 ((1r,2r)-2-[(2s,4e,6z,8r,9s,11r,13s,15s,16s)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclobutane-1-carboxylic acid)

PDB for NP0150566 ((1r,2r)-2-[(2s,4e,6z,8r,9s,11r,13s,15s,16s)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclobutane-1-carboxylic acid)

3D PDB for NP0150566 ((1r,2r)-2-[(2s,4e,6z,8r,9s,11r,13s,15s,16s)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclobutane-1-carboxylic acid)

SMILES for NP0150566 ((1r,2r)-2-[(2s,4e,6z,8r,9s,11r,13s,15s,16s)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclobutane-1-carboxylic acid)

INCHI for NP0150566 ((1r,2r)-2-[(2s,4e,6z,8r,9s,11r,13s,15s,16s)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclobutane-1-carboxylic acid)

Structure for NP0150566 ((1r,2r)-2-[(2s,4e,6z,8r,9s,11r,13s,15s,16s)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclobutane-1-carboxylic acid)

3D Structure for NP0150566 ((1r,2r)-2-[(2s,4e,6z,8r,9s,11r,13s,15s,16s)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclobutane-1-carboxylic acid)