NP-MRD: Showing NP-Card for (5s,10z)-5-propyl-1-oxa-4-azacyclopentadec-10-en-15-one (NP0177009)

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Record Information

Version

2.0

Created at

2022-09-03 14:46:18 UTC

Updated at

2022-09-03 14:46:18 UTC

NP-MRD ID

NP0177009

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5s,10z)-5-propyl-1-oxa-4-azacyclopentadec-10-en-15-one

Description

Epilachnene 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. (5s,10z)-5-propyl-1-oxa-4-azacyclopentadec-10-en-15-one is found in Epilachna varivestis. (5s,10z)-5-propyl-1-oxa-4-azacyclopentadec-10-en-15-one was first documented in 2008 (PMID: 18827463). Based on a literature review very few articles have been published on Epilachnene (PMID: 23345004).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 48 48  0  0  0  0  0  0  0  0999 V2000
    5.6885    0.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2851    0.8144    0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4161   -0.4263    0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9882   -0.1293    0.7542 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4288    0.8942   -0.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0581    1.1100    0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3499    2.4475    0.6996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8627    2.6357    0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4099    2.2627   -0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2564    1.2511   -0.7555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488    0.5038    0.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3150   -0.7918    0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2778   -1.7742   -0.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6478   -2.4409    0.6364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4803   -2.9411    1.4346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2992   -2.4551    0.7411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3201   -2.9037   -0.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7504   -1.8453   -0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2816   -1.3590    0.8304 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3985    1.2647    0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6842    0.1294   -1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9998   -0.4617    0.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8924    1.5599   -0.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3179    1.2192    1.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8606   -1.1666    1.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4790   -0.8763   -0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0393    0.3046    1.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9146    1.8698    0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6803    0.7090   -1.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6153    1.1211   -0.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4264    0.3348    0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0868    3.2471    0.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0201    2.4846    1.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3656    2.1793    1.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0157    3.7494    0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1016    2.8345   -1.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6554    0.9834   -1.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3830    1.0657    1.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8033    0.2271    1.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8158   -1.2019    0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0650   -0.5694   -0.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7761   -2.5371   -1.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5748   -1.1634   -1.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6451   -3.3086   -1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2185   -3.7536    0.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2854   -1.1017   -1.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5920   -2.2985   -0.9748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8610   -2.1172    1.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  1
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
M  END


  Mrv1652309032216462D          

 19 19  0  0  1  0            999 V2000
    2.3338    3.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0426    2.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5655    2.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2742    1.5504    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7971    0.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6112    1.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1341    0.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8524   -0.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1524   -1.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5143   -1.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8198   -1.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9235   -1.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4006   -0.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5865   -0.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2953   -1.6709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0636   -0.2609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3549    0.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1689    0.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4602    1.4166    0.0000 N   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
  4  3  1  1  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  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  4 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0177009

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC[C@H]1CCCC\C=C/CCCC(=O)OCCN1

> <INCHI_IDENTIFIER>
InChI=1S/C16H29NO2/c1-2-10-15-11-8-6-4-3-5-7-9-12-16(18)19-14-13-17-15/h3,5,15,17H,2,4,6-14H2,1H3/b5-3-/t15-/m0/s1

> <INCHI_KEY>
QDPAWHWSRVALOP-QTLSWZBMSA-N

> <FORMULA>
C16H29NO2

> <MOLECULAR_WEIGHT>
267.413

> <EXACT_MASS>
267.219829178

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
31.830840036254305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,10Z)-5-propyl-1-oxa-4-azacyclopentadec-10-en-15-one

> <JCHEM_LOGP>
3.9188729736666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.790203566731543

> <JCHEM_POLAR_SURFACE_AREA>
38.33

> <JCHEM_REFRACTIVITY>
79.89989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5S,10Z)-5-propyl-1-oxa-4-azacyclopentadec-10-en-15-one

> <JCHEM_VEBER_RULE>
1

$$$$

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       4.356   6.967   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.813   5.526   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.789   4.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.245   2.894   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.221   1.703   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.741   1.952   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.717   0.761   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.191  -0.840   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.751  -2.274   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.560  -3.250   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.264  -2.419   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590  -2.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.614  -1.429   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.095  -1.678   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.551  -3.119   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.119  -0.487   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.662   0.954   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.182   1.203   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.726   2.644   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
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                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    4                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
11-Propyl-12-azacyclotetradec-5-ene-14-olide	MeSH

Chemical Formula

C₁₆H₂₉NO₂

Average Mass

267.4130 Da

Monoisotopic Mass

267.21983 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC[C@H]1CCCC\C=C/CCCC(=O)OCCN1

InChI Identifier

InChI=1S/C16H29NO2/c1-2-10-15-11-8-6-4-3-5-7-9-12-16(18)19-14-13-17-15/h3,5,15,17H,2,4,6-14H2,1H3/b5-3-/t15-/m0/s1

InChI Key

QDPAWHWSRVALOP-QTLSWZBMSA-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
Epilachna varivestis	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
Amino acid or derivatives
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Organoheterocyclic compound
Azacycle
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Amine
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

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

4948196

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6444271

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang C, Yu M, Kyle AF, Jakubec P, Dixon DJ, Schrock RR, Hoveyda AH: Efficient and selective formation of macrocyclic disubstituted Z alkenes by ring-closing metathesis (RCM) reactions catalyzed by Mo- or W-based monoaryloxide pyrrolide (MAP) complexes: applications to total syntheses of epilachnene, yuzu lactone, ambrettolide, epothilone C, and nakadomarin A. Chemistry. 2013 Feb 18;19(8):2726-40. doi: 10.1002/chem.201204045. Epub 2013 Jan 23. [PubMed:23345004 ]
Kaku H: [Thermodynamically controlled deracemization utilizing inclusion complexation]. Yakugaku Zasshi. 2008 Oct;128(10):1431-41. doi: 10.1248/yakushi.128.1431. [PubMed:18827463 ]
LOTUS database [Link]

Showing NP-Card for (5s,10z)-5-propyl-1-oxa-4-azacyclopentadec-10-en-15-one (NP0177009)

MOL for NP0177009 ((5s,10z)-5-propyl-1-oxa-4-azacyclopentadec-10-en-15-one)

3D MOL for NP0177009 ((5s,10z)-5-propyl-1-oxa-4-azacyclopentadec-10-en-15-one)

3D SDF for NP0177009 ((5s,10z)-5-propyl-1-oxa-4-azacyclopentadec-10-en-15-one)

3D-SDF for NP0177009 ((5s,10z)-5-propyl-1-oxa-4-azacyclopentadec-10-en-15-one)

PDB for NP0177009 ((5s,10z)-5-propyl-1-oxa-4-azacyclopentadec-10-en-15-one)

3D PDB for NP0177009 ((5s,10z)-5-propyl-1-oxa-4-azacyclopentadec-10-en-15-one)

SMILES for NP0177009 ((5s,10z)-5-propyl-1-oxa-4-azacyclopentadec-10-en-15-one)

INCHI for NP0177009 ((5s,10z)-5-propyl-1-oxa-4-azacyclopentadec-10-en-15-one)

Structure for NP0177009 ((5s,10z)-5-propyl-1-oxa-4-azacyclopentadec-10-en-15-one)

3D Structure for NP0177009 ((5s,10z)-5-propyl-1-oxa-4-azacyclopentadec-10-en-15-one)