NP-MRD: Showing NP-Card for (7r,8s,13z,15z,17z)-2-[(2e,4e)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one (NP0247535)

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Record Information

Version

2.0

Created at

2022-09-07 09:25:22 UTC

Updated at

2022-09-07 09:25:22 UTC

NP-MRD ID

NP0247535

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(7r,8s,13z,15z,17z)-2-[(2e,4e)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one

Description

Fr252921 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. (7r,8s,13z,15z,17z)-2-[(2e,4e)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one is found in Pseudomonas fluorescens. (7r,8s,13z,15z,17z)-2-[(2e,4e)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one was first documented in 2007 (PMID: 17941643). Based on a literature review a small amount of articles have been published on fr252921 (PMID: 35274951) (PMID: 31436963) (PMID: 27818534) (PMID: 19219867).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072211252D          

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M  END


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    4.8212   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4487   -0.8341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8574   -1.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113   -1.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2913   -1.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4863   -1.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1758   -2.4362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7834   -1.2398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  4  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  4  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  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
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 13 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247535

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC\C=C\C=C(/C)C1CC(O)=NC[C@H](O)[C@H](C)C(O)=NCC\C=C/C=C\C=C/C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C29H44N2O5/c1-4-5-6-7-8-9-12-15-18-23(2)26-21-27(33)31-22-25(32)24(3)29(35)30-20-17-14-11-10-13-16-19-28(34)36-26/h10-16,18-19,24-26,32H,4-9,17,20-22H2,1-3H3,(H,30,35)(H,31,33)/b13-10-,14-11-,15-12+,19-16-,23-18+/t24-,25-,26?/m0/s1

> <INCHI_KEY>
BMWFPIGVZGRBAD-VRQYISITSA-N

> <FORMULA>
C29H44N2O5

> <MOLECULAR_WEIGHT>
500.68

> <EXACT_MASS>
500.325022525

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
57.59219559094397

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(7R,8S,13Z,15Z,17Z)-2-[(2E,4E)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one

> <JCHEM_LOGP>
5.004166690035005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.048411091960033

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4391588873772396

> <JCHEM_PKA_STRONGEST_BASIC>
6.2011128294635025

> <JCHEM_POLAR_SURFACE_AREA>
111.71000000000001

> <JCHEM_REFRACTIVITY>
149.93880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(7R,8S,13Z,15Z,17Z)-2-[(2E,4E)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0     -14.187  -1.896   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.853  -1.126   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.520  -1.896   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.186  -1.126   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.852  -1.896   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.519  -1.126   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.185  -1.896   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.851  -1.126   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.518  -1.896   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.184  -1.126   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.850  -1.896   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.850  -3.436   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.483  -1.126   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.057   0.317   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.099   1.856   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.624   2.068   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       0.361   3.326   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       1.273   4.567   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.538   5.444   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.881   6.837   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.020   5.863   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.851   7.394   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.558   5.778   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.895   7.281   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       6.985   5.199   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       8.146   4.188   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.916   2.854   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.211   1.342   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.000  -0.183   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.304  -1.557   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.200  -2.631   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.808  -3.288   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.277  -3.458   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.774  -3.121   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.195  -4.548   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.462  -2.314   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                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   36                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   13                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₄N₂O₅

Average Mass

500.6800 Da

Monoisotopic Mass

500.32502 Da

IUPAC Name

(7R,8S,13Z,15Z,17Z)-2-[(2E,4E)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one

Traditional Name

(7R,8S,13Z,15Z,17Z)-2-[(2E,4E)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one

CAS Registry Number

Not Available

SMILES

CCCCCCC\C=C\C=C(/C)C1CC(O)=NC[C@H](O)[C@H](C)C(O)=NCC\C=C/C=C\C=C/C(=O)O1

InChI Identifier

InChI=1S/C29H44N2O5/c1-4-5-6-7-8-9-12-15-18-23(2)26-21-27(33)31-22-25(32)24(3)29(35)30-20-17-14-11-10-13-16-19-28(34)36-26/h10-16,18-19,24-26,32H,4-9,17,20-22H2,1-3H3,(H,30,35)(H,31,33)/b13-10-,14-11-,15-12+,19-16-,23-18+/t24-,25-,26?/m0/s1

InChI Key

BMWFPIGVZGRBAD-VRQYISITSA-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
Pseudomonas fluorescens	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
Cyclic carboximidic acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Monocarboxylic acid or derivatives
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	5	ChemAxon
pKa (Strongest Acidic)	3.44	ChemAxon
pKa (Strongest Basic)	6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.71 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	149.94 m³·mol⁻¹	ChemAxon
Polarizability	57.59 Å³	ChemAxon
Number of Rings	1	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

78438142

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587425

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dethe DH, Kumar V, Beeralingappa NC, Mishra KB, Nirpal AK: Synthesis of Polyene Bioactive Natural Products: FR252921 and Vitamin A. Org Lett. 2022 Mar 25;24(11):2203-2207. doi: 10.1021/acs.orglett.2c00546. Epub 2022 Mar 11. [PubMed:35274951 ]
Chen Y, Coussanes G, Souris C, Aillard P, Kaldre D, Runggatscher K, Kubicek S, Di Mauro G, Maryasin B, Maulide N: A Domino 10-Step Total Synthesis of FR252921 and Its Analogues, Complex Macrocyclic Immunosuppressants. J Am Chem Soc. 2019 Sep 4;141(35):13772-13777. doi: 10.1021/jacs.9b07185. Epub 2019 Aug 22. [PubMed:31436963 ]
Ghosh AK, Rodriguez S: An enantioselective synthesis of the C3-C21 segment of the macrolide immunosuppressive agent FR252921. Tetrahedron Lett. 2016 Jun 29;57(26):2884-2887. doi: 10.1016/j.tetlet.2016.05.067. Epub 2016 May 18. [PubMed:27818534 ]
Amans D, Bellosta V, Cossy J: Synthesis of two bioactive natural products: FR252921 and pseudotrienic acid B. Chemistry. 2009;15(14):3457-73. doi: 10.1002/chem.200802649. [PubMed:19219867 ]
Amans D, Bellosta V, Cossy J: Synthesis of a promising immunosuppressant: FR252921. Org Lett. 2007 Nov 8;9(23):4761-4. doi: 10.1021/ol702110k. Epub 2007 Oct 17. [PubMed:17941643 ]
LOTUS database [Link]

Showing NP-Card for (7r,8s,13z,15z,17z)-2-[(2e,4e)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one (NP0247535)

MOL for NP0247535 ((7r,8s,13z,15z,17z)-2-[(2e,4e)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one)

3D MOL for NP0247535 ((7r,8s,13z,15z,17z)-2-[(2e,4e)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one)

3D SDF for NP0247535 ((7r,8s,13z,15z,17z)-2-[(2e,4e)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one)

3D-SDF for NP0247535 ((7r,8s,13z,15z,17z)-2-[(2e,4e)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one)

PDB for NP0247535 ((7r,8s,13z,15z,17z)-2-[(2e,4e)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one)

3D PDB for NP0247535 ((7r,8s,13z,15z,17z)-2-[(2e,4e)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one)

SMILES for NP0247535 ((7r,8s,13z,15z,17z)-2-[(2e,4e)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one)

INCHI for NP0247535 ((7r,8s,13z,15z,17z)-2-[(2e,4e)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one)

Structure for NP0247535 ((7r,8s,13z,15z,17z)-2-[(2e,4e)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one)

3D Structure for NP0247535 ((7r,8s,13z,15z,17z)-2-[(2e,4e)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one)